Textbook Of - Wild Rose College

Copyright © 1992, Wild Rose College of Natural Healing Ltd.©

Textbook OfAdvancedHerbology

byTerry Willard, Ph.D.

assisted by James McCormick, M.Sc.

Foreword by Christopher HobbsPreface by Joseph Pizzorno, N.D.

Wild Rose College of Natural Healing, Ltd.302, 1220 Kensington Rd. N.W.

Calgary, AlbertaT2N 3P5

Copyright © 1992, Wild Rose College of Natural Healing Ltd.

Disclaimer: Individuals seeking relief from illness should consult aqualified health practitioner. This book cannot, and is not meant to,replace the services of a health professional.

© 1992 Wild Rose College of Natural Healing, Ltd.

302- 1220 Kensington Rd. N.W.Calgary, Alberta, CANADAT2N 3P5Phone: (403) 270-0936FAX: (403) 283-0799

Illustrations by: Rob RenpenningNaomi Lewis

Illustrations, Chemical Diagrams and Charts by James McCormick

plus digital adaptations from materials in the public domain.

Figure 11.1 reproduced with the permission of CRC Press, Boca Raton,FL, U.S.A..

Minor typographic changes and enhancements ... October 1994

ISBN # 0-9691727-1-0

ii


Table of Contents

Foreword by Christopher Hobbs, M.H.Preface by Joseph Pizzorno, N.D.Acknowledgements

Introduction 1Chapter 1: A Background in the Medicinal Use of Plants 5Chapter 2: A Foundation in Chemistry 35Chapter 3: Carbohydrates and Related Compounds 67Chapter 4: Glycosides 99Chapter 5: Organic Acids, Aromatic Acids and Tannins 159Chapter 6: Lipids 175Chapter 7: Volatile Oils 213Chapter 8: Resins 253Chapter 9: Terpenoids, Sterols, Cardiac Glycosides, Etc. 273Chapter 10: Alkaloids 287Chapter 11: Herbal Product Assessment 315Chapter 12: Herbal Product Manufacture 331Chapter 13: Herbology and Pharmacological Research 353Chapter 14: Alchemy and Herbs 367Appendices

GRAS Information 385Periodic Table of the Elements 394

IndicesChemical 395General 406

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Copyright © 1992, Wild Rose College of Natural Healing Ltd.i v

Foreword

by Christopher Hobbs, Santa Cruz, CA.(Author of Echinacea: The Immune Herb )

I am pleased to have been asked by Terry Willard to write a Foreword tohis new textbook, Textbook of Advanced Herbology. Terry and I havebeen meeting and teaching together for several years at conferencesaround the United States. In that time, I have been increasingly im-pressed with his dedication to herbalism, and his amazing energy andenthusiasm.

Like other creative herbalists today, Terry is primarily interested in the"New World herbalism" being created out of the three major systems ofworld healing -- Traditional Chinese Medicine (TCM), Traditional Euro-pean Medicine (TEM) and Ayurveda. This is an exciting time forherbalism and herbalists -- a true Renaissance.

I can say with confidence that the Textbook of Advanced Herbology issolidly in the spirit of this new herbalism. It is well researched andorganized, and represents a tremendous number of hours of compilingand years of personal experience.

Of course, there are always critics of this kind of cutting-edge work.They will point out that some of this text is personal opinion, not provenscientific fact. But I know from my own work that it is hard to blendscience with one's own experience, especially in herbalism, when thereis so much that we don't know about the mysteries of the plant-humanhealing connection. The bottom line is that both "teachers" and "stu-dents" continue to learn every moment they practice their art. Thosewho stop learning can hardly be considered real herbalists.

Now for a few practical comments. In the Textbook of AdvancedHerbology, Terry has chosen to organize the book by the classes andtypes of active plant constituents. This offers several advantages. First, itemphasizes that knowledge of a plant's constituents can be extremelyhelpful in determining how an herb can be used in a given circumstanceand with a given person. Contraindications are also clearer.

For instance, once we know that tannins are astringent and that theyhave shown antiviral and antibacterial properties, we know that anyplant that contains them (such as lemon balm or oak bark) may be usefulfor diarrhea, burns or viral infections. Plants that contain high quantitiesof tannins might be irritating to the bowel in some conditions.


If we are familiar with the major plant toxins, like cardiac glycosides, andcan associate them with plant groups commonly containing them (suchas the figwort or lily family), we have an important piece of information.We will be sensitive to the toxicity of certain plants under certaincircumstances.

Second, plant constituents are a kind of modern Western energetics. Inconstitutional medicine, a herbalist is always interested in herbalenergetics. In other words, what taste, warming or cooling properties, orother regulatory effects a herb might embody. Traditional systems ofmedicine, such as TCM, always consider the energetics of herbs in atraditional way. I believe in the future, we will work out energetic andconstitutional correspondences for herbs, based on their individualconstituents.

For instance, plants that contain essential oil are "spicy cool" in TCM. Amodern biochemical understanding of this energetic category mightstate that essential oils (such as peppermint oil) can dilate peripheralvessels in and just below mucous membranes, which will "warm" thesurface (bringing extra blood and immune cells) and "cool" the interior,by moving some of the blood up to the surface, releasing heat. This isjust one example, but many more could be mentioned.

Third, an explanation within the conceptual framework in which we grewup is just right for our Western minds. This helps to create and develop astory about herbs that we can relate to. At the same time, we don't wantto stop at the constituent, biochemical level, and we want to connect the"mind" of scientific understanding with the "soul" of traditional medicine.This is where this textbook by Terry Willard excels -- it does go beyond asimple understanding of the plant constituents in a biochemical way -- italso brings in personal clinical experience and traditional medicalthought, enriching the process and making it much more usable. Mostpeople that read this text will be interested in the practice of herbalmedicine, not just the theory. Terry's extensive clinical experience willhelp keep the theory "on the ground."

In summary, I recommend this text as an excellent source of informationfor the student and practitioner of herbal medicine. I believe that therereally is "something for everybody."

v


Preface

by Joseph E. Pizzorno, Jr., N.D., President, Bastyr Naturopathic College,Seattle , WA. (Co-author of A Textbook of Natural Medicine )

Students and physicians of natural medicine lack good textbooks andreference materials on the pharmacognosy and clinical application ofbotanical medicines. It is a continuing problem. The few available textsusually focus somewhere on the spectrum of information -- perhapspharmacognosy from a botanist's point of view or the isolated constitu-ents of a pharmacologist. Authors may neglect the advances of modernpharmaceutical science or rely on works that were written a centuryago.

The serious student, looking to understand the underlying biochemistryof botanical medicines and then apply that knowledge clinically, comesaway frustrated. Fortunately, a few good books are now appearing, withthis work leading the way.

The Textbook provides an excellent discussion of the chemistry, bio-chemistry and toxicology of each of the major classes of herbal constitu-ents with known medicinal effects. With each class of constituents thereis a well-referenced scientific description, complete with easily under-stood discussions about the most common plant chemicals found in theclass. The discussions are sophisticated enough to satisfy the clinician'sneeds without bogging the reader down in unnecessary detail. Multiplefigures and diagrams further illustrate important concepts and relation-ships. I especially appreciate the way in which the Textbook utilizescommonly-used herbs to illustrate how the active constituents contrib-ute to or determine each herb's actions and potential toxicity. This leadsto a much better understanding of their clinical application.

Over the past fifty years, a huge body of scientific research on botanicalconstituents has been assembled. The Textbook does a good job ofpresenting a relevant summary of this research as well as key applica-tions. It maintains a comfortable balance between the pharmacology ofbotanical medicines and the centuries-old traditions of herbalism.Particularly impressive is the effort to integrate the Eastern and Westernherbal traditions -- to integrate both the traditional philosophies and thescientific underpinnings of traditional practice. The author has found adelicate way to balance the vitalistic and strictly chemical/materialisticapproaches. I applaud Terry Willard's goal of utilizing scientific researchto further our understanding of clinical traditions.

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Copyright © 1992, Wild Rose College of Natural Healing Ltd. vii

Another valuable section of the book discusses, frankly and comprehen-sively, how herbal products are manufactured and ways to evaluate thequality of commercial products. A continuing frustration for those of uswho prescribe botanicals has been the difficulty of evaluating andensuring the quality of these medicines. Misidentification, impropergathering techniques, careless storage, lack of standardization and theuse of inappropriate extraction processes are discussed in turn. Thiswork helps the conscientious clinician make better decisions aboutwhich herbal products to use. Hopefully, as this field matures, we willestablish widely accepted standards to ensure much-needed qualitycontrol.

I highly recommend this work to naturopathic students and physiciansand all others who are serious about advancing their understanding ofbotanical medicine. The Textbook of Advanced Herbology will develop thereader's understanding of botanical medicines and lead to more sophisti-cated clinical skills.


Acknowledgements

Like the two previous books in this series, the Textbook of AdvancedHerbology grew out of notes used to teach a course. In this case, theAdvanced Herbology course at Wild Rose College in Calgary was firsttaught in the early 80's. It's only fair therefore to acknowledge thestudents in the many courses held since then. They were the stimulus todevelop these chapters, they were the people most responsible forhelping to refine its content.

Direct contributors to this book were relatively few, partly due to theamazing reach of current computer technology. Seva Singh Khalsaedited classroom notes for the Advanced Herbology course in 1990.James McCormick, M.Sc., began work on the manuscript in the mid-80'sand did the bulk of editing, diagram creation and DTP work. He wouldlike to thank Diane Riley for her support during the production of thisbook.

Thanks are also due to Christopher Hobbs and Joe Pizzorno, N.D. fortheir respective Foreword and Preface. Additional thanks are owed toRob McCaleb from the Herb Research Foundation who provided a veryvaluable appendix on GRAS material. And to Shelley, Aiyana and Yarrowfor their patience while I finished The Textbook of Advanced Herbology.

Calgary, AlbertaNovember 1991

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1Copyright © 1992, Wild Rose College of Natural Healing Ltd.

Introduction

Wmy personal perspective of what a modern, Western advanced herb-ology should be.

To my mind, advanced herbology reflects a serious academic commitmentto go beyond what our teachers profess and to examine the subtleties ofboth herbs and herbology to the best of our ability. It is a desire to pushour knowledge forward in a clear (and usually written) manner -- to dealwith the subtlest ailments, to develop the broadest and deepest under-standing of the interaction of plants and the human body. In the Text-book of Advanced Herbology, the focus of this “going beyond” is agrounding in what is called “phytochemistry” -- grouping plants by theirbiochemical “family” and examining their impact on the human body.

Is this the only form of advanced herbology?

By no means! This text will briefly review the Oriental, Ayurvedic andNorth American Indian traditions of medical science which fully qualifyas “advanced” practice. It will conclude with an overview of Westernalchemy, an ancient technology full of knowledge about plants whichonly recently is making a public reappearance. The simple reality is thatalchemy and those other advanced approaches are well documentedelsewhere.

My approach blends modern scientific research in the area of pharma-cognosy and biochemistry with practical experience developed overyears of using herbs. This approach is also used by a modest number ofscholars and practitioners around the world but there has never been aclear text available for the herbalist or herbology student. This book is aresponse to that need.

hat is advanced herbology? How is it different from any otherkind? In choosing the title of this book, I sought to describe thekind of herbology which I practice and teach. This book outlines

Introduction

2 Copyright © 1992, Wild Rose College of Natural Healing Ltd.

Textbook of Advanced Herbology

I began developing this approach with beginning students and presentedit in The Textbook of Modern Herbology (2nd Revised Edition). It is furtherindicated in the Wild Rose Scientific Herbal (2nd Revised Edition), auseful desk reference for the practising herbalist. Colour photographsand line drawings of some herbs can be found in the field guide, Edibleand Medicinal Plants of the Rocky Mountains and Neighbouring Territories.Herbs found in those books are indicated with the symbols to the right.

In the two preceding books, I set the stage for introducing plants asmedicines from the perspective of botany, human physiology, biochem-istry and folklore. The goal in both texts was careful attention to refer-encing ideas when possible. In this book the chemical constituents inplants, briefly described before, are brought to the forefront for exami-nation.

Each family of medicinally active constituents is discussed from ascientific perspective, then the herbs which contain such constituentsare listed and reviewed. Where possible, I’ve added brief practicalapplications. Since this text is used as the basis for an AdvancedHerbology course at the Wild Rose College of Natural Healing, greaterelaboration on the practical aspects of each constituent family arecovered in the companion course workbook.

A careful reading of this book will acquaint you with the hows and whysof the medicinal effects of plants. Not the complete story -- since com-mon sense, experience and folklore will always have a role to play inherbology -- but at the very least an introduction to understanding plantsat a deeper, more profound level.

Sources of Knowledge for Advanced Herbology

When approaching herbology, the student must begin somewhere. Theacademic discipline which most clearly contributes to an advancedherbology is pharmacognosy.

Pharmacognosy is literally the study of pharmaceuticals. It is the earliestof the five major disciplines of pharmaceutic education. Even thoughpharmacognosy is a well respected science, it slipped out of prominencein university degree programs during the 70's and is only now experienc-ing a ‘comeback’.

The lack of academic interest is primarily due to modern methods ofsynthetically producing economical drugs. Such drugs are often strongerin their action, more consistent in their constitution and faster in reliev-ing symptoms than medicines derived from plants.

I take a slightly different point of view towards healing than many of mycolleagues in the field of herbology. Many herbalists, natural health

Ed

Sc2

Mo2


Introduction

practitioners, naturopaths and so on, feel that all synthetic pharmaceuti-cals are bad, “unnatural” and harmful to the body. I categoricallydisagree.

I do agree that pharmaceuticals are very strong and this strength shouldsuggest many precautions. One doesn’t tune a piano with a hammer. Thejob of any health practitioner should be to restore health, to create abalance or homeostasis, to maintain health and help to prevent healthproblems in the future. As it states in the Hippocratic Oath, “At the least,do no harm”. In acute situations, however, “the fire” has to put be out. Ifyou had a house fire, you would put out the fire before fixing faultywiring. It is sometimes necessary to use pharmaceuticals to move thebody out of an acute state. Side effects and further chronic problems canbe handled with natural ingredients. Our approach, after finding thecondition of our patient, is to use the natural biological intelligence of anindividual as much as possible. When you are in the “trenches” of aclinical practice, you need to get results. After you have stabilized thebody, you can go into the deeper cause of the problems.

Pharmaceuticals have a role in healing. Natural health practitionersmust, above all, be cognisant of the innate biological intelligence of thehuman body. What do I mean by biological intelligence? It is my firmbelief that our body has the innate ability to heal itself. As health practi-tioners, our sole concern is to assist the body, making sure that it hasthe proper nutrients, cleansing and building abilities, vital energies, andthe special ingredients needed to support this restorative process.Herbs satisfy many of the requirements for healing to take place. Butherbs are not the sole answer! There are many other ingredients neces-sary for good health -- exercise, good mental and emotional attitude, andadequate rest, to name a few.

What about synthetic pharmaceuticals? There is definitely a place forpharmaceuticals in the treatment of disease and support of health. Forexample, dramatic, acute disease situations and traumatic accidents areall too common in the industrialized world. In these situations a remedyof the strongest and fastest action is often necessary to ensure theimmediate survival of certain tissues, organs or even the individual. Thisis sometimes referred to as "battlefield medicine". The best naturaltherapies in the "battlefield" are acupuncture, and in some cases,homeopathy. Modern herbology, by contrast, deals with long termchronic care.

A case of severe strep throat in a young child, left untreated for even ashort amount of time, could cause irrevocable heart or kidney problems.The best approach, in my opinion, would be administration of an antibi-otic. Later we can use herbs and other natural ingredients to help buildup the child's body, working with the innate biological intelligence.



While there is a place for pharmaceuticals, their use should be muchmore limited than is common. Start with the most natural method first. Ifseverity or urgency demands, go on to stronger, faster remedies asneeded.

In this text I have found it necessary go off the track slightly in a fewareas, to give a more complete description of a particular botanical.This is particularly true when discussing the energetics of the herb.Occasionally, clinically related problems and therapies are reviewed(e.g. the chapter on lipids) to more thoroughly complete the subject.People who own copies of my other works might find a bit of redun-dancy. At the risk of be accused of repetition, the text gives morecomplete information on botanicals in each location. Cross-referencingto the other two texts was made where possible.

I have particular views on health and healing which, as I mentioned, arenot shared by all herbalists. This textbook provides the base for herbal-ists to push toward a greater level of sophistication about the materialsof their art -- the plants of the world. No matter what persuasion, I thinkthere will be something of value for all practising herbalists in thesepages and an avenue of study for student herbalists which shouldn’t beignored.


A Background in the Medicinal Use of Plants

A Backgroundin the MedicinalUse of Plants

1

The use of botanicals as medicine started with the first humans. Its rationalizationinto a separate discipline developed over time. In this chapter, we take a brief lookat pharmacognosy today and how it classifies plant material. We will furtherexplore three other advanced herbology systems, that base themselves on theenergetics or vitality of the plant material: Oriental, Ayurvedic & North Ameri-can Indian.

Synopsis:



Table of Contents

IntroductionPharmacognosy Today

Crude BotanicalsClassification of BotanicalsThe Chemistry of Botanicals

EnergeticsTraditional Chinese Medical TheoryAyurvedicNorth American Indian

Summary

List of Tables and Figures

Figure 1.1 - Master DiagramFigure 1.2 - Yin and YangFigure 1.3 - Five ElementsTable 1.1 - Elemental AssociationsTable 1.2 - Expanded Five Element RelationshipTable 1.3 - Tridosha QualitiesTable 1.4 - Samkhya View of Cosmic EvolutionTable 1.5 - Qualities of Vata, Pitta, KaphaFigure 1.4 - PipeFigure 1.5 - Sweat LodgeFigure 1.6 - Medicine BundleFigure 1.7 - Medicine Wheel



T he study of naturally occurring herbal medicines goes back manythousands of years -- back to the era of medicine men, wanderingherbalists, witches and superstition. Back, in fact, to a time when

most of the world’s peoples lived by hunting, fishing and gathering theedible plant resources of their environment. The wholistic medicalapproach, which emphasizes the integration of physical exercise,emotional harmony and proper diet is really a modern reacquaintancewith the living reality of our distant ancestors. What form of medicinecould our forebears have imagined except the combination of thespiritual, social, emotional and physical?

In such ancient circumstances, the empirical results of consumingcertain plants would be clear to observant humans -- which herbs werecathartic, which herbs were diuretic, which styptic, which tranquilizing.Observing animals probably added information to the cumulativewisdom of tribal cultures. We don’t often recognize that this informationwas acquired over the space of thousands of years of observation,change and practice.

Over time, as knowledge accumulated on the natural occurring sub-stances, the amount of information became too large for every individualin a human group to manage. The informal gifts of herbalist and midwifegrew into more formal apprenticeships in shamanism and healing. Withstill more time, the occupation of apothecary or pharmacist appeared.This final group of people specialized in the collection, preparation andcompounding of healing substances.

Introduction



Literacy appeared on planet Earth some 5,000 years ago. With writtenculture, the knowledge of generations of healers, collectors and “manu-facturers” could be stored, reviewed and transmitted across space andacross time. Thus appeared the first materia medica or groupings ofnatural medicinal materials. These materia medicas contained thesubstances and products derived from natural sources and were em-ployed by the physicians of each particular era.

Jumping forward across the millennia, the role of Islamic scholars inpreserving early Greek and Egyptian medical texts is well known. Muchof the early history of Europe and the Mediterranean is understoodbecause of the efforts of Arab doctors. Indeed, until the Renaissanceperiod, much of what we think of as medicine in the West was intellectu-ally centred in the Muslim world.

Meanwhile, farther east, the literate cultures of India and the Orient wereable to develop medical traditions beginning 5000 years before theCurrent Era (C.E.). These medical traditions were inseparable from thephilosophies, both social and natural, which were evolving in thecultures. Later in this chapter we look at the specific medical theoriesfrom these cultures which are the outgrowth of thousands of years ofresearch and observation.

In 1815 the term pharmacognosy was introduced by C.A. Seydler, amedical student in Halle/Saole, Germany. This term was formed from twoGreek words: pharmakon, drug, and gnosis, knowledge. The most com-prehensive explanation covering the scope of pharmacognosy waspresented by Flukeges who stated that, “it is the simultaneous applica-tion of various scientific disciplines with the object of acquiring knowl-edge of drugs from every point of view”.

Pharmacognosy Today

Pharmacognosy is presently defined as “an applied science which dealswith the biological, biochemical, economic features of natural drugs andtheir constituents.” It is the study of drugs which have their origin in theplant and animal kingdom. It deals with crude drugs, such as the wholeleaf of a medicinal plant and its natural derivatives. For example: digitalisleaf and its isolated glycoside, digitoxin; rauwolfia root and its purifiedalkaloid, reserpine.

We will only be dealing with one aspect of pharmacognosy though thefield covers both natural and synthetic substances. These substancescan often be easily distinguished by physical or chemical tests. Forexample, natural camphor is obtained by steam distillation from thecamphor tree. It is dextrorotary (d-camphor) in its reaction to polarized



light. In contrast, synthetic camphor can be manufactured either by totalsynthesis from vinyl chloride and cyclopentadiene (a completelysynthetic process) or by semi-synthesis from pinene derived from pinestump (not an entirely synthetic process but a chemical modification ofa natural product). Synthetic camphor is racemic and can be differenti-ated easily from the natural form. In the Textbook of Advanced Herbology,we will be focusing on the properties of natural substances. Let’s firstlook at crude botanicals.

Crude Botanicals

Crude botanicals are natural substances that have undergone no humanprocessing other than collection and drying. The term “natural sub-stance” refers to those substances found in nature comprised of thefollowing; whole plants and herbs, the anatomical parts thereof, veg-etable saps, extracts, secretions and other constituents thereof. Theterm “crude” used in reference to natural products, means any productthat has not been advanced in value or improved in condition by shred-ding, grinding, chipping, crushing, distilling, evaporating, extracting,artificial mixing with other substances or any other process or treatmentbeyond that which is essential to its proper packaging and the preven-tion of decay or deterioration pending manufacturing. The term “ad-vanced”, used in relation to natural products, means any product whichhas been advanced in value or improved in condition from its crudestate by any mechanical or physical process whatsoever, beyond thatwhich is essential to its proper packaging. We will be looking at manu-facturing techniques in Chapter 12.

Crude botanicals are rarely used as therapeutic agents. Most often thechief principals (the principal active components) are separated byvarious means. Often the crude botanical is put through a grindingprocess and encapsulated, either as a single herb or as a herbal formula.The chief principals are often separated and are known as derivatives orextractions.

Extractions will remove only those substances that can be dissolved inliquid or a liquid mixture referred to as the solvent or specifically, as themenstruum. Alcohol would be the menstruum in a tincture. Theundissolved portion of the drug that remains after extraction is com-pleted is called the marc.



Classification of Botanicals

The Textbook of Modern Herbology, a basic herbology text, describedseveral different classification systems for plants. Three were used forintroductory study:

1) Morphological features: e.g., herbs, shrubs.2) Linnaean binomial system (Family, genus, and species): e.g.,

Artemisia frigida is in the Compositae family.3) Therapeutic properties: e.g., stimulant, tonic, cathartic.

A fourth type of classification is chemical. This is the system we willemphasize throughout this text. Unfortunately, modern drug/plantinvestigations are far from exhaustive. Most plants contain a variety ofconstituents. Some are therapeutically active, others only chemicallyactive. Some are even antagonistic to one another. By studying thechemical characteristics of plants we can often establish the relation-ships between different plants and classify them by their respectivephytochemical groups.

The Chemistry of Botanicals

A living plant may be considered a biosynthetic laboratory -- not onlycreating chemical compounds (carbohydrates, protein, fats) that areutilized as food by man and animal, but also creating a multitude ofcompounds (glycosides, alkaloids, volatile oils) that exert a physiologi-cal influence.

One of the phases of pharmacognosy that is of particular interest toadvanced herbology students is the study of the biochemical pathwaysleading to the formation of secondary constituents. This study is calledbiogenesis (also called drug biosynthesis). It comes down to a fewquestions repeated over and over again. What sort of compound causesthis action? Where is its source?

These fundamental reaction sequences, which lead to the different typesof secondary constituents used as drugs, will be presented in the variouschapters that follow. To facilitate a general understanding of the path-ways involved and their interrelationships, refer to Figure 1.1 where theyare summarized. This figure may at first seem ominous. We will deal withit slowly, one step at a time throughout the text.

Chemistry, as we stated earlier, merely studies the “body” of a plant.Many herbal traditions go beyond this physical reality and work with the“energies” of a plant, sometimes even the “personalities” of a plant. Overcenturies, very sophisticated methods for the study of these energieshave developed.



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Energetics

Though we’ll deal with energetics later in the text, a herbalist shouldalways keep the subject in mind. The chemistry of a plant describes the“body”. Herbology is concerned with much more. Herbology is part of avitalist tradition. This tradition is poorly regarded by the generalscientific community at the moment. Non-vitalists (variously describedas particularists or materialists) feel the universe is just a big complexmachine. They feel that if one understands the component parts, thebehavior of an entire system should be predictable. Greater knowledgesimply requires more and more refined understanding and investigationof the “parts”.

Vitalists believe that “components” do influence a system’s behavior butthat living systems carry a conforming energy that also influences thecomponents -- a vital energy that flows through the Universe and con-nects all living and non-living things.

Most people feel they are much more than a body. People have emo-tions, intelligence, personality and spiritual concepts. Herbs are alsomuch more than a physical body. Most of the medical traditions of ourplanet discuss herbs in a broader energetic framework. Traditionalherbalists don't deny the chemical properties that we’ll study in this text-- but they, and we, want to place that knowledge in the broader contextof the plant’s full nature.

The current Western allopathic point of view has tied itself very closelyto the materialist scientific perspective in order to be accepted. Fromthis relatively recent stance, the notion has arisen that if somethingcannot be proven with materialist methods, it is somehow less “real”.Many medical doctors take a mechanical view of the body, not remem-bering that the person has emotions and feelings. In the clinical settingthis often causes problems. Emotional problems often arise that enhancethe disease process. They can’t be ignored simply because they can’t beprecisely measured. Becoming an effective practitioner means looking atboth the science and the art of healing.

Many cultures, around the world and throughout history, have devel-oped healing methods with little relation to modern Western science.These systems are complete, self-contained and use energetics fortherapeutic and diagnostic classification. The two most prominenttheoretical schemes are traditional Chinese and Ayurvedic (Indian)medicine. Before looking at the chemistry of plants, let’s review theseancient systems to remind ourselves that energetics is also an importantpart of herbology.



Figure 1.3Five Element Diagram

Wood(Liver)

Cycles ofgeneration

Cycles ofdestruction

Figure 1.2Yin/Yang Diagram

Traditional Chinese Medical Theory

Traditional Chinese physiological and medical texts use definitionswhich come out of the fabric of nature. The central concept of thislogically consistent medical system is energy flow. Energy flow is Qi(pronounced “chee” and sometime written chi). This nutrient Qi energyis the basic substance of the Universe. It is more important than thechemical nutrients we get from food, or the oxygen we take from the air,but it is contained in them.

The types of Qi are split into many forms. There is pre-natal Qi and post-natal Qi -- the Qi we were born with and the Qi we get from the worldaround us. Qi, having no known direct chemical counterpart, is the basicenergy behind everything. It flows through our physical body, in riversand streams which are reflected by the acupuncture meridians. “Dis-ease”, in Chinese terms, results from blockages, excesses or imbalancesin Qi flow.

Earth(Spleen)

Water(Kidneys)

Metal(Lung)

Fire(Heart)

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Qi is further split into Yin and Yang (Figure 1.2). These two terms can bevisualized as dualities -- night and day, cold and hot, back and front,female and male, and so on. These opposite pairs have to be in balance.The meridians are set up in paired structures also -- Yin and Yang. Themeridian energy reflects the function of the corresponding organ.

In classical acupuncture, meridians are split into five pairs. Each pair isrepresented by an energy system from nature: Wood, Fire, Earth, Metal,Water. The energy systems work in a creative cycle, called the mother -son relationship. Wood (plus energy) creates Fire; Fire (becoming ash)creates Earth; Earth (over time) creates Metal; Metal creates Water(water condenses out of the air onto metal, dew); Water creates wood(trees need water); and the cycle continues.

Elemental Associations of The Organs & Viscera

Table 1.1Elemental Associations

Energy Element WOOD FIRE EARTH METAL WATER

Yin

Yang BladderLargeIntestineStomach

SmallIntestine

Gall-bladder

ORGAN

HOLLOWVISCERA

In addition to the creative cycle, there is a cycle of injury or insult. Woodinjures earth (roots penetrate the earth); Earth controls water (as in adam); Water insults Fire (suffocating it); Fire destroys metal (melting it);metal destroys wood (by chopping it down or sawing it). These easy-to-remember relationships, modeled on natural processes, have additionallevels of profundity when fully studied. Each of the attributes is associ-ated with organ systems. And the organ systems themselves haveadditional unique attributes.

Each of these elements have both a solid, yin organ and a hollow, yangorgan (Table 1.1). This system functions very simply. If, for example,there is a tree that is drying out because the sun (fire) is too hot, onecould say too much Qi is flowing from the wood to the fire. Controllingthe problem is easy. Any gardener knows. You simply water the tree.Water gives Qi to the tree (wood) and lowers the heat (insults fire). So ifsomeone with an over-heated liver appears in a clinic, by stimulating thekidneys a practitioner can alleviate their problem. We don’t give any-thing to stimulate the liver, it is already too energized.

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From a Western point of view, we can see that by increasing flow to thekidneys, we can pull more toxins from the body and lower the stress onthe liver. This law of balance, called the Five Element Theory, can havemany combinations and permutations. It is one simple system amongmany used to explain the energetic relationships between parts of thebody.

All existence has Qi. It is the flow and the balance of this Qi that deter-mines our health. Environmental factors have various forms of Qi, as dopathogenic organisms. Such organisms will only attack us if there is asuitable energy niche for them in our own Qi pattern. A botanical has itsown Qi patterns which have an affinity toward certain acupuncturemeridians. In this way we can say a herb has a downward action on theLung meridian thereby indicating both direction and area of potentialtreatment. Classifying herbs by this energetic system can help usdetermine their action in the body.

One form of personal Qi is defense Qi (wei Qi). This somewhat “military”Qi, defends us from attack by outside Qi. If external Qi is stronger thanour defense Qi we get an imbalance and suffer from a disease (e.g, aninfluenza). If our internal Qi is to strong or too hot, we can also suffer adisease (an autoimmune disease such as arthritis). It is all a matter ofbalance. Stagnated Qi can equally become a problem. Perhaps ananalogy will help us visualize the concept.

If a beaver formed a dam in a river, we would get a pond forming behindit. In this pond we would have stagnating water. This would, of course,provide a breeding ground for mosquitoes. Approximately 80% of themosquitoes’ life cycle is that of a “garbage man” -- cleaning up or recy-cling material in the pond. The larval mosquitoes clean up the excrementof other organisms in the pond. The other 20% of the life cycle is in theform of the insect we know all too well. We might consider the mosquitoan environmental dis-comfort or a environmental dis-ease, but it wouldbe absurd to think of the mosquito as the cause of the pond.

In Western allopathic medicine, most diseases are blamed on microor-ganisms because of their local association with the disease process. InChinese medicine, it would be said that the flow of Qi was dammed,causing a Qi pool or stagnant Qi. This Qi pool is a perfect ecologicalniche for micro-organisms to thrive in. The micro-organism is not thecause of the disease but the result of the Qi pool. The goal is not to justget rid of the microorganisms, but to clean up the Qi blockage. This isthe purpose behind many forms of acupuncture. If there is a blockage inan acupuncture meridian (river of Qi), a practitioner opens the blockage.Certain herbs have affinity to specific meridians. They may tonify,cleanse, heat up, cool down or have other influences on the meridian. Inthis way, the nutrient Qi of the botanical influences the body. This is notto say that the chemistry of the plant has nothing to do with the healing



process, or to say that merely some esoteric energy is all that is in-volved. From the perspective of an advanced herbology, the chemistryis a physical “signature” of the Qi energies involved.

Since the environment has its own Qi patterns, one has to consider theenvironment in the energy equation. An influenza caused by cold winterdampness would be treated quite differently than a summer influenzacaused by excessive heat. Some herbs will disperse heat patterns,others will warm a meridian. Once again, this simple system deals withbalance, flow and Qi strengths. Even though the individual parts aresimple and easy to understand, complexities can be very deep andprofound when creating a Qi pattern picture encompassing: Yin/Yang,Five Elements, Pre-natal/Post-natal Qi, Qi Flow and Balance. Byoverlaying all of these concepts (and often other factors) a Chinesepractitioner works out a strategy for herbal and/or acupuncturetreatment. Chinese practitioners are always looking at the balance ofEight Principles: Exterior/Interior, Hot/Cold, Excess/Deficiency and Yin/Yang.

There are many good books in English on Chinese medicine and theselection is growing year by year. These are a few of my favourites andare meant as a guide only:

Fundamentals of Chinese Medicine (East Asian Medical Studies Society), ParadigmPublications, Brookline, MA, 1985.

Maciocia, G., Tongue Diagnosis in Chinese Medicine , Eastland Press, Seattle, WA,1987.

Kaptchuk, Ted, The Web that Has No Weaver, Congdon & Weed, NewYork, 1983.

Matsumoto, K. and S. Birch, Five Elements and Ten Stems, Paradigm Publications,Brookline, MA, 1983.

Hsu, Hong-Yen, Oriental Materia Medica, a concise guide, Oriental Healing ArtsInstitute, Los Angeles, CA, 1986.

Bensky, D., Gamble, A., Chinese Herbal Medicine, Materia Medica, Eastland Press,Seattle, WA, 1986.

Ayurvedic Medical Theory

From the ancient medicine of India a healing art developed that is stillvery practical. ( Ayur = Life and Veda = Science). In Ayurvedic medicine,the basic energy of the universe is also split into five elements. Theseelements are Ether, Air, Fire, Water, Earth which in turn blend into threeprinciples or humours called tridosha. This basic theory of Tridosha, likethe Chinese system, is one in which a normal balance sustains health.The Tridoshas are Vata, Pitta and Kapha. Vata dosha is made up of etherand air. Fire and water constitute pitta. Kapha is the combination ofwater and earth. The Tridosha govern biological, psychological andphysiopathological functions of mind, consciousness and the body. Aperson’s constitution is determined at conception. Both father andmother contribute elements to the fetus.



This gives us seven basic constitutions:

1. vata2. pitta3. kapha4. vata-pitta5. pitta-kapha6. vata-kapha7. vata-pitta-kapha

There can be subtle variations of these constitutions. The basic constitu-tion remains the same throughout a person’s life. Change in environ-ment, food, and medicines can determine physiopathological changes.The goal is to balance to vata-pitta-kapha of environment, with personalconstitution.

Qualities of Tridosha

Vata: has the quality of movement. This subtle energy of bodily air,governs biological movement. It governs breathing, blinking of theeyelids, muscular and tissue movement, heart beats, contractions andexpansion, cytoplasmic and cell membrane movement. The emotionsthat vata corresponds to are nervousness, fear, anxiety, pain, tremor andspasms. The seats of vata are the large intestine, pelvic area, bones, skin,ears, and thighs.

Pitta: this fire energy can be seen as body heat energy. It governsdigestion, absorption, assimilation, body temperature, skin colouration,and lustre of the eyes as well as intelligence and understanding. Anger,hate and jealousy are the major emotions associated with pitta.

Kapha: made of water and earth, its quality is the cement of the bodyproviding the material for the physical structure. Kapha gives us resis-tance, and strength, lubricating joints, provides skin moisture andpromotes wound healing. It gives us biological strength, memory reten-tion, energy of the heart and lungs. Emotional attachments, greed andlong standing envy as well as calmness, forgiveness and love are gov-erned by kapha.

The goal is to have a proper balance of the Tridosha governing metabo-lism: the activity of anabolism (kapha), catabolism (vata), and metabo-lism (pitta). Table 1.3 is a summary chart.



Aspect of Vata Pitta KaphaConstitution

Frame Thin Moderate ThickWeight Low Moderate OverweightSkin Dry, Rough, Soft, Oily, Thick, Oily

Cool, Brown Warm, Fair Cool, PaleBlack Red, Yellow White

Hair Black, Dry Soft, Oily Thick, Oily, WavyKinky Yellow, Early Dark or Light

Gray, RedTeeth Protruded, Moderate Strong, White

Big, Crooked Soft GumsGums YellowishEmaciated

Eyes Small, Dull Sharp Big, AttractiveDry,Brown Soft Gum Blue, ThickBlack Green, Gray Eyelashes

YellowAppetite Variable Good, Excessive Slow but Steady

Scanty UnbearableTaste Sweet, Sour Sweet, Bitter Pungent, Bitter,

Saline Astringent AstringentThirst Variable Excessive ScantyElimination Dry, Hard Soft, Oily Thick, Oily

Constipation Loose Heavy, SlowPhysical Very Active Moderate LethargicActivityMind Restless Aggressive, Calm, Slow

Active IntelligentEmotional Fearful, Aggressive Calm, GreedyTemperament Insecure Irritable Attached

Unpredictable JealousFaith Changeable Fanatic SteadyMemory Recent Memory Sharp Slow but

Good, Remote prolongedMemory poor

Dreams Fearful, Fiery,Anger Watery, RiverFlying, Violent, War Ocean, Lakes,Jumping, Swimming, RomanticRunning

Sleep Scanty Little but Heavy, ProlongedInterrupted Sound

Speech Fast Sharp and Slow, MonotonousCutting

Financial Poor, Spends Moderate, Spends RichStatus Money quickly on Luxuries Money saver, Spends

on Trifles on Food

Pulse Thready, Feeble Moderate, Broad, Slow,Moves like a Jumping like Moves like aSnake Frog Swan

Source: Lad, V., The Science of Self-Healing.

Table 1.3Elemental Associations



Tridosha Qualities

Vata Pitta Kapha(Air & Space) (Fire & Water) (Water & Earth)

Movement Body Heat StabilityBreathing Temperature EnergyNatural Urges Digestion LubricationTransformation Perception Unctuousness

of TissueMotor Functions Understanding ForgivenessSensory Function Hunger GreedUngroundedness Thirst AttachmentSecretions Intelligence AccumulationExcretions Anger HoldingFear Hate PossessivenessEmptiness Jealousy Anxiety

Table 1.5Qualities of Vata, Pitta and Kapha

Table 1.4Samkhya View of Cosmic Evolution

Prakriti (unmanifested)

Mahat (cosmic matter)

Ahamkara (self-sense)

Satva Rajas Tamas(Vaikrita) (Taijas) (Bhutas)

Gnanendriyas Karmendriyas Mana 5 Tanmatras(senses) (actions) (mind) (subtle material

potencies)

Sight Tongue Akasha (Ether)Touch Arms Vayu (Air)Hearing Legs Teja (Fire)Taste Anus Aap (Water)Smell Reproductive organ Prithvi (Earth)

↓

↓

↓ ↓

↓ ↓↓ ↓

↓

→→→→→

→→→→→

→

→→

→→



Constitutions of Individuals

A person is made up of a combination of all three dosha, with one ormore prominent. The following are the major constitutional attributes ofthe Tridoshas.

Vata Constitution these flat chested individuals, appear underdevel-oped with muscle, tendons and veins visible. Complexion is brown,rough, dry, cracked with cold skin. Dark moles are often present. Thinframes, revealing prominent joints, poor muscle development and beingdistinctly tall or short. Eyelashes are thin, eyes lustreless, often sunken,small, dry, active with conjunctiva. The nails are rough and brittle, hairis curly and scanty. The nose is often bent and turned up.

Vata people desire sweets, sour and salty taste and hot drinks. The urineis scanty, feces are dry, hard, and small. They have cold hands and feetand perspire little. Vata types need less sleep and may have more sleepdisturbance than other types. Creative, active, alert, restless; talking andwalking fast but with little endurance.

Psychologically vata have quick mental understanding, short memory,little willpower, tendency toward mental instability, with little tolerance,confidence or boldness. Being anxious and fearful, these nervous peoplehave poor reasoning power. Vata can earn money quickly, spending itjust as quickly and therefore often being poor.

Pitta Constitution Medium height, slender with often delicate frames.Mole and freckles are common, being bluish or brownish-red in colour.Muscle development, veins, and tendons are moderate. Complexion maybe coppery, yellowish, reddish or fair with soft, cool wrinkled skin. Thenails are soft, hair thin, greying, early hair loss. The eyes are sharp, gray,green, copper-brown and of medium size. Good appetites, digestion,desiring lots of food and liquids. Craving sweets, bitter and astringenttastes enjoying cold drinks. Urine and feces are of large quantity,yellowish, liquid, and soft. Hands and feet are warm, perspiring exces-sively. These people do not like hard work, sunlight, or heat.

Psychologically they have good power of comprehension, very intelli-gent, sharp and are good orators. Emotionally, they are quick to hate,anger and jealousy. Liking to be leaders, they appreciate materialprosperity and enjoy exhibiting their wealth and luxurious possessions.

Kapha Constitution These physically well developed individuals oftenbecome overweight and are broad chested. Muscular development isgood and the skin is thick, bones are not prominent. Their soft skin isoily with a cold lustre and pale with a fair and bright complexion. Theirlarge attractive eyes are dense, black or blue with very white scleras.



They have cravings for pungent, bitter and astringent foods, have aregular appetite, and slow digestion. Stools are pale, soft and slow.Kapha constitutions lend good stamina. They shine out in their strongvitality, being healthy, happy and peaceful. They are usually tolerant,calm, forgiving, and loving but with greed, attachment, envy, and posses-siveness. Comprehension is slow but solid. Kapha tend to becomewealthy and able to hold it.

The Human Constitution (Prakruti)

Medicinal substances are represented by:

rasa: tasteguna: qualitiesvirya or veeya: potencyvipaka: taste arising after digestion.

1. Rasa is split into six tastes:

i. Madhura (sweet)ii. Amla (sour)iii. Lavan (saline)iv. Katu (pungent)v. Tikta (bitter)vi. Kasaya (astringent)

2. Gunas are made up of ten pairs or twenty items:

i. Guru (heavy) Laghu (light)ii. Manda (dull) Tikshna (sharp)iii. Shita (cold) Ushna (hot)iv. Snigdha (unctuous) Rooksha (ununctuous)v. Slaksan (smooth) Khara (rough)vi. Sanda (dense) Drava (liquid)vii. Mrida (soft) Kathina (hard)viii. Sthira (stable) Sara (unstable)ix. Suksma (subtle) Sthula (gross)x. Visada (nonslime) Piccila (slime)

3. Virya is the potency of a drug action, split into eight categories:

i. Sitta Pacifies pitta, Exhilarant, moistening, cooling life,promoting, aggravates kapha and vata. Increasessemen.

ii. Ushna Pacifies kapha and vata, Heating, digestive, causes lossof consciousness, aggravates pitta. thrust,diaphoresis, emesis, purgation, solution, vertigo:decrease semen.



iii. Snigdha Pacifies vata, Oleation, bulk increasing, sexual vigour;prevents old age

iv. Ruksa Aggravates vata, Astringent, roughening, healingpacifies kapha.

v. Guru Pacifies vata. Anointing bulk increasing; promotingunion of sexual vigour and semen.

vi. Laghu Pacifies kapha. Roughening, fluid absorbing, healing:reduce fat and body weight.

vii. Mridu Pacifies pitta Saturates rakta and mamsa, softeningviii.Tiksna Pacifies kapha. Constipation, promoting secretions,

tearing.

4. Vipaka is the transformed state of an ingested substance.

In Ayurvedic medicine, the “diagnosis” is always related back to thebalance of the Tridosha. Diagnosis is usually based upon observation ofthe tongue, pulse, face, eyes, nails and lips to provide subtle indicators.The goal is to check for signs regularly so imbalance can be found ininitial stages, making it easier to correct. Ayurvedic medicine can workon acute and chronic problems but prides itself on early detection ofproblems -- the basis for preventive medicine.

Treatment by Ayurvedic methods involves matching the imbalances ofvata-pitta-kapha with protocols to return them to balance. Herbs, diet,exercise, enemas, massage and even blood-letting are potential thera-pies. Most initial treatment programs start with some kind of detoxifica-tion procedure.

For more information, I highly recommend books authored by DavidFrawley and Vasant Lad, Ayurvedic Healing, Ayurveda: the Science of Self-Healing and The Yoga of Herbs or perhaps Ayurveda: Indian Art andScience of Medicine by Dr. C.G. Thakkur. An Ayurvedic materia medica ispresented in Kapoor, L.D., Handbook of Ayurvedic Medicinal Plants, CRCPress, 1990.

North American Indian Medicine

Most of the books dealing with American Indian medicine emphasize itsshamanistic aspect. A shaman is a medicine man, witch doctor or healer.While rituals played an important part in Indian curing procedure, therewas also extensive use of what has been called “rational therapy”. In thisrational therapy, indigenous botanical drugs played an extraordinarypart.



At the time Europeans discovered North America, Indian herbal medi-cine was probably at par with European herbology, with the exception ofbirth control. The Indians used several methods of birth control thatwere very effective. Some of these botanicals have guided presentmedical research in the area.

Indian treatment of external injuries, where the origin of the ailment wasperfectly obvious, was usually rational and effective. In cases of persis-tent internal diseases, where the cause was not obvious, the usual Indiancustom was to attribute the disease to supernatural agents.

If ordinary medicine did not soon bring relief, they resorted to shamanis-tic methods, such as incantations, charms, prayers, dances, shaking ofrattles, and beating of drums. The effect of this would have a strongpsychological and maybe even psychic effect on the patient. In Indianterms, it would raise the energy of Good Medicine in the area so badspirits could not live there.

Most of these internal diseases were attributed to animals or spiritintrusion. If a hunter didn’t treat an animal body properly after killing it,or didn’t observe proper taboos, the spirit of this animal would enter hisbody.

It is often suggested that Indian medicine is pure superstition. Dr. R.Bergman, a psychiatric doctor who has been assigned to oversee aMedicine Man School funded by the National Institute of Mental Health, aUnited States federal agency, has changed his opinion on superstition.He says,”I usually answer that question by pointing out the properdefinition of the word superstition is -- my knowledge, your belief, hissuperstition. Superstition is a word which conveys a lot of things withoutconveying a whole lot of information.”

It should be emphasized that for a Indian medicine man to reach thehigher levels of the art, the education would take many years and extendfor a lifetime. It is reasonable to say that the level of dedication requiredis equivalent to undertaking a modern Ph.D. or an M.D. Even though theAmerindian system is quite different, it is logically consistent. By that wemean that it begins with some primary assumptions about the way theworld “works” and then expands upon those first principles in a logicalmanner. In the case of North American Indian medicine, it is an oraltradition, passed from generation to generation.

The most important elements of medicine power are:

1. Vision Quest, usually undertaken at puberty and sometimesrepeated later in life. A vision quest involved self-denial, with nofood, water or shelter, continuing til the person had what theyconsidered a suitable vision.



2. A reliance on Vision, was also a very important. To pursue thepath of life directed by one’s personal visions and dreams.

3. A personal song, allowed one to attune oneself to the primalsound of the cosmic vibration of the Great Spirit.

4. Partnership with the spirit world. It was sometimes necessary tomake contact with the Grandfathers and Grandmothers whohave changed planes of existence.

5. Non-linear time sense, was necessary in order to deal with thespirit world.

6. Omnipresence, to know that the Great Spirit may be foundeverywhere and in everything.

7. Passion for the Earth Mother, and an awareness of one’s place inthe web of life, and one’s responsibility toward all plants andanimals.

8. A total commitment to one’s belief, that permeates every aspectof one’s life to enable one to truly walk in balance.

Even though the dogma varied from tribe to tribe and Nation to Nation,the personal way was most important. The tribe’s rituals were alwaysconsidered secondary to the guidance a medicine person received fromtheir personal vision. In the Navajo school for medicine men, at RoughRock, Arizona, after 3-4 years of full time study, a medicine person onlylearns two or three ceremonies. Traditionally, medicine men knew manyceremonies. The important ceremonies take five to nine nights toperform, with a difficulty and elaborateness approaching that of openheart surgery.

These ceremonies demand that the entire extended family be present.The attendance of the patient’s most distant social connections are alsodesired. Many of these people are employed in important roles duringthe ceremony. The singer medicine-man is required to do a letter-perfectperformance of up to one hundred hours of ritual chanting. The featcould be compared to a perfect recitation of the New Testament frommemory. In addition, the medicine man has to produce many sanddrawings, recite myths and manage a very large group of people.

It must be remembered that a Indian medicine man was as much amental/spiritual councillor as they were a person that healed wounds.The medicine man tradition is not dead today. In fact, a revival is inprocess. The revival involves as many non-natives as it does natives.Some of the new ‘Medicine Tradition’ is evolving into slightly differentforms with the addition of traditional elements from around the world.



Figure 1.4Pipe

The American Indian uses the term medicine to embrace much morethan the cure of disease and the healing of injuries. Medicine, in theIndian sense, connected most things that were good.

Besides the botanical that might or might not be used in a healing, thereare three major components: the medicine pipe, the sweat lodge and aperson’s medicine bundle. To these were added masks, rattles and otherimplements.

The Pipe

The medicine pipe was used to open ceremonies, to initiate deal-making,for healing or to start the healing process itself. First the pipe wascleansed in ritualistic smoke. The botanicals used for this were usuallyone of three sacred plants: sweetgrass, artemisia sage, or juniper.Depending on the circumstances one of these would be chosen, burnedas an incense, with the smoke being used to ‘wash’ the pipe. The pipewould then be filled with a smoking mixture.

The first smoke would be offered to the heavens, the next to the spiritsof the four directions. Prayers accompany all of this ceremony in askingfor aid of the spirits in the healing process. The pipe was always passedonto the next person (usually part of a circle) in a sunwise (clockwise)direction. When passing the pipe, it would be rotated in a small sunwisecircle, with the stem of the pipe offered to the next person.

The pipes were made of carved stone (often red stone - hematite) withpipe stems decorated with a person’s own power symbols.

Sweat lodge

The sweat lodge is a small domed structure made out of bent willowbranches, covered with hides, tarps or blankets. Inside the structure, thefloor is usually covered with juniper and/or sage with a pit in the center.Sweat lodge ceremonies were used to heal physical ailments, to startvision quests, and as an important preparation for most major ceremo-nies. Ceremonies differ from location to location, with sweat lodgeleaders in control of the details.



The dome is usually dark. After the person or group enters, hot rocksare passed in to be placed in the pit. These stones are heated up in a bigfire to the east of the sweat lodge. Before the sweat sessions are started,there is a ceremony of bringing in single rocks. The first rock is broughtin with the first steam being sent to the heavens, the next four rocks areagain for the spirits of the four directions, thus starting the sweat. Thesweat is a series of four sessions. For each session, a group of rocks arebrought in, the door is closed, and water is poured on the hot rocks.

As the steam accumulates the heat inside the sweat lodge becomes veryhot, with each session the heat gets even more intense. An eagle featherfan is often used to increase the intensity of the heat. Songs and chantsare often sung in the sweat lodge. These can be group songs, but aremost often individual songs for each person. As the heat increases, theperson usually escapes into their song more. By the third or fourthsession, if you don’t escape into your song (almost escaping your body)it is felt you will not make it to the end of the session due to the extremeheat. To be able to escape into one’s song was in itself considered goodmedicine.

Often diaphoretic teas such as yarrow or geranium are drunk to stimu-late sweating before starting the sweats. Inside the lodge, herbs such aswormwood sage are often rubbed on the body, stimulating sweat anddetoxifying the body.

It is easy to see that the sweat lodge can have medicinal qualities and themodern tradition of saunas, steamrooms and hot tubs is a reflection ofthis ancient ritual. The tradition of sweating (in saunas) was verycommon to the European healing tradition at the time of the Europeandiscovery of North America and is still used heavily in the Scandinaviancountries and in naturopathic medicine. The medicinal quality of theherbs used could also increase the healing potential. The greatesthealing quality that the Indians attributed to the sweat lodge was tocleanse out the spirit, forcing evil spirits to leave the body. Speakingfrom personal experience, a person certainly does feel more enlivened,fresher and cleansed after a sweat lodge ceremony.

Figure 1.5Sweat Lodge



The Medicine Bundle

One of the most dramatic parts of the training of a Native Americanhealer was the experiential aspect. A ‘Medicine Person’ takes theirhealing energies from the power of a ‘totem’ or ‘ally’. If you wanted toobtain a personal ‘totem’ or ‘ally’ for your medicine bundle, you have toexperience the power of the animal, (plant or mineral) to obtain awisdom or power over and through it, for use in healing energy.

Let’s say you want to obtain the very powerful totem of the eagle. Thiswould mean, after four days of fasting and purification sweats, you wouldgo up into the hills and dig a pit. Over this pit you would put somebranches, tethering a hare upon them. With a eagle bone whistle andchanting, you would call an eagle to you. This could take many hours ordays. When the eagle swoops down to pick up the hare, you would haveto reach up and grab its razor sharp talons, pull it down into the pit andwring its neck to kill it. Great speed must be used in order to avoidinjury. To do this would take extreme concentration and an “oneness”with the eagle spirit. The eagle would be hypnotized by you. Thus youobtain one of many articles in your medicine bundle. As can be imagined,many do not make it through the educational system of a medicine man.They quit or die.

After obtaining an article for the medicine bundle, a medicine personcould call on the spirit to aid in the healing process, sometimes toconquer the evil spirit that was causing the problem.

Figure 1.6The Medicine Bundle



EW

N

S

White Buffalo

Yellow EagleBlack Bear

Green Mouse

The Medicine Wheel

In some Indian traditions, the information of the medicine ways wastransferred in an oral tradition with the aid of a group of stones placed ina circle and called the Medicine Wheel. Each direction (east, north, westand south) represented an animal, colour and attribute.

The medicine wheel represents the philosophy behind the medicineway. It represents our planet, how we perceive ourselves and howothers perceive us. It indicates how we can share in our group percep-tion and thus heal each other.

Each person may perceive the world differently; with the industrious-ness of a mouse, the sneakiness of a weasel, the cunning of a fox, or thewisdom of an owl. By sharing in this council, the group would be stron-ger and healthier. This represents the tribe, the nation, or even one’sindividual person (body, soul and spirit). In this tradition, it is felt thatthe universe is a mirror of the person and each person is a mirror toevery other person.

In the medicine circle the light comes in from the illumination of the east,which represents the far-sightedness of the yellow eagle. The southrepresents the innocence and industriousness of the green mouse. Theintrospection of the great black bear takes up the position of the west.The north is left to the wisdom of the white buffalo. These are but fourperceptions with many varying perceptions in between. Each perceptionhas subperceptions inside itself. The white buffalo of wisdom also needsto understand the yellow farsightness of wisdom, the green innocence ofwisdom as well as the black introspection of wisdom.

Figure 1.7The Medicine Wheel



Native American Medicine in Perspective

The evolution of the medicine person can be represented by the stagesof the Medicine Wheel they have conquered. People often wear the namerepresenting their personal energies (e.g., Green Buffalochild), withgreat people becoming chiefs or the nation’s powerful medicine men -- asstubborn as Sitting Bull.

An example of a particular type of Indian medicine way can be found inH. Storm’s “Seven Arrows”.1 As can be seen, the uses of the wordmedicine varied. One meaning involved power -- this dance has “greatmedicine” -- meaning great power. It might be the Bull Dance, to help in abuffalo hunt, or an Eagle Dance, to help them see far and to gain illumina-tion.

It should be noted at this point that not all medicine men were or aresincere -- just as is the case in modern Western society. They were notalways above trickery in making their patients think that they werereleased from these animal/spirit intrusions. This approach might havepositive psychological effects but it should also be remembered that ashaman usually demanded payment in advance, and that the trickerywas not always in the patient’s interest.

When a medicine man decided that an evil spirit had entered the body ofa patient, he would try to scare it out. Through the shaking of rattles, bydancing, by wearing masks, and by chanting for hours or even days, theshaman was eventually sure that the evil spirit had left the body. An-other method was to suck the spirit out. This was done by sucking on ahollow stick or bone inserted into the wound or into an incision made bythe medicine man. This usually resulted in the recovery of some foreignobject.

Sucking or extraction obviously helped in some cases, (e.g. if the personhad a sliver) but in other cases the medicine man was not above sleight-of-hand tricks. For example, a medicine man might suck an eagle clawfrom a sick man -- this was the spirit inside the patient -- even though thepatient had not been anywhere near an eagle before his sickness.

There were different types of medicine men. For example, in the Ojibwatribes there were four ranks:

1. Priest and highest rank, to which membership was gained byinitiations.

2. “Dawning Men”: practitioners of medicinal magic, huntingmedicine and love powers.

3. Seers and prophets, revealers of hidden truths, possessors of thegift of clairvoyance.



4. Herbalists, who knew about mysterious properties of a variety ofplants, herbs, roots and berries. The powers were revealed uponthe payment of a fee.

The herbalists were often women. It was not unusual for a person to bein more than one rank. Often those of the priest rank also were herbal-ists. In some tribes, one person would have the medicine for someailments while another person had the medicine for others. The specificinformation was passed on to a new generation after a payment wasgiven to the previous owner of the knowledge. The knowledge of thenatural world could offer a Native American both social and financialbenefits.

There are four basic components of cure set up in the Indian tradition.These four components are similar to allopathic (orthodox, Westernmedicine) traditions, as well as most healing traditions throughout thecultures of the world. They include:

1. The naming process: By giving a name or cause to the ailment thepatient is often put at ease. One of the most frightening things inhuman experience is the Unknown. Naming lets the patient know thatthe practitioner has come across their situation before and recognizesit. Of course the names in Native American lore are not those ofallopaths (e.g. cancer of the prostate,) it is more like a “spirit of thebear is biting your behind.”

2. The personal characteristics of the healer: The charisma of thehealer/doctor is very important. The patient has to feel that thepractitioner is caring, convincing and genuine.

3. The patient’s expectations: It is common practice for doctor/healersall over the world to use much the same method of raising theirpatient’s expectations. Physical stimulus like rattles, amulets, stetho-scopes and diplomas are common ways to increase patient expecta-tion. It can be commonly observed that the farther a patient has totravel to see a healer, the greater the chances of cure.

4. The doctor/healers training: All sincere healers go through atraining period that takes several years of rigorous work. The insin-cere usually drop out in the process.

We tend to think of things done in a medical center as scientific whereassomething done in a tipi is magical. But the methodology seems to bevery similar. Many of the herbs that the Indians use in their healingprocesses have been shown to have active pharmaceutical actions, withbiochemical rationale. The old Indian who had a backache never looked



at bearberry leaves and said, “That plant has arbutin in it. That arbutinwill undergo hydrolysis in my body and change to hydroquinone beta-glycoside in my kidneys to act as a local antibiotic, thus relieving theinflammation in my kidney, to stop the pain in my back.” He just knewthat a certain type of pain in the back could be overcome by the strongspirit in bearberry (Arctostaphylos uva-ursi).

The Indian medical tradition was mostly oral, with several societieswithin the tribe responsible for different remedies. This helped build upa mystique about the healer, much as medical terminology does today.Plants transferred in an oral tradition had many stories attached tothem. The knowledge of the herbs came from the ancestors. This usuallymeant powerful medicine people had a specific plant(s) as their ally ortotem. By fully understanding the ‘spirit’ of the plant they could tell howit could heal the body. This information, once learned and tested, waspassed on to future generations. This is not very different from herbal-ists in Europe up to the present day. Even though scientific rationale hasbeen assigned many of these plants, and synthetic and more economicaldrugs have been created as copies of the botanical, much of the originalinformation for the botanical’s use comes from folklore.

Summary

Though only one of several advanced herbologies on the planet, NativeAmerican medicine has special significance for all North Americans. Thistradition can potentially re-establish the "roots" of Western herbalism onthe continent. It's heartening to see this medical tradition undergoing arenaissance.

In this chapter we have listed three traditions that are all forms ofadvanced herbology. We have included them to remind readers thatdifferent traditions may have different theoretical structures but they alladhere to principles of logic and consistency. In addition, we can seethat these three traditions also place great emphasis on “energetics” --the internal energies of healer, patient and herbal substance. This focuson energy, rather than rote prescription, is a hallmark of advancedherbologies around the world.

Even though the focus of this text is not energetics, it is important tokeep in mind that the subject of humans and healing involves more thanpure chemistry. As indicated earlier, learning about the chemistry or“body” of the herbs is very useful. Through it, we can understand themajor mechanism of how a herb works. Western medical scienceconsiders this the total attribute of an herb. Herbalists, however, feelthat such information is only part of a herb’s attributes. Having a solidinsight into the chemistry of botanicals will help us a great deal in theselection and use of the proper herb in a broader clinical setting.

Ed

Sc2

Mo2



1 Storm, Hyemeyohsts, Seven Arrows,Ballantine Books, New York, 1972.

References




A Foundation in Chemistry

Synopsis:

A basis for understanding the function of herbs can be rooted in chemistry. In thischapter, we will look at the Periodic Table, the first eight elements, chemicalbonding, organic versus inorganic chemistry, the shape of organic compounds,functional groups and their reactions. We finish up the chapter with a very brieflook at the biochemical basis of life and the macro nutrients of carbohydrates,lipids, proteins and nucleic acids.

AFoundationInChemistry

2



IntroductionElectronic Structure of Atoms

HydrogenHeliumLithiumBerylliumBoronCarbonNitrogenOxygenWater

Bonding MoleculesInorganic and Organic ChemistryShape of Organic Compounds

Table 2.1 Shortened Periodic TableFigure 2.1 The AtomFigure 2.2 Hydrogen AtomFigure 2.3 Ionization of the Hydrogen AtomFigure 2.4. Isolated hydrogen moleculeFigure 2.5. Formation of He++, an alpha

particleFigure 2.6. Electronic configuration of the

lithium atomFigure 2.7. Beryllium atomFigure 2.8. Boron atomFigure 2.9. Carbon atomFigure 2.10. Nitrogen atomFigure 2.11 AmmoniaFigure 2.12. Oxygen atomFigure 2.13. Structure of waterFigure 2.14. A Covalent BondTable 2.2 Comparison of inorganic/organic

chemistryTable 2.3 Simple organic structures17. Double/Triple bonds of carbonFigure 2.15 Representative organic moleculesFigure 2.16. Benzene ringFigure 2.17 MethaneFigure 2.18 GlyceraldehydeFigure 2.19 Stereo-isomers of glyceraldehydeFigure 2.20 Fischer projection formula of l-

isoleucine or (2S),(3S)-isoleucine.

Figure 2.21 Planar zigzag - carbon atoms

Table 2.6 Oxidation/Reduction TableFigure 2.22 Cis and Trans isomers (Maleic

and fumaric acids)Figure 2.23. Functional groups in Organic

compoundsTable 2.5 Functional groups in Organic

compoundsFigure 2.24 Type 2 Oxidation/Reduction

rectionFigure 2.25 Type 3 Oxidation/Reduction

reactionFigure 2.26 Sample AlcoholsFigure 2.27 Sample ester foramtionfigure 2.28 Sample exidation reactionsFigure 2.29 Aldehydes/KetonesFigure 2.30 Sample aldehydes/ketonesFigure 2.31 Oxidation of aldehydesFigure 2.32 Hemiacetal formationfigure 2.33 Aldol condensationFigure 2.34 Conversion to enol formfigure 2.35 Carboxylic acidsFigure 2.36 Disassociation of carboxylic acidsfigure 2.37 Amide formation of carboxylic

acidsfigure 2.38 AminesFigure 2.39 Disassociation of AminesFigure 2.40 EstersFigure 2.41 Amidesfigure 2.42 Sulfur-Containing Compounds

(Skeleton)Figure 2.43 Examples of sulfur compoundsFigure 2.44 Reduction of sulfur compounds


Table of Contents

Functional Groups in Organic CompoundsOxidation-Reduction Reactions

Major Functional Groups(A) Alcohols(B) Carbonyl Compounds

Aldehyde and Ketones(C) Carboxylic Acids(D) Amines(E) Esters(F) Amides(G) Sulfur-Containing Compounds

Biochemistry Basis of LifeSummary.



s stated in the Introduction, this chapter reviews the broadsubject of chemistry. It is just an overview. For the herbalist whowants to learn advanced herbology as practiced by clinicalA

herbalists, chemistry is an important area. Greater detail and a basis forpersonal research can be found in courses offered by communitycolleges or universities.

Starting with the basics, this chapter builds toward practical informationfor herbalists. Readers already familiar with chemistry can skim thischapter as a review. The information in this chapter is necessary inorder to understand many of the subjects in future chapters.

The study of chemistry has drawn thousands of people in the lastcentury. While few pursue it as a career, a curiosity about the constitu-ents of the natural materials around us is common. Simple chemicalconcepts are often introduced in elementary schools. What is the thecolouring matter in leaves and flowers? What is the make up of plantsand animals, medicines and poisons? What are the chemicals in thehuman body? How are they composed and transformed by naturalprocesses?

Chemistry might initially look a little abstract, even esoteric. We mustkeep in mind the practical applications of the knowledge -- how it relatesto herbology and human physiology. By constantly making this link inour minds, studying chemical principles becomes less intimidating andmore rewarding.

Introduction



Figure 2.1The Atom

electron ( - )

neutron the nucleusproton ( +)

Group 0 I II III IV V VI VII

H

He Li Be B C N O (F)

Ne Na Mg Al Si P S Cl

Ar K Ca Se Br

Kr Rb I

Xe Cs

Table 2.1Abbreviated Periodic Table

Full table as Appendix

Electronic Structure of Atoms

Atoms consist of three major components: neutrons, protons, andelectrons. Electrons are negatively charged, protons are positivelycharged, neutrons have no relative charge. The Periodic Table (seeAppendix) classes the known elements in a systematic manner based onthe increasing number of protons (and therefore electrons). Each atomof a certain type is called an element, e.g., hydrogen, oxygen and nitro-gen. Electrons and protons are equal in number resulting in a neutrallycharged atom. The Periodic Table got its name from the pattern orperiod of classification of elements by atomic size -- 2, 8, 10, 18 and so on.



There are eight groups. Each group has certain properties in common.Starting with hydrogen and proceeding from left to right in the PeriodicTable, each new element has one more electron and one more protonthan the previous element and a sufficient number of neutrons to makeup the appropriate atomic mass. Atoms with the same number ofprotons, but a different number of neutrons, are called isotopes and aresometimes radioactive.

Electrons travel in orbitals around the nucleus of the atom, which iscomposed of neutrons and protons (see Figure 2.2). These orbitals aremore or less “shells” (like the inner surface of a ball). They are notactually fixed “orbits”, more like “volume spaces”. These volume spaces(orbitals) are designated s, p, d or f, (sharp, principle, diffuse or funda-mental). The s-orbital is spherically symmetric about the nucleus, the p-orbital may be described as dumbbell-shaped. The d and f orbitals dealwith elements we won’t normally consider in this text. Each orbitalcontains two electrons with opposite spins. Each shell contains one ormore types of orbitals than the preceding shell.

Electrons do not travel around the nucleus in neat orbitals. They can befound somewhere in a volume space. Figure 2.2 show the electrondensity of a hydrogen atom. The electron(s) can be anywhere in thisspace at any particular time. By looking at the first several elements, wecan become familiar with how orbitals work. These elements are alsosome of the more common in the world around us and are central to ourstudy of plants.

Hydrogen, H: The first element, hydrogen, has the atomic number one.An atom of hydrogen has only one electron and one proton. The elec-trons travel in a sphere around the nucleus. For convenience, the sphereis represented as a circle. The electron in the hydrogen atom is denoted(1s) (Fig. 2.3) -- having one electron in the first s orbital. We can also

Figure 2.2The Hydrogen Atom



Figure 2.4Isolated Hydrogen Molecule

H2

Figure 2.3Ionization of the Hydrogen Atom

H,(s)1 H+,(1s) 0

+e-

represent the hydrogen atom as H. If we remove the one electron we areleft with the hydrogen ion, or proton H+ (Fig. 2.3). If we take two hydro-gen atoms and bind them together, (H2) their orbitals overlap (Fig. 2.4).The outer orbital is most balanced when it is complete. Both hydrogenatoms have one electron in their outer orbital and desire two. By bindingtogether and giving up their electron to the other they now both havetwo. This puts the hydrogen atoms in a more stable state.

Helium, He: With one more electron and one more proton (and theappropriate number of neutrons), we get a helium atom, (1s)2, com-pletely filling both the first orbital and first shell. The atom can give uptwo electrons. He++, is also known as an alpha-particle (sometimesrepresented by the Greek symbol α), (Fig. 2.5). Elements which fill a shell(not just an orbital) are found in group 0 of the Periodic Table and arecalled rare gases. This group used to be called inert gases because theatoms are complete in their outer shell.

→→



Figure 2.5Formation of He++, an α particle

He,(s)2 He++,(1s) 0

1s + 2e -

Lithium, Li: In lithium (atomic number 3) the 1s orbital is filled and wehave one electron in the 2s orbital (Li, (1s)2 (2s)1 ). Like the hydrogenatom, lithium contains one outer electron; the 2s electron can be do-nated or given up (Fig. 2.6) giving us Li+.

Figure 2.6Configuration of the lithium atom

Li,(1s) 2(2s)1 Li+,(1s) 2

1s

2s

+e-

Beryllium, Be: Here we have the 2s orbitals filled (1s)2 (2s)2, but it is nota rare gas because the second shell also contains p orbitals.

Boron, B: Although the two s orbitals are spherical, the third or porbitals are dumbbell-shaped (volumes directed at 90 degrees to eachother along the three axes of a Cartesian coordinate system), (Fig. 2.8).The orbitals do not overlap. In boron we have one electron in the porbital. B, (1s) 2 (2s) 2 (2p)1.

→→

→→



Figure 2.9Carbon atom

Figure 2.7Beryllium atom

Be,(1s)2(2s)2

1s

2s

2s

1s

2p y

2p x

2p z

C,(1s) 2(2s)2(2p)2

B,(1s) 2(2s)2(2p)1

Figure 2.8Boron atom

2s

1s

2p y

2p x

2p z



Carbon, C: Because of the repulsive nature of electrons, (two negativecharges repulse each other), the two electrons are in different orbitals.In Figure 2.9 the two representations are the same. This gives twoorbitals, with one electron each. Since it is possible to have six electronlocations, carbon needs four electrons to be “at rest”. This is the goldenrule of organic chemistry. Carbon always has to have four bonds full.

Figure 2.10Nitrogen atom

N,(1s)2(2s)2(2px)(2p

y)(2p

z)

Nitrogen, N: Here we have one electron in all three of the 2p orbitals(Fig. 2.10). If we were to bond hydrogen, (which has one electron) to thisfigure, we could fill up the orbital by bonding three H atoms, to produceNH3 (ammonia). In this situation, the H atoms would be bonded at 90degrees to each other.

Oxygen, O: In oxygen, two of the four electrons in the p orbitals mustoccupy the same p orbital. This leaves oxygen two positive spaces if it isto fill up the shell O - - or O -2. An oxygen atom can bind to another oxygenatom, sharing two electrons from each oxygen atom to satisfy the steadystate or O2. If two hydrogen attach themselves to an oxygen we get water(H2O).

2s

1s

2p y

2p x

2p z

N

H

H H

Figure 2.11Ammonia



Figure 2.13Structure of Water

H

H

O

Water

Water is of special interest to humans. It is the most abundant substanceon the surface of our planet and in our body. The physical properties ofwater differ from any other solvent. It has a different melting point thanother hydrides. There is a strong inter-electrical force seen in water,making it electrically dipolar (having two electrically charged poles).

The actual polar shape of water might prove to be very significant in theprocess of natural healing. Although it is mostly postulation, someresearchers feel small variations in the angle of the hydrogens in relation

Figure 2.12Oxygen atom

O,(1s) 2(2s)2(2p)4

2s

1s

2p y

2p x

2p z

104.5o



Group 0 I II III IV V VI VII

H

He Li Be B C N O (F)

Ne Na Mg Al Si P S Cl

Ar K Ca Se Br

Kr Rb I

Xe Cs

Table 2.1Abbreviated Periodic Table

Full table as Appendix

to each other represent homeopathic remedies. Can water be a storagemechanism behind some forms of vibrational medicine? I think it is tooearly to tell, but it is an interesting concept. If these small variations inthe electromagnetic fields do hold a secret for vibrational medicine,molecular structure might provide a way to quantify the influence. Inturn, this would lead to greater acceptance and acceptability of vibra-tional concepts in the general scientific community.

Bonding Molecules

In several of the elements discussed, we have added two or moretogether. These combinations are called molecules. Water, for example,is a molecule made up of 2 hydrogens and 1 oxygen. The bonding of thismolecule follows specific rules.

Because of the electron configuration, atoms in groups I, II and III of thePeriodic Table tend to lose their valence electrons to form ions, (e.g. H+,Na+), whereas atoms on the right hand side of the table tend to gainelectrons (e.g. Cl-, O-2, Br -). In both instances, they acquire the number ofelectrons of a rare gas. Elements at either extreme end of the shortPeriodic Table are usually ionic, e.g. Na+, Cl-, K+, Br-. They produce ionicbonds. (The elements form an ionic valence and then bond. e.g. H+ andCl- form HCl).

Elements in the center of the Periodic Table, especially carbon, neithergain nor lose electrons readily to form ionic bonds. Instead, they shareelectron pairs to form covalent bonds. The covalent bonds can becarbon-carbon bonds, carbon-hydrogen bonds and so on.



Figure 2.14A Covalent Bond (Methane represented in Lewis Structure)

C HH

H

H

In summary then, ionic bonds are made from elements that lose or gainelectrons, where as covalent bonds are formed from elements of sharedelectrons. Two examples are: HCl with ionic bonding and methane withcovalent. In the former case, the hydrogen gives up it electron to chlo-rine. In a water solution they will be present as H+ and Cl-. Methane (CH4),however, has four covalent carbon-hydrogen bonds (see Figure 2.14). Asyou can see, the covalent bond is somewhat stronger and will not form asolution with water -- an important consideration during our examinationof phytochemicals.

Inorganic and Organic Chemistry

Inorganic chemistry deals with all 103 elements but the principles areoften demonstrated with roughly the first 70 -- (Table 2.2). Organicchemistry focuses on the carbon atom and the compounds it formsnaturally. Formations occur mainly with twenty elements, in particularhydrogen, oxygen and nitrogen. Organic chemistry is often defined as“the chemistry of carbon compounds”. In Table 2.2 you will see acomparison of inorganic and organic chemistry. Table 2.3 highlightssome simple organic structures. In the second column are the Lewisstructures. The third column shows bonding as a line. Both are equiva-lent methods of molecule description.

Since carbon forms covalent bonds by sharing electrons, carbon chainsmay be continued indefinitely or joined to form ring structures. Theymay contain double (-C=C-) and sometime triple (-C=C-) bonds(seeFigure 2.15), . Both single and double bonds are found in all classes ofnaturally occurring organic compounds. Triple bonds are quite rare.Molecules containing double and triple bonds are called unsaturatedcompounds.



Criterion Inorganic* Organic

elements involved all 103 relatively few (mainlyC, H, O, N, S, P, F, Cl,Br, I).

bonding ionic covalent (shared electronpairs)

rates of reaction:at room temperature fast slowat higher temperature very fast moderately fast to explosive

catalyst required? no yes, often.mechanism of reaction usually ionic ionic, free-radical, and

othersside reactions no, many are yes, nearly always.

quantitative.physical properties:

conductivity of salts electrolytes nonelectrolytesmelting point > 700o < 300o

volatility nonvolatile readily distilled (oftenat low pressure)

solubility:in water yes noin nonaqueous organic

solvents no yeselectrical conduction in

solutions and melts yes no

* There are exceptions to every entry in this table.

Table 2.2Comparison of inorganic and organic chemistry

The bonding of carbon to other carbon (C) atoms and to nitrogen (N),oxygen (O), hydrogen (H), and sulfur (S) is of major biological signifi-cance. Through such bonds (or bonds to other groups of atoms) func-tional groups along carbon chains are created. In Figure 2.23 we will seesome of the most common functional groups.

Table 2.4 shows a variety of carbon chains and rings. One biologicallyimportant organic structure, the benzene ring, contains covalent bondswhich are electrically intermediate between single and double bonds.Although the benzene ring is written as alternating single and doublebonds -- all the bonds in the ring are electronically equivalent(see Fig.2.16).

With properties between those of a single and of a double bond, theelectrons are equally distributed over all the carbon atoms in the ring.Molecules containing one or more benzene rings are classified as



CC C O

CC NC S

C CCC

Figure 2.15Example of double and triple bonds formed by carbon

Molecular formula Lewis Open Lineand name structure structure

CH4

methane

CH3Cl

methyl chloride

CH3Cl

2methylene chloride

CHCL3

chloroform

CCl4

carbon tetrachloride

CH3OH

methyl alcohol

HHH

C ClH

H

Cl

Table 2.3Some simple organic structures

H H

CH

C

H

HH

H

H

C ClH

H

ClCH

Cl

Cl

Cl

ClCl C

Cl

C

H

H

H O

C

CC C

CC

C

C

CN

C C CC

HCH

ClH

HCCl

ClH

ClC ClCl

H

ClClC

ClCl

O HCH

H



CH3 CH3

Molecular formula Open Line Condensed Lineand name structure structure

C CH H

C C

CHH

HH

CH2H2C

CH2

CH2

H2C

H2C

H2

C

CH

2

Table 2.4Representative organic molecules

C2H

6

ethane

C3H

6

cyclopropane

C6H

1 2

cyclohexane

C2H

4

ethylene

C2H

2

acetylene

C6H

8

benzene

C5H

5N

pyridine

C

H

H

HH

HCH2CH2

C CHCH

H

H

H

H

H

H

H

H

HH

HC

CC

C

H

H

HH

H

H

HH

H

C

CC

C

CN

H2C

H H

HH

H H

HH

HH

H

C

CC

C

CHHH

HH

H

CC

C HH

CC

H

H

N



aromatic compounds. This has nothing to do with scent. Some of thearomatic compounds of hydrocarbons first discovered did have a strongscent but many compounds since have none. Nevertheless, they are allstill called aromatic ring structures.

H

H

H

H

H

H

H

H

H

H

H

HC

C

C

Figure 2.16A Benzene Ring

Figure 2.17A Methane Molecule

H

Shape of Organic Compounds

A very important and very interesting quality of carbon, is its ability toform a tetrahedral structure. Organic compounds are not planar (in two-dimensions), but are three-dimensional shapes. The shape of the orbitalof the carbon electron provides that third dimension. The four valencebonds of carbon are directed at the four corners of an equilateral tetra-hedron (or four-sided pyramid), with the carbon atom at the center: Acarbon atom, to which four different atoms or different types of atomsare attached, is known as an asymmetric carbon molecule. Such acarbon molecule is found in glyceraldehyde.

We can draw two different forms of glyceraldehyde. Note the location ofthe middle -OH (Figure 2.18). As you can see, the atoms and groups arethe same but their arrangement in space is different. The molecules aremirror images. Such spatially different molecules are known as isomers.Since shape and fit are so important in biology, only one of the abovemolecules is biologically active. The two isomers would have many ofthe same physical properties (e.g. melting point) which makes it veryhard for most analytical techniques to tell them apart.

CC

C

HC

H

H



Figure 2.18Glyceraldehyde

CHO

H C OH

CH2OH

CHO

HO C H

CH2OH

L-(-)-GlyceraldehydeD-(+) -Glyceraldehyde

One distinctive property used for identification is the rotation of polar-ized light as it passes through a solution of optical isomers. If the lightrotates to the right (+) the isomer is prefixed D- (dextro: Latin for right),or if light rotates to the left (-) the isomer is prefixed L- (levo: Latin forleft). Even though this is a somewhat old naming system for molecules itis still prominently used.

Since optical rotation only considers one carbon atom, the system doeshave some limitations. R and S classification of isomers is a moremodern method. For example, isoleucine (an amino acid - Figure 2.20) isknown as L-isoleucine but is more correctly called (2S), (3S)- isoleucine:

As we examine larger organic compounds, their shapes become morebent, twisted and irregular, and they are capable of a large number ofdifferent spatial arrangements. In the more complex biologically impor-

CHO

H C OH

CH2OH

CHO

HO C H

CH2OH

OHH

Figure 2.19Stereoisomers of Glyceraldehyde

H

CH2OH CH2OHHO

CC

CHOCHO



tant molecules (containing hundreds of atoms), shape itself will deter-mine the substance’s biochemical action. This is occasionally the majordifference between a chemical found in a herb and the same one made ina laboratory. Although “chemically” the same, they are particularisomers and as such work differently in the body.

When you have three or more single bonded carbons (-C-C-C-) in a chain,there will be rotation around the bond presenting a zig zag phenomena.The angle between single-bonded carbons is 114o, all things being equal.When there is a double bond (-C=C-) the possible rotation is restricted.This means the active groups of atoms occupy different sides of the solidstructure. These two isomers are then prefixed cis- and trans-. Againthere is great biological significance in these two shapes. Some arebiologically active and other are not. Often both the two forms are activebut have different functions. Examples are maleic and fumaric acids (seeFig. 2.22).

*Asymmetric carbon atom

Figure 2.20Fischer projection formula of L-isoleucine ( (2s),(3s)-isoleucine)

114o

114o

114o

Figure 2.21Planar zig-zag of carbon atoms

COOH

H2N *C H

H3C *C H

CH2

CH3



Functional Groups in Organic Compounds

In Figure 2.23 and Table 2.5 we see some of the most common functionalgroups in organic compounds. As mentioned above, the bonding ofcarbon to other carbon (C) atoms and to nitrogen (N), oxygen (O),hydrogen (H) and sulfur (S) is of great significance. The bonding ofcarbons to these other atoms, or groups of atoms creates functionalgroups along or at the end of carbon chains.

Figure 2.22Examples of cis and trans isomers

(Maleic and fumaric acid)

HOOC H

C

C

H COOH

H COOH

C

C

H COOH

A B

C

C

A B

B A

C

C

A B

TransCis Maleic acid (cis) Fumaric acid (trans)

Figure 2.23Functional Groups in Organic Compounds

Carboxyl

aldehyde

hydroxyl

keto (oxy)

amino

sulfhydryl

phosphate (pronated)

O

C OH

O

C H

OH

O

NH2

SH

O

O P OH

OH



Table 2.5Functional Groups in Organic Compounds

Functional GroupClasses of compounds

Name Symbol containing group

Hydroxyl C OH alcohols

Carbonyl C O aldehydes, ketones

Carboxyl C O Carboxylic acidsHO

Amino C NH2 Amines

Sulfhydryl C SH Thiols O

phosphate C O P OH Phosphates

OH

A basic understanding of these functional groups reveals the functionand interplay of chemicals in botanical substances. This interplayundergoes many reactions. One of the most significant is the oxidation-reduction reaction.

Oxidation-Reduction Reactions

Oxidation-reduction reactions are very important in biological systems.These are coupled reactions: every time one compound is oxidized,another molecule is reduced simultaneously. There are three possibleways for coupled oxidation-reduction reactions to occur.

Remember: a hydrogen atom consists of an electron (e-) and a proton(H+). Oxidation-reduction reactions in biological systems are usuallytype 2 or type 3. The most common hydrogen donor is NADH. The mostcommon hydrogen acceptor is NAD+. NADH and NAD+ are the majorhydrogen transfer systems in animal physiology.



Oxidation Reduction

1. Addition of oxygen Removal of oxygen2. Removal of hydrogen atom Addition of hydrogen atom3. Removal of an electron Addition of an electron

Table 2.6Functional Groups in Organic Compounds

An example of a type 2 oxidation-reduction reaction is the oxidation ofan alcohol to an aldehyde with the concomitant reduction of NAD+ toNADH (Figure 2.24).

In this reaction, the NAD+ has received two electrons and one proton. Anexample of a type 3 oxidation-reduction reaction is the reduction of Fe3+to Fe2+. In biological systems, this would occur as follows (Figure 2.25):

H

R C OH+ NAD+

H

R C O + NADH + H+

H

Alcohol Aldehyde

Figure 2.24Type 2 Oxidation-Reduction Reaction

Fe3+ + NADH Fe2+ + NAD+ + H+

Ferric Ion Ferrous Ion

Figure 2.25Type 3 Oxidation-Reduction Reaction



Major Functional Groups

(A) Alcohols

Alcohols are compounds that contain one or more hydroxyl groups.Naturally occurring alcohols include (Figure 2.26):

H O

R C O C R' + H2O

H

H O

R C OH+ R' C OH

H

Alcohol Carboxylic Acid(organic)

Ester

H O

R1 C O P OH + H2O

R2 OH

H O

R1 C OH+ HO P OH

R2 OH

Figure 2.27Ester Formation

Phosphoric Acid(inorganic)

Alcohol Phosphate ester

Chemicals in the natural world usually don’t stay static. They arecontinuously undergoing reaction and changing forms. We will often findan ester of a compound along with an alcohol of the compound in thesame plant. The following are some of the most common reactions inorganic chemistry.

Figure 2.26Naturally Occurring Alcohols

H

H C OH

HO C H

H C OH

H

H H

H C C OH

H H

Ethanol Glycerol(a trihydroxy alcohol)

Serine(an amino acid)

Phenol(an aromatic

alcohol)

OH

H H O

H C C C OH

HO NH2



Figure 2.30Naturally Occurring Aldehydes and Ketones

H O H O

H C C C C OH

H H

H O

H C C

H H

O O

H3C C C OH

Acetoacetic acid Acetaldehyde Pyruvic acid(a keto acid)

Naturally occurring aldehydes and ketones include:

O

R1 C R2

O

R C

H

Aldehyde Ketone

Figure 2.29General Formulas of Aldehyde and Ketone

R1

C O

R2

H

R1 C OH

R2

O

R C

H

H

R C OH

H

-2[H] -2[H]

PrimaryAlcohol

Aldehyde SecondaryAlcohol

Ketone

Figure 2.28Oxidation

Reactions of alcohols

1. Ester formation. An ester is formed when an alcohol and an acidcombine, releasing water. The acid can be organic or inorganic. (R in allthe following diagrams represents a “general” radical ( ie., a hydrogen,sugar or some complex molecule.)

2. Oxidation. Depending on its structure, the removal of two hydrogenatoms from an alcohol produces an aldehyde or a ketone.

(B) Carbonyl compounds: Aldehydes and Ketones

Both aldehydes and ketones contain a carbonyl group (see Table 2.5).Their general chemical formulas are:



O

R C OH

O

R C H+ [O]

Figure 2.31Reactions of Aldehydes and Ketones -- Oxidation

Aldehyde Carboxylic Acid

OH H

R C O C R

H H

O H

R C H + R' C OH

H

Aldehyde Alcohol Hemiacetal

Figure 2.32Reactions of Aldehydes and Ketones -- Hemiacetal formation

H H H

R C C C O

HO H

O H H

R C H + H C C O

H

Aldehyde Aldehyde Aldol

Figure 2.33Reactions of Aldehydes and Ketones -- Aldol formation

Reactions of aldehydes and ketones

1. Oxidation. The addition of oxygen to an aldehyde produces a car-boxylic acid.

2. Reduction. The carbonyl group in both aldehydes and ketone can behydrogenated to produce an alcohol (see Alcohols, reaction 2).

3. Hemiacetal formation. The reaction between an aldehyde and analcohol produces a hemiacetal.

4. Aldol condensation. Under basic (low pH, see under (C) Carboxylicacids) conditions, aldehydes can react with each other (condense) toform aldols.



5. Conversion to enol form. Aldehydes and ketones are converted totheir enol form when a hydrogen atom moves to the oxygen atom andthe position of the double bond shifts.

Figure 2.35Example of Carboxylic Acids

H H O

H C C C OH

H NH2

H O

H C (CH2)14 C OH

H

H O

H C C OH

H

H O

H C C OH

O

H C C OH

H

Acetic acid Succinic acid(a dicarboxylic acid)

Palmitic acid(a fatty acid)

Alanine(an amino acid)

(C) Carboxylic acids

The functional group in carboxylic acids is the carbonyl group. Biologi-cally important carboxylic acids include:

Figure 2.34Reactions of Aldehydes and Ketones -- Enol conversion

H O

R1 C C R2

H

H

R1 C C R2

OH

Ketone Enol



O

R C OH

Carboxylic acid Anion Proton

Figure 2.36Dissociation of Carboxylic Acids

Reactions of Carboxylic Acids

l. Dissociation. Monocarboxylic acids dissociate in water, releasing oneproton and the negatively charged anion (R-, e.g., Cl-).

This dissociation (seen in Figure 2.36) is readily reversible. The extent ofdissociation is proportional to the concentration of hydrogen ions (H+) inthe solution (i.e. the pH of the solution). The pH represents the power ofhydrogen or how acid/alkaline a solution is. Water has a pH of 7. A pHlower than 7 is acidic, with a pH of 1 being very acidic. A pH high than 7would be alkaline with a pH of 13 being very alkaline or very basic.

At pH 7 and above, carboxylic acids exist almost entirely in their dissoci-ated forms. As the pH of the solution is lowered (i.e. acid is increased) agreater percentage of the acid molecules are in the uncharged form.

2. Ester formation. See alcohols, reaction 2.

3. Amide formation. When carboxylic acid combines with an amine, withthe release of water, an amide is formed.

Figure 2.37Amide formation of Carboxylic Acids

O H

R C OH+ R' C NH2

H

Carboxylic acid AmideAmine Water

O H H

R C N C R' + H2O

H

O

R C O - + H -



H

R C NH2 + H +

H

H

R C NH3

H

Figure 2.39Dissociation of amines

Amine Proton Cation

H H

C C NH2

HO H

H H

HO C C NH2

H H

HO

HOEthanolamine Epinephrine

H H H O

H3C C C C C OH

H3C H NH2

NH2

CN

N

N

NH

HCCH

Adenine Leucine (an amino acid)

Figure 2.38Examples of amines

(D) Amines

Amines are compounds containing an amino group. Naturally occurringamines include:

Reactions of Amines

1 . Dissociation. In solution, amines exist in both a charged and un-charged form.

As with the dissociation of carboxylic acids, this reaction is readilyreversible and the direction of the reaction depends upon the pH of thesolution. At pH 7 and below, the amine is in its cationic (R+, e.g., Na+)form. As the pH increases (i.e. the concentration of H+ decreases), theamine is converted to its uncharged form.

C

C



2. Amide formation. See carboxylic acids, reaction 3.

(E) Esters

Esters are formed when organic or inorganic acids react with alcohols.

Reaction of Esters

1. Hydrolysis. Esters are cleaved into their constituents (alcohol andacid) by the addition of water across the ester bond. This reaction is thereverse of their formation (see Alcohols, reaction 2).

(F) Amides

Amides are the product of a reaction between an amine and a carboxylicacid. Naturally occurring amides include:

Reactions of Amides

1. Hydrolysis. Amides are similar to esters and are cleaved into theirconstituents, acid and amine, by the addition of water across the amidebond. This reaction is the reverse of their formation (see carboxylicacids, reaction 3).

O H H

H3C C O C C N(CH3)3

H H

H O

H C O C (CH2)14CH3

O

C O C H

O

H C O C (CH2)14CH3

H

CH3(CH2)14Acetylcholine

Tripalmitate(a triglyceride)

H

H C OH

HO C H O

H C O P OH

H OH

Glycerol phosphate

Figure 2.40Examples of esters



H H O H H O H H O

N C C N C C N C C

R1 R2 R3

A protein

O

C NH2

H C H

H C H

H C NH2

C OH

O

Glutamine

Figure 2.41Examples of amides

H

Figure 2.43Naturally occurring sulfur compounds

H O

H2N C C OH

H C H

H C H

S

CH3

Cysteine(an amino acid)

Acetyl coenzyme A(a thioester)

Methionine(an amino acid)

H

R C SH

H

O

R C S R'

Thioalcohols(mercaptans)

Thioesters

Figure 2.42Sulfur containing compounds (skeleton)

Although they are relatively few, there are some important naturallyoccurring sulfur compounds, including:

H O

H2N C C OH

H C H

SH

H O

H C C S C o A

H

(G) Sulfur-containing compounds

Sulfur, which is in the same group in the Periodic Table as oxygen, canform similar types of compounds. As a result, the following compoundsare analogous to oxygen-containing compounds.



Reaction of Sulfur compounds

1. Reduction. When two thiols react with the removal of hydrogen, adisulfide is formed.

H H

R C S S C R'

H H

Disulfide

- 2 [H]H H

R C SH + R' C SH

H H

Thiol Thiol

Figure 2.44Reduction of sulfur compounds

Biochemical Basis of Life

Even though all of the molecules of living systems obey the rules ofchemistry, not one single compound of a cell has life. The energy of thecell or the organism is necessary for the chemical to have life. A liveorganism exhibits extreme organization of energy and is capable of self-repair. When the organization stops, the energy goes and self-repaircapacity disappears. The chemicals stop having life.

In a biological system, chemicals reach great degrees of organization.Beyond the functional groups mentioned above, biological system createmacro-molecules that are necessary for life. The four major groups ofmacro-molecules are carbohydrates, lipids, proteins and nucleic acids.

Carbohydrates are described in more detail in the next chapter. Thisgroup of chemicals is the product of photosynthesis, one of the mostimportant chemical reactions. It brings solar energy into the livingorganism. Most of the other reactions in a living system rely on theenergy captured from the sun.

Lipids are described more fully in Chapter 6. These substances aremajor storage and structural components in biological systems.

Proteins make up much of the structure of animals. They also formenzymes that have complex shapes, catalyzing chemical reactions. Madeup of complex arrangements of amino acids, proteins are important froma nutritional point of view but are not central to a study of advancedherbology.



Nucleic acids are the major component of DNA and RNA along with asugar. As such they are the basis of the genetic code, determining thecolour of your hair or whether an egg will become a frog or a goat. Theyprovide the “code” for protein -- in turn, shaping organisms.

These final two categories of molecules are studied in general biochem-istry and nutrition. Any good textbook on these topics can give you afirm foundation or more detailed information.

Summary

Chemistry is one of the great keys to unravelling the mystery of life,medicine and how herbs work in our body. The world of chemistry ismade up of protons, neutrons and electrons as major building blocks.The number of these building blocks that makes up an atom give it astructure and a signature, determining how it interacts with otherstructures. The Periodic Table shows how these atoms can be classifiedby size, and by how they will bond to each other. Just like any system,there is a struggle for order. Atoms bond to other atoms to create astable order for the outer shell of electrons. This creates both ionic andcovalent forms of bonding. Ionic bonds both gain and lose electrons,while covalent bonding shares electrons.

Carbon occupies a strategic position in the chemistry of living systems.Its ability to form covalent bonds with a number of substances and itsversatility in bonding (single, double and triple bonds) are critical.Carbon’s ability to link into long chains and to form rings, makes it theperfect backbone for a large variety of structures.

The asymmetry of the tetrahedral carbon in its covalent bonding isconsidered biologically important. The symmetry, or cis-trans form (indouble bonded carbons), will determine how and if a molecule will beactive in a biological system. The process of oxidation and reduction isone of the major processes that chemicals undergo during biosynthesisin biological systems.

Functional groups of the organic compounds such as alcohols (hy-droxyls), carboxyl, aldehydes, ketones (oxy), amino acids, sulfhydryland phosphates determine both the chemical group as well as thereaction of the substance. The macro-molecules in the body have greatsignificance. Carbohydrates, proteins, lipids and nucleic acids are allimportant building blocks of our body. A clinical herbalist should haveknowledge of their basic role in human nutrition.



Understanding chemistry is the foundation for better appreciation of thephysical processes that botanicals undergo in the body. This allows usto use herbs more creatively, more dependably. It also gives us the soliddata necessary to bring herbal use into the mainstream of modernmedicine. For more information, browse the introductory texts forcollege chemistry courses.


Carbohydrates

The first group of chemicals that are produced in plants by photosynthesis arecarbohydrates. We can divide the sugars into mono- , di- and polysaccharides. Thesimple sugars have few medicinal uses and in fact have some adverse effects onthe body. Polysaccharides have medicinal uses as gums, mucilages and fibers.Complex, branched immuno-stimulating polysaccharides are of special interest tothe modern herbalist.

Synopsis:

CarbohydratesAnd RelatedCompounds

3



Table of Contents

IntroductionBiosynthesis of CarbohydratesSugar and Sugar-Containing BotanicalsSucrose

A Hidden PoisonGums and Mucilages

Karaya GumSodium AlginateKelpPsyllium SeedGuar Gum

Dietary Fiber: An OverviewSummary on Fibers

Immuno-Stimulating PolysaccharidesChlorellaEchinaceaReishiShiitakeAstragalus

SummaryMini-Materia Medica -- Carbohydrates


Figure 3.1 Sample sugar moleculesFigure 3.2 GlucoseFigure 3.3 Carbon dioxide fixation in photosynthesisFigure 3.4 SucroseTable 3.1 Relative SweetnessTable 3.2 Gums and MucilagesTable 3.3 Fiber componentsFigure 3.5 Immunostimulating polysaccharidesFigure 3.6 EchinaceaFigure 3.7 EchinaceinFigure 3.8 Ganoderic acidFigure 3.9 Reishi ideogramsFigure 3.10 AstragalusFigure 3.11 AstragalinTable 3.4 Stimulation of phagocytes


Carbohydrates

arbohydrates are the most widely distributed biological substancefound in nature. Judged by mass they are also the most abundant.Commonly called sugars, carbohydrates are formed during

photosynthesis. This process is very important. It is the mechanism bywhich solar energy is transferred into life energy on our planet.

Although simple carbohydrates don’t play much of a role in the medici-nal effects of herbs, the more complex forms of carbohydrates hold avery prominent place in herbology. Our discussion of plant biosyntheticpathways starts with carbohydrates because they are the first in thepathway after photosynthesis.

Carbohydrates are key compounds in the biochemistry of green plants.Ultimately all other compounds can be derived from them. Besidesacting as precursors, carbohydrates play many roles. Both starch andsimple sugars are involved in the storage and utilization of energyrequired for the processes of growth, ion transport and water uptake.Forms of cellulose and hemicelluloses (complex carbohydrates) contrib-ute to the structural strengths and binding of the cell in plants. Some ofthe other functions seem more obscure, involving protection fromparasitic action.

Carbohydrates are aldehyde or ketone alcohols containing carbon,hydrogen, and oxygen, in which the hydrogen and oxygen are generallyin the same ratio as water. A carbohydrate is an aldehyde if the terminalcarbon contains a carbonyl oxygen ( - CHO ). It is a ketone if the terminalcarbon has a carbonyl oxygen bonded to it ( C=O ). This is the startingpoint from which, by subsequent organic reaction, the plants synthesizea great number of other constituents.

C

Introduction



Carbohydrates, can be split into simple sugars and polysaccharides. Thesimple sugars are called monosaccharides (e.g. glucose). Oligosacchar-ides (e.g., sucrose) yield two to ten monosaccharide molecules (onhydrolysis). The monosaccharides are classified by the number ofcarbons they contain: if four carbon atoms are present the monosaccha-ride is named tetrose, five carbon atoms, pentose and six carbon atoms,hexose. We will be focusing primarily on the hexose group. These simplesugars are crystalline, soluble in water and taste sweet.

The polysaccharides are more complex. They have a higher molecularweight and examples include starch, insulin, glycogen and cellulose.Polysaccharides have ten or more monosaccharides in a row. Often thenumber goes up into the thousands. These polysaccharides usuallyhydrolyse to produce hexose components and therefore are calledhexosans. Starches containing glucose are known as glucosans, whileinsulin-yielding fructose is known as a fructosan. Cellulose is a glucosan,a complex polysaccharide forming the primary cell walls in plants. It hasvery little solubility. Hemicellulose and other compounds associatedwith cellulose have a greater degree of solubility and are more easilyhydrolysed.

Polysaccharides can be homoglycan, containing only one monosaccha-ride, such as starch or cellulose. If it contains more than one monosac-charide it is called heteroglycan. Closely related to hemicellulose are thegums, mucilages and pectin that we will discuss in this chapter.

Glucose (also called dextrose), fructose, sucrose and maltose are thesimple sugars most commonly occurring in botanicals. We also find, inlimited amounts, the monosaccharides; mannose and galactose (aconstituent of lactose and raffinose) and the disaccharides; trehaloseand lactose.

Figure 3.1Sample sugar molecules

D - Glucose D -Fructose

CH2OH

C O

HO C H

H C OH

H C OH

CH2OH

CHO

H C OH

HO C H

H C OH

H C OH

CH2OH


Carbohydrates

In solution, glucose (and many other saccharides for that matter) areclosed-ring molecules rather than linear.

Biosynthesis of Carbohydrates

Photosynthesis is the process during which monosaccharides areproduced. Photosynthesis has two broad stages:

1. Light Stage: the actual conversion of electromagnetic energy intochemical potential.

2. Dark Stage: a series of enzymatic reactions which turns carbondioxide into sugar.

The pathway, worked out by Calvin and co-workers is seen in Figure 3.3.There is no need to memorize the pathway but it is worth carefulexamination.

Sugar and Sugar-containing Botanicals

In nature, the most abundant oligosaccharide is sucrose. Sucrose, ortable sugar, is a disaccharide of D-glucose and D-fructose. Lactose, acomponent of milk, is made from D-galactose and D-glucose.

Sucrose

Sucrose is a sugar obtained from Saccharum officinarum (sugar cane)and Beta vulgaris (sugar beet).

Figure 3.2Glucose

CH2OH

O

H H H

OH OH H OH

H OH



Figure 3.3Path of Carbon dioxide fixation in photosynthesis

Figure 3.4Sucrose

Sucrose (sometimes called saccharum) is obtained from sugar cane bycrushing the stems between a series of heavy iron rollers and extractingthe juice. This is boiled with lime to neutralize the plant acids (the plantacid would change the sucrose to non-usable sugar) and to coagulatealbumins. The juice is filtered, usually decolorized with sulfur dioxide,concentrated and crystallized. When all crystals of sugar are obtained,the residue, a dark coloured syrup called molasses, is left behind.

Sucrose from sugar beets is produced differently. The beet is dug up,washed, and sliced into small slivers. The slivers are then put on aconveyor belt and carried through a diffusion battery, where they are

CH2OH

O

H H H

OH OH H

H OH

O

CH2OH H

OH H CH2OH

H OH

2ATP

2PGA

ADP +P

3ATPLight

Ribulose

ATP

CO2

2H2O O2

4 H +

2NADPH2

2ADP + 2P

4e -

Sugars

3ADP + 3P

→

↓

↑

↑

O

↑

↑↑

↑

↑

↑


Carbohydrates

Table 3.1Relative Sweetness of the Sugars

mixed with hot water as they move through a series of cells. The waterdiffuses the sucrose from the slices and the raw juice is then subjectedto the same purification process described above. It takes approximatelysixteen feet of one-inch-diameter sugar cane to produce one teaspoon ofsugar! As you can see, this is quite a purification process.

Sugars, mono- and disaccharide are considered to be sweet. In Table3.1, a relative sweetness index is presented (Table sugar = 100). Notethat fructose is much sweeter. This means a person can use less fructoseto get the same sweetness and by doing so have fewer calories in aproduct. This is often the strategy in candies and confectionaries.

A Hidden Poison

The North American population consumes 120pounds of sugar per person, per year. The largestconsumption is in the form of soft drinks, 500 12 oz.cans/person/year in 1980 with a steady increasesince then, accounting for 30 pounds of sugar. Thishigh consumption is associated with diabetes (3-5%of population), hypoglycemia (low blood sugar, 12-55million people in North America), obesity (20-25% ofpopulation), coronary thrombosis (one of the top 5killers), periodontal disease (90% of population over30 years) and a host of other problems. Even thoughthere is a great industry associated with sucrose, it isa major killer and one could even say, a hiddenpoison.1 , 2

Relative Sweetness of Some Sugars

Sugar Relative Sweetness

Sucrose 100Glucose 74Fructose 173Galactose 32Maltose 32Lactose 16



Gums and Mucilages

Gums are a form of polysaccharide or salts of polysaccharide and areoften produced in higher plants as a protective mechanism againstinjury. We find botanicals with gum and mucilaginous properties oftenused in bulk laxative formulas because their chemical action bothcleanses and soothes mucous membranes. This effect categorizes themas demulcents.

Both of these gums and mucilages usually contain more than one type ofmonosaccharide. Normally uronic acid is also present. Gums andmucilages are generally soluble in water or strongly hydrophilic (takesup moisture).

The most common gums and mucilages along with their components arelisted below:

Name Sources Hydrolysis Products

GUMS

Gum Arabic Acacia spp. D-galactose, L arabinoseL-rhamnose, D-glucuronic acid

Mesquite gum Prosopis spp. L-arabinose, D-galactose4-O-methyl-D-glucuronic acid

Cherry Gum Prunus sp. L-arabinose, D-xylose, D-mannose,D-galactose, D-glucuronic acid

MUCILAGES

Flax seed Linum spp. D-xylose,L-galactose, L-rhamnose,D-galacturonic acid

Blond Psyllium Plantago sp. D-xylose, L-arabinose, L-rhamnose,D-galacturonic acid

Slippery Elm Ulmus fulva D-galactose, 3-0-methyl-D-galactose,L-rhamnose, D-galacturonic acid.

Table 3.2Gums and Mucilages


Carbohydrates

Examples of Gums and Mucilages

Karaya gum or Sterculia gum

Karaya gum is an exudation of Sterculia urens and S. villose, native plantsof India. This gum exudes naturally from the tree or can be stimulated byincisions in the heartwood. The powder of the gum absorbs water andswells to several times its original bulk. The Karaya gum is used as a bulklaxative, a demulcent and emollient, as well as a dental adhesive. 3

Sodium Alginate

Sodium Alginate is the purified carbohydrate product extracted frombrown seaweeds. It is usually obtained from Macrocystro pyrifera. SodiumAlginate is an odourless and tasteless yellowish-white powder that isquite soluble in water. It is used throughout the food industry (icecream, chocolate milk, salad dressing) as a suspension agent.

Alginates are hydrophilic, colloidal substances. They have a water-absorbing and retaining properties greater than methylcellulose. Theydo not swell up in an acid environment. This of course has made themuseful as bulk laxatives with acid-neutralizing, buffering action andhemostatic properties also favoured for ulcer treatment. 4,5

Sodium Alginate is known to reduce strontium absorption. SodiumAlginate has also been shown to decrease the retention of other radioac-tive divalent metallic ions in rats. Its strength of extraction in order isBa > Sr > Sn > Cd> Mn > Zn > Hg. The Ba level has been “reduced to 3%of control value and Cd and Mn level at about 50% in three weeks.” Bothalginic acid and sodium alginate have been shown to reduce plasma and/or liver cholesterol in rats.6

Kelp

Kelp has been shown to have activity against many pathogenic micro-organisms, including Gram positive and Gram negative bacteria such asStaphylococcus, Streptococcus, Brucella bacillus, Klebsiella, Proteus, E. coliand Salmonella. The active principal is now felt to be the brominatedphenolic compound and not iodine as originally suggested.7

In Japanese studies a direct correlation between kelp consumption andprevention of breast cancer has been established. It is felt the fiber andmore particularly the algin is responsible. Kelp extract has had up to a95% success rate in inhibiting Ehrlich and Sarcoma 180 models. It hasbeen further shown to enhance the immune system functioning. It istheorized the alginates stimulate the T - cells, (other polysaccharideshave also been shown to do this).8

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Psyllium Seed

Psyllium seed, plantago seed or plantain seed is the cleaned, dried, ripeseed of Plantago psyllium. This plant is an annual, coalescent, glandular,pubescent herb native to the Mediterranean.

The major component of psyllium is a mucilage. The concentration isbetween 10 - 30%, mostly in the husks. The mucilage is a polysaccharide,consisting primarily of D-xylose with L-arabinose and an aldobiuronicacid. Other constituents include some monoterpene alkaloids such as(+)-boschniakine and indocyanine, a glucoside aucubin, saccharides,planteose, sucrose, glucose and fructose, sterols (beta-sitosterol,stigmasterol and campesterol).9,10,11

The seeds and the husk (preferred) are hydrophilic bulking agentswhich swell 8 - 14 times their original size in water. This property hasbeen used in diet aids to fill the stomach of weight watchers, as a bulklaxative, for diarrhea and as a base for an internal poultice (bolus).12,13

The amount of liquid present in the diet determines whether psylliumwill have a laxative or astringent effect. If over six cups of fluid are takenin the day, psyllium becomes a bulking laxative. If little fluid is taken, itwill draw moisture from the GI tract and act as an astringent.

Blond psyllium (P. ovata) has been shown to lower blood pressure inanaesthetized dogs and cats. It inhibits isolated hearts of rabbits andfrogs and stimulates rabbit, rat and guinea pig ileum and has cholinergic(acetylcholine-like) properties.14

Psyllium husks have been shown to depress growth in chickens by 15%when 2% of the husk is added to their well balanced diet. Blond psylliumseeds have been reported to have strong antidote effect on 2% sodiumcyclamate supplementation, 2% FD & C Red Dye No. 2, and 4%polyoxyethylene (20) sorbitan monostearate in rats.15

Chinese energetics: (related species P. asiatica) is sweet, bland andcold; entering the Kidney, Bladder, Small intestine, Lung and Livermeridians. Its action is to regulate water metabolism, remove heat, clearvision, disperse phlegm and control coughs.16,17

Ayurvedic energetics: (related species P. ovata) Rasa - madhur; Guna -snigdha (pacifies vata), guru (heavy), pichil; Veerya - sheeta; Vipak -madhura (sweet). Action: Vata-pitta samak, dah prasman, sanahan,balya, brihan, jawaraghana.18

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Carbohydrates

Guar gum

Guar Gum is the powdered endosperm of the seed of Cyamopsistetragonolobus (Guar bean). This powder produces a bulk mucilage thatis gaining increasing acceptance as a bulk laxative and cleanser. It isbeing used as a binder in some health food breads, as it has a higherfiber content than bran. It is a specific aid for people with obesityproblems and low blood sugar problems, especially useful for toxiccolons.

Pectin

Pectin is obtained from a dilute acid extract of the inner portion of therind of citrus fruit or from apple. It is a popular gelling agent in the foodindustry and also has medicinal uses.

Pectin is classified as a protectant and a suspension agent and is oftenused as an antidiarrhetic. Pectin has a wonderful ability to absorb toxinsfrom the body and pass them out through the colon. In digestive distur-bances, pectin’s colloidal nature increases surface area, and seems to doa thorough cleansing of the villi and microvilli of the small intestine.

Dietary Fiber: An Overview

Dietary fiber is the sum total of all the indigestible lignin and polysaccha-rides in the plant foods that we eat. Fiber is made up of the cell walls ofplant cells. Fiber is not a single substance but rather a mixture of manydifferent complex organic substances. Not all fiber is in a solid form.Pectin for example is water soluble and can be found in a liquid form. Allplant fibers are made up of long chains of various sugars bound togetherso tightly that they cannot be broken down by digestion.

In general, the less soluble fibers such as bran have been shown to bemore effective in increasing fecal bulk while the soluble fibers such asguar and pectin have more effect on carbohydrate and lipid metabo-lism.19

Concern about the health benefits of food fiber is not new. In the fifthcentury B.C. the “Father of Medicine”, the Greek physician Hippocrates,suggested that unrefined flour be used for making bread. In the nine-teenth century in the United States, Sylvester Graham advocated ahigher fiber intake and gave his name to the high fiber Graham cracker.

Unfortunately fiber was not considered a nutrient nor studied by nutri-tionists until relatively recently. Only during the last twenty years hasthe full attention of the scientific community been directed at dietaryfiber.



The fiber hypothesis is a concept popularized by Burkitt and Trowell.20

This hypothesis suggests that a diet high in fiber containing grains,legumes, fruits and vegetables protects against many diseases and that adiet low in fiber is a causative agent in the etiology of these diseases andincreases the effects of the other factors on these diseases.21

The research of Burkitt found that as a traditional or aboriginal diet(primarily plant based) becomes “Westernized”, obesity and diabetesstart to appear. As this westernization process continues, constipation,hemorrhoids, varicose veins and appendicitis become common. In afully Westernized diet, the preceding conditions are augmented byischemic heart disease (cause of death for about 30% of men and 15% ofwomen in our society), diverticular disease (occurring in an estimated40% of “over 40” Americans), hiatal hernia and cancer.

Colon cancer is particularly noticeable (70,000 new cases of colon andrectal cancer are diagnosed in the U.S. each year). All of the diseasesmentioned are extremely rare in the original aboriginal plant baseddiet.22,23 This research has lead to a greater emphasis on fiber in bothmedical literature and in the popular press.24 Researchers have sug-gested that Westerners should increase their daily intake of fiber fromthe average of 4 to 5 grams a day to 12 to 20 grams per day.25

The most commonly known benefit of increased dietary fiber is as a bulkforming laxative. Water insoluble hydrophilic (water-attracting) fiberssuch as cellulose (in brans) increases the weight and size of stools and

Table 3.3Fiber components

Fiber components

I polysaccharides

cellulose structural part of plant cell wallshemicellulose structural part of plant cell wallspectin intracellular cement of plantsalgal polysaccharides found in algae and seaweedsgums plant secretionsmucilages plant seed secretions

II non-polysaccharides

lignin structure in woody plant tissue


Carbohydrates

all fibers reduce transit time (the time it takes for food to travel from themouth to the anus). Bran can absorb approximately 200 times its dryweight in water.

The Expert Advisory Committee on Dietary Fibre reported to the Cana-dian Health Protection Branch that “... there is consistent evidence [of]improved bowel function and/or relief of constipation in humans inresponse to maize, wheat and soy fibres.” 26

A larger bulkier stool passes through the intestine faster, with less effortand with less abdominal pressure required. This reduces conditionssuch as diverticulosis and hemorrhoids. It is interesting to note that fiberhas a normalizing effect. While fiber generally speeds up the transit timeif it is too slow (up to 48 hours in the typical North American diet), it alsowill also slow it down if it is too fast (less than 24 hours). In a traditionalhigh fiber diet the average transit time will be about 30 hours. It hasbeen hypothesized that by improving transit time fiber reduces the timein which food components and bile acids can be changed to carcino-genic substances and damage the colon.27

Fiber also has the capacity to retard the emptying time of the stomach.With certain fibers, e.g., guar gum, a slower emptying of the stomachdiminishes the hyperglycemia (raised blood sugar) that usually occursafter a meal in both diabetic and normal persons. Increased dietary fiberalso stimulates the production of digestive enzymes by the pancreas andmakes bile more soluble. Both of these factors improve digestion offoods. A high fiber diet also improves the balance of beneficial overpathogenic microorganisms in the colon.

One of the most important health benefits of high fiber consumption is areduction in the blood cholesterol and triglyceride levels. Coronaryheart disease, largely due to cholesterol accumulation in the arteries, isthe major cause of death for North Americans. Increasing dietary fiberintake reduces LDL cholesterol (the bad kind) and increases HDL (aprotective factor against cholesterol) and lowers the body’s synthesisand absorption of cholesterol. One study on the effect of high fiber onincreased blood lipids due to a high carbohydrate diet found that thefiber had a protective effect against triglycerides. But there was noapparent lowering of cholesterol while on a high carbohydrate diet.28

The most effective cholesterol lowering fibers (5.7 grams two times aday lowered cholesterol levels by 16%) are the mucilages, particularlyguar gum (Cyamopsis tetragonolobus), which is often used as a stabilizerand thickener in the food industry.29 Guar gum (discussed earlier) is alsothe most studied medicinally useful fiber.

Inadequate dietary fiber intake has been clearly linked by both epide-miological and experimental research to diabetes mellitus. A high fiber,



high complex carbohydrate diet reduces the increase of blood sugarafter a meal by delaying stomach emptying and increasing tissue sensi-tivity to insulin.30 A high fiber diet reduces both blood sugar levels andurinary C-peptide excretion in diabetics.31 In addition to flattening theblood sugar curve after a carbohydrate meal, fiber added to the diet ofdiabetics also reduces the insulin needs of people on a artificial pan-creas. Over the longer term, fiber lowers the loss of glucose in the urineand increases general control over diabetes.32 Because of these resultsdiabetics have been advised by major diabetic associations and aCanadian federal Expert Advisory Committee to consume higher com-plex, carbohydrate, fiber rich diets.33

The most impressive results of increased fiber intake in diabetics areseen with guar gum. Guar has been shown to reduce blood glucoselevels in both diabetics and normal subjects.34 Several short term studieshave indicated that wheat bran has little of this effect. A recent long termstudy of the effect of bran, however, has shown a reduction of post mealblood glucose.

It was also found that twenty-four hour urinary glucose excretion wasreduced by about 30% during the periods of the study in which fiber wasconsumed. In those consuming the fiber, total cholesterol was reducedand the proportion of HDL increased, serum triglycerides (blood fats)were not decreased. The patients’ insulin was also reduced from anaverage of 52 to 51.35 Research on the effect of guar at a lower dose (4grams given 4 times a day) to non-insulin-dependant diabetics (NIDDM)indicated that insulin and blood sugar levels were moderated and therewas a significant reduction of both LDL and total cholesterol and anincrease in HDL.36

Another study examined total serum cholesterol (TSC) of female diabet-ics fed 5 grams of guar in bread. This research found that the degree ofTSC lowering increased with time. In 4 weeks it was reduced by 7.3%,8.3% after 8 weeks and 13.8% lower than the initial levels after 12weeks.37 A mixture of guar gum with carob bean powder has been foundto be valuable in lowering post meal hyperglycemia in diabetics and isreported to be well tolerated.38

Fiber consumption has also been linked to gall stone formation byresearchers in Japan. The study found that increased incidence of gallstones was related to the consumption of more fat and less crude fiber inthe diet.39

Diets deficient in dietary fiber have been shown to be related to thedevelopment of obesity. Fiber has its effect by slowing the eating pro-cess, by increasing chewing, intensifying caloric loss though the feces,altering digestive hormone secretions, improving glucose tolerance,delaying nutrient absorption, and satisfying appetite by increasing


Carbohydrates

stomach filling, releasing cholesytokinin, and through intestinal bulk-ing.40 Guar has been found to decrease body weight and reduce hungerratings when given to obese persons.41,42 In a study of obese females, 10%guar gum was used in pasta, the product had excellent palatability andno gastrointestinal side effects. The guar pasta beneficially moderatedglucose and insulin response as well as lowering "total fasting" choles-terol.43

Summary on fiber

Dietary fiber has important scientifically established benefits in reducingdisease and moderating body weight. The most promising fiber is guargum, however different fibers offer a number of benefits. Much of thebenefit of fiber is lost however due to poor compliance. Benefit is afactor which can be determined by the effectiveness of a health productmultiplied by the compliance with an effective dose. Much of the benefitsof fiber are long term. Effectiveness is limited if consumption is reducedor stopped too soon. This problem is resolved if the product tastes good,is easy and handy to consume and is appealing in ways outside of it’s“medicinal” effect.

The fiber aspect of polysaccharides is not their only medicinal effect.Modern research has reported many immuno-modulating properties ofpolysaccharides, often confirming traditional uses that are centuries old.

Immuno-stimulating Polysaccharides

Generally, structural polysaccharides are longstraight chains, whereas “food reserve”polysaccharides tend to be branched (Figure 3.5).Branched polysaccharides are more easilydispersed in water and are therefore more

Figure 3.5Immunostimulating polysaccharides

O

OH

HO

CH2OHO OO

OH

HO

CH2

O

OH

HO

CH2OH

O

OH

HO

CH2OHO OO

OH

HO

CH2

O

OH

HO

CH2OH

O

OHHO

CH2OHO

O O



hydrophillic, colloidal systems that are often viscous. It appears that theimmune-modulating polysaccharides generally have a beta 1,3 glucanlinkage. There have been many studies of this group of branchedpolysaccharides with clear evidence for their immuno-modulatingfunction. One of the most common and successful tests is the actionthese herbs or extracts of these herbs have on Sarcoma 180 tumor inmice (a common test model). These polysaccharides have beenreported to cause complete regression in many studies.

What seems to be the activation site? Most of these polysaccharidescontain beta 1,3, beta 1,6 and alpha 1,4 linkages (see Figure 3.5).Through a series of studies it has been shown that the activity still existsif the 1,6 linkage is cut by specific enzymes. If the 1,3 or 1,4 is cut theactivity decreases dramatically. It has been concluded that a beta 1,3linkage at position six, having a side branch alpha 1,4 linkage, yields thehighest activity.

The shape of the polysaccharide seems also to be significant. The shapeis controlled by an associated protein. When the protein is denatured,the activity of the polysaccharide goes down. The activity of a polysac-charide cannot be determined by the chemical assay, only by biologicaltesting. There are many herbs and mushrooms in this category. Some ofthe most commonly known ones are ginseng, Siberian ginseng,epimedium, astragalus, echinacea, chlorella, reishi, shiitake andcordyceps.

Active research on these herbs in the last few years has centered ontheir effect on AIDS, ARC, cancer and CFS (Chronic Fatigue Syndrome).How the actual mechanism works is not completely clear at this time.Some researchers feel that the body recognizes these long chain struc-tures as possible allergins and thus increases immune response. It isprobably much more complex than that. Increased immune responsewill occur in people who already have immune compromised systemsfrom an over-stimulating (other) antigen.

How are the polysaccharides absorbed into the body in a way whichaffects the immune system? It’s an interesting question. Theoretically,the polysaccharide should be split into smaller units, likely monosaccha-ride, before being absorbed. If this is true, polysaccharides should haveno more influence on the body than sugar. Some researchers, however,feel that these branched chain polysaccharides are absorbed by pinocy-tosis, a process whereby large molecules can be absorbed into the bodyintact. Another prominent theory is that stimulation of the immunesystem takes place in the gastro-intestinal tract itself, at receptor sites,such as Peyer’s patches in the intestine.

One of the most encouraging fields in the study of polysaccharides istheir effectiveness against tumors. Polysaccharides are notably different


Carbohydrates

from allopathic cancer drugs -- there is no cytotoxic effect. Instead, thepolysaccharides promote the immune system’s attack on the tumor. Oneof the most successful herbs is the mushroom Reishi (Ganodermalucidum), which has had 80 - 98% success in repeated studies. Anotherheavily studied mushroom is shiitake (Lentinus edodes), for both cancerand ARC\AIDS problems.

Three of the biggest players in the research on these immune stimulat-ing herbs are:

1. Dr. Wagner from Germany, at the University of Munich, with hisresearch on Echinacea. He calls this type of immune therapyUmstimnungs therapie, which translates literally as “to tune”.

2. Dr. Sun Yan, head of Cancer surgery at the Beijing Cancer Hospital,with his study of herbs based on the ancient concept of Fu Zhengtherapy. Some of the most notable herbs in this area are Astragalusand Ligusticum.

3. Dr. Breckhman, of the USSR, coined the now very popular term“adaptogen”. Adaptogen means a substance that increases resis-tance to a wide range of environmental, physical, biological andemotional stressors. One of the major herbs he worked on wasSiberian ginseng.

These three independent groups of researchers have reported amazingeffects of a few herbs on human immunological capacity. Let’s look morespecifically at some botanicals which demonstrate similar attributes.

Chlorella

Chlorella (Chlorella pyrenoidosa) is a single-celled, fresh-water greenalgae. The name chlorella orginated from the fact that it contains thehighest concentration of chlorophyll of any known plant (algae areplants!). Chlorella is also known to be the first form of cellular plant tohave evolved a true nucleus, existing on Earth for over 2.5 billion years,since the Pre-Cambrian Period. Its survival into the modern era isattributed to genetic stability -- an unusually effective DNA-repairmechanism.44 Many feel that the mere fact that this species has survivedso long, shows that it has incredible strength of vital energy. This vitalenergy is the major ingredient that is sought by health enthusiasts.Today, chlorella is the second largest selling supplement in Japan, with ayearly production of over 1,000 tons.

Sc2



In reviewing the material on chlorella it is easy to split up the activeingredients into four categories:

1) Chlorophyll.2) The cell wall.3) Beta Carotene.4) Chlorella Growth Factor (CGF).

The content per 100 grams of the following are: Chlorophyll A (1,469mg), Chlorophyll B (613 mg), Beta Carotene ( 55,500 I.U., 180.8 mg),vitamin C (15.6 mg), thiamine (1.5 mg), riboflavin (4.8 mg), pyridoxine(1.7mg), niacin (23.8 mg), pantothenic acid (1.3 mg), folic acid (26.9 mg),B-12 (125.9 mcg), biotin (191.6 mg), Vit K., inositol (165. mg), parmino-benzoic acid, with a mineral content of phosphorus (989 mg), potassium,magnesium (315 mg), sulphur, iron (167 mg), calcium (203 mg), manga-nese, copper (0.08 mg), zinc (71.0 mg) and cobalt.45,46,47 It also containsdietary fiber, nucleic acids, amino acids, enzymes, anti-cancer agents,anti-viral agents and Chlorella Growth Factor (CGF).48

Chlorella Stimulates the Immune System It has been shown that thehot extract of chlorella stimulates the production of interferon. Thesubstance responsible for this is known as chlorellan, which resides inthe chemical group of very large branched polysaccharides. This grouphas been receiving great attention lately for its interferon stimulatingqualities. This substance stimulates macrophage activity, thus function-ing as an immune stimulant. There are many papers that have beenwritten on the immunostimulatory effect of chlorella.49-55

Chlorella has been shown to increase the number of macrophages intumor-bearing mice, producing an anti-tumor effect and prolonging thelives of these animals.56 There are several papers on the direct orindirect influence of chlorella on the prevention or inhibition of cancer.There are also many papers on the photodynamic qualities of chloro-phyll (found in very high quantities in chlorella) against canceroustumor.57,58

Chlorella was first found (1967) to be very effective against viruses witha lipid coat. Its antiviral factors were shown to stimulate both B and Tcells. Chlorella has been shown to be specific for Epstein-Barr virus andcytomegalovirus.59,60,61

Chlorella has been shown to be more active than chlorophyll alone,apparently due to the CGF in the chlorella.62 An inflammation of thepancreas (pancreatitis) is often caused by excessive alcohol consump-tion, by gallstones, poor nutrition, excessive calcium or fats in the blood.It is quite painful and often life threatening. There have been severalstudies showing that chlorophyll in concentrations found in chlorella ishelpful in the treatment of pancreatitis. The use of chlorophyll in the


Carbohydrates

treatment of pancreatitis is fairly prominent in the Japanese scientificliterature. The chlorophyll derivative inhibits the proteases enzymesthat are involved with the inflammation.63

Chlorophyll has been shown to tighten the teeth (contributing to thecessation of bleeding from the gums) and grow new tissue. Chlorella in agranular form has been mixed with water (1 tsp. per pint of water) andapplied through a “Water Pik”R to create these results.64

The detoxification capability of chlorella seems to be due to the struc-ture of the cell walls. In both animal and human studies chlorella hasbeen shown to be a great detoxifier of cadmium.65 “When Chlorella wasgiven for 12 days, cadmium in the excretions of the patients increased 3times over the baseline. After 24 days of chlorella the cadmium in theurine had increased to 7 times greater than baseline and the pain ofpatients was markedly reduced.”66

Detoxification of other heavy minerals such as uranium, mercury,copper and lead have also been shown to increase with the use ofchlorella. Chlorella has been shown to be very effective in removingpesticides, insecticides and polychloridebiphenyl (P.C.B.). from thehuman body. Additional medical effects are noted for liver toxicity,alcohol hangover prevention, bowel toxicity, constipation, anti-viralregimes, ulcers, skin problems, allergies, arthritis, atherosclerosis, highcholesterol levels, hypertension and heart problems.67

Echinacea

Echinacea is known for its anti-inflammatory activity, for acceleratingwound healing, treating viral infections, stimulating the immune systemand has been found useful in urology, gynecology, internal medicine anddermatology. Echinacea sp. possesses antibiotic activity, has a cortisone-like activity, inhibits hyaluronidase enzyme activity and activatesmacrophages.68,69,70,71

The immunostimulatory action is credited to echinacea’s inulin content.Besides the antitumour lipid component of Echinacea, echinacin hasbeen found to have anti-viral activity. E. purpurea root extract has beenshown to have interferon-like activity.72,73,74 Wagner and Proksch haveisolated a high molecular weight polysaccharide from the above groundparts of E. purpurea that has a pronounced immune stimulant activityattributable to a polysaccharide.75 As an alternative to the hypothesis ofinduction of interferon production, the authors suggest that the polysac-charide blocks the virus receptors on cell surfaces and thereby preventincorporation of the viral particles. The actual mechanism of the an-tiviral activity is not known and further study is required. Many organ-isms secrete hyaluronidase which increases connective permeabilityand allows the organism to become more invasive. The link mightinvolve the polysaccharide in this way.76,77

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Mo2

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Antibacterial properties are relatively mild but have be proven effectiveagainst Staphylococcus aureus, Corynebacterium diphtheria and Proteusvulgaris .78 Echinacea (most likely a lipid-soluble component) has alsobeen shown to increase properdin that stimulates alternative comple-ment pathways, thus mediating antibiotic and antineoplastic activity.This same component has shown significant inhibition of the growth ofWalker carcinosarcoma and lymphocytic leukemia.79

This same effect also helps in stopping wrinkles as the heteroglycanfound in humans is hyaluronic acid abundant in connective tissue.Echinacea supports this by inhibiting hyaluronidase from breaking downconnective tissue, thus stopping wrinkling.80 The major chemical ingredi-ent of Echinacea are two very long polysaccharides with molecularweight of 40,000 - 50,000; containing arabinose, xylose, galactose anduronic acid. These carbohydrates are thought to bind to the cell surfaceof T-lymphocytes which turn on the production of interferon.

Reishi

Reishi mushroom, known in China as Ling-zhi, has been considered themost valuable herb of the Orient, outpacing the reputation of evenginseng. The mystical qualities attributed to this herb might be ex-plained by the rarity of this plant. Only 2 - 3 mushrooms are found forevery 10,000 dead plum or hemlock logs. In light of new scientificevidence, this herb of longevity deserves a second look.

The nature of Reishi mushroom is documented in Shen nung tsao ching(56 B.C.). It is described as having the most extensive and effective

Figure 3.6Echinacea

Sc2

Mo2


Carbohydrates

O

OHR

R1

Figure 3.8Ganoderic Acid

healing powers. Since that time it has been considered number oneamongst the higher herbs. Over the centuries it has gone by manynames: Happy herb, herb of spiritual potency, Ling-zhi, Ten-thousand-year mushroom, Miraculous chi, Auspicious herb and Good omen plant.Folklore has it that the herb was considered so valuable that if a personfound one they would not even tell their closest friends or relatives.

When one reads the list of ailments it is supposed to cure, there is animmediate impression of a “snake oil” product. A cure-all! It is tempting

Figure 3.7Echinacein

O

N

H

COOHO

R3

H

H

H

R2



to consider the stories about Reishi just as wive’s tales, with lore suchas: “the gods planting it in the mountain, for only the special to find”. Onthe other hand, Nissan, (one of the three largest conglomerates inJapan), has conducted extensive research on reishi and is the majorworld supplier of the herb. This activity, when linked with the new floodof information on this herb, suggests the evidence should be consideredseriously.

Traditional Uses As noted above, the list of traditional uses is long.Cast in the terms of traditional Chinese medicine, it includes: nourishing,supplementing, toning, removing toxins, dispersing accumulation. It isindicated for neurasthenia, nervousness, dizziness, insomnia, high bloodpressure, high cholesterol, chronic hepatitis, cancer, AIDS/ARC,nephritis, bronchial asthma, allergies, pneumonia, stomach disease,coronary heart disease, diabetes, angina, mushroom poisoning, fatigueand for enhancing longevity. You add up this list and it is easy to call itan adaptogen (a substance that aids the body in resistance against awide range of physical, biological and environmental stress).

Active Ingredients What makes this herb so special? The activeingredients include: polysaccharide (Gandelan A & B), lanostan, couma-rin, ergosterol, triterpenes, germanium, organic acids and resins. Thekey phrase which describes the adaptogen effect of this herb is itsability to “dispel old blood”. By strengthening the energy or Qi of theblood, all systems in the body should be aided by this herb.

Pharmacological Activity Reishi has been examined extensivelythrough both traditional and modern scientific methods. The followingareas are noteworthy:

Figure 3.9Reishi Chinese ideograms

"Rain - together"deep rain forest

Three mouths

Shaman

Special Mushroom


Carbohydrates

Nervous System Both the ethanol and aqueous extracts have beenfound to inhibit the central nervous system of mice and act additionallyas an expectorant. It has been used for nervous problems like insomniaand paranoid conditions in humans.81

Antioxidant Reishi can be justifiably considered an antioxidant. It isvery likely that this feature contributed to its reputation as a longevityherb in Chinese medicine. It has been shown to be very effective inscavenging the hydroxyl radical in blood plasma.82

Respiratory Ailments For respiratory problems it has demonstrateda 60% recovery rate for allergy-related chronic bronchitis. In the sameresearch, improvement was noted in 97.9% of the cases. Chinese studieshave shown benefit for 87.5% of bronchial asthmatics with a cure rate of48%. For sinus problems the cure rate is over 50% with effectivenessbeing approx. 80%. Reduction of asthma prevention in guinea pigs, andcontact dermatitis in mice, has been considered remarkable by Japaneseresearchers.83 Reishi was shown to significantly inhibit histamine releaseand to be effective against Img-E related allergies.84,85

Cholesterol and Fatty Acid Reishi protected mice from accumulatedfatty acid and cholesterol when taken along with a fatty diet. The herbalso showed significant results in lowering blood lipids and fatty depos-its in the liver. In a small study done on 10 cholesterol patients, signifi-cant drops in cholesterol and triglyceride levels were noted after twomonths of taking Reishi mushrooms.

Blood Pressure Injection of the extract has lowered blood pressure inboth dogs and rabbits, while increasing urine volume. In a study con-ducted on genetically hypertensive (high blood pressure) mice, bloodpressure was lowered by 20% after consuming reishi for two weeks.Another study involving 10 patients with high blood pressure, deter-mined a 70% improvement in blood pressure (especially diastolic) afterremoval of medication and use of reishi. A third study with 10 patientsover 20 weeks produced significant improvement using reishi andpharmaceutical preparations compared with patients only using thepharmaceutical. In another study done on 53 patients, reishi was shownto reduce blood pressure, with no side effects, while reducing bloodlipids.8 6

The active ingredient for circulation has been isolated. It is a triterpenewhich inhibits angiotensin converting enzyme (responsible for narrow-ing the arteries in high blood pressure).87 Reishi has been verified toinhibit excessive platelet accumulation and to reinforce the outermembrane of the red corpuscle.88 Reishi is known to stop thrombiformations (blood clots).89 In China it was shown to be effective in 80% ofmyocardial infarction and angina cases while being curative in 25%.90



Anti-Bacterial This fungi has antibacterial effects on Bacillus pneumo-nia, staphylococci and streptococci bacteria. It can be used as anantidote in mushroom poisoning.91

Cancer Studies done in Japan have confirmed that reishi can beresponsible for arresting metastic cancer in laboratory mice. TheJapanese Cancer Society has found reishi effective against sarcomas.The active ingredients responsible for this are the polysaccharides.92,93,94

Blood Sugar Gandelan A & B are the known factors responsible forreishi’s sugar regulating ability.95

Digestive Tract In the digestive tract, reishi has shown an 80% curerate for ulcers. The difficult problem of chronic hepatitis has shown a10% cure rate in 2 months with 40% reduction of symptoms. Reishireduced the symptoms associated with hepatitis in carbon tetrachloride-induced hepatic mice.

Toxicity The toxicity of this mushroom can be considered completelynegligible with an LD50 of > 5,000 mg/Kg, with no toxic effect at this levelafter 30 days of consumption. This means that no toxic signs would befound in humans if they consumed 350 grams a day, 40 - 300 times thetherapeutic dose.96

Initial Response to the Herb During the initial period of intake, somepeople have observed dizziness, sore bones, itchy skin, increased bowelmovements, hardened feces, and/or pimple-like eruptions. These can beconsidered normal signs of the reishi excreting body toxins. Thesedisturbances vary from person to person and will disappear when intakecontinues.

Shiitake

Shiitake (Lentinus edodes) is a common food in the Orient, often found inSushi bars. This mushroom, and especially the polysaccharide lentinan,has been studied since 1925. Its major areas of uses is for cancer, AIDS/ARC, colds/flu, anti-viral, cholesterol and general immune stimulation.Lentinan has been used as an antitumour drug since 1986.

Some other immuno-stimulating mushrooms from the Orient are:Coreolus versicolor (Yun zhi), Tremella spp. (white tree ear, Yiner orbaimuer), Grifola umbellata (Zhuling), Poria cocos (Hoelen), Cordyceps(dongzhong or chancao, winter worm, summer grass), and Armillariamellea (mihuajun).


Carbohydrates

Figure 3.10Astragalus

Astragalus

Astragalus (Milk Vetch) is an Oriental herb that has been used forcenturies to build energy in the system. Its Chinese name translates as“Yellow Qi (energy),” meaning that it builds energy while working as amild antibiotic. The specific area of influence of this herb is the lungsand spleen. Its energy building qualities have been indicated by increas-ing body weight and prolonging swimming time in mice. By feeding micemilk vetch, their glycogen (energy) supplies in the liver were protectedfrom the environmental toxicity of carbon tetrachloride. Milk vetch hasbeen shown to have cardiotonic effect (significantly lowering bloodpressure in dogs, cats and rabbits). It dilates blood vessels. It alsoincreases the contraction of normal hearts, having a more dramaticeffect in hearts exhausted by fatigue or poisons. In vitro studies haveshown this herb to have antimicrobial effect against Shigella dysenteriae,Streptococcus haemolyticus, Diploccus pneumonia and Staphylococcusaureus. As a diuretic it has been shown to increase urine flow and totreat kidney and bladder infections. 97,98

OH

HO OOH

O - glu

Figure 3.11Astragalin

O

Mo2

Ed



Chinese energetics: Sweet, slightly warm; entering the Spleen and Lungmeridians. It is used to supplement qi, increase yang, consolidatesurfaces, control diaphoresis by stabilizing exterior, promote urinationand the discharge of pus. 99,100

Summary

Carbohydrates, also called sugars, are a product of photosynthesis. Thisis the primary source of life energy at the metabolic level. Monosacchar-ides contain one sugar, an oligosaccharide contains between two andten, and a polysaccharide contains more then ten monosaccharides.

The most abundant oligosaccharide is sucrose, also called table sugar.Sucrose is composed of D-glucose and D-fructose. It is usually extractedfrom sugar cane or sugar beet. The most common polysaccharides arecellulose (plant structure), plant starches (nutrient storage), and animalglycogen. Gums and mucilages have a demulcent effect as well as ahydrophilic bulking quality that makes them perfect for bulk laxative.These polysaccharides are also useful for absorbing toxins.

Immuno-stimulating polysaccharides are a very big area of herbalresearch. These polysaccharides have been shown to be effectiveagainst: AIDS, ARC, CFS, cancer as well as many other areas. The immunestimulating qualities of the polysaccharides explain many new and

Source of Concentration % increasePolysaccharide (mg/ml) in Phagocytosis

with control (%)

Arnica montana 0.001 44Achyrocline satureidoides, foliage 0.001 33Calendula officinalis, flowers 0.001 ***Echinacea purpurea, foliage 0.001 27E. purpurea, root 0.01 27E. angustifolia, foliage 0.01 23E. angustifolia, root 0.01 32Baptisia tinctoria, root 0.01 ***Chamomilla recutita, flower 0.01 31Eupatorium perfoliatum. foliage 0.001 28E. cannabinum, foliage 0.001 42Sabal serrulate, fruit 0.01 36Eleutherococcus senticosus, root 0.01 52

Table 3.4 101

Stimulation of Phagocytes by various Plant Extracts containing Polysaccharides


Carbohydrates

ancient therapies such as Umstimnungs therapie, adaptogen therapyand Fu Zheng therapy. Some major herbs used in these therapies areChlorella, Echinacea, Reishi, Shiitake, numerous Oriental mushroomsand Astragalus.

Mini- Materia Medica -- Carbohydrates

Adder Fern (Polypodium vulgare)Constituents: sugary mucilage, resinous bitter compound and

essential oils.Therapeutic action: used to treat infection of the respiratory tract, a

cholagogic and as a purge. Listed as anthelminthic, cholagogic,purgative and able to soothe coughs.

Barley (Hordeum vulgare)Constituents: mucilage, Vitamin B and E, protein, fat, starch (70-80%)

and enzymes.Therapeutic action: used since ancient Greece where physicians

used the mucilage to treat inflammation and infection of thedigestive system.

Borage (Borago officinalis)Constituents: mucilages, tannin and trace of essential oils.Therapeutic action: demulcent, emollient, sudorific and diuretic.

The oil of the seeds contains both Ω 3 & 6 essential fatty acids.Coltsfoot (Tussilago farfara)

Constituents: rich in mucilage, inulin, xanthophyll, pentose, galac-tose and uronic acid plus caoutchouc, a saponin, volatile oil,phytosterols, tussilagine and resin.

Therapeutic action: a specific demulcent for the lungs and bron-chial area, coltsfoot has been used for asthma, pleurisy andwhooping cough. It has also been found to be antibacterial andantifungal.

Marshmallow (Althaea officinalis)Constituents: mucilage (10% of root), sugar, pectin, and traces of

asparagine.Therapeutic action: emollient, demulcent, is used for irritations of

the bronchial, gastrointestinal and urinary tract.Plantain (Plantago sp.)

Constituents: mucilage and a heteroside -- aucuboside.Therapeutic action: used for bronchial catarrh, bronchitis, asthma,

tuberculosis and as a diuretic. Used for healing wounds, hemor-rhoids.

Ed

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Mo2

Mo2

Ed



Soy Beans (Glycine soja)Constituents: 20% mucilage (holoside, pentosans, galactosans)

Vitamins B & E, carotenoids, flavonoids and essential aminoacids.

Therapeutic action: used as a food with four times the number ofcalories as beef. Ideal food for diabetics as its sugar has poorassimilation.

References Cited

1 Bland Jeffrey, Your Health UnderSiege, Stephen Greene Press,Vermont, 1981, p151.

2 Borrmann, W., Comprehensive Answerto Nutrition, New Horizon Publ.,Chicago, 1979, p.1-5.

3 Tyler, V., Brady, L., Robbers, J.,Pharmacognosy, (7th ed.), Lea &Febiger, Phila., PA, 1976. p.68.

4Spoerke, D.G., Herbal Medications,Ibid.

5Leung, A.Y., Encyclopedia of commonnatural ingredients used in food,drugs, and cosmetics, Ibid.


7Biard, J.F., et al., Algues fixees de lacote atlantique francaise contentantdes substance antibacteriennes etantifungiques, Planta MedicaSupplement 136-51, 1980.

8 Chenieuc, J.C., et al., Algaes fixees dela cote atlantique francaise contenaitdes substances antimitotiques,Planta Medica Supplement, 152-162,1980.

9 Leung, A.Y., Encyclopedia of commonnatural ingredients used in food,drugs, and cosmetics, John Wiley &Sons Inc., New York, 1980. p.272.

10Spoerke, D.G., Herbal Medications,Woodbridge Press Publ. Co., SantaBarbara CA, 1980. p.146.

11Grieve, M., A Modern Herbal, JonathanCape, London, 1931, p.643.


13Grieve, M., Ibid.14Leung, A.Y., Ibid.15Leung, A.Y., Ibid.16Hsu, H.Y., Chen, Y.P., et al., Oriental

Materia Medica: a concise guide,Oriental Healing Arts Institute, LongBeach, CA, 1986, p.298-299.

17Bensky, D. and Gamble, A., ChineseHerbal Medicine: Materia Medica,Eastland Press, Seattle, WA, 1986,p.204-206.

18Kapoor, L.D., CRC Handbook ofAyurvedic Medicinal Plants, CRCPress, Boca Raton, FL, 1990, p.267.

19 Health Protection Branch, Report ofExpert Advisory Committee on DietaryFibre Information Letter No. 700,Health Protection Branch, Health andWelfare Canada, Dec. 6, 1985.

20Burkitt, D. and H. Trowell, WesternDiseases: Their Emergence andPrevention. Harvard University Press,Cambridge, Mass. 1981.

21Vahouny, G. and D. Kritchevsky,Dietary Fiber in Health and Disease.Plenum Press, New York, N.Y., 1982.

22Worthington-Roberts, B., Contempo-rary Developments in Nutrition CVMosby, St. Louis, Mo. 1981.

23Goodhart, R. and M. Shils, ModernNutrition in Health and Disease. Leaand Febinger, Philadelphia, Pa. 1980.

24Kritchevski, D., The role of fiber inhealth and disease. J. Environ. Pathol.Toxicol. Oncol., 6(3-4):273-84, Mar-Apr, 1986.

25McNutt, K.W. Perspective: Fiber.Journal of Nutrition Education8(4):150, 1976.

26Health Protection Branch, Report ofExpert Advisory Committee on DietaryFibre Information Letter No. 700,Health Protection Branch, Health andWelfare Canada, Dec. 6, 1985.

27Leveille, G.A., Dietary Fiber. Contempo-rary Nutrition, 1976.

28Abrink, M.J. and I.H. Ullrich, Interactionof dietary sucrose and fiber on serumlipids in healthy young men fed highcarbohydrate diets. Am. J. Clin. Nutr.,43. 419-428, March, 1986.


Carbohydrates

29Penagini, R., et al., The effect of dietaryguar on serum cholesterol, Am. J.Gastroenterol., 81(2):123-5, Feb.,1986.

30Vahouny, G. and D. Kritchevsky,Dietary Fiber in Health and Disease.Plenum Press, New York, N.Y., 1982.

31Iodice, M., et al., The effect of a dietwith high fiber contents on a C-peptideexcretion in therapeutic managementof type II diabetes. Rass. Med. Sper.32(7/8):147-15, 1985.

32Jenkins, D.J. and A.L. Jenkins, Dietaryfiber and glycemic response. Proc.Soc. Exp. Biol. Med. 180(3):422-31,Dec., 1985.

33Health Protection Branch, Report ofExpert Advisory Committee on DietaryFibre Information Letter No. 700,Health Protection Branch, Health andWelfare Canada, Dec. 6, 1985.

34Trinick, T.R., et al., Effect of guar onsecond-meal glucose tolerance innormal man. Clin. Sci., 71(1):49-55,July, 1986.

35Vaaler, S., et al. Diabetic Control isImproved by Guar gum and WheatBran Supplementation, DiabeticMedicine 3(3) :230-233 (may, 1986.

36Tagliaferro, V., et al., Moderate gaur-gum addition to usual diet improvesperipheral sensitivity to insulin andlipaemic profile in NIDDM. DiabetesMetab. 11(6):380-5, Dec., 1985.

37McNaughton, J.P., et al. Changes inserum cholesterol of diabetics fed 5grams guar gum daily. Nutr. Rep. Int.31(3):505-520, 1985.

38Bommartini, F., et al., Guar-carob beanassociation in the control of post-prandial hyperglycemia. G. Gerontol.33(6):497-504, 1985.

39Kameda, H., et al. Clinical andnutritional study on gallstone diseasein Japan. Jpn. J. Med. 23(2):109-113,1984.

40Schneeman, B.O., Effects of nutrientsand nonnutrients on food intake. Am.J. Clin. Nutr., 42(5 Suppl.):966-72,Nov., 1985.

41Morgan, L.M., et al., The effect of guargum on carbohydrate, fat, and protein-stimulated gut hormone secretion:modification of post-prandial gastricinhibitory polypeptide and gastrinreponses. Br. J. Nutr. 53(3):467-75,May, 1985.

42Schneeman, B.O., and D. Gallaher,Effects of dietary fiber on digestiveenzyme activity and bile acids in thesmall intestine. Proc. Soc. Exp. Biol.Med., 180(3):409-14, Dec., 1985.

43Tognarelli, M., et al., Guar-pasta : anew diet for obese subjects? ActaDiabetol. Lat. 23(1):77-80, Jan-Mar.,1986.

44Schopf WJ; Precambrian Micro-organism and evolutionary EventsPrior to the Origin of Vascular Plants.Biol Rev. 1970 45 pp 319-352.

45Steenblock, D., Chlorella: NaturalMedicinal Algae, Aging ResearchInstitute, El Toro, CA, 1987, p.2.

46Tamiya, H., Role of Algae as Food,Proceeding of the Symposium onAlpology, New Delhi, 1959 pp 379-389.

47Bewicke, D., Potter, B., Chlorella, TheEmerald Food. Ronin Pub. Inc.,Berkeley, CA, 1984.

48Steenblock, D., Ibid.49Kojima, M., Kasajima, T. et al., A New

Chlorella Polysaccharide and itsaccelerating Effect on the PhagocyticActivity of the ReticuloendothelialSystem, Recent Adv. R.E.S. Res 13:11,1973.

50Neveu, P.J., Morin, O. et al., Modula-tion of antibody synthesis by anti-tumor algae, Experientia 34:12,p.1644-45, 1978.

51Yamaguchi, N., Shimizu S, et al.,Immunomodulation by single cellularalgae (Chlorella pyrenoidosa) andanti-tumor activities for tumor-bearing mice. Third InternationalCongress of Developmental andComparative Immunology, ReinFrance July 7-13 1985.

52Kobayashi, S., Japanese Reticuloendo-thelial Society 10, 83, 1971.

53Kobayashi, S., Agricultural Chemistry46, 373, 1972.

54Kobayashi, S., Influence of Chlorellaextract on reticuloendothelialphagocytosis of rats, Health andIndustry Newsletter, March 25 1978.Agri. Chem. Conv. Japan.

55Nakamura, M., et al., Promotion ofreticuloendothelial function bychlorella components, Health andIndustry Newsletter, March 25, 1978.

56Yamaguchi, N., Ibid.



57Konishi, F., Tanaka, K., et al.,Antitumor effect induced by a hotwater extract of Chlorellavulgaris(CE): Resistance to Meth-Atumor growth mediated by CE-induced polymorphonuclearleukocytes, Cancer Immun.Immunother. 1985 19:73-78.

58Umezaawa, I., Komiyama, K., et al., AnAcidic Polysaccharide, chlon A, fromChlorella pyrenoidosa, Chemotherapy30(9), 1041-45, 1982.

59Shirota, Minoru, et al., Regarding theanti-virus components extractedfrom Chlorella, Show 42 nen Nihonnogika gakkai koen yori, 1967.

60Murayama, T., Leng-Feng, et al., Effectsof Various Products Derived fromChlorella pyrenoidosa cells on defensemechanisms of Organisms (Immuno-logical Resistance) The 21st JapanBacter. Conv. Nov 1984.

61Steenblock, D., Ibid.62Steenblock, D., Ibid.63Steenblock, D., Ibid.64Steenblock, D., Ibid.65Nagano, T, et al., Absorption and

Excretion of Cadmium by Ratsadministered Cadmium-containingChlorella. Eisei Kagaku 24(4), 182-86,1978.

66Steenblock, D., Ibid.67Steenblock, D., Ibid.68Koch, E., and Haaze, H., Arzeimittel

Forschung 2, 464 1952.69Koch, E., Uebel, Arzeimittel 1, 16,

1953.70Busing, K.H., Hyaluronidasehemmung

durch echinacin, Arzneim Forsch2:467-9 1952.

71Kuhn, O., Arzeimittel Forsh. 1, 194,1953.

72Mose, J., Effect of echinacin onphagocytosis and natural killer cells.,Med. Welt 34:1463-7 1983.

73Wagner, V., Proksch, A., et al.,Immunostimulating polysaccharides(heteroglycans) of higher plants /preliminary communication, ArzneimForsch 34:659 -60, 1984.

74Vomel, V., Influence of a non-specificimmune stimulant on phagocytosis oferythrocytes and ink by reticuloen-dothelial system of isolated perfusedrat liver of different ages, ArzneimForsch. 34:691-5 1984.

75Wagner, V., Proksch,A ibid.76Wacker, A., Hilbig, W., Virus-inhition

by echinacea purpurea, PlantaMedica 33:89-102, 1978.

77Hopp, E., and Burn, H., Groundsubstance in the nose in health andinfection, Annal. Otto. Rhino.Laryngol. 65:480-9, 1956.

78Cizmarik, J., Matle, I., Examination ofthe chemical composition of propolisI: Isolation and identification of the3,4 dihydroxycinnamic acid (caffeicacid) from propolis, Experentia26:713, 1970.

79Voaden, D.J., Jacobson, M., Journal ofMedicinal Chemistry 15(6), 619-23,1972.

80Busing KH ibid.81 Gengtao L, Tiantong B, et al; Some

Pharmacological actions of the sporesof Ganderma lucidum and themycelium of Ganoderma capensecultivated submerged fermation; ChinMed J 92 (7) 496-500 1979.

82Wang J, Zhang J, Chen W; Study of theaction of Gandoderma lucidum onScavenging hydroxyl radical fromblood plasma J Trad Chin Med 5 (1)55-60 1985.

83Nogami M, Ito M, Kubo M et al; Studyon Ganoderma lucidum VII. Antiallergic effect; Yakugak Zasshi 106 (7)1986 600-604.

84Nogami m, Tsuji Y, et al; Studies onGanoderma lucidum VI. Anti Allergiceffect; Yakugaku Zasshi 106 (7) 1986,594-599.

85Koda H, Tokumoto W, et al; Thebiologically active constituents ofGanoderma lucidum Histaminerelease-inhibitory triterpenes ChemPharm Bull (Tokyo 33(4) 1367-741984.

86Kanmatsuse K, Kajiwara N, Hayashi K,et al; Studies on Ganoderma lucidum.Efficacy against hypertension and sideeffects, Yakugo Zasshi, 1985, 105(10):942-947.

87Morigiwa A, Kitabatake K, Fujimoto Yet al; Angiotensin converting enzyme-inhibition triterpenes from Ganodermalucidum; Chem Pharm Bull(Tokyo34(7) 1986; 3025-3028.


Carbohydrates

88Shimizu A., Yano T, Saito Y et al;Isolation of an inhibitor of Plateletaggregation from a fungus Ganodermalucidum; Chem Pharm Bull (Tokyo)33(7) 3012-3015 1985.

89Kubo, M., Matsuda H, Nogami M; et al;Ganoderma lucidum IV. Effects onDisseminated Intra Vascular Coagula-tion; Yakugaku Zasshi 103 (8) 871-8771983.

90 Fu, H., Wang Z; The Clinical effects ofGanoderma lucidum spore preparationin 10 cases of Atrophic Myotonia; JTradit Chin Med 2 (1) 63-65 1982.

91Hsu H Y, Chen Y P, et al; OrientalMateria Medica; a concise guide;Oriental Healing Arts Institute 604-641; 1986.

92Sone Y, Okuda R, Wada n, Miskai A,Structures and antitumor Activity ofthe Polysaccharides Isolated fromFriuting Body and the GrowingCulture of Mycelium of Ganodermalucidum , Agric.Biol Chem. 49(9)2641-2653. March 4 1985.

93Miyazaki T, Nishijima M; Studies onFungal Polysaccharide 27 Structureexamination of a water soluble anti-tumor saccharide of Ganodermalucidum ; Chem Pharm Bull (Tokyo)29 (12) 3611-16 1981.

94Kim B, Chung H, Chung K et al: Antineoplastic components of KoreanBasidiomycetes; Korean J Mycol 8 (2)107-114 1980.

95Hikino H, Konno C, Mirin Y et al;Isolation and Hypoglycemic activityof Ganoderan A & B glycans ofGanoderma lucidum fruit bodiedPlanta Med 0 (4) 339-340 1985.

96Kim M J, Kim HW Lee Y et al; Studieson Safety of Ganoderma lucidum ;Koren J Mycol 14 (1) 49-60 1986.

97 Hsu, H.Y., Oriental Materia Medica: aconcise guide, Oriental Healing ArtsInstitute, Los Angeles, CA, 1986,p.521.

98 Bensky, D., Gamble, S., ChineseHerbal Medicine - Materia Medica,Eastland Press, Seattle, WA, 1986,p.457.



101Wagner, Proksch, ibid.




Glycosides

4Glycosides

Synopsis:

Glycosides, the second group we are looking at, is very active medicinally. Wewill examine eight of the eleven groups of glycosides. These glycosides representcathartics, pseudo-hormone regulators, analgesics, counter-irritants, antioxi-dants, diuretics and more. This exciting group of chemicals is a gold mine in thehands of herbalists.



Table of Contents

IntroductionAnthroquinone Glycosides

Cascara sagradaAloeRhubarbSennaLapacho

Saponin GlycosidesBiosynthesis of Saponin Glycosides

TriterpenesLicoriceSarsaparillaDioscoreaGinseng

Cyanophose GlycosidesApricot Kernels (Laetrile)Wild CherryBitter Almond

Isothiocyanate GlycosidesMustardHorseradish Root

Flavonol GlycosidesGingkoMilk ThistleHawthorne Berry

Alcohol GlycosidesSalicinPoplar bud

Aldehyde GlycosidesLactose GlycosidesPhenol Glycosides

Uva UrsiOther Glycosides

GentianSaffron

SummaryMini-Materia Medica - Glycosides


Figure 4.1 Alpha and Beta GlycosideFigure 4.2 Anthraquinone StructureFigure 4.3 Anthraquinone ConversionFigure 4.4 Biosynthesis of emodinFigure 4.5 Chrysophanol 8 glycosideFigure 4.6 Cascara sagradaFigure 4.7 AloeFigure 4.8 Aloe 8 glucosideFigure 4.9 BarbaloinFigure 4.10 Turkey RhubarbFigure 4.11 SennaFigure 4.12 Sennosides C & DTable 4.1 Quinones in TabebuiaFigure 4.13 LapachoFigure 4.14 Saponin Glycoside StructureFigure 4.15 LicoriceFigure 4.16 Chemicals associated with

LicoriceFigure 4.17 SarsasapogeninFigure 4.18 Diosgenin

Figure 4.19 GinsengFigure 4.20 Ginsenoside SkeletonFigure 4.21 Hydrolysis of amygdalinFigure 4.22 Hydrocyanic acidFigure 4.23 AmygdalinFigure 4.24 Isothiocyanate parentFigure 4.25 Hydrolysis of sinigrinFigure 4.26 Flavonoid skeletonFigure 4.27 Flavonoid with Heterocyclic ringFigure 4.28 Examples of flavonoidsFigure 4.29 GingkoFigure 4.30 Gingko chemicalFigure 4.31 Milk ThistleFigure 4.32 SilybinFigure 4.33 Proanthocyanidin B2

Figure 4.34 HawthornFigure 4.35 Biosynthesis ofsaligeninFigure 4.36 Uva ursiFigure 4.37 Transformation of arbutinFigure 4.38 Crocin


Glycosides

n the most simple terms glycosides are sugar ethers (an organiccompound in which an oxygen attaches to two carbon atoms,neither of which is a carbonyl carbon). A chemist would say thatI

glycosides are hydroxyls of a sugar, capable of forming ethers (seeChapter 2) with other alcohols. The ether group is condensed with ahydroxyl group of the non-sugar component, and the secondary hy-droxyl is condensed within the sugar molecule itself to form an oxidering. The non-sugar component is known as the aglycone. The sugarcomponent is called the glycone. Glycosides are distinguished fromother ethers by their ease of hydrolysis. By boiling a glycoside in diluteacids, the sugar will come away from the aglycone.

Glycosides are designated by taking the “-ose” (found in sugars) andreplacing it with “-oside” e.g. methyl-glucoside. Many of the glycosidesare known by their common name, e.g., arbutin.

Both alpha (α) and beta (β) glycosides are possible, as illustrated by theformulae for methyl glucoside (an alias for methyl glycoside) (Figure4.1). We will only be dealing with the beta form -- all that occurs in plants.Most glycosides have glucose as their sugar (glycone), however othersugars can be found.

From the plant’s point of view, glycosides have an important regulatory,protective and sanitary function. One might expect that we would findmany therapeutically active agents in this group because of theirregulatory roles in the plant and such is indeed the case. In fact, thegroup contributes to almost every class of herbal remedy. We findcardiac specific glycosides from digitalis, strophanthus, squill and

Introduction



others. Cathartic botanicals based on glycosides include senna, aloe,rhubarb, cascara sagrada and frangula containing emodin and otheranthraquinone glycosides. Sinigrin, a glycoside from black mustardyields allyl-isothiocyanate, a powerful local irritant, while gaultherinfrom wintergreen yields methyl salicylate, an analgesic.

Classification of glycosides from a chemical point of view is not an easymatter. The general description is that of the sugar residue beingcoupled to an aglycone. Once this glycoside is formed, other enzymesmay act to transfer another sugar unit to the monosaccharide to pro-duce di-, tri- or higher saccharides. For example, many flavonoids havetwo sugars.

Glycoside-containing botanicals are basically split into eleven types,based primarily on their aglycone group.

1) cardioactive group2) anthraquinone group3) saponin group4) cyanophose group5) isothiocyanate group6) flavonol group7) alcohol group8) aldehyde group9) lactone group10) phenol group and11) others.

We will deal with the cardioactive group in Chapter 9.

Figure 4.1Alpha (α) and Beta (β) Methyl-Glycoside

H OCH3

C

H C OH

HO C H O

H C OH

H C

H C OH

H

H3CO H

C

H C OH

HO C H O

H C OH

H C

H C OH

H


Glycosides

Figure 4.3Anthroquinone Conversion

HH

anthroneanthraquinone anthranol

Anthraquinone Glycosides

This is the largest group of naturally occurring quinones. They areimportant as dyeing agents and cathartics. The botanical families richestin anthraquinone glycosides are: Rubiaceae, Rhamnaceae and Poly-gonaceae. The basic structure, along with ring-numbering system is:

Figure 4.2Anthroquinone Structure

29

34

106

7

8 1

It is very common to find hydroxylated radicals at C-1 and C-2 (ie.,positions 1 & 2 in Figure 4.2), although these hydrolated compoundsmight be the results of extraction, preparation or analysis techniques.The actual anthraquinones found in plants are not completely deter-mined. They convert very easily. Aging, extraction, or analytical process-ing often encourage these changes. This points out the very dynamicnature of their chemistry. Constant chemical interchanges are going onin the living plant and in the prepared herb.

Many herbs that are cathartic in nature have anthracene relatedaglycones. Examples include Cascara Sagrada, aloe, rhubarb and senna.Besides the anthraquinone found in these plants, anthranol andanthrone (chemical derivatives) make significant contributions to thetherapeutic value of the herb.

The native glycosides often have their aglycone as a reduced form of theanthraquinone. The dynamic nature of this exchange can be seen inFigure 4.3. Note that the anthranol has a -OH, usually on the ninthcarbon, and an -O in C-9 in the anthrones.

O

5

O

O

O OH

←→←→

O



C C C C

CO CO CO CO

C C C C

CO CO CO CO

O

CH3OH

O O O O CH3

C C C C

C C C COOH

O O O

Figure 4.4Biosynthesis of emodin

8 Acetate Poly - β- ketomethylene acidintermediate

Emodin(or related derivatives)

Enzymatic (or chemical) hydrolysis of C-9 of anthranol is followed byoxidation of anthrone to form a anthraquinone, if oxygen is present.

Many anthraquinone and related glycosides are stimulant cathartics andexert their action by increasing the tone of the smooth muscle in the wallof the large intestine. The glycoside of the related anthranols andanthrones elicits a more drastic action than the corresponding anthra-quinone glycoside. If there is too large a quantity of the former constitu-ents (anthranols and anthrones) in the glycosidic mixture there is oftena discomforting griping action. The anthraquinone cathartics are nothabit-forming, while anthranol and anthrone often are.

The complex interplay of chemical structures depends on many factors.There is often literally a symphony of chemicals and derivatives in aplant. It is interesting to note that folklore has found ways to encouragethese transformations. Though ignorant of the chemical structure,centuries of tradition dictate that Cascara sagrada should be stored for ayear before use. This encourages the slow hydrolysing anthraquinone toform from its derivatives.

The actual formation of an anthraquinone in the plants can be summa-rized in Figure 4.4-- the production of emodin (found in Cascarasagrada). Here we have 8 acetates combining to form a Poly-b-keto-methylene acid which produces emodin. The anthranols and anthronesare most likely intermediates between the second and third steps.Now let’s examine some example herbs from this category in greaterdetail.

→ →

OH OHO


Glycosides

Figure 4.6Cascara sagrada

CH3

C6H11O5 - O

Figure 4.5Chrysophanol 8 glucoside

Cascara sagrada - Rhamnus purshianus

In this plant we use the dried bark that has been aged for at least oneyear prior to therapeutic use. This year changes the emodin-typeglycosides to the anthraquinone form (via slow hydrolysis). Many of theglycosides are in the anthranol and anthrone form when freshly picked.Delayed use gives the herb a milder and less griping cathartic activity.

The name Cascara sagrada is Spanish for sacred bark. The generic nameRhamnus is the ancient classical name for buckthorn. Purshean was thename of a famous German botanist. Cascara sagrada is found mostabundantly in the Pacific North West where it grows up to 10 meters inheight. Today’s market supply is mostly from Oregon, Washington andsouthern British Columbia. The bark is stripped from the tree trunk andlarge branches, and dried in the sun without exposing the inner surfaceto the sun.

This plant contains 6-9 anthraquinone glycosides which are normallymade up of 10 - 20% O-glycosides (based on emodin), 80 - 90% C-glyco-sides (aloin-like). There are a dozen substances represented. Two of theC-glycosides are barbaloin and chrysaloin (deoxybarbaloin), four arecascarosides A, B, C, and D. The major mode of action is to increase thetone of the colon wall while also stimulating peristalsis of the colon.Large doses also greatly influence the small intestine and stimulate mildbile flow. 1,2,3,4

O

OHO

Ed

Sc2

Mo2



The C-glycoside, chrysotain converts into chrysophanic acid. Thischemical gives a very strong laxative effect by stimulating the colonmuscle. On the other hand, emodin (O-glycoside) tends to control theeffect of chrysophanic acid. If the emodin were not present, we wouldget extreme looseness of the bowel. The two chemicals have a balancingaction.5,6,7,8 Other chemicals found in this herb are a volatile oil, glucose,malic and tannic acid (giving it a slight astringent effect also).9

The action of Cascara sagrada is primarily due to stimulation of in-creased colonic peristalsis.10-13 Peristalsis is stimulated through theautonomic nervous system rather than through the local irritativemechanism as is sometimes proposed. The active principals are ab-sorbed through the small intestine, enter the systemic circulation,stimulate the Auerbach plexus and in turn excite peristalsis.14 Cascara ismild in action and generally doesn’t cause griping. It is considered theleast griping of the emodin cathartics.15

When too much Cascara is taken alone, or when the bark is not oldenough, strong diarrhea might result. To treat this, administer Redmondclay, dolomite, magnesium oxide or charcoal as an antidote. Cascaranormally induces a solid or semisolid stool in eight hours. It is not anaddictive cathartic. It acts to build up the muscle tone of the colon.

Dosage: Capsules: 1-3, 2-3 times dailyFluid extract BP: 6 drops - 1 dramPowder extract: 2-10 grains.

Cascara sagrada powdered bark is listed as between 0.10 and 8.0 gramsin the literature.16-22

Merck Index and the U.S. Dispensary 0.60 to 2.0 grams23,24

B.P.C., 1934 lists the dose as 0.10 to 4.0 grams25

1.0 gram Cascara extract is equal to3.0 grams Cascara, usual dose is 300 mg.26

Cascara produces its action 6-8 hours after ingestion27

Toxicity: Large doses can cause extensive diarrhea accompanied bynausea, vomiting and cramping. The cascarosides are “generally consid-ered to be safe drugs with a minimum of side effects...”.28 Toxicityappears to be an issue in excessively large doses which may causeirritation.2 9

The Merck Index lists the upper therapeutic dose as 8 grams.Cascarosides may enter a mother’s milk and act as a laxative for thechild. Long term use may induce chronic diarrhea or a melanin pigmen-tation of the colon and rectal mucosa.30,31 This pigmentation is reversiblein four to twelve months after use is discontinued.32 Some authors note


Glycosides

that excessive doses can result in cramping, vomiting, and nausea.33,34

These side effects are generally countered by the administration of acarminative such as ginger or fennel.

The younger the bark, the more pronounced the side effects. The ratio ofanthrone to anthraquinone constituents changes as the bark is stored.The less predominant and more desirable anthraquinone cascarosidesbecome more common due to a slow process of hydrolysis of theconstituent glycosides.35,36 Grieve37 states that “the action of the barkbecomes milder and less emetic by keeping. Matured bark, three yearsold, is preferred for pharmaceutical purposes”.

Aloe Aloe vera or A. barbadensis

Aloe has become a very popular herb in the health food business inrecent years, especially as a cosmetic. It is usually found as a gel incosmetics or as suspensions of the gel, stabilized juice or as a derivativeof the gel. It is used as an external application with many other herbsand natural ingredients. The gel (juice from the aloe plant) is also usedinternally to cleanse the system and is a mild to moderate cathartic. Apowder, obtained from the dried juice of the plant is a very stronggriping cathartic even in moderate doses.

Aloe juice comes from the leaves of Aloe vera or A. barbadensis. Aloe isfrom the Arabic word alloeh or the Hebrew word halal, meaning shinybitter substance. Vera is from the Latin verus, meaning true. Of the 150species, most have fleshy leaves from which the juice can be extracted.Aloe contains a number of anthraquinone glycosides, principallybarbaloin (aloe-emodin anthrone C-10 glucoside).38

Even though most aloes contain 5-30% barbaloin, Aloe vera carries littleif any. All aloe also contains free non-glycosidal aloe-emodin andanthranol. Chrysophanic acid has also been found in this botanical. Wealso find socaloin (7.5 - 10%), capaloin (4.5-9%) and resinoltannol (16-23%), varying, like all ingredients, from species to species.39,40,41

The powder gives its strong cathartic action by stimulation of theperistaltic muscle, especially of the lower bowel. This powder is evenmore irritating than senna or large doses of Cascara sagrada. Actionusually starts 12-19 hours after ingestion. It is necessary to have bile inthe GI tract for the cathartic action to work. This powder has also beeneffective in eliminating several microorganisms, notably Pseudomonasaeruginosa (a diarrhea-causing bacteria).42,43

The oral administration of aloe has been effective in treating chronicbronchial asthma. It was effectively treated after a six month period. Theextract had to be kept in the dark at 4o C for seven days before adminis-tration. This produced a change in the glycoprotein and polysac-

Sc2

Mo2



Figure 4.7Aloe

O

O

CH2OH

Figure 4.8Aloe-emodin - 8 - glucoside

charides.44,45 Scientific research has been sparked by apparent prophy-laxis and treatment of leukopenia (caused by exposure to cobalt 60) andits anti-tumor activity against Sarcoma 180 and Ehrlich ascites.46,47,48

The fresh mucilaginous juice of the leaves of Aloe vera has been used forcenturies to treat burns. Today it is successful in treating all types ofburns, including third degree X-ray burns. It is even advocated as apossible aid for atomic radiation burns. 49

Dosage: Gel 1oz - 2 pintsPowder 1 - 10 grainsTincture 10 - 40 dropsFluid extract 1/2 - 1 tsp.Powder extract 1-5 grainsB.P. 1/2 - 2 oz.U.S.P. 30 drops.

OHC6H11O5 - O


Glycosides

Toxicity: Toxicity varies with variety. Barbaloin can be very griping(especially in a dried form) causing severe intestinal irritation. Aloe vera(which has very little if any barbaloin) seems to be non-toxic. It shouldnot be used internally during pregnancy50, however, because of itscathartic properties.

Chinese energetics: bitter flavour, cold property, entering the liver,stomach and large intestine meridians.51 Bensky says it enters Liver,Heart and Spleen meridian.52

Ayurvedic energetics: (Kumari) Rasa - madhur, tikta; Guna - guru,snigdha, pichila; Veerya - sheeta; Vipak - katu.

Rhubarb (Turkey or Chinese)Rheum officinale or Rheum palmatum

The dried rhizome or root (without periderm) tissue of Rheum officinaleor Rheum palmatum or most other Rheum species (excepting Rheumrhaponticum, common garden rhubarb) is used. Rheum comes from theLatin Rha, the name of the Volga River near which species of Rheumgrow. Palmatum refers to the large spreading leaves.

The principal constituents of the botanical are rhein anthrones. They areanthraquinone derivatives of emodin, chrysophanol and aloe-emodin. Aswe have seen in Cascara sagrada, the combinations of emodin andchrysophanol type components give these botanicals both “brisk andeffective” cathartic action while they “check diarrhea” as Mrs. Grievesays. Some of the rhubarb’s astringent effects undoubtedly come fromthe tannic acid (Rheo-tannic). 53-56

Figure 4.9Barbaloin

O OH

CH2OH

OH

H C6H11O5

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Dosage: Powder - 5 - 60 grainsDecoction - 3 ozFluid extract - 1/4 tspTincture - 1/2 - 1 tspSyrup - 1 tsp

Official Preparations: Fluid extractum, Rhei, U.S.P. 57

Rhubarb extract N.F. 1935.Extractum Rhei B.P.C. 1914 58,59

Aromatic Rhubarb Tincture 60

Infusum Rhei B.P. 1914, Fr. Codex 61

Extractum Rhei B.P. 1914, U.S.P. 190562

Tinctura Rhei et Gentianae N.F. 1905 63

Tinctura Rhei Vinosa N.F. 1905 64

GRAS 172.51065

Toxicity: In very large doses rhubarb can be griping and cathartic. Theleaf of any rhubarb is very poisonous, causing vomiting with severekidney and liver damage. Past researchers felt the oxalates caused thetoxic effect but it has now been shown to be caused by monoanthrones.66

Chinese energetics: a bitter and cold property; entering the Stomach,Colon, Liver, Spleen and Pericardium meridians. Its action is to drainheat, remove stool, drain dampness, cool blood, regulate menstruation,disperse stagnant blood and invigorate blood.67,68

Ayurvedic energetics: (related species R. emodi) Rasa - amala; Guna -laghu (light), rooksha (oily), tikshna (sharp); Veerya - ushna (hot); Vipak- amla (sour). Action: Kapha vat samak, pittawardhak, dipan, pachan,anuloman, bedhan, hridotajek swas har, hicaahar.69

Figure 4.10Turkey Rhubarb


Glycosides

Senna Cassia acutifolia

The dried leaflets (and sometimes seed pods) Cassia acutifolia (Alexan-dria senna) and Cassia angustifolia (Tinnevelly senna) also containanthraquinone glycosides. The name senna is from senna, the nativeArabian name of the botanical, Cassia is from the Hebrew getsial, mean-ing to cut off, and refers to the fact that the bark of some of the specieswas once peeled off and used. Acutifolia is Latin referring to sharplypointed leaflets and angustifolia means narrow-leaved. These plants arelow branching shrubs. C. acutifolia grows wild near the Nile River fromAswan to Kordofon and C. angustifolia grows wild in Somalia, the Arabianpeninsula and in India. Most of the commercial supply of this botanical iscollected from cultivated plants in southern India. It is cultivated on wetland resembling rice paddies.

The principal active constituents of senna are dimeric glycosides (1.5-3.0%), and aglycones, which are comprised of aloe-emodin and/or rhein.Those present in greatest concentration are sennosides A and B, a pairof optical isomers in which the aglycones are rhein dianthrone (sennidinA and B). Sennosides C and D are minor constituents having dimericaglycones comprised of one of aloe-emodin. 70,71,72 The leaflets alsocontain myricyl alcohol, salicylic acid, a phytosterbain mucilage andcalcium oxalate. 73,74

In the growing phase chrysophanol is the first constituent formed inyoung senna seedlings. The aloe-emodin related chemicals then appear,followed by the rhein. This herb is usually dried in the light, causingsome of the less active glycosides to change into more active ones.During fruit development the amount of simple aloe-emodin glycosideand rhein glycoside falls dramatically and the sennosides increase. Thisis why the plants are usually harvested during the pod stage. The podsthemselves are also sometimes used as they contain basically the sameconstituents as the leaflets, along with a highly active (cathartic) 10sugar rhein dianthrone. 75,76,77

Senna has a strong purgative action with griping. Because of the griping,senna is seldom used alone and is most often mixed with an aromatic,the best being ginger (3 parts senna to one part ginger) though cloves,cinnamon or fennel also works. Senna’s action is to increase the peristal-tic movements of the colon by local action upon the intestine wall. Overlong periods senna seems to become addictive -- it is necessary toincrease dosages to continue to have proper bowel movements. It isusually used for short periods of time because of this. If senna is takenby a nursing mother the purgative effect is transferred to the sucklinginfant.78

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Figure 4.12Sennoside C and D

H

It should be noted that senna reacts poorly when in combination withPeruvian bark (Cinchona), mineral lime and mineral acids.

Chinese energetics: (Fan Hsieh Yeh) sweet, bitter and extremely cold;entering the Colon meridians. Its action is to cleanse heat and removestagnancy.79

Ayurvedic energetics: Rasa - tikta (bitter), katu (pungent); Guna - laghu(light), rooksha (oily), teekshna; Veerya - ushna (hot); Vipak - katu(pungent). Action: Kapha vat samak. lakhan, vamak, anuloman, sansarn,krimighan, rakt sodhak.80

Figure 4.11Senna

OHO

COOH

COOHH

OHOC6H11O5- O

C6H11O5 - O


Glycosides

Dosage: Powder - 10 - 60 grainsInfusion - 2 ozFluid extract - 1/2 tspTincture - 30 - 40 drops

Toxicity: Senna can be griping and habit forming but is consideredfairly safe. Extended use can cause damage to the colon.81

LaPacho (Pau D’Arco)

LaPacho (Tabebuia avellanedae) is a native plant to South Americawhere it is called Pau D’Arco, Tahebo or Ipe Roxo. The inner bark hasbeen used for medicinal purposes for centuries as a folk remedy for awide variety of afflictions including boils, chlorosis, colitis, diarrhea,dysentery, enuresis, fever, pharyngitis, snakebites, syphilis, wounds,cancer, ulcers, respiratory problems, arthritis, cystitis, constipation,prostatitis, poor circulation and constipation. With a list this long, oneimmediately wonders if it is a cure-all. Surely it can’t do all of thesethings? After looking at some of the current scientific research on thisherb, many of the claims are substantiated in the lab, with animal studiesand in human studies.82,83,84

During the past century, Lapacho came under scientific scrutiny. Thefirst active constituent studied was lapachol in 1882.85 Lapacho has alarge range of quinones of both the anthraquinones and naphthoquinonegroups (see Table 4.1). One of the most important areas of research isLapacho’s antimicrobial activity. As early as 1956 it was shown to beeffective against a large array of Gram positive bacteria and fungi. Someof the most significant organisms are Candida albicans, Staphylococcus,Trichophyton, malaria, Brucella sp., tuberculosis and dysentery.86-89

Lapacho’s antiviral activity has proven effective against Herpes I and II,influenza virus, polio virus and Vesicula stomatitis virus. LaPacho haseven been shown to inhibit reverse transcriptase. This has prompted itsuse in several current studies on HIV+ and HLBV subjects (the impli-cated viruses in AIDS and Chronic Fatigue Syndrome).90-97

Antiparasitic activity of Lapacho has also been studied. Its action seemsto come from increasing oxygen supply at the local level, destroyingbacteria, viruses, fungi and parasites. The National Cancer Institute(U.S.A.) has done several studies on the components of Lapacho. Thebest results came from an ingredient Lapachol (Figure 4.13), that (in1968) had over 90% confidence rate against Walker 256 tumors. Studieswere stopped due to presumed toxicity. The head of the study laterfound this toxicity concern to be erroneous. He published a paperproving that Lapacho was less toxic than coffee. It appears that eco-

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nomic/political pressure of the time had much to do with cancellingfurther study on this herb in the U.S.A. The mechanism of action hassince been worked out by many other researchers in the search for anadequate “patent-able” cancer drug. In clinical studies Lapacho has alsoshown significant anti-inflammatory activity.98 - 102

Lapacho apparently works through a combination of all of the quinonesbut lapachol seems to be the most active and most studied quinone.Lapachol, like many napthoquinones, acts as a respiratory poison byinterfering with electron transport. It inhibits malarial parasites bystopping oxygen uptake ability. Mitochondrial respiration is inhibited inmicro-organisms by 50% at a lapachol 110 mmol/L. Its antitumor effectseems to be based on the same principle.

NaphthoquinoneLapacholMenaquinoneDeoxylapacholα-lapachoneβ-lapachoneDehydro-alpha-lapachone

Anthraquinone2-Methylanthraquinone2-Hydroxymethylanthraquinone2-AcetoxymethylanthraquinoneAnthraquinone-2-aldehyde1-Hydroxyanthraquinone1-Methoxyanthraquinone2-Hydroxy-3-methylquinoneTabebulin

Table 4.1Quinones in Tabebuia avellanedae

O

O

OH

CH2CH C(CH3)2

Figure 4.13lapachol


Glycosides

Clinically Lapacho is being used heavily for it anti-microbial properties.It is clearly successful against Candida, both the systemic varieties andthose found in the vagina. The clinical applications for Lapacho are quitebroad. Its control of many micro-organisms (which are responsible for awide array of diseases) explains its folklore.

Toxicity: there is no report of human toxicity in the literature, even inlight of its abundant use throughout the U.S.A., Japan, Europe and SouthAmerica over the last ten years. Reports have shown it to be less toxicthan coffee.103

Dosage: Boiling the bark is the most effective way to take this herb. Onetablespoon is boiled in two - three cups of water for ten minutes. Arecommended dose is to drink between 2 - 8 cups a day. In extract form,dosage is usually 15 - 30 drops, two - eight times daily.

Saponin Glycosides

This group of glycosides is fairly common in higher plants. Saponins arecharacterized by forming a colloidal solution in water that foams uponshaking. These plants have a bitter, acrid taste. Many botanicals thatcontain them have a sternutatory (cause sneezing) and otherwiseirritating effect on the mucous membranes. Saponins have been knownto destroy red blood corpuscles by hemolysis and are often toxic tocold-blooded animals. Some are used as fish poisons. The most poison-ous saponins are usually called “sapotoxins”.

This background seems intimidating until one recalls there are manyherbs in this group that are very useful: licorice root, sarsaparilla, yam,yucca, Devil’s claw root and ginseng. Current research indicates seaorganisms in the Echinodermata phylum contain saponins that havepromising uses for humans. One of special note is sea cucumber(Holothuria aggazia) which contains a triterpenoid type compound. It isinteresting that this Chinese delicacy, with holothurins, hascardioactivity even at low doses. It is also neuroactive, cytotoxic,antitumor and antifungal.

The humble starfish also has a large range of toxic attributes from itsasterosaponins. It is lethal to fish, annelids, arthropods, mollusc andvertebrates. Its components are also hypotensive, analgesic, causeneuromuscular junction blocking, and have protein metabolism interfer-ing properties.104 There has been a fair amount of scientific researchconducted on saponin-containing plants because they have precursorsto cortisone (steroidal sapogenins).



Figure 4.14Saponin Glycoside Structure

A B

C D

EF

Biosynthesis of Saponin Glycosides

Saponin glycosides are divided into two different types based upon thechemical structure of their aglycones (sapogenins).

The so-called neutral saponins are steroid derivatives with spiroketalside chains (Fig. 4.14). The other saponins have a triterpenoid structure.Triterpenoid biosynthesis-leading sapogenins (aglycones) involve head-to-toe coupling of acetate units. There is branching which leads tosteroids in one direction and cyclic triterpenoids in the other. Terpeneswill be examined throughout this text in the chapters on volatile oils ( 7),resins (8) and cardioactive and miscellanous compounds (9).

Triterpenes

Triterpenoids are of great interest as they often have hormonal-likeactivity in the human body. Some of the most active and regulative herbscan be found in this classification. Terpenes take their name from the“turp” in turpentine. Found in oily substances (essential oils), resins andsaps of plants, the fragrance of pine and of citrus is due to their terpe-nes. Pinene (turpentine) and limonene are among the more commonlyknown.

Triterpenes are found in Siberian ginseng (Eleutherococcus senticosus),Reishi (Ganoderma lucidum) and in Gotu Kola (Centella asiatica), three ofthe more renowned longevity herbs of the Orient. The medicinal activityof Gotu Kola, a creeping herb that grows close to the ground, is mainlyfound in triterpenes known as “asiaticosides”. Applications of the herb in

O

O


Glycosides

the traditional medicine of China bear obvious similarities to that ofReishi (mentioned in Chapter 3). It is primarily used to treat the respira-tory tract and as a blood tonic applied in fevers. Sedative and immuno-enhancing activities offer further similarities.

According to Daniel B. Mowrey, Ph. D., in his highly recommended bookGuaranteed Potency Herbs: Next Generation Herbal Medicine, 105 there aremany tales of centagenarian Gotu Kola ingesters in the regions where itgrows: Pakistan, Madagascar and India. In Chinese folk-history, a herbal-ist named Li-Ching Yun is said to have attained a life-span of 256 yearsfrom partaking of the herb. Gotu Kola is noted by the local peoplesbecause of the fact that elephants enjoy it and live for so long. The herbis also cooked and eaten raw in salads.

Triterpenes also occur in soybeans in the form of saponins. Soybeansare listed in ancient herbal records for use in treating inflammation andcounteracting the aging process.106

There are triterpenes in “Hoelen” (Poria cocos Wolf), a fungus that growson pine roots in China. In ancient times adepts in search of longevity orimmortality frequently ingested the growth. Also known to Chineseherbalists today as “Fu-ling”, Poria cocos is the one fungus most fre-quently used in Oriental herbal formulas where it is found in 30% ofprescriptions.

Fu-ling protected mice during laboratory studies from the formation ofstress-induced ulcers and taken orally caused a remarkable inhibition ofcontact dermatitis. But for the most part, Fu-ling remains an enigma topharmacologists who are at a loss to find a “chemical rationale” toexplain its uses in folk-medicine. Such uses include: antispasmodic,diuretic and promoting stomach function. Although the fungus hasshown only weak antitumour action, anticancer applications are re-corded as well. On the other hand, the mycelium has significantantitumour activity owing to immuno-modulating polysaccharides.107,108,109

Fu-ling is one of the elixir plants of the ancient Taoists and was classedas a “superior” medicine, meaning it is a substance that brings ease tothe body and prolongs life.

An in-depth discussion of this aspect of Chinese herbal medicines isgiven by Stephen Fulder, Ph. D. in his book The Tao of Medicine: OrientalRemedies and the Pharmacology of Harmony.110 Fulder presents a “hor-mone-tuning model” to explain the traditional use of ginseng as a restor-ative agent rather than as an “instant cure”. This amounts to a harmoniz-ing of the actions of the glands which both secrete and are affected by



hormones in response to stress from the environment. He explains thattriterpenoids are regarded as analogous to the steroids in the body ofman and beast (e.g. cholesterol, estrogen, testosterone, cortisol whichcontrols sugar metabolism and aldosterone which controls water levelsin the body) and that chemically they are closely related.

Fulder senses that “it is more than coincidence that the active principlesof most of the harmony remedies are triterpenoids.” That their chemicalstructure is so reminiscent of steroids should tell us something more.The effect of hormones on improving sensory awareness, memory,learning and relearning with less errors are improvements of the samekind as those noticed with the triterpenoidal plant remedies. Fulderfound a link through the element of stress, which is consistently less andin some cases, far less taxing with the ingestion of these triterpene-containing herbs. Experiments with literally thousands of animals haveshown that resistance to all manner of stress is increased and that theability of these herbs to “restore harmony” is made evident in thepresence of greater stress.

The effect of ginseng on the hormonal response to stress is the mainfocus of Fulder’s hypothesis. If ginseng increases both the responsive-ness of the adrenal glands and their ability to stop excreting when thestress has stopped, the work of these glands is conserved, they recoverfaster and the body is subjected to less adrenaline. Fulder proposes thatbecause of the similarity of the triterpenoids to the body’s hormones,they are able to occupy and act in the same sites of action (almosteverywhere in the body). Because of this, the glands would have tomanufacture less to achieve the same effect. Put another way, thetriterpenoidal herbs “amplify” glandular effects.

Fulder went on to initiate the first experiments ever conducted todetermine whether ginseng acts on the hypothalamus - the hormonecommand center where the response of the mind mediates the release ofhormones in the body. If his hypothesis was going to stand, there wouldbe no better place to look. The first experiments found that true to hisdeductions, ginseng caused the area where the hypothalamus resides -“the lower brain that regulates and monitors internal harmony” - to beimmensely sensitized.

Because it is only when stressful situations arise that these kinds ofherbs function to aid the body in adjusting to or harmonizing with theenvironment, Soviet scientists decided to name them “adaptogens”.Fulder’s “harmony drugs” have essentially the same meaning. The term“adaptogenic” was devised in 1958 by N.V. Lazarev, given to describe theeffects of “dibazol”; a narcotic that increased the non-specific resistanceof an organism “to adverse influences”. Ten years later, Drs. I.I.Brekhman and I.V. Dardymov reasoned this sort of action was already


Glycosides

common in folk-medicine and later followed their hunch with a survey.Of 189 medicinal plants prescribed in Southeast Asia, those conformingto this action prevailed in herbal formulas used in the treatment ofanemia, atherosclerosis, cancer, diabetes, hypertension, “and someother diseases”. Particularly noted was their ability to stimulate “produc-tion of immune bodies”.

Today we have scarcely more than a partial understanding of theactivity and mechanisms of adaptogens. Considering that to qualifyunder this category a substance must be innocuous, causing only aminimum interference with body functions, it’s no wonder that Westernscience has paid them little attention. And although an adaptogen mayhave a regulatory or “normalizing” action, as a stiffer requirement itmust also enhance resistance to health endangering influences, whetherof a chemical, biological or physical nature.

Brekhman and Dardymov decided Siberian ginseng and its close familyrelative Panax ginseng, conformed to every specification of “adaptogen”.These two plants took first and second place in all of the 189 medicinalplants examined. Activity studies showed positive effects in animalsfrom both ginsengs against the effects of radiation, fatigue, and narcot-ics. For reasons unknown, protection against the toxic effects ofanticancer drugs was stronger and more consistent from Siberianginseng than Panax ginseng.

The triterpenes in ginseng are closely related to a triterpenoid found inthe resin of “dammar” or resin trees (Agathis species) of New Zealand,New Guinea and the East Indies, and so they are called “dammarane-type” triterpenoids. Those in Ganoderma are made up of highly oxygen-ated lanostane-type triterpenoids. Including sterols, oxygenated com-pounds discovered in Ganoderma lucidum so far total at least 41 distinctkinds. The lanostane types are similar to and therefore take their namefrom lanosterol, a sterol occurring in the wool-grease of sheep.Lanosterol is also the main precursor of “parent steroid” found inanimals, a fact which may prove of greater significance as Fulder’sHormone Hypothesis and the secrets of plants of longevity unfold in theyears ahead.

Licorice Root Glycyrrhiza glabra

Licorice root is the dried rhizome and roots of Glycyrrhiza glabra.Glycyrrhiza is of Greek origin and means sweet root; glabra meanssmooth and refers to the smooth seed pods of this species.

Until 1870, Spain was the largest Western producer of licorice root butnow Turkey, Greece, and Asia Minor supply most of the licorice. Ap-proximately 60,000,000 pounds of licorice root and 350,000 pounds of

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licorice extract are imported into the United States yearly. Glycyrrhizacontains a saponin-like glycoside, glycyrrhizin (glycyrrhizic acid), whichis 150 times as sweet as table sugar.

Glycyrrhetic acid is a pentacyclic triterpene derivative of the b-aminetype. Glycyrrhizin (5-10% of the root), which is the potassium andcalcium salt of the glycyrrhizic acid, is very soluble in hot water andalcohol. Recent clinical investigation has shown licorice root is useful intreating rheumatoid arthritis (probably due to the saponins), Addison’sdisease and various types of inflammatory problems. Licorice, having asteroid component, has been shown to have a mild mineralocorticoid orcortisone steroid-like reaction on inflammation. These steroid-likecompounds can change to estradiol and estrone which are estrogenprecursors and therefore produce mild estrogenic properties.111,112

The unique glycosides in licorice root have the ability to purge excessfluid from the lungs and throat, eliminating them from the body throughthe urinary tract. It should be noted that some patients do get an allergicreaction to licorice. Symptoms include swelling at the ankles, increase inweight, water retention (edema) and loss of potassium.

Licorice’s ability to treat ulcers is well documented. We can also findsignificant activity as a detoxifying agent, antispasmodic, anti-allergic,immune suppressant, for chronic bronchial asthma, for lowering choles-terol and anti-neoplastic activity. 113,114,115

Figure 4.15Licorice


Glycosides

HOO - glu.

HO

O

O - glu.

HO O

OOHOH

O

licoricone

glycyrol

liquiritin

isoliquiritin

Figure 4.16Chemicals associated with Licorice

HO O

HO

OMe

OMe

Glycyrrhizin exhibits a regulatory action over estrogen metabolism, i.e.when estrogen levels are too high it inhibits estrogen action, and whenestrogen is too low, glycyrrhizin potentiates it. This factor can be used inthe clinic for many female hormonal problems, including P.M.S.

The major constituent is 5 - 24% glycyrrhizin (a triterpene glycoside).Upon hydrolysis, glycyrrhizin yields glycyrrhizic acid and two moleculesof glucuronic acid. Other constituents are flavonoids, starch (2 - 20%), 3 -14% sugar (glucose and sucrose), lignin, 2-4% asparagine, a complexvolatile oil, and a trace of tannin.116-125

Dosage: Powdered root - 1/2 - 1 dram126

Fluid extract - 1 - 4 drams127

Solid extract - 1 dram128

Toxicity: Licorice is a very safe herb in moderate doses. In large dosesit can cause sodium retention and potassium depletion and thereforecan lead to hypertension and edema. It is not recommended for patientswith heart or blood pressure problems.129

COOH

Oglu. A

glycyrrhizin

O

O

OHO

O



Chinese energetics: (Gan Cao)(raw) sweet and neutral; (toasted) sweetand warm. Licorice enters all twelve primary meridians, especially theSpleen and Lung. It tonifies the Spleen, replenishes Qi, clears heat,removes toxins, moistens lungs, controls coughs, harmonizes thestomach and spleen, harmonizes all drugs, soothes spasms and acts asthe great antidote.130,131,132

Ayurvedic energetics: (Yashtimadhu) Rasa - mahura; Guna - guru(heavy), snigdha (pacifies vata); Veerya - sheeta; Vipak - madur. Action:Vat pitta samak, daha, samak, shura bardhak, kapha nisarak, vata-nuloman, kantaya, raket sthambk, jawar nasak, jiviniya, sandhaniya,rasayan, balya.133

Sarsaparilla Smilax spp.

Sarsaparilla is the dried root of many of the Smilax species. The chiefconstituents of sarsaparilla are 1.8 -2.4% steroid saponins sarsa-parilloside and smilasaponin, the glycosides of the steroids aglyconesarsapogenin and isosarsapogenin, smilagenin and pollinastanol. It alsocontains other phytosterols such as sitosterol and stigmasterol. Theparillin and smilagen that have been previously reported are, in fact,impure forms of sarsasaponin.134-138

Sarsaparilla has been clinically used for many years for psoriasis,rheumatism, syphilis (effective in 90% of acute and 50% of chroniccases) and other venereal and skin diseases. The successful treatmentseems to stem back to the presence of the saponins. It should be notedthat Yucca also contains sarsasapogenins. The particular alkaloidswhich seem to be similar to spikenard have a peculiar molecularstructure that allows them to penetrate dense masses of hardenedmaterial and soften them. This factor seems to be the reason for itsbeneficent but sometimes limited effect on multiple sclerosis. Thealkaloids, along with saponins, attach themselves to germicidalmicrobes, weakening their activity. This is probably why it has beensuccessful in treating syphilis and virulent gonorrhea, but it has beenfound to work better in combination with sassafras and burdock ratherthan alone. The volatile oil in sarsaparilla has been shown to help theabsorption of other drugs into the system and therefore the assimilationof other herbs when combined with them.139 - 143

Some of the effects of sarsaparilla seem to be due to its endotoxinbinding capability. Endotoxins are toxins from bacterial cell wallsabsorbed through the intestines. When these circulate, they overtax theliver and are theorised to be one of the major cause of psoriasis. Thisendotoxin binding effect will also help reduce liver stress, gout andarthritis.1 4 4

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Glycosides

The steroidal properties of Smilax has made it very popular with bodybuilders. Many of the users find increased muscular size and strength.Some users find that it makes them more aggressive. It works in a similarway as anebolic steroids and will pass undetected in urine drug tests.145

Sarsaparilla is considered to be an excellent expectorant and tonic andis often used as a flavouring agent.

Dosage: Powder - 30 - 60 grainsDecoction - 3 ozTincture - 5 - 15 dropsFluid extract - 2 - 4 tsp

Toxicity: No cases of toxicity were reported in the references re-viewed.

Chinese energetics: (Tu Fu Ling) sweet, bland and neutral; entering theLiver and Stomach meridians. It clears damp heat poison, aids the skinand opens channels.146,147

Yam Dioscorea spiculifora or Dioscorea floribunda

Yam, or Wild Yam as it is often called, should not be confused with someDioscorea species which are eaten as table yams (or with its relative, thesweet potato).

The medicinal yams, Dioscorea spiculifora, source of botogenin anddiosgenin and Dioscorea floribunda (Mexican Yam), represent a richsource of principals used as cortisone precursors. Dr. Russell E. Makerhas been successful in synthesizing the pregnancy hormone progester-one (in five steps) and male hormone testosterone (in eight steps) fromthe saponin in this plant. It should be emphasized that this was done in alaboratory, not a body, and does not necessarily mean that thesehormones can be produced in the body from this herb.148,149

Figure 4.17Sarsasapogenin

O

O

HO



Dioscorea has been used as the raw material to synthesize many of thesteroidal drugs now presently on the market. The most notable arecortisone and female hormones. Beta-carotene is often extracted fromyam.

Wild Yam is employed as an antispasmodic, especially for bilious colicand abdominal cramps. This botanical yields an alkaloid substancewhich relaxes the muscles of the stomach and entire abdominal regionby working as a sedative on the local nerves.151-153 It’s estimated thatmore than 200 million prescriptions a year are sold containing yamderivatives.1 5 4

Dosage: Powder - 30 - 60 grainsInfusion - 30 - 60 grainsDecoction - 30 - 60 grainsFluid extract - 2 - 4 mlTincture - 2 - 10 ml

Toxicity: No toxicity was found but the fish poisoning attribute ofdioscin suggests that more than triple dose should be avoided.155

Chinese energetics: (dried rhizome of related species of D. opposita) issweet and neutral properties; entering the Spleen, Lung and Kidneymeridians. The action is to tonify the spleen and stomach, benefit thelungs, and nourish the kidneys. 156

Ayurvedic energetics: (related species D. bulbifera) Rasa - katu (pun-gent), tikta (bitter), madhur; Guna - laghu (light), snigdha (pacifies vata);Veerya - ushna (hot); Vipak - katu (pungent). Action: Tridosha har,bran ropan, dipan, anuloman, krimighan, rakt sodhak, veersya,prameghan, kustaghan, balya, rasayan.157

O

Figure 4.18Diosgenin150

HO

O


Glycosides

Ginseng Panax quinquefolium

Space prohibits more than an introductory glance at ginseng. Anyonedesiring more information on this exciting herb should consult The Taoof Medicine by Stephen Fulder, the Wild Rose Scientific Herbal orMowrey’s Next Generation Herbal Medicine. Panax quinquefolium andother ginseng have been studied rather thoroughly, primarily by theChinese and Russians. The species is known to contain several saponinglycosides including ginsenosides and panaxosides. There is also 3%volatile oil containing a camphoraceous substance, a resin, arabinose,mucilage and starch. It contains small amounts of pantothenic acid,biotin, vitamins B1,B2,B12, nicotinic acid, choline, citric, fumaric, malic,maleic, panaxic and tartaric acids and traces of Mn, V, Cu, Co, S andAs.158 - 161

The therapeutic attributes can really only be summed up by the word“adaptogen” -- to increase the resistance to a wide variety of physical,chemical and biological stresses. Panaxin has been shown to stimulatethe midbrain, heart and blood vessels. Panax acid is a stimulant to theheart and to general metabolism. Panaguillin stimulates internal secre-tions and panacen and sapogenin (volatile oils) stimulate the centralnervous system.162,163

For reducing blood sugar, ginseng has the chemical gensenin. It has alsobeen found that ginseng has a general stimulant effect on the adrenalcortex. There is an increase of corticosteroid content in the urine bymore than 60% and eosinophil cell count decreases after ginseng admin-istration. There are other studies that show ginseng increases bothmental and physical efficiency.164,165,166

Figure 4.19Ginseng

Sc2

Mo2



During stress the amount of Vitamin C is normally decreased dramati-cally in the adrenal glands of a healthy individual. When ginseng isadministered it has been shown that the time of decreased Vitamin C ismuch shorter. This has been considered by some researchers as thefoundation of its adaptogenic effect. Ginseng also stimulates an aerobicand anaerobic glycolysis in the liver and kidney with no significantincrease in oxygen consumption. As a histamine liberator the saponin inginseng has proven to be effective. The muscles seem to be affecteddirectly by ginseng in its ability to bring about expenditures of energystored as ATP. This is why many athletes use it to build skeletal muscletone and for weight gain. It is therefore sometimes called “a biocatalyst”.167,168,169

Dosage: 2 - 8 gms

Toxicity: This herb has a very low toxicity with an LD50 of 1167mg/Kg.When 100ml of 3% tincture is ingested by humans a mild degree ofunrest is seen; 200 ml causes symptoms of systemic rash, pruritus,vertigo, headaches, fever, and in severe cases, hemorrhage. One case ofconsumption of 500ml was fatal.170

Chinese energetics: Chinese ginseng is sweet, slightly bitter and warmproperty; entering the Lung and Spleen meridians. A powerful tonic oforiginal Qi, expels “evil” Qi, supplements lung yin (vital essence), while itbenefits yin and generates fluid.171,172 American ginseng is bitter, sweet,mild and cooling properties; entering the Lung, Stomach and Kidneys. Itnourishes Yin, cleanses heat, depresses fire.173,174

Figure 4.20Ginsenoside Skeleton

RO

R'

HOR ' 'O


Glycosides

O C6H10O4 O C6H11O5

CH

CN

+ H 2O

C6H12O6++ HCN

MandelonitrileglucosideAmygdalin

Figure 4.21Hydrolysis of amygdalin

Cyanophose Glycosides

This is the largest group of naturally occurring nitriles (organic cya-nides):

Like many other glycosides, the cyanophose group are colourless,soluble in water and (to some extent) in alcohol but insoluble in fatsolvents. They occur throughout the plant kingdom (including someferns and fungi) with a strong representation amongst the Rosaceae.175

Amygdalin and mandelonitrile are the most common cyanophoseglycosides. The glycosides in Fig. 4.21 can be hydrolyzed into benzalde-hyde and are therefore sometimes classified in the aldehyde glycosidegroup. Amygdalin is found in large quantities in bitter almonds, in thekernels of apricots, cherries, peaches, plums and may other seeds of theRosaceae genus. 176

Preparations from plant materials containing cyanogenic glycosides arewidely employed as flavouring agents. An amygdalin-containing prepara-tion, known as laetrile or vitamin B17, is claimed by many to be ananticancer “drug”. Claims have also been made for the control of sicklecell anemia.

+ H 2O+ C6H12O6

Mandelonitrile Benzaldehyde Hydrocyanic acid

OH

CH

CN

→

O C6H11O5

CH

CN

↑

↑↑

H

C O



Apricot Kernels (Laetrile)

Apricot pits have been used for many years as the source of laetrile.Even though laetrile is not officially permitted in the USA or Canada, it isused heavily in Mexico and smuggled throughout the rest of NorthAmerica. Laetrile is really amygdalin, the source of the bitter taste foundin many plants such as almonds, cherries and plums. It is felt that smallamounts of laetrile over a period of time will accumulate in cancer tissueresulting in tissue anoxia (lack of oxygen) and thus the cancer cell’sdestruction.

It is known that cancer tissue has greater beta-glucosidase activity thannormal body tissue and is less capable of detoxifying cyanide. It isknown also that cyanide causes asphyxiation in brain tissue. Manyresearchers do not believe this theory. No animal model research hasreported antitumor activity for amygdalin. It also should be noted thatseveral people taking laetrile have died evidencing hydrocyanic acidpoisoning symptoms. On the other hand, there are also many cases ofpeople whose cancer has reversed while using laetrile. Even though thetheoretical model is interesting, “the jury is out” on this product.177

Wild Cherry Prunus serotina or Prunus virginiana

The dried bark is obtained from Prunus serotina for this botanical. Prunusis the classical name of the plum tree. Serotina means later or backward,referring to the time of flowering and fruiting of this species. Prunusvirginiana also exhibits medicinal characteristics.

Wild Cherry Bark contains a cyanogenic glycoside and prunasin (aderivative of amygdalin), an enzyme, pronase (an emulsive, which onhydrolysis forms hydrocyanic acid (HCN)), gallic acid, tannins, salts ofcalcium, potassium and iron.178

The amount of hydrocyanic acid varies from plant to plant and with thetime of the year. There is a higher quantity in plant parts that aredirectly exposed to the sun. Bark that is tinted green from thechloroplastids caused by increased photosynthesis also has an in-creased percentage of prunasin (C 14H17O6N).

Figure 4.22Hydrocyanic acid

O β Glucose

CCN

H

Ed


Glycosides

Prunasin with the enzyme pronase yields hydrocyanic acid, benzalde-hyde and dextrose. This greenish bark, when harvested in the fall, is thebest. Bark of less commercial value is more yellowish in colour.

In cases where cyanide content is in question, the test forhydrocyanic acid is as follows: Take 1.0 grams of smallpieces of the bark and put into a test tube with 1.1 ml ofwater, close test tube with a cork holding a strip ofmoistened sodium nitrate paper between the cork andtube. The HCN evolved over a period of 30 minutes willchange the yellow of the nitrate to a brick red.

Even though hydrocyanic acid is extremely poisonous, in small quanti-ties, and from a natural source, it works as an excellent expectorant andmild sedative. It seems to increase oxygen pickup of the blood byreacting with the oxygen barometer in the carotid and aorta arteries,affecting vascular dilation from the medulla centre.

Not only is it an excellent flavouring agent, the above qualities areexcellent reasons for its use as the base of many traditional coughsyrups. It also shows us that some chemicals (HCN) in a natural state (inmoderation) are very therapeutic. The same chemical in a syntheticform is extremely poisonous.

Figure 4.23Amygdalin

Bitter Almond Prunus amygdalus

Bitter Almond is considered more fully in a later chapter. It containsamygdalin and emulsions which yield benzaldehyde, hydrocyanic acidand glucose on hydrolysis. It therefore has some of the same attributesas Wild Cherry.

O β Gentiobiose

CCN

H



Isothiocyanate Glycosides

In the seeds of many cruciferous plants there are glycosides whoseaglycones are isothiocyanate. Principal among these glycosides aresinigrin from black mustard, sinalbin from white mustard and gluconapinfrom rapeseed. When these glycosides are hydrolyzed by the enzymemyosin, they yield mustard oils.

Most of the isothiocyanates are colourless liquids with sharp, irritatingodor and the ability to raise blisters on skin. The diagram below indi-cates the general structure. Most of these groups undergo hydrolysis,causing the aglycone rearranging.179

The "R" can be a simple alkyl group or much more complex. These“mustard oils” are thought to protect the plants against parasites. Manyresearchers feel that this group has the strongest antibiotic activity ofthe higher plants.180

Mustard Brassica nigra or B. juncea

Black mustard and Brown Mustard are the dried ripe seed varieties ofBrassica nigra or B. juncea. These plants come from the family Cruciferaewhich in Latin means cross-bearing, refering to the shape of the petalsarranged crosswise. Brassica is from the Celtic bresic, meaning cabbage.Juncea is Latin meaning rush or seed, nigra is Latin meaning black. Theterm mustard is believed to be derived from the use of the seeds as acondiment. The sweet must (fermenting juice) of old wine was mixedwith crushed seeds to form a paste called “ mustum arden” (hot must),hence the name mustard.

Figure 4.24Isothiocyanate Parent

R S -- β - Glucosyl

C

N

O

O S O

O --


Glycosides

Black mustard’s principal constituent is the glycoside sinigrin (potas-sium myronate). In adjacent cells the enzyme myosin is present. If wateris combined with the crushed powdered seed, the myosin brings abouthydrolysis of sinigrin (Figure 4.25).181,182

The product commonly called mustard oil is the allyl isothiocyanate.This chemical works as a local irritant (rubefacient) that increasesvasodilation. Used in small amounts internally, it stimulates digestionand in large amounts it is an effective emetic. Externally, mustard packs(mustard seed, flour, water) have been used for centuries to break upcongestion in the lungs and bronchials.

The mixture is applied on the thoracic area by first applying alayer of cloth or waxed paper (to avoid excessive local skinirritation), then the mustard mixture, a piece of waxed paper, thena towel to keep the heat in. This pack should be checked every fiveminutes to ensure that excessive skin irritation isn’t present.Within 10 - 20 minutes extreme loosening of the bronchial area willbe observed.

Horseradish Root Cochlearia armoracia

This herb, which also contains sinigrin and the enzyme myosin, whenfreshly grated and added to water or especially apple cider vinegar,produces a volatile oil containing allyl isothiocyanate. It also contains abitter resin, sugar, starch, gum, albumin and acetate.183,184

S C6H11O5

C3H5 N C

OSO3K

+ H2O

Sinigrin + (Myrosin)

Figure 4.25Hydrolysis of sinigrin

Allyl isothiocyanate + Pot. acid + Glucose(Mustard Oil) sulfate

S C N CH2 CH CH2 + KHSO4 + C6H12O6

Take 1/4 teaspoon of freshly grated horseradish root and combinethis with 1/4 teaspoon of apple cider vinegar. Immediately chew themixture thoroughly, with the mouth closed, causes the volatile oil torise into the sinuses, cleansing and restoring the mucus membranethere. This routine is usually followed twice daily. Increase both partsby one-quarter teaspoon every four days until 1 level teaspoon ofeach ingredient is reached. This is continued for two months, six daysa week. Sinus symptoms usually leave within one week but for athorough cleansing of the sinuses and to ensure the symptoms do notreturn, two months is recommended.

→

→

Sc2

Mo2



These vapours are also inhibiting to micro-organisms. Horseradish rootis a mild stimulant to the stomach. It does not causing emesis unlesstaken in very large doses.185,186,187

Flavonol Glycosides

The aglycone-containing glycosides are generally called flavonoids.These chemicals are widely distributed throughout the higher plants,giving them a yellowish pigmentation. Some of the most commonflavonoids are: rutin, quercitin and bioflavonoids (including hesperidin,hesperetin, diosmin and naringen).

The flavonoid group may be described as a series of C 6 - C3 - C6 com-pounds. The carbon skeleton usually consists of two C 6 groups (oftenbenzene rings) connected by a three-carbon aliphatic chain.

Often an oxygen-heterocyclic ring and hydroxyl group provide the nameof the flavonoid. There are approximately 150 flavonoids. Two of themost popular are rutin and hesperidin -- generally referred to as vitaminP or permeability factor. A great deal of research has been focused onthese chemicals in recent years. The results indicate these flavonoidsdecrease permeability and fragility of vessels in the capillary beds.

Figure 4.26Flavonoid skeleton

C C C

Figure 4.27Flavonoid skeleton with oxygen heterocyclic ring

1

2

345

6

78

1 '2 ' 3 '

4 '

5 '6 '

O


Glycosides

HO

HO

HO

O - Rutinose

Figure 4.28Examples of flavonoids

Rutin

Hesperetin

Quercetin

The physiological action is due to direct interaction of the flavonoids onthe capillary bed. Increased epinephrine supply was also discovered,which might be a factor. The utilization of vitamin C was found toincrease manyfold when accompanied with flavonoids. This is one of themajor reasons why vitamin C containing flavonoids in the health foodindustry is considered much more effective than “straight” ascorbic acidfound in drug stores.188

Therapeutically, the flavonoids are used when a health problem ischaracterized by capillary bleeding associated with increased capillaryfragility. These include: easy bruising, vascular disease, allergic states,hemorrhoids, diabetes mellitus and edema. Many of the bioflavonoidsare great antioxidants and are appropriate in anti-radiation treatment.Quercitin has been shown to be effective against food-based allergiesthrough its ability to bind up IgG. 189

Flavonoids seem to function as “biological response modifiers” inhumans. They modify the body’s response to allergens, viruses andcarcinogens. At the same time, they are anti-inflammatory, anti-allergic,antiviral, and anti-carcinogenic. Flavonoids also are active against a widerange of free radicals, controlling a larger range than most other antioxi-dants. We can find these therapeutic abilities in milk thistle (Silybummarianum), Ginkgo biloba and hawthorn berry (Crataegus oxycantha).190

OCH3

OOH

OH O

OOH

OH

OCH3

OHO

OHOOH

OHO



As mentioned above, one of the most useful bioflavonoids in the area ofallergies is quercitin. In addition to its antioxidant capabilities, quercitininhibits the release of histamine and other inflammatory molecules fromthe mast cells in both the gut and respiratory tract. Quercitin has alsoshown significant anti-tumor properties.191

Some of the best sources of flavonoids are the inner yellowish surface ofcitrus fruit, green peppers, rosehips and acerola cherries. Let’s examinea few prime examples of botanicals which contain significant quantitiesof flavonol glycosides: gingko, milk thistle and hawthorn berry.

Ginkgo Gingko biloba

Ginkgo is the oldest living species of tree, surviving both ice ages andheatwaves during its 200 million year history. An individual tree can liveas long as 1,000 years and grow to a height of 120 feet with a 4 footdiameter. Ginkgo biloba has been marketed in Europe, in the form of astandard extract of the leaves, for many years. Its effect on circulation isastounding. It influences the arteries, capillaries, veins and myocardium.Its physiological actions include vasodilation, enhanced ATP synthesis,increased cellular glucose uptake, inhibition of platelet aggregation, freeradical scavenging and modulation of calcium flux. The extract has alsoshown improvement of neural transmission, making it useful in cases ofdegenerative senility.

The active ingredients are terpene, flavonoids, proanthocyanidins, andginkgo heterosides (flavoglycosides). It also contains lactones, ananthocyanin and organic acids.192 - 195 This herb is often standardized to24% flavoglycoside (10% of which should be quercetin).196 This extract isoften described as Ginkgo biloba extract (Gbx).

Clinically ginkgo has shown statistically significant abilities in improving

Figure 4.29Gingko

Sc2

Mo2


Glycosides

cerebral vascular insufficiency. It alleviates vertigo headaches, tinnitus,short term memory loss, depression and lack of vigilance -- all “age-related cerebral disorders”. It not only improves blood supply to thecerebral area, it also improves oxygen and glucose utilization. Ginkgohas been reported to decrease depression. It apparently acts to normal-ize muscarinic acetylcholine receptors in the hippocampus whileinducing significant changes in CABS neurotransmission, similar totricyclic antidepressants.197,198,199

By aiding peripheral circulation, inhibiting platelet aggregation andacting as a free radical scavenger, ginkgo has provided excellent resultsin cases of arteriolar sclerosis, high blood pressure and arterial insuffi-ciency. The standard dose is 40 mg three times daily of the solid extract.

Chinese energetics: (Yin Hsing) The nut of ginkgo is sweet, bitter,astringent and neutral but slightly poisonous. It enters the Lung andKidney meridians. It expels phlegm, stops discharges, stabilizes thelower burners and stops wheezing.200,201,202

Milk Thistle Silybum marianum

Milk Thistle (Silybum marianum) is a stout annual or biennial, found indry rocky soil, in southwestern Europe and to a lesser degree in theUnited States. It contains silymarin, a mixture of flavonoids consistingchiefly of silybin, silydianin and silychristine. Silybin is considered themost active.

OH O

HO

R2O

Figure 4.30Chemical constituents in Gingko

Compound R1 R2 R3

Amentoflavone H H HBilobetin CH3 H HIsoginkgetin CH3 H CH3Ginkgetin CH3 CH3 HSciadopitysin CH3 CH3 CH3

O

OR1OR3

OOH

O

Sc2



Figure 4.32Silybin

The standard extract (usually containing 70% silymarin) is a widely usedpharmaceutical drug in Europe for liver disorders (protecting the liverbetter than any other known substance). The mode of action seems tobe free radical and leukotriene inhibition, coupled with the extract’sability to stimulate liver protein synthesis.

Silybum has been shown prevent depletion of glutathione (GSH) and alsoincrease its basal rate by as much as 35%. Glutathione takes up andgives off hydrogen and is fundamentally important in cellularrespiration. Silybum’s ability to increase basal rate during poisoning isimportant to pump the poisons out. It is similiar to “walking” anoverdosed person. One of the most dramatic examples of this effect isinhibition of mushroom poisoning. Mushrooms as toxic as Amanitaphalloides (Deathcap or Death Angel) can be counteracted with 100%effectiveness. In contrast, other therapies fail, resulting in death in 90%of subjects.203,204

HO

OH

CH2OHH

H

Figure 4.31Milk Thistle

O

OOHH

O

O

H

OCH3

OH


Glycosides

Clinically milk thistle can be used for all forms of liver toxicity anddamage from hepatitis to alcohol-damaged livers. In some tough cases ofpsoriasis, milk thistle has also been found effective.

Dosage is based on silymarin content and is 70 - 210 mg, three timesdaily. The dosage of the solid extract (70% silymarin) is 100 - 300 mg.three times daily.

Hawthorn berry Crataegus oxyacantha

Crataegus comes from the Greek word kratos, meaning hardness (of thewood) while oxus means sharp and akantha means a thorn. The leaves,berries and blossoms of this plant contain many biologically activeflavonoids, particularly anthocyanidins and proanthocyanidins (poly-mers of anthocyanidins also known as bioflavans or procyanidins).These flavonoids provide the red and blue colour of hawthorn berries.The flowers are particularly rich in the flavonoids (quercetin, quercetin-3-galactoside, vitexin, vitexin-4-rhamnoside) and proanthocyanidins.

We also find cardiotonic amines (e.g., phenylethylamine, O-methoxy-phenylethylamine, tyramine, isobutylamine), choline and acetylcholine,purine derivatives (e.g. adenosine, adenine, guanine and caffeic acid),amygdalin, pectin and triterpene acids (ursolic, oleonolic and crategolicacid). Proanthocyanidins in hawthorn berries and flowers seems tounderly the botanical’s effect on the human cardiovascular system.205 - 208

HO

OH

OH

Figure 4.33Proanthocyanidin B2

OH

OH

HO

OH

OH

OH

OH

O

O

Ed

Sc2

Mo2



The flavonoids of hawthorn berry are very strong “vitamin P” factorsand also increase intracellular vitamin C levels. Clinically, they havebeen shown to cause significant stabilizing of collagen by preventingcrosslinking destruction. They act as free radical scavengers, inhibitenzyme cleavage during inflammation, inhibit inflammation factors likehistamine, serine proteases prostaglandins and leukotrienes.

By increasing blood supply to the coronary vessels, improving heartmuscle contraction, eliminating rhythm disturbances and inhibitingangiotensin converting enzyme (ACE), hawthorn is effective in reducingblood pressure, angina attacks and serum cholesterol while preventingdeposits of cholesterol.209

Dosage is 3-5 gm of dried herb, 4-5 ml of tincture (1:5), 1-2 ml of fluidextract (1:1), standardized concentrate (1.8% vitexin-4-rhamnoside) 100-250 mg.

Chinese energetics: (Shan Cha) sour, sweet and warm properties;entering the Spleen, Stomach and Liver meridians. Hawthorn dissolvesfood, conducts stagnation, transforms congealed blood, dissipatesmasses and expels phlegm.210,211

Figure 4.34Hawthorn


Glycosides

Alcohol Glycosides

There are many glycosides in this group. The common plant compoundis cinnamic acid. We will limit our discussion to salicin and closelyrelated compounds found in willow (Salix), poplar (Populus) and birch(Betula).

Salicin

This glycoside is obtained from many Salix (willow), Populus (poplar),Betula (birch) and wintergreen species. Populin (benzoylsalicin), alsoassociated with salicin, is found mostly in poplars and birches.

Salicin is hydrolyzed into D-glucose and saligenin (salicyl alcohol) byemulsin. Salicin resembles salicylic acid (ASA, aspirins) and is probablyoxidized into salicylic acid in the human system. Salicin exhibits definiteantirheumatic properties. It has been shown that populin (which con-verts into salicin) exhibits a slightly greater nervine effect than straightsalicin.

Poplar Bud Populus candicans and other spp.

Balm of Gilead is derived from the resinous buds of several species ofpoplar. Some confusion surrounds the question of which species ofpoplar is the official herb. This is compounded by the hybridization ofthe species within the genus. Most poplar species, apart from aspen (P.tremuloides), are effective to varying degrees.

The most significant chemicals in poplar are two glycosides, populin(salicin benzoate) and salicin. The volatile oil (2%) is mainly humulene.Other chemicals are gallic acid, malic acid, mannite, chrysin,tectochrysin and a fixed oil.212 -215

Figure 4.35Biosynthesis of saligenin

CH2OH

OH

Saligenin

+ C6H12O6

CH2OH

O C6H11O5

+ H2O→

Ed

Sc2

Mo2

Salicin



Populin and salicin have antipyretic, antirheumatic and analgesic pro-perties along with many of the properties of salicylates. The terpene inthe resin is also thought to produce some of the therapeutic effects. Inthe plant, some antioxidant prevents the rancidity of the oil. Externally,the oil made of poplar (Balm of Gilead) works as a very good musclerelaxant and antirheumatic. This plant has been used in many pharma-ceutical cough preparations.216 - 221

Dosage: Solid extract - 5 - 10 grainsTincture - 1 - 4 dramsFluid extract - 1 - 2 dramsExtract of bark - 5 - 15 grains

Toxicity: There is no case of serious poisoning from this plant. Prob-ably, very large doses could have the normal methyl salicylate toxiceffects.222,223

Chinese energetics: (related species P. euphratica) is salty, bitter beingextremely cold property. It cleanses heat and removes toxins.224

Aldehyde Glycosides

The major glycoside that is employed in this group is vanillin, found notsurprisingly, in vanilla. It is used as a flavouring agent.

Vanilla Vanilla planifolia or V. tahitensis

A well-known flavouring agent, vanilla is cultivated in Mexico and Tahiti.The name comes from the Spanish vania , a sheath-like pod and illa,small. Planifolia is from planus, flat and folium, leaf.

The major constituent is vanillin with 10% sugar, 10% fixed oil andcalcium oxalate. The herb is reported to be an aphrodisiac, carminative,stimulant, emmenagogue and vulnerary. It is also known to stop toothdecay.225 There are no other important herbs containing significantquantities of aldehyde glycosides.

Lactose Glycosides

No useful herbal plants have lactose glycosides as a major constituent.


Glycosides

Phenol Glycosides

There are many naturally occurring glycosides that are phenolic incharacter. Arbutin, found in uva ursi is in this group. Hesperidin, (foundin various citrus fruits) already discussed under the flavonol group,could also be classified as a phenol glycoside. Phloridzin, found in theroot bark of rosaceous plants, baptisin, from Baptisia and iridin from theIris species are also examples of phenol glycosides.

We’ll take a close look at the botanical containing a phenol glycosidewhich has most importance for North American herbology: uva-ursi.

Uva-ursi Arctostaphylos uva-ursi

Uva-ursi or Bearberry typically refers to the dried leaf of Arctostaphylosuva-ursi. This procumbent evergreen shrub is found throughout Europe,Asia and the northern United States and Canada.

Arbutin (5.0-18.%), the major chemical found in uva-ursi, changes tohydroquinone and glucose or dextrose. Uva-ursi also containsmethylarbutin, ericinol, ericolin, ursone, flavonoids, allantoin, tannins (6-40% of the gallic and ellagic types), ursolic acid (0.4 to 0.75%), phenolicacids, uvaol, a trace of volatile oil and resin. The flavonoids in the plantare represented by quercetin (tetraoxyflavonol) and isoquercetin.Ursolic acid (urson) and isoquercetin are strong diuretics in concentra-tions of 1:100,000.226 - 231

Figure 4.36Uva ursi

Ed

Sc2

Mo2



Arbutin changes either in the GI tract before assimilation or in theglomerulus. Whichever the case, it has an antiseptic action in thekidneys from the nephridia tubes down to the bladder.232 - 236 Hydroqui-none is most effective in alkaline urine with a low specific gravity.237

Quercetin (isoquercetin) and ursolic acid have been shown to providethe diuretic effect in uva-ursi. Uva-ursi’s astringent action is due totannins (and derivatives).

Uva-ursi has been shown to be strongly antibiotic against many organ-isms including Staphylococcus and E. coli. This plant has also been founduseful for killing snails (Biomphalaria glabrata -- known to carry tropicalparasites) in concentrations as low as 50 ppm.238,239

Dosage: Powder - 20 - 60 grainsInfusion - 3 - 5 ozTincture - 10 - 20 dropsFluid extract - 1/2 - 1 tsp

Average dose 2.0 gram 240,241

U.S. Dispensary 1.3 to 4.0 grams 242

Merck Index 1.0 to 4.0 grams 243

4.0 ml. 244

Infusum Uvae Ursi Recens B.P.C. 15 to 30ml. 245

Toxicity: While large doses of bearberry could prove toxic, Spoerke246

considers this herb to be relatively safe and to produce no symptoms oftoxicity in the amounts generally available.

CH2OH

Figure 4.37Transformation of Arbutin

ArbutinOH

O C6H11O5

OH

+ C6H12O6+ H2O

GlucoseHydroquinoneWater

→


Glycosides

Other Glycosides

Gentian Gentiana lutea

The herb known as gentian or gentian root is the dried rhizome androots of Gentiana lutea. This large perennial herb is indigenous to centraland southern Europe and Asia Minor. The roots are usually gathered inthe autumn and are heaped in piles. As they ferment, they take on areddish yellow colour. The principal constituent is the bitter glycosidegentiopicrin (1-2%) which acts as a bitter stomachic, 0.6 - 0.8%gentianine, gentialutine (two alkaloids), xanthones, gentianose (afructose derivative) and volatile oils.247 - 255

Gentian exhibits choleretic activities in animals. Gentianine also exhibitsstrong anti-inflammatory properties in laboratory animals.256 Gentian hasproduced remarkable increases in gastric secretion in dogs.257,258 It hasbeen used for centuries as a digestive tonic, useful in both acid oralkaline conditions.259 Gentiopicrin is highly poisonous to plasmodiumwhich lead to gentian’s use for malaria.260

Dosage: Fluid extract - 1/2 - 1 dramCompound infusion - B.P. 1/2 - 1 dramTincture - 1/2 - 1 dramSolid Extract - 2 - 8 grains

Toxicity: It is usually taken in small doses as larger doses will sedatedigestion and even cause nausea or vomiting. It is contraindicated forexpectant mothers and people with high blood pressure.261 Approved bythe FDA as GRAS 172.510.

Chinese energetics: (related species G. macrophylla, Chin Chiu) is bitter,acrid (pungent), with a neutral property. Chin Chiu enters the Stomach,Liver and Gall bladder, expelling wind dampness, and removes defi-ciency heat.262,263

Saffron Crocus sativa

Crocus or Spanish Saffron is the dried stigma of Crocus sativa. It takesthe stigmas of about 100,000 flowers to make a kilo of the botanical,hence the high price. There are two glycosides in this plant and avolatile oil. The source of medicinal effect of the glycoside has not yetbeen established.

Saffron contains 2% crocin-1, 2% picrocrocin, small amounts of crocin-2, -3 and -4, free crocetin and derivatives, quercitin, 13% starch, Vitamins B1

and B2, iron and lots of potassium, 8 - 13% fixed oils, carotenoids, 0.4 -1.3% volatile oil (consisting of safranal, oxysafranal, pinene, cineole,isophorone, naphthalene, and others).264,265

Sc2

Mo2

Sc2



Saffron has been used for centuries as a respiratory stimulant in asthma,tuberculosis and whooping cough. It lowers blood pressure with a strongeffect on isolated toad and rat hearts. In addition to its use as anabortifacient (abortion-causing), claims are also made for its aphrodisiacproperties.

Saffron has been widely used for treating cancer but has been recentlyoutlawed for consumption in the United States because of a U.S. Foodand Drug Agency report saying it can cause cancer in rats.266

Dosage: Powder - 1 - 10 grainsTincture - 5 - 15 drops 267

Syrup - 1 dram - 1 oz

Toxicity: Deaths have occurred when used as an abortifacient (24grains).268 Other symptoms are vertigo, vomiting, bradycardia andstupor.269,270

Chinese energetics: (Fan Hung Hua) a pungent flavour with a warmproperty; entering the Spleen and Liver meridians. The action is toinvigorate blood circulation, smoothe menses, control pain, dispersestagnant blood and improve bile secretion.271

Ayurvedic energetics: (Kumkuma) Rasa - katu (pungent), tikta (bitter);Guna - snigdha (pacifies vata), laghu (light); Veerya - ushna (hot); Vipak -katu (pungent). Action: Tridoshahar, varyna sothahar, dipan, pachan,grahi, hridya, vajikarn, jwaraghan, rasayan.

Figure 4.38Crocin

CH3CH3

O

O - gentiobose

O - gentiobose

O

CH3CH3


Glycosides

Summary

The length of this chapter demonstrates the variety and extent of thegroup of chemicals called glycosides. Glycosides are non-reducingsubstances which, on hydrolysis (brought about by enzymes or re-agents) yield one or more sugars among the products of the reaction.The non-sugar part is called aglycone.

We classified the glycosides into eleven groups according to aglyconeand activity. They are as follows:

1) Cardioactive group (dealt with in a later chapter).

2) Anthraquinone Glycosides which included:a) Cascara Sagrada, containing emodin; and aloin-like barbaloin and

chrysaloin (converting to chrysophanic acid), which increasedperistalsis in the colon along with colon muscle tone.

b) Aloe: containing barbaloin, chrysophanic acid -- both increasingperistaltic action in the colon.

c) Rhubarb: containing rhein anthrones, anthraquinone derivative ofemodin, chrysophanol which again exhibits cathartic action, alongwith a slight astringent effect.

d) Senna: containing sennosides, aloe-emodin and chrysophanol,causing strong purgative action with griping.

e) Lapacho: whose anthraquinone and naphthoquinones contributedtherapeutic aids against parasites, arthritis, cancer, wounds, consti-pation, viruses and reverse transcriptase to name a few.

3) Saponin Group, which contains many steroid-like compounds, somesimilar to cortisone. Triterpenes seem to be of special interest due totheir hormone-like action. Present in many of the elixir plants,triterpenes have a wide range of activity. Examples discussed were:

a) Glycyrrhiza (licorice) which contains glycyrrhizin, affecting sugarand insulin levels and acting as an anti-inflammatory agent andpossible hormone precursor (maybe cortisone and estrogen).

b) Sarsaparilla, containing sarsaponin and smilagenin, used as an anti-inflammatory and anti-syphilitic.

c) Dioscorea, containing a cortisone-like substance.d) Ginseng known as an adaptogen.

4) Cyanophose group which are used as flavouring agents, anticancerherbs and nervines. Examples discussed were:

a) Wild Cherry containing hydrocyanic acid, which is found to be anexcellent expectorant and mild sedative.

b) Bitter Almond which is similar to Wild Cherry.



5) Isothiocyanate group, usually acting as a local irritants:a) Mustard contains sinigrin and myosin which combine to form

mustard oil, causing local vasodilation, producing a counter-irritanteffect and working as an emetic.

b) Horseradish, also containing sinigrin and myosin, producing avolatile form of mustard oil which cleanses the sinuses and in-creases gastric secretion.

6) Flavonol group, containing the chemicals quercetin, hesperitin andrutin. These chemicals work together with Vitamin C and decreasecapillary permeability and fragility. They are found in citrus fruit,rosehips, green peppers and many other plants.

a) Ginkgo, contains flavonols and terpenes that aid in improvingcerebral vascular circulation, enhances ATP synthesis, increasesbrain activity, works as a free radical scavenger, aiding in arterio-sclerosis and blood pressure.

b) Milk Thistle, has a mixture of flavonoids that are very effective intreating liver toxicity, been effective enough to reverse the livertoxicity caused by some of the world’s most poisonous mushrooms.

c) Hawthorn contains flavonoids that are effective in strengthening theheart and blood circulation, while inhibiting rhythm disturbancesand preventing cholesterol deposits.

7) Alcohol group, where we looked at salicin and populin found in theSalix, poplar, birch and wintergreen species. These chemicals producesalicylic acid in the body and have a nervine effect.

8) Aldehyde group, where we saw vanillin found in vanilla, used as aflavouring agent.

9) Lactose group has little therapeutic value.

10) Phenol group, in which we discussed uva-ursi and the chemicalarbutin. Arbutin hydrolyses into hydroquinone which acts as an antisep-tic in the kidneys.

11) Other glycosides included:a) Gentian, containing gentiopicrin which acts as a bitter stomachic.b) Saffron having glycosides acting as a respiratory stimulant,

abortient and aphrodisiac (maybe).

All the plants containing glycosides have not been included in thischapter but the preceding examples help us understand the role of thespecific plants containing glycosides in these various groups.


Glycosides

Mini - Materia Medica -- Glycosides

Asparagus Fern (Asparagus officinalis)Constituents: saponins, asparagine, rutoside, tannin, potassium and

traces of fluorides.Therapeutic Action: diuretic, used in gout and for dropsy.

Aloe (Aloe sp.)Constituents: aloe-emodin, barbaloin.Therapeutic Action: purgative, emollient, stomachic. Used exter-

nally to treat burns and as a cosmetic.Almonds (Prunus amygdalus)

Constituents: 2-4% amygdalin, fatty acids, vitamin E.Therapeutic Action: emulsion, anti-microbial, stops coughing.

Bearberry (Arctostaphylos uva-ursi)Constituents: the glycosides arbutin and methyl arbutin, as well as

catechin and diuretic flavones.Therapeutic Action: disinfectant, diuretic effect upon the urinary

tract (best when urine is alkaline).Black Poplar (Populus nigra)

Constituents: populin and flavonic derivatives.Therapeutic Action: anti-arthritic, diuretic, diaphoretic, expecto-

rant, treating hemorrhoids, bronchitis, infection of urinary tract.Used mostly externally as an ointment.

Blackthorn (Prunus spinosa)Constituents: the flower contains the glycosides kaempferol and

amygdalin (lost upon drying).Therapeutic Action: diuretic, mildly laxative, tonic effect upon the

stomach and bladder.Buckthorn (Rhamnus catharticus)

Constituents: several anthraquinone glycosides.Therapeutic Action: purgative and diuretic.

Chervil (Anthriscus cerefolium)Constituents: essential oil (atraol), glycoside (apiine).Therapeutic Action: mild diuretic and depurgative. Used in folk

medicine to lower blood pressure. It is also used as a seasoning.Chickweed (Stellaria media)

Constituents: saponins.Therapeutic Action: emollient, demulcent, internal “knitter”.

Cleaver (Gallium aparines)Constituents: glycoside asperuloside.Therapeutic Action: vulnerary, reduces blood-pressure and tem-

perature.

Sc2

Mo2

Ed

Sc2

Mo2

Ed

Sc2

Sc2

Mo2

Mo2

Ed



Elder (Sambucus nigra)Constituents: essential oils (terpenes), rutin, quercitin, mucilage and

tannins. Fruit high in Vit. C.Therapeutic Action: diaphoretic, antispasmodic and antirheumatic.

Used for pharyngitis, tonsilitis, and stomach problems.Figwort (Scrophularia nodosa)

Constituents: saponins (diosinine and hesperidin).Therapeutic Action: diuretic.

Goldenrod (Solidago virgaurea)Constituents: saponins, flavonoids, essential oils, a bitter compound

and tannin.Therapeutic Action: diuretic, expectorant and antidiarrheal. Used

as a wash to soothe inflammations, eczema, internal to treatchronic nephritis, arthritis and menorrhagia.

Ginseng (Panax spp.)Constituents: triterpene saponins (ginsenosides).Therapeutic Action: adaptogen.

Hawthorn (Crataegus oxycanthus)Constituents: flavonoids (hyperoside, vitexin-rhamnoside),

leucoanthocyanidins and their triterpene derivatives, crataegolic,ursolic and oleanolic acids.

Therapeutic Action: cardiotonic, treats both high and low bloodpressure, tachycardia and arrhythmias. It is also an antispas-modic sedative.

Horse Chestnut (Aesculus hippocatanum)Constituents: several saponins (aescine the most important),

tannins, glycosides (esculoside, becomes coumarin) and fla-vones.

Therapeutic Action: antiphlogistic, diuretic, increase blood supplyto gastric and prostate areas. The fluid extract has been used toprotect the skin from harmful effects of the sun.

Horsetail (Equisetum arvense)Constituents: rich in silica, glycosides (isoquercitin, luteolin, and

kaempferol), equisetin (saponin) and traces of nicotine.Therapeutic Action: diuretic, haemostatic, vulnerary. Used for

internal bleeding and for pulmonary tuberculosis.Ivy (Hedera helix)

Constituents: all parts contain saponins (hederacoside),hederagenine and an acid.

Therapeutic Action: antispasmodic specific for whooping cough.The berries are toxic with skin irritating properties.

Knotgrass (Polygonum aviculare)Constituents: silica, mucilage, tannins, flavonoids (avicuroside,

quercitol and kaempferol.Therapeutic Action: a decoction is used for enteritis, diarrhea and

dysentery, with astringent, anti-diarrheal, diuretic, hemostaticand vulnerary properties.

Ed

Ed

Sc2

Mo2

Sc2

Mo2

Ed

Sc2

Ed


Glycosides

Licorice (Glycyrrhiza glabra)Constituents: saponoside, glycyrhhizin, glycyrrhizic acid,

triterpenes.Therapeutic Action: antispasmodic, treats ulcers, expectorant, mild

diuretic.Meadowsweet (Spiraea ulmaria, syn. Filipendula ulmaria)

Constituents: glycosides , salicylic aldehydes, spireine, methylsalicylate, gaultherin, flavonoids, spiraeoside, tannins.

Therapeutic Action: Hydrochloric acid regulator, antirheumatic,diuretic, diaphoretic and mild spasmolytic.

Milk Thistle (Silybum marianum)Constituents: flavonoid (silymarine)Therapeutic Action: produces bile flow, anti-hepatotoxic.

Mullein (Verbascum thapsus)Constituents: saponins and pigments (crozetine and xanthophyll).Therapeutic Action: soothing, expectorant, demulcent.

Pansy (Viola tricolor)Constituents: saponins, salicylates, flavonoid (violaquercetin).Therapeutic Action: diuretic, expectorant, depurgative, used to

treat skin eruptions.Rhubarb (Rheum palmatum)

Constituents: anthrones and dianthrones , aloe-emodin,chrysophanol, rhein, rhaponticine and tannins.

Therapeutic Action: in small amounts -- antidiarrheal, largeramounts purgative.

Sarsaparilla (Smilax spp.)Constituents: saponins that hydrolyse to form sarsapogenin,

essential oil and resin.Therapeutic Action: diuretic, sudorific, increases the metabolic

processes.Senna (Cassia angustifolia)

Constituents: sennosides A,B,C and D, flavonoids and polysacchar-ides.

Therapeutic Action: laxative.Shepherd’s Purse (Capsella bursa-pastoris)

Constituents: amino-alcohols, choline, acetylcholine, amino-phenol,tyramine and the flavonoid diosmin.

Therapeutic Action: used for menorrhagia, dysmenorrhoea anduterine hemorrhages. It can stop bleeding throughout the body.Tyramine is sympathomimetic and hypertensive.

Silver Birch (Betula pendula)Constituents: saponins, flavonoids (hyperoside), sesquiterpenes

and tannins.Therapeutic Action: the leaves are diuretic, heart tonic. It is used to

treat urinary insufficiencies, dropsy, rheumatism and infectedurinary tracts.

Sc2

Mo2

Ed

Sc2

Mo2

Sc2

Mo2

Ed

Sc2

Sc2

Mo2

Ed

Ed



Silverweed (Potentilla anserina)Constituents: tannins, flavonoid, an alcohol and tormentol.Therapeutic Action: antispasmodic, astringent and antidiarrhetic.

White Willow (Salix alba)Constituents: salicin, salicortine and tannin.Therapeutic Action: tonic, febrifuge and antirheumatic. Used for

similar ailments as aspirin.Wintergreen (Pyrola rotundifolia)

Constituents: arbutin, flavones and tannins.Therapeutic Action: astringent, disinfectant, vulnerary. Used for

cystitis.


2 Morton, J.F., Major Medicinal Plants:Botany, Culture and Uses, Charles C.Thomas, Springfield, IL, p.201.

3 Leung, A.Y., Encyclopedia of CommonNatural Ingredients, A Wiley-Interscience Pub., Toronto, ON, 1980,p.97.

4 Trease, G.E., Evans, W.C.,Pharmacognosy (11th ed.),Bailliere,Tindall, London, Eng., 1978, p.384.

5 Martindale, The Extra Pharmacopeia,The Pharmaceutical Press, London,Eng., 1941. p.376.


7 The British Pharmaceutical Codex1934, The Pharmaceutical Press,London, Eng., 1934, p.290.

8 Merck Index (5th ed.), Merck & Co.Inc., Rahway, NJ, 1940, p.124.


10Wood, H.C. and Osol, A., U.S.Dispensatory, 23rd ed.,

11Martindale: The Extra Pharmacopeia,Ibid.

12Spoerke, D.G., Herbal Medications,Woodbridge Press Publ. Co., 1980.

13Leung, A.Y., Encyclopedia of commonnatural ingredients used in food,drugs, and cosmetics, John Wiley &Sons Inc., New York, 1980. p.79.

14Remington’s Pharmaceutical Sciences(16th ed.), Ibid., p.741.

15Remington’s Pharmaceutical Sciences(16th ed.), Ibid.

16The British Pharmaceutical Codex1934. Ibid.

17The Merck Index 5th ed., Merck & Co.Inc., Rahway NJ, 1940. p.124.

18Martindale: The Extra Pharmacopeia,Ibid., p.377.

19Wood, H.C. and Osol, A., Ibid.20Grieve, M., A Modern Herbal, Dover,

New York, 1971.21Wren, R.C., Potter’s New Cyclopaedia

of Botanical Drugs and Preparations,Ibid.

22Morton, J.F., Major Medicinal Plants:Botany, Culture and Uses, Charles C.Thomas Inc, Springfield IL, 1977.p.202.

23The Merck Index 5th ed., Ibid.24Wood, H.C. and Osol, A., Ibid.25The British Pharmaceutical Codex

1934. Ibid.26Remington’s Pharmaceutical Sciences

(16th ed.), Ibid.27Williams, L.O., Drug and Condiment

Plants, Agricultural Handbook 172,U.S.D.A., Washington, D.C., 1960.p.74.

28Leung, A.Y., Encyclopedia of commonnatural ingredients used in food,drugs, and cosmetics, Ibid., p.97.

29Wood, H.C. and Osol, A., Dispensatoryof the United States of America 23rded., Ibid.

30Remington’s Pharmaceutical Sciences(16th ed.), Ibid.

References

Ed

Ed

Ed


Glycosides


32Williams, L.O., Drug and CondimentPlants, Agricultural Handbook 172,Ibid., p.69.

33Spoerke, D.G., Herbal Medications,Ibid., p,51.

34Morton, J.F., Major Medicinal Plants:Botany, Culture and Uses, Ibid.

35Griffenberg, G.B. and Hawkins, L.L.,Handbook of Non-Prescription Drugs(1973 ed.), American PharmaceuticalAssoc., Washington, D.C., 1973.p.122.

36Kinglet, R., Studies in the field ofDrugs containing AnthraceneDerivatives XVII. The quantitativedetermination of the anthracenederivatives of Rhamnus purshianabark., Lloydia Vol. 31, No.1, pp. 17 -22, 1968. p.17.

37Grieve, M., Ibid.38 Leung, A.Y., Encyclopedia of Common

Natural Ingredients, A Wiley-Interscience Pub., Toronto, ON, 1980,p.24.

39 Spoerke, D., Herbal Medications,Woodbridge Press Publ. Co., SantaBarbara, CA, 1980, p.21.


41 Morton, J.F., Major Medicinal Plants:Botany, Culture and Uses, Charles C.Thomas, Springfield, IL, p.48.



44Shida, T., et al., Proceeding ofWakananyaku Symposium 13, 1980,pp. 47-51.

45Shih, T., et al., Effect of aloe extract onperipheral phagocytosis in adultbronchial asthma, Plant Medica, 273-275, 1985.

46Soeda, M., et al., Studies on theantitumor activity of Cape Aloe,Nippon Act. Radiol., 23, 1109-1112,1964.

47Yagi, A., et al.; Aloe manna, polysac-charide from aloe, Planta Med. 31(1),17-20, 1977.

48Arendarevslii, L.F., Factors effectingthe efficiency of chemotherapy andrecurrence of tumors, Onkologiya(Kiev), No. 2, 15-22 (Russ) 1971.


50Spoerke, D.G., Ibid., p.21.51Hsu, H.Y., Chen, Y.P., et al., Oriental

Materia Medica: a concise guide,Oriental Healing Arts Institute, LongBeach, CA, 1986, p.88.

52Bensky, D. and Gamble, A., ChineseHerbal Medicine: Materia Medica,Eastland Press, Seattle, WA, 1986,p.171.

53 Grieve, M., A Modern Herbal,Jonathan Cape, London, 1931, p.677.



56 Duke, J., CRC Handbook of MedicinalHerbs, CRC Press, Boca Raton, FL,1985, p.404.

57The National Formulary 6th ed.,American Pharmaceutical Associa-tion, Washington DC, 1935. p.175.

58Martindale: The Extra Pharmacopeia,The Pharmaceutical Press, London,1941. p.898.

59The British Pharmaceutical Codex1934. The Pharmaceutical Press,London, 1934. p.904.

60Youngken, H.W., Textbook ofPharmacognosy, Blakiston, Toronto,1950. p.297.

61Lucus, E.W. and Stevens, H.B., TheBook of Pharmacopeias, J & HChurchill, London, 1915. p.153.

62Lucus, E.W. and Stevens, H.B., Ibid.,p.116.

63Lucus, E.W. and Stevens, H.B., Ibid.,p.404.

64Lucus, E.W. and Stevens, H.B., Ibid.65Leung, A.Y., Ibid.66Leung, A.Y., Ibid.67Bensky, D. and Gamble, A., Chinese

Herbal Medicine: Materia Medica,Eastland Press, Seattle, WA, 1986,p.166-168.

68Hsu, H.Y., Chen, Y.P., et al., OrientalMateria Medica: a concise guide,Oriental Healing Arts Institute, LongBeach, CA, 1986, p.92-93.












78Willard T.L.; Clinical observation.79Hsu, H.Y., Chen, Y.P., et al., Oriental



81Leung, A.Y., Ibid.82 Duke, J., CRC Handbook of Medicinal

Herbs, CRC Press, Boca Raton, FL,1985, p.470.

83Bernarde, A., A Pocket book ofBrazilian Herbs (Folklore - History -Uses), Shogun Editoria Rio deJaneiro, Brazil, 1984. p.22-23.

84Duke, J.A., Ibid.85 Duke, J., CRC Handbook of Medicinal

Herbs, CRC Press, Boca Raton, FL,1985, p.470.

86de Lima, O.G., et al., PrimeiraObservacoea sobre a acaoantimicrobiana do Lapachol. Anaisda Sociedad de Biologica dePernambuco XIV:129-35 1956.

87de Lima, O.G. et al., Antibiotica isolasado Pau D’Arco, Tabebuia sp. Anaisda Sociedad de Biologica dePernambuco XIV:136-40 1956.

88Burnett, A.R., and Thomson, R.H.,Naturally occurring quinones. Part Xthe quinonoid constituent ofTabebuia avellanedae (Bignoniaceae).J. Chem. Soc., pp. 2100-4, 1967.

89Gershon, H., and Shanks, L.,Fungitoxicity of 1,4-naphthoquinoneto Candida albicans and Trichophytonmentagrophytes. Can. J. Microbiol.21:1317-21, 1975.

90de Lima, O.G., et al., Ibid. p.129-135.91Largrota, M., et al., Antiviral activity of

Lapachol, Rev. Microbiol. 14:21-26,1983.

92Lopes, J.N., et al., In vitro and in vivoevaluation of toxicity of 1,4-naphthoquinone and 1,2-naphthoquinone derivatives againstTrypanosoma cruzi., Ann. Trop. Med.Parasit. 72:523-531, 1978.

93 Schuerch, A.R., and Wehrli, W., b-Lapachone, an inhibitor of oncornavi-rus reverse transcriptase andeukaryotic DNA polymerase-a:inhibitory effect, thiol dependencyand specificity. Eur. J. Biochem.84:197-205, 1978.

94Pinto, A.V., et al., Schistosomiasismansoni: blockage of cercarial skinpenetration by chemical agents: I.naphthoquinones and derivatives.Trans. Royal Soc. Trop. Med. Hyg.71:133-135, 1977.

95de Lima, O.G., et al., Comunicacao II.Antividade antimicrobiana de algunsderivados do lapachol emcomparacao com a xiloidona, Novaortoaftoquinona natural isolada deextractos do cerne do “Pau d’Arco”roxo, Tabebuia avellanedae Lor. ex.Griseb. Substancias antimicrobianasde plantas superiores. Revista doInstituto de Antibioticos Recife 4,1962.

96Shapiro, A., et al., In vivo and in vitroactivity by diverse chelators againstTrypanosoma brucei. J. Protozool.29:85-90, 1982.

97Morrison, R.K., et al., Oral toxicologystudies with lapachol. Toxicol. Appl.Pharm. 17:1-11, 1970.


Glycosides

98de Lima, O.G., et al., PrimeirasObservacoes sobre a acaoantimicrobiana do lapachol, Anais daSociedade de biologica depernambuco XIV:129-135, 1956.

99Austin, F.G., Schistosoma mansonichemoprophylaxis with dietarylapachol. Am. J. Trop. Med. Hygiene23:412-419, 1974.

100Gilbert, B., et al., Schistosomiasis.Protection against infection byterpenoids. An. Acad. Brasil Cienc.42(supl):397-400, 1970.

101Goijman, S.G., and Stoppani, A.O.M.,Oxygen radicals and macromoleculeturnover in Trypanosoma cruzi. LifeChem. Rep. suppl. 2, 1984. pp. 216-221.

102Docampo, R., et al., b-Lapachoneenhancement of lipid peroxidationand superoxide anion and hydrogenperoxide formation by sarcoma 180ascites tumor cells. Biochem.Pharmacol. 28:723-728, 1979.

103 Leung, A.Y., Encyclopedia ofCommon Natural Ingredients, AWiley-Interscience Pub., Toronto,ON, 1980, p.297.

104 Marderosian, A.D., Liberti, L., NaturalProduct Medicine, George F. StickleyCo., Phila., PA, 1988, p.223.

105 Marderosian, A.D., Liberti, L., NaturalProduct Medicine, George F. StickleyCo., Phila., PA, 1988, p.32-43.

106 Robinson, T., The Organic Constitu-ents of Higher Plants (4th ed.),Cordus Press, North Amherst, Mass.,1980, p.156.



109Liu Bo; Fungi Pharmacopeia (sinica);The Kinko Co; Oakland Ca; 1980;p202

110Leung, A.Y., Ibid.111 Bensky, D., Gamble, S., Chinese

Herbal Medicine - Materia Medica,Eastland Press, Seattle, WA, 1986,p.463.


113 Weiss, R.F., Herbal Medicine (6th ed.Eng. trans.), AB Arcanium,Gothenburg, Sweden, BeaconsfieldPubl., Beaconsfield, Eng., 1988, p.60.



116 Leung, A.Y., Encyclopedia ofcommon natural ingredients used infood, drugs, and cosmetics, JohnWiley & Sons Inc., New York, 1980.p.221.



119Textbook of Pharmacognosy, J. & A.Churchill Ltd., Rahway, N.J., 1976.(citation not confirmed) p.386.

120Wood, H.C. and Osol, A.,Dispensatory of the United States ofAmerica 23rd ed.,J.B. Lippincott,Montreal, P.Q., 1943. p.500.

121Gathercoal, E.N. and Wirth, E.H.,Pharmacognosy, Lea & Febiger,Phila. PA, 1936. p.354.

122Herbal Pharmacology in the People’sRepublic of China, Trip Report of theAmerican Herbal PharmacologyDelegation, National Academy ofSciences, Washington DC, 1975.p.156.

123Wallis, T.E., Textbook ofPharmacognosy, J & H Churchill,London, 1967. p.385.

124Remington’s Pharmaceutical Sciences(16th ed.), Mack Publ. Co., EastonPA, 1980. p.1233.

125Osol, A. and Pratt, R. (eds.), TheUnited States Dispensary (27th ed.),J.B. Lippincott, Phila. PA, 1983. p.563.

126Grieve, M., Ibid.127Grieve, M., Ibid128Grieve, M., Ibid129Spoerke, D.G., Herbal Medications,

Ibid.130Hsu, H.Y., Chen, Y.P., et al., Oriental





132Tierra, M., Planetary Herbology,Lotus Press, Santa Fe, NM, 1988,p.295-296.

133Kapoor, L.D., CRC Handbook ofAyurvedic Medicinal Plants, CRCPress, Boca Raton, FL, 1990, p.194-195.

134Tyler, V.E. et al., Pharmacognosy (7thed.), Lea & Febiger, Phila. PA, 1976,p.91.



137Grieve, M., A Modern Herbal,Jonathan Cape, London, 1931, p.713.

138Heinerman, J., The Science of HerbalMedicine, BiWorld Publ., Orem UT,1979. p.177.

139Heinerman, J., The Science of HerbalMedicine, Ibid.

140Leung, A.Y., Ibid.141Duke, J.A., Handbook of Medicinal

Herbs, CRC Press Inc., Boca RatonFL, 1985. p.446.

142Ohigashi, H., et al., Antimicrobialsubstances in higher plants, Botyu-Kagak 38(3), 165-80, 1973.

143Heinerman, J., The Science of HerbalMedicine, Ibid.

144 Mowrey, D.B., The Scientific Vali-dation of Herbal Medicine, Cormo-rant Books, 1986, p.19.

145Willard T.L.; Clinical experience.146Bensky, D. and Gamble, A., Chinese


147Hsu, H.Y., Chen, Y.P., et al., OrientalMateria Medica: a concise guide,Oriental Healing Arts Institute, LongBeach, CA, 1986, p.233.




151Herbal Pharmacology in the People’sRepublic of China., Trip Report of theAmerican Herbal PharmacologyDelegation, National Academy ofSciences., Washington, D.C., 1975,p.137.

152The Merck Index 5th. ed., Merck &Co. Inc., Rahway, N.J., 1940, p.203.

153Veninga, L. and Zaricor, B.R.,Goldenseal/Etc. A Pharmacognosy ofWild Herbs, Ruka Publications, SantaCruz, CA., 1976, p.178.

154Duke, J.A., Handbook of MedicinalHerbs, CRC Press,Inc., Boca RatonFL, 1985, p.168.

155Veninga, L. and Zaricor, B.R., Ibid.156Bensky, D. and Gamble, A., Chinese

Herbal Medicine: Materia Medica,Eastland Press, Seattle, WA, 1986,p.459.

157Kapoor, L.D., CRC Handbook ofAyurvedic Medicinal Plants, CRCPress, Boca Raton, FL, 1990, p.164-165.

158Duke, J.A., CRC Handbook ofMedicinal Herbs, CRC Press, BocaRaton, FL, 1985, p.340-341.

159Mowrey, D.B., Guaranteed PotencyHerbs- Next Generation HerbalMedicine, Keats Pub., New Canaan,Conn., p 87-107, 1990.

160Bensky D., Gamble A., Chinese HerbalMedicine: Materia Medica, EastlandPress, Seattle, 1986. p. 450-54.

161Hsu Hong-yen, Chen Yuh-Pan, et al;Oriental Materia Medica: a conciseguide, Oriental Healing Arts Institute;Long Beach CA., 1986. p 528-30

162 Hsu, H.Y., Oriental Materia Medica: aconcise guide, Oriental Healing ArtsInstitute, Los Angeles, CA, 1986,p.596-97.





Glycosides

166Fulder, S., The Tao of Medicine,Destiny Books, New York, 1982.



169 Fulder, S., The Tao of Medicine,Destiny Books, New York, 1982.

170Bensky, D. and Gamble, A., Ibid.171Bensky, D. and Gamble, A., Chinese



173Bensky, D. and Gamble, A., ChineseHerbal Medicine: Materia Medica,Eastland Press, Seattle, WA, 1986,p.518.


175 Robinson, T., The Organic Constitu-ents of Higher Plants (4th ed.),Cordus Press, North Amherst, Mass.,1980, p.323-326.








183 Spoerke, D.G., Herbal Medications,Woodbridge Press Publ. Co.,SantaBarbara CA, 1980. p.91.

184Grieve, M., A Modern Herbal,Jonathan Cape, London, 1931, p.417.





189 Pizzorno, J., Murray, M., Textbook ofNatural Healing, John Bastyr CollegePubl., Seattle, WA., 1988, p.V: carflav2-4.

190 Pizzorno, J., Murray, M., Textbook ofNatural Healing, John Bastyr CollegePubl., Seattle, WA., 1988, p.ibid..

191 List, P.H., Schmidt, P.C.,Phytopharmaceutical Technology,CRC Press, Boca Raton, FL, 1989,p.Quer - 3.

192Bunello, N., et al., Pharm. Res. Comm.17:1063, 1985.

193Karcher L., et al., Naum.-Schmied.Arch. Pharmacol. 327:31, 1984.

194Vorberg, G., Clin. Trial. J. 22:149 1985.195Mowrey D; Guaranteed Potency

Herbs, Next Generation HerbalMedicine; Keats, New Cannaan, Con,1990, p63-86

196Mowrey, D.B., Ibid.197 Mowrey, D., Guaranteed Potency

Herbs, Next Generation HerbalMedicine, Keats Publ., New Canaan,Conn., 1990, p.63-86.


199 Pizzorno, J., Murray, M., Textbook ofNatural Healing, John Bastyr CollegePubl., Seattle, WA., 1988, p.V:Ginkgo.

200Hsu Hong-yen, Chen Yuh-Pan, et al.,Oriental Materia Medica: a conciseGuide, Oriental Healing Arts Institute,Long Beach CA.; 1986. p 610-11.



201Bensky D., Gamble A.; Chinese HerbalMedicine:Materia Medica; EastlandPress Seattle; 1986. p 560-61.

202Tierra M.; Planetary Herbology; LotusPress; Santa Fe; 1988 p 345.

203 Mowrey, D., Guaranteed PotencyHerbs, Next Generation HerbalMedicine, Keats Publ., New Canaan,Conn., 1990, p.108-126.

204 Pizzorno, J., Murray, M., Textbook ofNatural Healing, John Bastyr CollegePubl., Seattle, WA., 1988,p.V:silybum.

205 Pizzorno, J., Murray, M., Textbook ofNatural Healing, John Bastyr CollegePubl., Seattle, WA., 1988, p.V:crata.




209 Pizzorno, J., Murray, M., Textbook ofNatural Healing, John Bastyr CollegePubl., Seattle, WA., 1988, p.ibid..



212 Tyler, V.E. et al., Pharmacognosy(7th ed.), Lea & Febiger, Phila. PA,1976. p.189.



215Felter, H.W., Eclectic Materia Medica,Pharmacology and Therapeutics,Eclectic Medical Publ., Portland OR,1922 (1983). pp.612,561.

216The British Pharmaceutical Codex1934. The Pharmaceutical Press, London, 1934. p.918.

217Tyler, V.E. et al., Pharmacognosy (7thed.), Ibid.

218Leung, A.Y., Ibid.219Spoerke, D.G., Herbal Medications,

Ibid.

220British Herbal Pharmacopeia Section1, British Herbal Medicine Associa-tion, London, 1971.

221Felter, H.W., Eclectic Materia Medica,Pharmacology and Therapeutics,Ibid.


Ibid.224Hsu, H.Y., Chen, Y.P., et al., Oriental



226Allport, N.L., Chemistry and Phar-macy of Vegetable Drugs, GeorgeNewnes Ltd., London, 1943, p. 144.

227Leung, A.Y., Encyclopedia of CommonNatural Ingredients used in Food,Drugs, and Cosmetics., John Wileyand Sons, Inc., New York, 1980,p.316.

228Spoerke, D.G., Herbal Medications,Woodbridge Press, Santa Barbara,Ca., 1980, p.30.

229Wood, H.C. and Osol, A., TheDispensatory of the United States ofAmerica 23rd. ed., J. B. Lippincott,Montreal, P.Q., 1943, p.1204.

230Wallis, T.E., Textbook ofPharmacognosy, J & H Churchill,London, 1967, p.128.

231Duke, J.A., Handbook of MedicinalHerbs, CRC Press,Inc., Boca RatonFL, 1985, p.56.

232Leung, A.Y., Ibid.233Spoerke, D.G., Ibid.234Wallis, T.E., Ibid.235The Merck Index 5th. ed., Merck &

Co. Inc., Rahway, .J., 1940, p.53/571.236Trease, G.E. and Evans, W.C.,

Pharmacognosy 11th ed., BailliereTindall, London, 1978, p. 362.

237Wood, H.C. and Osol, A., Ibid.238Benigi, R., Richere sulla presenza di

sostanze ad azione antibiotica nellepiante superiori, Fitoterapia 19(3), 1-2.

239Schaufelberger, D., et al., On themulloscicidal activity of tannin-containing plants, Vol.16, [Journalunknown] 865-69, 1975.

240Duke, J.A., Ibid.241Youngken, H.W., Ibid.242Wood, H.C. and Osol, A., Ibid.


Glycosides

243The Merck Index 5th. ed., Ibid.244The British Pharmaceutical Codex

1934, Pharmaceutical Press, London,1934, p.1091.

245The British Pharmaceutical Codex1934, Ibid.

246Spoerke, D.G., Ibid. 128247 The British Pharmaceutical Codex

1934. The Pharmaceutical Press,London, 1934. p.482.





252 Wood, H.C. and Osol, A.,Dispensatory of the United States ofAmerica 23rd ed., J.B. Lippincott,Montreal, P.Q., 1943. p.489.

253 Gathercoal, E.N. and Wirth, E.H.,Pharmacognosy, Lea & Febiger,Phila. PA, 1936. p.570.

254 Trease, G.E. and Evans, W.C.,Pharmacognosy 11 ed., BailliereTindall, London, 1978. p.510

255Duke, J.A., Handbook of MedicinalHerbs, CRC Press Inc., Boca RatonFL, 1985.p.207.



258Wood, H.C. and Osol, A.,Dispensatory of the United States ofAmerica 23rd ed., Ibid.

259Martindale: The Extra Pharmacopeia,The Pharmaceutical Press, London,1941. p.546.


261Duke, J.A., Ibid.262Hsu, H.Y., Chen, Y.P., et al., Oriental



264 Leung, A.Y., Encyclopedia ofcommon natural ingredients used infood, drugs, and cosmetics, JohnWiley & Sons Inc., New York, 1980.p.289.

265Duke, J.A., Handbook of MedicinalHerbs, CRC Press Inc., Boca RatonFL, 1985. p.149.

266Leung, A.Y., Ibid.267Grieve, M., Ibid.268Spoerke, D.G., Herbal Medications,

Ibid., p.152.269Spoerke, D.G., Herbal Medications,

Ibid.,270Brinker, F., An Introduction to the

Toxicology of Common BotanicalMedicinal Substances, thesis,National Coll. of NaturopathicMedicine, Portland OR, 1982 - 83,n.p..





Organic Acids, Aromatic Acids & Tannins

Organic Acids,Aromatic Acidsand Tannins

Synopsis:

Plant acids are a very basic part of plant chemistry. We can find some acids inmost vascular plants, often working as a mild “background” component to thestronger effect of active constituents. Other plants have various acids in highenough concentrations to be the primary driving force behind the botanical's use.In this chapter we will briefly look at some common citric cycle acids, non-citriccycle acids, aromatic acids, tannins and their derivatives. Acid-containingbotanicals include Witch Hazel, Tormentil, Bearberry, Bayberry, Oak bark &galls, Guarana, Coffee, Tea and Maté.

5



Table of Contents

IntroductionAromatic AcidsTannins

Botanicals containing catecholBotanicals containing pyrogallotanninsBotanicals containing pseudotannins

Biosynthesis of TanninsCatechol Tannins

Witch HazelTormentilBearberryBayberry

Pyrogallol TanninsOak Bark and Oak Gall

PseudotanninsGuaranaCoffeeTeaMate’

SummaryMini-Materia Medica


Figure 5.1 Citric acid cycleTable 5.1 Non-citric cycle acidsFigure 5.2 Gallic acidFigure 5.3 Gallic acid pathwayFigure 5.4 Alternate gallic acid pathwayFigure 5.5 Biosynthesis of catechinFigure 5.6 Witch HazelFigure 5.7 BayberryFigure 5.8 Oak



Figure 5.1Citric acid cycle

ArginineHistidineGlutamineProline

PhenylalanineTyrosineLeucineTryptophan

AlanineCysteineSerineGlycineThreonine

LeucineIsoleucineTryptophan

CarbohydratesGlycerolFatty acidsAcetoacetylCoenzyme A

Pyruvic acid

Acetyl Coenzyme A

Fumaric acidfrom the urea cycle

TyrosinePhenylalanine Valine

MethionineIsoleucine

Citricacid

Isocitricacid

α α - Ketoglutaricacid

Succinicacid

Fumaricacid

Malicacid

Oxaloaceticacid

Citric Acid(Kreb)Cycle

here are many free acids found in plants. An especially largeaccumulation of specific acids is found in vascular sap. Thisaccumulation of acids typically results in a pH of 2 or 3. Many of theT

most common plant acids are in the citric acid cycle. It is theorized thatthey are just normal metabolic by-products but we can find specificplants with large accumulations: e.g. citric acid in lemon (Citruslimonica), isocitric acid in blackberries (Rubus spp.) and malic acid inapples (Malus spp.).

Introduction

↑↑

↑↑

↑

↑

↑↑

↑

↑

↑

↑

↑

↑

↑



CH3

CHCH2COOH

CH3

Vitis spp.

Table 5.1Non-citric cycle acids

Stinging Nettle Hair(Urtica urens)

Formic

Butyric

Esterified in fruit,essential oils.

L- (+) - tartaric

glycolic

widespread

many Leguminosae

Malonic

Valeriana spp.

Isovaleric

widespread in roots,germinating seeds

D- (+) - lactic

Oxalic

Oxalis spp.

During the formation of fruit, some acids (citric and tartaric acids) are intheir greatest concentrations, playing a significant role in the plant’sdevelopment. We can find acid in combination with alkaloids, essentialoils, mucilages, pectins, sugars and of course tannins (such as tannicacid and gallic acid).

Citric acids and tartaric acid have a role in human physiology. Theystimulate saliva, cleansing the mouth, while reducing the bacteria whichcan cause dental caries and infection. They also are gently laxative anddiuretic in nature, absorbing very slowly through the mucosa thuskeeping the stool soft. These acids are also useful in cases of hemor-rhoids and after surgery when abdominal muscle use should be reduced.

Gallic, tannic and malic acids are astringent in nature and have a role inthe treatment of dysentery and diarrhea. Oxalic acid, however, is an acidto be wary of, either in its free state or as a calcium or potassium salt. It

HCOOH

CH3CH2CH2COOH

CH2OH

COOH

CH3COOHEsterified in fruit,essential oils.

Acetic

COOH

COOH

COOHOHOH

Shikimic

widespread

COOH

CH2

COOH

COOH

HCOH

HCOH

COOH

COOH

HCOH

CH3

HO OH



can cause kidney stones or even kidney failure. It also reduces thecalcium proportion of the blood affecting the function of the heartindirectly. We find oxalic acid in Rumex (sorrel), Oxalos (wood sorrel)and Rheum (rhubarb) species. As a result, long term use of these plantsis typically contraindicated in herbal texts.Some of the non-citric cycleacids are seen in the Table 5.1.

Aromatic acids

As discussed in Chapter 2, aromatic compounds have little to do witharoma. The adjective refers to chemical structure -- having at least onebenzene ring. Some aromatics are simple acids with carboxyl as the onlyfunctional group, while many have other functional groups as well. Someof these free acids are: caffeic acid (widespread), ferulic acid (wide-spread), coumaric acid (widespread) and rosmarinic acid (Rosmarinusofficinalis).

Tannins

Tannins are complex substances, the molecules of which seem to bebuilt up from a simple phenol acid. We find many tannins associated withsimple sugars and they appear to be glucosidal in nature.

The tannins are a very large group of complex substances that are seenin almost every family of the plant kingdom. The tannins are usuallyisolated in specific parts of the plant such as leaves, fruits, bark andstems.

We find tannins in fairly large quantities in unripe fruit, disappearing asthe fruit matures. It is theorized that the fruit employs the energyliberated from tannins on oxidation for its metabolic processes. It hasalso been shown that tannins are the source of many fruit acids. Sincetannins are antiseptic in nature we can also theorize that the actionhelps prevent damage by insects and fungi during the maturationprocess. This theory is backed up by the large quantities of tannins ininsect galls where they appear to act as a protective agent for the rest ofthe plant. Besides being a protective agent for plants during the growingphase, we also see tannins as the end product of metabolism in deadtissue. This appears as a protective barrier, e.g., outer cork, heartwoodand galls. There are also large quantities of tannins in fallen deciduousleaves. This leads one to the conclusion that if tannins are metabolicwaste products, deciduous processes would be a logical way to releasethe tannins from the plant as a whole.



Chemically we find tannin to be a noncrystalizable compound that formsa colloidal solution with water, also producing an acid reaction. Thissolution gives a typical astringent taste or “puckering action”.

Tannins precipitate proteins from solutions and are able to combinewith them rendering them resistant to proteolytic enzymes. Whenapplied to living tissue, we get an astringent action, revealing tannins’basis as a therapeutic aid. Many tannin-bearing botanicals, especiallyones with tannic acid and acetyltannic acid are employed as astringents,both in the gastro-intestinal tract and on skin abrasions. An example ofthe latter is the protein of exposed tissue in burns. Tannins form aprecipitate resulting in a mildly antiseptic, protective coating underwhich regeneration of new tissue can take place.

This ability to precipitate protein is also used in the tanning industry inthe process of vegetable tanning of hides. We can use this information totoughen up feet before that first hike of the season or when breaking innew boots. Practitioners of the martial arts use tannins to toughen upboth feet and hands before a tournament or exhibition.

Tannins also have the ability to precipitate gelatin and alkaloids and areemployed in laboratories as reagents to detect these substances. Usefulto our purpose are tannins’ ability to precipitate alkaloids. They can beadapted as antidotal treatment of alkaloid poisoning, being extremelyvaluable for deactivating the alkaloid by formation of insoluble tannates.

As mentioned earlier, some tannins appear to be glucosidal in nature buton hydrolysis yield relatively simple polyhydric phenol, proving theglucosidal ‘tag’ not to be true.

The most common polyhydric phenols are:

1. Gallic acid, which is broken down to be pyrogallol.2. Protocatechuic acid, which is broken down to catechol.3. Ellagic acid and other phenols.

Figure 5.2Gallic acid

HO

HO

HO

COOH



The classification of tannins is based upon the colour obtained whenmixed with iron salts. Catechol type tannins, with two adjacent phenolicgroups, give a green colour with ferric iron. Pyrogallol, with threeadjacent phenolic groups, gives a blue colour. However useful this is in alaboratory, many of our botanicals have both groups present. Thedominant group will mask the presence of the lesser.

Tannins are usually classified in the following manner.1

1. Catechol (Pyrocatechol) Tannins or Phlobatanninsa) When heated they yield catechol.b) When boiled with HCl they yield insoluble red with FeC13TS.d) They form a precipitate with bromine tannin salt (TS).

2. Pyrogallotannins have these characteristics:a) When heated, they yield pyrogallol.b) When boiled with HCl, they yield gallic acid or ellagic acid.c) They form a blue colour with FeC13TS.d) They do not form a precipitate with bromine TS.

The following is a list of some of the most important botanicals contain-ing Catechol Tannins, Pyrogallotannins and Pseudotannins.

Botanicals containing catechol (tannins)a) Barks - Cinnamon, wild cherry, cinchona, willow, acacia, oak and

hamamelis.b) Roots and Rhizome - Krameria and male fern.c) Seeds - Cocoa, guarana, kola and areca.d) Leaves - Hamamelis and tea (table tea) especially green tea, witch

hazel, bayberry leaves and chestnut leaves.e) Extracts and dried juices - Catechin, acacia.

Botanicals containing pyrogallotannins (non-catechol,gallo-tannins)

a) Ellagitannins - Pomegranate rind, pomegranate bark, myrobalans,Turkish galls, eucalyptus leaves, kousso, some Australian kinos, andoak bark and galls.

b) Callitannins - Rhubarb, cloves, red rose petals, bearberry leaves,Chinese galls, lopwood and oak galls.

c) Mixed Gallitannins and Catechol - Hamamelis leaves and bark,bark of Acacia arabic, some kinds of tea.

Botanicals containing pseudotannins (gallic acids)a) Gallic Acid - Rhubarb and most material containing gallitannins.b) Catechins - acacia, most Australian kinos, cocoa, guarana.c) Chlorogenic Acid - Maté, coffee (particularly unroasted), nux

vomica.d) Ipecacuanhic Acid - Ipecacuanha.



HO

HO

HO

3,4,5 - Trihydroxycinnamic acid

CH CH COOH

HO

HO

caffeic acid

CH CH COOH

HO

HO

HO

gallic acid

CH CH COOH

CH CH COOH

CH2 CH COOH

NH2

phenylalanine

cinnamic acid

ρ - coumaric acid

Figure 5.4Alternate Gallic acid pathway

HO

COOH

HO

HO

HO HO

Figure 5.3Gallic acid pathway

O

5 - dehydroshikimic acidShikimic acid

Biosynthesis of tannins

Describing the biosynthesis of tannins is no simple matter, so we willlimit our discussion to the biochemical pathways of a few individualchemicals. In Figure 5.3, we can see the pathway for gallic acid via 5-dehydroshikimic acid. This chemical is found in certain micro-organismswhich produce galls in higher plants. Galls are sometimes seen on treesor small plants. They look like bulges or tumours on trunks or branches.

An alternative pathway in plants themselves can be seen in Figure 5.4starting with phenylalanine. The biosynthesis of catechin (Fig. 5.5) startswith three acetates and the same cinnamic acid as in the second gallicacid pathway.

HO→ →COOH HO

HO

gallic acid

COOH

COOH

↑

↑

↑

↑

HO

↑



Figure 5.6Witch Hazel

Catechol Tannins

Witch hazel Hamamelis virginiana

Witch hazel leaves are the dried leaf of Hamamelis virginiana. Hamamelisis from the Greek word hama meaning “at the same time” and melismeaning “fruit”. The flowers appear in the fall at the same time as thefruit from the previous year ripens. Virginiana indicates the plant is

Figure 5.5Biosynthesis of catechin

C

COC

CO COC

3 AcetateHOOC

gallic acid

HO

O

OHOH

OH

OH

catechin

↑

↑

Sc2



found in Virginia, but it can actually be found from New Brunswick westto Minnesota and southward to Florida and Texas. This shrub (some-times small tree) grows to 8 meters in height and lives in low, dampwoods. The leaves are usually collected throughout the summer anddried in open air under shade to preserve the green colour. The majorcommercial supply comes from the Blue Mountain Ridge region inVirginia, North Carolina and Tennessee.

Witch hazel contains 2.3 - 9.5% of tannins called hamamelitannins as themajor ingredient. There is also the presence of gallic acid and deriva-tives, hexose sugar, calcium oxalate, free hamamelose, saponins, cho-line, resins (circa 7% hamalin and hamamelin), flavonoids (quercetin,kaempferol, astragalin, etc.), a eugenol-like compound, safrole andvolatile oil.2,3,4

Hamamelitannins reduce internal secretions and discharges and act as ahaemostatic (stop bleeding). Distilled witch hazel is often found in drugstores but it contains no hamamelitannins, in contrast to a straighttincture which does. Witch hazel has been used for centuries for itsprotein precipitating, astringent action and haemostatic properties. Itwas applied in cases of diarrhea, gonorrhea, hemorrhoids and varicosevein problems. 5,6

Dosage:7 Fluid extract - 5 -15 dropsTincture - 30 - 60 drops

Toxicity: There is no toxicity recorded, but it should be noted thatwitch hazel does contain safrole (a known toxin). The small amount isfelt to have no significant toxicological effect.

Tormentil Potentilla tormentilla, P.erecta, P. silvestris

A very important astringent herb, tormentil contains 15-20% of tannicacid. Tormentil is most often used in clinical situations for diarrhea andexternally for mucous membranes of the mouth and throat.

Bearberry Arctostaphylos uva-ursi

Beside containing arbutin (discussed in the previous chapter on glyco-sides), bearberry also contains 6 - 15% tannins. It has been used by manygroups of Native peoples for tanning hides and even to toughen up feet.It is still used to toughen up hiker’s feet first thing in the season. Besidesworking as a great diuretic for cystitis, it also works as an astringent incases of diarrhea.

Ed

Sc2

Mo2



Figure 5.7Bayberry

Bayberry Myrica cerifera

This is a very important astringent containing tannins and gallic acid. Ithas been applied in many different clinical situations for its alterativeand astringent qualities. It is also considered a diaphoretic and tonic. Infolklore, it has been used for boils, cankers, carbuncles, catarrh, cholera,diarrhea, dysentery, fever, goiter, hemorrhages, jaundice, leucorrhea,scarlet fever and ulcers. Besides the astringent factor contributed bytannic acid, the mixed resins also add to its astringent effect. The waxysubstance in bayberry, which contributes to its pharmacological role, is5 - 10%, but reported as high as 25% in some plants. The preferred plantshave the most waxy taste. The activity of the volatile oils will be dealtwith in greater detail in a later chapter.

Pyrogallol Tannins

Oak bark and Oak gall (nutgall)

Oak produces some of the highest quantities and qualities of tannins,ellagic acid (ellagitannins) and gallic acid available from plants. The gallsare particularly high in such chemicals. The twigs of Quercus infectoriaand other Quercus species are the principal source of Oak gall (Nutgalls).

Sc2

Mo2

Sc2

Mo2



Figure 5.8Oak

These galls (excrescences) are due to the puncture of a hymenopterousinsect, Cynips tinctoria, and the presence of the deposited ovum. It isinteresting to follow the stages of development of the gall correspondingto the development of the insect:8

1. When the larva begins to develop and the gall to enlarge, the cells ofthe outer and central zones of the gall contain numerous smallstarch grains.

2. When the chrysalis stage is reached, the starch near the middle ofthe gall is replaced in part by gallic acid, but the peripheral andcentral cells contain masses of tannic acid.

3. As the winged insect develops, nearly all the cells contain masses oftannic acid with a slight amount of adhering gallic acid.

4. When the insect emerges from the gall, a hole to the central cavity isformed. Thus, the tannic acid, due to the presence of moisture andair, may be oxidized into an insoluble product.

The constituents of a mature gall are 50 - 75% a tannic acid (gallotannicacid), 2 - 4% gallic acid, ellagic acid, starch and resin. The galls are usedas a chief source of tannic acid for the tanning and dyeing industry.Medicinally, it is a very strong astringent and styptic. The oak barkcontains 15 - 20% quercitannic acid and other tannins.9,10,11,12

Amazingly, tannins are not irritating to the skin. Oak tannins have beenused as protein precipitant and astringent aiding in diarrhea, hemor-rhoids, as a gargle for sore throats, for cankers and as a vaginal douche.The tannins are also very useful for treating bedsores. The tannic acidsin oak have been shown to have antiviral, antimicrobial and growthdepressant effects (in rats).13,14,15



Dosage: Powder - 5 - 30 grainsFluid extract - 5 - 20 dropsTincture - 1 tsp.

Toxicity: Includes abdominal pain, constipation, diarrhea and in severeoverdoses, liver damage.16

Chinese energetics: (Insect galls) bitter, and warm; entering theLungs, Spleen, and Kidneys. It stimulates tissue regeneration, reproducessperm, calms spirit, warms the stomach and spleen (middle burner),astringes, quenches thirsts, darkens hair.17 Bark: bitter flavour having anastringing action, while dispersing blood and expelling worms.18 Fruit: isbitter, astringent; with a mild, warm property; entering the Colon,Spleen, and kidney meridians. It has a astringent action in the intestine.19

Pseudotannins

Guarana

This rather popular herb, is the crushed seed of Pallinea cupana, andwas sold under the tradename Zoom® as well as many other “stimulant”pick-me-ups or Pep® commercial products.

Guarana contains 2.6 - 7% caffeine, other alkaloids include theophylline,theobromine, xanthine, adenine, guanine, hypoxanthine. In additionthere are 12% tannins, 3% fats, 5-6% starches, 7% resin, a saponin,mucilage and choline.20,21

It is used medicinally as a nervine, central nervous system stimulant,slightly narcotic stimulant, aphrodisiac and febrifuge. Grieve considersits action very similar to both coffee and cocaine combined, as it hascaffeine in high abundance and chemical constituents similar to cocaine.It certainly has a stimulant nervine effect and is therefore often used bytruck drivers and students to stay awake. Guarana has been used forheadache or depressions that accompany menstrual problems. It wasused by the native South Americans for treating chronic diarrhea.22,23

Used occasionally, it can be useful, but overconsumption brings outguarana’s addictive and constipating effects (as is the case with coffee).Guarana is a much stronger stimulant than coffee.

Sc2



Coffee

The seed of Coffea arabica and other species of Coffea contain 1 - 1.3%caffeine, tannin and caffeotannic acid.

Tea

The leaves of Thea sinensis contains 1 - 9% caffeine and 10 - 25% tannins,and small quantities of theobromines, theophylline and volatile oils.

Maté

The leaves of Ilex paraguariensis or I. cassine contain between 0.2 - 2.0%caffeine, 7% caffeotannic acid and a little volatile oil with a high vitamincontent.

Summary

There are many acids found in plants -- from free acids of the citric acidcycle to other simple acids. Aromatic acids and the tannin family ofcompounds have an astringent effect and appear in a wide variety ofplants. Tannins can chemically be divided into three groups: catecholtannins, pyrogallotannins and pseudotannins. Even though there is asignificant chemical difference between these groups, little separatestheir therapeutic application.

Tannins have the property of rendering proteins resistant to attack byproteolytic enzymes while precipitating soluble protein. Tannins act asantidotes to alkaloid poisoning by forming insoluble tannate precipi-tates. Tannins are generally used for their astringent and styptic action.

Mini-Materia Medica -- Organic Acids, Aromatic Acids & Tannins

Crab Apples (Malus silvestris)Constituents: pectin, malic and citric acids, sugars, arabane,

galactane, tannin, quercetin and enzymes.Therapeutic Action: antidiarrhetic, used for gastro-enteritis in

young children.Grapes (Vitis vinifera)

Constituents: tartaric and malic acids, tartrates, sugar, pectin andtannins.

Therapeutic Action: laxative and diuretic, used to reverse obesityand in some cardiorenal conditions.

Sc2



Male Fern (Dryopteris filix-mas)Constituents: filicin, consisting of aspidinol, albaspidine, phlorapine

and filicinic acid.Therapeutic Action: vermifuge if taken with an saline purgative and

no oil or alcohol (to prevent toxicity).Raspberry (Rubus idaeus)

Constituents: fruit has 1-2% of organic acids, 90% of which is citricacid. Vitamin C, pectin and sugars.

Therapeutic Action: the leaves are astringent and used duringpregnancy.

Sorrel, Wood (Oxalis acetosella)Constituents: potassium oxalate, oxalic acid.Therapeutic Action: stomachic (extended use can cause hemor-

rhaging, diarrhea and kidney stones and renal failure).

References


2Leung, A.Y., Encyclopedia of commonnatural ingredients used in food,drugs and cosmetics, John Wiley &Sons, New York, 1980, p.322-323.


4Duke, J.A., Handbook of MedicinalHerbs, CRC Press, Boca Raton, FL,1985, p.221.

5 Duke, J., CRC Handbook of MedicinalHerbs, CRC Press, Boca Raton, FL,1985, ibid..

6 Leung, A.Y., Encyclopedia of CommonNatural Ingredients, A Wiley-Interscience Pub., Toronto, ON, 1980,ibid..

7Grieve, M., Ibid.8 Tyler, V., Brady, L., Robbers, J.,

Pharmacognosy, (7th ed.), Lea &Febiger, Phila., PA, 1976. p.109.

9Leung, A.Y., Encyclopedia of commonnatural ingredients used in food,drugs, and cosmetics, John Wiley &Sons Inc., New York, 1980, p.305.

10Spoerke, D.G., Herbal Medications,Woodbridge Press Publ. Co., SantaBarbara, CA, 1980, p.129.


12Morton, J.F., Major Medicinal Plants:Botany, Culture, and Uses, Charles C.Thomas, Springfield, IL, 1977, p.361

13Leung, A.Y., Ibid., p.305.14Spoerke, D.G., Ibid., p.129.15Grieve, M., Ibid., p.593.16 Kapoor, L.D., CRC Handbook of

Ayurvedic Medicinal Plants, CRCPress, Boca Raton, FL, 1990, p.129.


18Hsu, H.Y., Chen, Y.P., et al., Ibid.,p.837-838.

19Hsu, H.Y., Chen, Y.P., et al., Ibid.,p.621-622.




23Grieve, M., Ibid.

Sc2

Mo2

Ed

Sc2

Mo2




Lipids

Lipids are not only important nutrients for health but cause some of the majorhealth problems in our society. The chemistry of lipids is relatively simple butaffects every aspect of our life. We use lipids as a major source of calories(energy) storage, hormone production, prostaglandin production, immuneresponse, lubrication of skin, eyes and joints. The way we cook, manufacture andtreat oils can have significance in present and future health. Some of the lipids,essential fatty acids, are similar to vitamins (called Vit. F at one time). We cannotmanufacture them and they must, therefore, be obtained from dietary sources.Not obtaining enough of these essential fatty acids can cause a myriad of healthproblems. Cholesterol levels and atherosclerosis problems are grave healthconcerns. Understanding some of the mechanisms behind these problems as wellas some therapeutic aids will help the herbalist. The final area we will cover onlipids is phospholipids and their function upon the cell membranes, along with theantidepressant qualities of phosphatidyl choline.

Synopsis:

Lipids 6




Figure 6.1 Oil Extraction ChartFigure 6.2 Basic Structure of a Fatty AcidFigure 6.3 Omega numbering systemTable 6.1 Common saturated fatty acidsTable 6.2 Common unsaturated fatty acidsFigure 6.4 A TriglycerolFigure 6.5 Cis- and Trans- MoleculesFigure 6.6 Linoleic AcidFigure 6.7 Linolenic AcidFigure 6.8 Conversion of Omega 6 oils & Omega 3 oilsFigure 6.9 Arachidonic Acid CascadeFigure 6.10 Function of Delta-6-DesatureaseFigure 6.11 Conversion of linolenic Acid to ProstaglandinsFigure 6.12 Evening PrimroseFigure 6.13 CurrantFigure 6.14 FeverfewTable 6.3 Composition of serumFigure 6.15 Lipoprotein metabolismTable 6.4 Major LipoproteinsFigure 6.16 CholesterolFigure 6.17 PhospholipidsFigure 6.18 Structure of a biological membraneFigure 6.19 Biological membrane transferFigure 6.20 Phosphatidyl choline

Table of Contents

BorageCurrantFeverfewPearl Powder

AtherosclerosisOverview of LipoproteinsCholesterol

The Other Side of CholesterolThe Injury HypothesisMicronutrient HypothesisMonoclonal HypothesisPlatelet AggregationOther Organs AffectedSource of CholesterolCholesterol and Our DietMeasuring Blood CholesterolObjectives in overcoming

AtherosclerosisHerbs and Other Nutrients

that Lower CholesterolAlfalfaGingerGarlicCayenneNiacinPyridoxine (Vitamin B6 )CopperSeleniumChromium

Phospholipids and Cell MembranesPhosphatidyl Choline

Summary

IntroductionFixed Oils and FatsFatty AcidsTriglyceridesHydrogenationHerbalist Use of OilsEssential Fatty Acids

BackgroundTo Cook or Not to CookChemistry of Essential Fatty AcidsConversion of Omega-6 OilsOmega-3 FamilyNeed for EFAThe Function of D-6-D in EFA MetabolismEvening Primrose Oil

Atopic EczemaPremenstrual SyndromeHigh Cholesterol LevelsAlcoholismDry Eye Syndrome (Sjogren’s

Syndrome)Other areas where EPO is usefulHyperactivity (Attention Deficit

Disorder)HypertensionDiabetesTender and Lumpy BreastPlatelet AggregationVascular ObstructionImmunity and InflammationOther Areas of EPO study

Plants Containing EFAs


Lipids

ipids, for the purposes of this text, are the fixed oils, fats, fattyacids, phospholipids (phosphatides) and waxes composed ofalcohols or closely related derivatives. The major differenceL

between these substances is the type of alcohol employed. In fixed oilsand fats, glycerol combines with the fatty acids. As the waxes have ahigher molecular weight, more complex alcohols are involved.

In the last few years several of these lipid compounds have come intothe therapeutic “limelight”. One prominent group is the essential fattyacids of the omega 3 and omega 6 series (Ω3 & Ω6) . Short chain fattyacids, such as caprylic acid, have also shown therapeutic value. We findfats and fixed oils in plants (olive oil, peanut oil) and animals (lard).Their primary function is food (energy) storage.

Fixed oils and fats

These substances differ only in their melting points. Fixed oils are liquidat normal room temperature whereas fats are semisolid or solid at roomtemperature.

Fixed oils and fats of vegetable origin are normally obtained by expres-sion in hydraulic presses. If the expression is done under relatively mildtemperatures (50 - 95oC), the oil is known as cold-pressed (a totallymeaningless term) in contrast to “hot pressed oil” (95 - 100oC) in whichhigher temperatures are present. Organic solvents are also often usedfor extraction of oil from botanicals.

Introduction



We can find oils in many parts of plants but, as a general rule, the seedscontain the largest quantities. There is a large industry built around oilextraction and delivery. It is an industry, however, that many people feeldoesn’t have the health of the consumer in mind. An interesting reviewof this topic, as well as many other aspects of the fats and oil story, canbe found in the book: Fat and Oils: the complete guide to fats and oils inHealth and Nutrition by Udo Erasmus.1

Fatty Acids

Chemically, the fixed oils and fats are glycerides of fatty acids. Fattyacids have two basic parts, the fat and the acid. One end has a methyl(- CH3) group. The other end has the weak acid we have become familiarwith, the carboxyl (-COOH) group. In Figure 6.2 we have the basicstructure of a fatty acid.

Figure 6.1Industrial Oil Processing (adapted from Erasmus, 1986.)

Raw Materials

Expeller Press orSolvent Extract

Shipment forfurther processing

Caustic Soda Crude Oil Fuller's Earthor Soda Ash

Emulsion or Degum, Refine,Washes or Neutralize, BleachSoap Stock

Splitting Filter Press Fuller's Earth residueVats

Fat Acid Filtered Oil RefinedTrap Oil Bleached Oil

paints, soaps Deodorizechemi- deter-cals, gents, Deodorized Oiletc. etc.

Margarines,shortenings,etc.


Lipids

There can be any number of carbons in a fatty carbon chain. Most oftenthough, it is between 4 carbons (e.g. butyric acid, found in butter) and 24carbons (found in fish and the human brain). An important feature of thefatty acid is its carbon bonding. If there are no double bonds the fattyacid is considered saturated. Each carbon is ‘saturated’ with as manyhydrogens as it can possibly hold. If there is double bonding then thefat is unsaturated. A poly-unsaturated fatty acid has two or more doublebonds. The double bonding is very significant. It gives the fatty acid theability to react with other chemical or environmental conditions, such aslight. Unsaturated fatty acids are less stable chemically than saturatedfatty acids.

To clarify the naming process of fatty acids, chemists have developed anumbering system called the omega (Ω) system. In this system thecarbons are numbered from the methyl end as seen in Figure 6.3.

Figure 6.3The Omega Numbering System

1 3 5 7 9 11 13

2 4 6 8 10 12 14

Methyl End (Ω) Carboxyl End (δ)

H H H O

H C C C C

H H H O H

Fatty Acid

Figure 6.2Basic Structure of a Fatty Acid

Methyl GroupOmega (Ω) end(CH3)

Carboxyl GroupDelta (δ) end(-COOH)

CarbonChainMiddle

O

OH

H H H O

H C C C C

H H H O H

H H H H H O

H C C C C C C

H H H H H O H

H H H H

H C C C C

H H H H

H H

C C

H H

H H H O

C C C C

H H H O H

H H H H

H C C C C

H H H H

H H

C C

H H

H H

C C

H H

H H H H

H C C C C

H H H H

H H

C C

H H

H H

C C

H H

H H

C C

H H

H H H O

C C C C

H H H O H

H H H H

H C C C C

H H H H

H H

C C

H H

H H

C C

H H

H H

C C

H H

H H

C C

H H

H H H O

C C C C

H H H O H

H H H H

H C C C C

H H H H

H H

C C

H H

H H

C C

H H

H H

C C

H H

H H

C C

H H

H H H O

C C C C

H H H O H

H H

C C

H H

4:0Butyric acid

Caproic acid6:0

Caprylic acid8:0

Capric acid10:0

Lauric acid12:0

Myristic acid14:0

Palmitic acid16:0

Stearic acid18:0

H H H O

C C C C

H H H O H

H H H H

H C C C C

H H H H

H H H O

C C C C

H H H O H

H H H O

C C C C

H H H O H

H H H H

H C C C C

H H H H

H H

C C

H H

H H

C C

H H

H H

C C

H H

C C

H H

H H H O

C C C C

H H H O H

H H

C C

H H

H H H H

H C C C C

H H H H

H H

C C

H

H H

C C

H

H H

C C

H H

C C

H H

H H H O

C C C C

H H H O H

H H

C C

H H

H H H H

H C C C C

H H

H H

C C

H

H H

C C

H

H H

C C

H H

C C

H H

H H H O

C C C C

H H H O H

H H

C C

H H

H H H H

H C C C C

H H H H

H H

C C

H

H H

C C

H

H H

C C

H H

C C

H

H H H O

C C C C

H H H O H

H H

C C

H

H H H H

H C C C C

H H H H

H H

C C

H H

H H

C C

H H

C C

H H

H H

C C

H H

Palmitoleic acid (POA)16:1ΩΩ7

Oleic acid (OA)18:1ΩΩ9

Linoleic acid (LA)18:2ΩΩ6

Linolenic acid (LNA)18:3ΩΩ3

Gamma (γ)-Linolenic acid(GLA)

20:4ΩΩ6

Stearidonic acid (SDA)18:4ΩΩ3

H H H O

C C C C

H H H O H

H H H H

H C C C C

H H

H H

C C

H

H H

C C

H

H H

C C

H H

C C

H

H H

C C

H

H H

C C

H H H O

C C C C

H H H O H

H H H H

H C C C C

H H

H H

C C

H

H H

C C

H

H H

C C

H H

C C

H

H H H O

C C C C

H H H O H

H H

C C

H

H H H H

H C C C C

H H

H H

C C

H

H H

C C

H

H H

C C

H H

C C

H

H H

C C

H

H H

C C

H

H H H O

C C C C

H H O H

H H

C C

H H

C C

H H

C C

H

H H

C C

H

H H

C C

H H

C C

H

H H

C C

H

H H H H

H C C C C

H H H H

Docosahexaenoic acid(DHA)

Eicosapentoenoic acid(EPA)

18:3ΩΩ6

Arachidonic acid (AA)

20:5ΩΩ3

22:6ΩΩ3

Fatty

acid

s ma

de f

rom

EFAs

(lin

olenic

acid

)Fa

tty a

cids

made

fro

m EF

As (

linole

ic ac

id)Es

sent

ial F

atty

Acid

s(E

FA's

)M

onos

atur

ated

Fat

tyAc

ids



In Table 6.1, common saturated fatty acid are listed and unsaturatedfatty acids are listed in Table 6.2. As indicated in Table 6.2, two of theunsaturated fatty acids are “essential” coming from the Omega (Ω)3 andOmega (Ω)6 groups. We will be discussing them in more detail later. Assuggested by their name, like vitamins these fatty acids are essential forhuman survival. They have a very significant action in our body.

Triglycerides

Fatty acids usually come in groups of threes. Ninety five percent of allthe fats we eat are triglycerides. This is also the way we store most ofour own body fat. Fat is the primary way our body stores energy forfuture use. If our diet is good, a significant number of essential fatty acidsare also stored in our body.

A triglycerol has a glycerol backbone, with one fatty acid hooked tothree of its carbon atoms to form a 3 pronged fork-like structure (Figure6.4).

The ideal fat form for the human body is two outside fatty acids (satu-rated), while the middle one is an essential fatty acid. This is not alwaysthe case though. Beef fat contains very small amounts of essential fattyacids. It is mostly comprised of saturated and monounsaturated fattyacid in all positions. Completely hydrogenated fats carry almost 100%saturated fatty acids. Flax and safflower oils, however, carry essentialfatty acid in most positions because they are composed of more than70% essential fatty acids.

The positioning of fatty acids found in our food sources is not thatimportant. It is the ratio and total amounts of the various fatty acids inour diet that has significance. We break down these triglycerides in ourdigestive system into the glycerol and fatty acid components for easierabsorption. We reconstruct them again according to our needs. We burnmany of the fatty acids for energy and store the essential fatty acids forthe significant structural and metabolic processes.

Usually glycerides of unsaturated fatty acids are liquid, while theglycerides of saturated fatty acids, of sufficient chain length, are solid.The predominance of one or another substance in any mixture willdetermine whether it is liquid or solid.


Lipids

Figure 6.4Structure of a Triglycerol

CH2

CH

C

OC

O

O

C

Hydrogenation

Under proper conditions double bonds in the unsaturated fatty acidscan undergo hydrogenation by taking up a hydrogen. This of coursetakes the liquid, unsaturated fatty acid, and converts it to a semi-solidfat.

Hydrogenation of oils takes place by passing hydrogen, in the presenceof nickel or palladium, through oil heated to 160 - 200 degrees C. Thisprocess is often undertaken for culinary reasons, such as changingvegetable oil into margarine.

Herbalist Use of Oils

From a herbalist’s point of view, oils are often used as emollients,cosmetics and as a medium for other herbs. They rarely play otherspecific medicinal roles. Some of the medicinally useful oils are:

1. Castor Bean Oil (Ricinus communis) used as a stimulant tonic.2. Linseed or Flaxseed Oil (Linum hesitatiasimum) used as a demulcent,

emollient, mild laxative.3. Olive Oil (Olea europaea) used as a demulcent, emollient, mild

laxative, solvent, hepatic and for its rich mineral content.4. Peanut Oil (Archis hyprogaea)used as a solvent.

CH2

O

O

O



Essential Fatty Acids

Background

It has long been known that certain fatty acids are essential for life.These fatty acids have been given the name essential fatty acids (EFA)and at one time were known as vitamin F. Even though these fatty acidsare not vitamins as such, the name is somewhat appropriate in that itindicates the relative importance of these substances.

There are a variety of ways to refer to fats. The most common refers tosaturation levels. We will often find a product claiming to be polyunsatu-rated (PUFA), especially since the U.S. Heart Foundation recommends adiet high in polyunsaturated oils. A partially informed consumer can bevery confused by this. The U.S. Cancer Foundation has simultaneouslysuggested decreasing polyunsaturated oils. By looking more into thechemistry of oils will sort out this problem.

To Cook or Not to Cook

Polyunsaturated oils used at room temperature (e.g., on salads) aresome of the strongest preventative substances for heart problems. Wehave had a dramatic decline (20-25%) in heart problems in NorthAmerica as the increased use of polyunsaturated oils has made its wayinto the dietary habits of the general public.

Cooking with these oils can cause carcinogenic chemicals.The cookingof polyunsaturated fatty acids can produce free radicals 2 or peroxidesupon heating. This causes a drain on the immune system and a potentialcarcinogenic environment.3 It is for this reason that cancer researchershave found a correlation between polyunsaturated oil and cancer.

Cooking should be done with saturated oils, like butter or as the peopleof India have been doing for centuries, ghee (clarified butter). Themaking of margarine from polyunsaturated vegetable oil (hydrogena-tion) is very similar to cooking with polyunsaturated oils (with the same"downside"). To keep the vegetable oil solid at room temperature it ispartly saturated. This causes the formation of trans fatty acids, a form ofoil which blocks utilization of the cis form and is therefore not good foryour health (Figure 6.5).

The cis form has both hydrogens on the same side, while the trans formhas the hydrogens on the opposite sides. The conversion happens attemperatures above 160oC. This slight change may seem insignificant,but it is quite drastic in its implications for the human body. As you cansee, the cis form bends, while the trans form doesn’t. The trans formcannot change into the prostaglandins -- very significant products we willdiscuss later.


Lipids

Figure 6.5Structure of Cis and Trans Molecules

The problem doesn’t stop there. The trans form locks up the absorptionsite of the cis form, further lowering the amount of the cis form that canbe processed in the body. The average intake of trans-fatty acid is 9.1grams per day in Canada (12 grams per day in U.S.A.). This representsapproximately 10% of our fat intake. Most of these trans fatty acids comefrom hydrogenated (human-manipulated) oils.4

The following examples show the percentage of trans fatty acids invarious food products:

Stick margarine contains 25 - 35% trans fatty acidsTub margarine 15 - 25% "Shortening 20 - 30% "Salad dressing 0 -15% "

Chemistry of Essential fatty acids

One of the essential fatty acids is linoleic acid, an 18-carbon long fattyacid. As stated earlier, these fatty acids have a delta end (the carboxyl -COOH) and an omega (methyl - CH3) end as seen in Figure 6.2 . Linoleicacid’s first double bonded carbon is the sixth carbon from the omegaend (Figure 6.6). Human beings have no internal ability to manufacture adouble carbon bond earlier than the seventh location on a long fattyacid. Nonetheless we need chemicals like linoleic acid for many pro-cesses in our body as we will see later.

Linoleic acid’s structure makes it a 18:2 omega (Ω)-6 fatty acid -- an 18carbon fatty acid with the first double bond at the sixth carbon from theomega end and a total of two double bonds in the molecule. Plantsources of polyunsaturated oil often have at least some omega-6 fattyacids. Some sources include safflower oil (>90%), oil of evening primroseand borage.

C C

H H

H

C C

H

Cis- Configuration BentMolecule

Trans- ConfigurationStraight Molecule



Figure 6.6Structure of Linoleic Acid

Another very important fatty acid is Ω 3, α-linolenic acid. It can be foundin unsaturated oils, typically in leafy green vegetables in northernclimates (which contain the oils in response to the cold). Omega-3 isfound in highest quantities in fish body oil, but it is also found in soy oil(3%), walnut oil (10-20%), and linseed (55%). The omega-3 oil and theomega-6 oils cannot convert to each other.

Figure 6.8 indicates that the end results of the omega-6 oil pathway isarachidonic acid, a 20 carbon fatty acid. Two prostaglandins are alsoformed in the process.

In the omega 3 series, again we can see that fish oil or EPA (eicosapenta-enoic acid) is a 20 carbon fatty acid. Because of this, it competes witharachidonic acid in our body for the muscle fat storage. This tendency iscritical. EPA produces PG3, which is quite beneficial for humans. Arachi-donic acid, in contrast, can produce leukotrienes, which are 1,000 to10,000 times more inflammatory then histamines.

Figure 6.8 explains why oil of evening primrose, though it has tremen-dous therapeutic benefits (discussed below), is best taken with EPA. Itforces the end pathways more toward PG1 and PG3 production (bothbeneficial) and away from PG2 production and the resulting leukotrieneinflammation.

Need for EFA

The need for these EFAs in the human diet is incontrovertible. Threemajor points should be made before we examine the subject:5,6,7

Figure 6.7Structure of Linolenic Acid

O

OH

OH

O


Lipids

1. EFAs are a major component of all membranes in the body. WithoutEFAs cell membranes will become stiff and unstable. EFAs are present inthe structure of all tissue in the body. Especially large amounts are foundin the brain.

2. EFAs control the ratio of high density and low density lipoproteins(HDL/LDL). As a result, they play a major role in problems associatedwith cholesterol in the bloodstream.

3. EFAs give rise to the very short lived prostaglandins (PGs), whichplay a role in regulating second-by-second functions of every part of thebody. Each organ produces its own PGs, which are made from the tissueEFAs. They inhibit/cause inflammation, functioning as an arm of theimmune system. These particular prostaglandins (especially PG3 fromEPA) stop platelet aggregation and increase bleeding time, and thus areeffective in lowering arterial plaquing.

The Function of delta (D)-6-desatureasein EFA metabolism

It is vital to understand the role of the gatekeeper, delta-6-desaturease(D-6-D), in the role of these essential fatty acids.

Figure 6.8Conversion of Omega Oils

Omega ( Ω Ω ) 3 Fatty Acids Omega ( Ω Ω ) 6 Fatty Acids

Alpha-Linolenic acid(LNA) (18:3W3, 3, 6,9)Flax, pumpkin seed, soybean, dark green vegetables

Linoleic acid(LA) (18:2W6, 6,9)Safflower, sunflower,sesame seed, flax.

Stearidonic acid(SDA) (18:4W3, 3, 6,9, 12)

Dihomogamma- Linolenic acid(GLA) (20:3W6, 6,9,12)

Eicosatetranoic acid(20:4W3, 3, 6,9, 12) Fish

Gamma- Linolenic acid(GLA) (18:3W6, 6,9,12)Evening Primrose, Currant,Borage

Arachidonic acid (AA)(20:4W6, 6,9,12,15)

Docosapentanoic acid(22:5W6, 6,9,12,15,18)

Adrenic acid(22:4W6, 6,9,12,15)

Docosahexaenoic acid (DHA)(22:6W3,3,6,9, 12,15,18)

Clupanodonic acid(22:5W3, 3, 6,9, 12,15)

Eicosapentaenoic acid(20:5W3, 3, 6,9, 12,15)

Delta - 6 - desaturase(D-6-D)

Delta - 5 - desaturase

PG1 series

PG2 seriesPG3 series

↓ ↓

↓

↓

↓

↓

↓

↓

↓

↓



(blocked by aspirin and relatednon-steroidal anti-inflammatory)

Figure 6.9The Arachidonic Cascade

Figure 6.10 demonstrates that both the omega-3 and omega-6 families ofEFAs require D-6-D for some of the initial conversions. It converts cis-linoleic acid to gamma-linoleic acid (GLA), and α-linolenic acid (found insome plant sources) to 18:4 omega-3. Unfortunately, many things havebeen shown to block D-6-D’s gatekeeper function:8,9

1. Saturated fats inhibit D-6-D.2. Trans fatty acids formed by processing vegetable oil (margarine)

inhibit D-6-D.3. Diabetics have low activity of D-6-D in their body.4. Alcohol inhibits D-6-D.5. Aging leads to a reduction of D-6-D activity. Less than 3% of dietary

linoleic acid is converted to GLA after adolescence.6. Adrenalin inhibits D-6-D, as does the effect of beta-blockers. This is a

point that is often overlooked in the prescription of beta-blockers forcardiovascular problems (an area where D-6-D is also very neces-sary).

7. Starvation inhibits D-6-D but a low calorie intake diet has beenshown to increase D-6-D threefold.

8. Glucocorticoids inhibit D-6-D.9. Very low protein intake inhibits D-6-D, whereas very high protein

intake activates it. This is presuming the high protein intake doesnot also contain high saturated fat content. Eating fish rather thanred meat would be preferable and either might be better than avegetarian diet.

10. Large intake of glucose inhibits D-6-D.11. Oncogenic viruses and ionizing radiation inhibit D-6-D.12. High blood cholesterol inhibits D-6-D.13. Atopy. Atopy is an inherited susceptibility to many diseases such

as eczema, asthma and allergic rhinitis. One in six North Americans

(blocked by anti-inflammatorysteroid and PGE1)↓

↓

↓↓

↓

(blocked by Vitamin E and hydroxyacid derived from DGLA)

Arachidonic acid in membrane store

Free Arachidonic acid

Lipoxygenase Cyclooxygenase

Leukotrienes PG and Thromboxane A2


Lipids

is atopic and the ailment is an underlying factor in 70% of hyperac-tive kids and women suffering from P.M.S. Atopy was first discov-ered in 1937 by Arid Hansen, and remained virtually unknown to thescientific community for over forty years. It has been shown that theinhibition of D-6-D plays a very important role in atopic conditions.

Because so many physiological conditions can inhibit D-6-D, manynutritionists recommend that dietary EFAs in both the omega-3 andomega-6 families come from sources further down the pathway, i.e., afterthe D-6-D point. Referring back to Figure 6.8, we can see a source fromthe omega-6 family is GLA, for the omega-3 family -- eicosapentaenoicacid (EPA). We find GLA in human milk, Evening Primrose seed oil andBorage oil. EPA is found in cold water fish body oil.

A further look at Figure 6.8 indicates that three EFAs can form PGs:dihomogamma-linoleic acid (DGLA), arachidonic acid (AA) and EPA. PG1,created from DGLA, is an activator of cyclic AMP formation, an inhibitorof platelet formation, a vasodilator, an inhibitor of inflammatory reactionand an activator of T-lymphocyte function. 10,11 For this process to occurwe also need vitamin B6, zinc and Vitamin C.

AA on the other hand (Figure 6.8), gives us an undesirable prostaglandinsuch as PGI2 that causes platelet aggregation, or TXA2 which has undesir-able effects such as vasospasm, thrombosis and inflammation throughthe cyclo-oxgenase pathway. The lipoxygenase pathway providesleukotrienes (strong inflammatories). It should be noted that aspirin andother non-steroidal anti-inflammatories block the cyclo-oxygenasepathway forcing AA to transform into leukotrienes (see Figure 6.9). Thisappears to be the mechanism behind aspirin-induced asthma. The herb,feverfew, also inhibits this process above the AA level. AA appears in

delta-6-desaturase(D6D)

elongation

delta-5-desaturase

cis-linoleic acid

gamma-linolenic acid (GLA)

Dihomogammalinolenic acid (DGLA)

arachidonic acid (AA)

longer chain fatty acids

alpha - linolenic acid

18:4 n3 (stearidonic acid)

20:4 n3

eicosapentaenoic acid (EPA)

longer chain fatty acids

Figure 6.10The Function of D-6-D in EFA Metabolism

3 series PGs

1 series PGs

2 series PGs

↓ ↓

↓↓

↓

↓

↓

↓

18:3 n6

18:3 n3

↓

↓

↓

20:5 n3



dietary form primarily in red meat. Some is found in seafood. Shrimp area particularly rich source.

EPA produces PG3. PG3 has been shown to affect the cellular membrane(body-wide) by making it more fluid and giving it better electricalconduction in neural transmission. But one of its most important fea-tures is its competition with AA. AA is a twenty carbon chain, as is EPA.The presence of EPA in the body reduces the formation of AA. Thisforces more omega-6 fatty acids into PG1, a very desirable thing. Manyresearchers are suggesting the EPO will work better if EPA is present.In Figure 6.11 we can see the shape changes that occur to form pros-taglandins.

To review, the characteristics of each fatty acid are:

1. The length of the chain2. The number of double links3. The location of double bond links4. Whether the fatty acid is cis or trans

COOHH3C

H3C

H3C

H3C

COOH

COOH

COOH

CarboxylMethyl

18:4 W-3

Alpha Linolenic Acid 18:3 W-3

20:4 W-3

20:5 W-3Eicosanpentaenoic Acid

Figure 6.11Conversion of Linolenic Acid to Prostaglandins

COOH

CH3

CH3

COOH

COOH

O

O

Prostaglandin PGH3

↓

↓

↓

↓

↓

Prostacyclin PGI3

Thromboxane TXA3


Lipids

Evening primrose oil (EPO)

Evening primrose (Oenothera biennis) has a long history of medicinaluse. It was one of the first plants the early settlers of North Americabrought back to Europe, where it picked up the common name, King’sCure-All. This plant can be found in wastelands throughout NorthAmerica. The Algonquin Indians used the seeds of Evening primrose fortreating skin diseases and breathing problems.12

The seed oil of Evening primrose contains between 1-15% GLA. Occasion-ally higher levels are found. In 1978 a British seed company set up asubsidiary, Efamol Ltd., to develop the seed oil of evening primrose as anutritional product. They produced a strain of evening primrose thatgives a consistent quality of 9% GLA. Manual harvesting techniques,which are absolutely necessary, and the loss of many seeds when theseed pod bursts during ripening keeps the cost of this oil is relativelyhigh.

In the last ten years, over 300 extensive scientific investigations into EPOhave been conducted. Over half were double blind studies. Researchinto EPO continues. GLA and EPO have a number of proven clinicalapplications:

Atopic Eczema As noted earlier, some families have a susceptibilityto atopic problems (supporting the homeopathic theory of psoricmiasms). These cases of eczema usually start in early childhood andoften progress to asthma later in life. It has been shown conclusively thatlow D-6-D in these individuals causes them to have a problem convertinglinoleic acid to GLA.13 During breast feeding (mother’s milk is high inGLA), these children have no problems. A double blind study conductedat Bristol University in England, carried out on both adults and children,determined that EPO in doses of 3 grams a day produced substantialchanges in eczema patients. Results usually occur within eight weeksand the dose is cut in half after three months because cell membranesstart to saturate with PUFA.

Premenstrual Syndrome (P.M.S.) Many cases of P.M.S. have anatopic (eczema, arthritic related disease) dimension. Sufferers will oftencome from atopic families and may show eczema, asthma or arthriticsymptoms themselves. D-6-D metabolic problems also are common.Some authorities estimate that more than 70% of P.M.S. patients havesome atopic factor as an underlying cause. Three double blind studies atthe universities of Dundee, Wales and Helsinki have shown that EPO wasvery effective in treating cases of P.M.S. Another study with 150 womenwho had failed to respond to other P.M.S. treatment modalities foundthat EPO brought 67% of the subjects relief and an additional 25%, partialrelief. The dosage was eight capsules of EPO daily throughout the men-strual cycle for three months. Dosage was cut in half at that point. 14,15,16



High Cholesterol levels We would expect EPO to lower cholesterolbecause other PUFAs do. The surprise lies in EPO’s power to lowercholesterol, reportedly 100-163 times as effective as other vegetable oils,even without dietary changes.17 - 20 Strangely, EPO did not lower choles-terol in patients with normal or low cholesterol. LDL was the form ofcholesterol changed in all subjects treated. There was no effect on HDL.LDL/HDL ratio was 3.20:1 before treatment and 2.38:1 after.

Alcoholism As noted earlier, high intake of alcohol inhibits D-6-D andtherefore the formation of GLA from LA. A Scottish study (involving morethan 200 alcoholics) indicated EPO substantially reducing the sideeffects of alcohol withdrawal and the need for tranquilizers duringwithdrawal.21 EPO returned liver function to normal more rapidly,producing improvements in brain function as recorded by psychologicaltests. It was also shown that EPO lowered the craving for alcohol. A yearlater, significantly lower numbers in the EPO group had not returned todrinking in comparison to the placebo group.

Dry Eye Syndrome (Sjogren’s Syndrome) With the extensive use ofcomputer terminals, the incidence of this syndrome is on the increase inthe developed world. It is the result of a poor production of tears and ischaracterized by a difficulty in wearing contact lenses, ‘gritty’ eyes,having a hard time watching TV or movies. EFAs are necessary in theproduction of tears. A large study at Glasgow University in Scotland anda controlled study at University of Copenhagen, have shown that EPO iseffective in controlling this syndrome.22

Other areas where EPO is useful Besides the above areas that havebeen proven by more than one double blind study, many other areas

Figure 6.12Evening Primrose


Lipids

have been researched. Many have shown good to moderate results butonly in small studies and are presently undergoing more extensiveresearch.

Hyperactivity (Attention Deficit Disorder) Many children withhyperactivity have underlying atopic problems (some authoritiessuggest up to 70% of hyperactive children). Researchers noticed thatmany of the additives and foods barred from consumption on theFeingold Diet (for hyperactivity) were substances that block EFA conver-sion to PGs, suggesting that hyperactivity was a metabolic problemsimilar to eczema.23 A New Zealand study found significantly reducedEFAs in hyperactive children. In England a Hyperactive Children’sSupport Group started administering EPO to over 200 children. Four outof five responded (the youngest responding best).

Mild cases of hyperactivity apparently responded to EPO alone, whilemore severe cases needed vitamins and the Feingold diet. Significantly,the English study found little rebounding effect. Children on the Feingolddiet are shown to have dramatic deterioration in behavior if they cheat(at a party, for example). Children on a EPO regime didn’t seem to be assensitive to occasional dietary “binges”. There are three double blindstudies being conducted on this topic. Very favourable results arereported so far.

Hypertension EPO has been shown to lower blood pressure inhypertensive models during animal studies. Several studies on humansare presently under way. One study on pregnant women found thatblood pressure was lowered through the use of EPO.24 In another studyon obese patients at Tulane University, EPO apparently reduced bloodpressure in mildly hypertensive cases.25

Diabetes Insulin is a factor in D-6-D conversion of LA to GLA. Bothdiabetic animals and humans seem to have low GLA and PGE1 levels.Researchers are studying this lack as a possible cause of some of thesecondary effects of diabetes. A five year study at the University ofRotterdam in Holland found high doses of LA reduced damage done toeyes, heart and kidneys in diabetics.26 Substantial improvements inblood sugar levels can occur after administration of large amounts ofGLAs. Since diabetics are known to have inhibited D-6-D, it has beensuggested that the large amounts are needed to overcome low D-6-D.

Tender and lumpy breasts Double blind studies conducted in thelate seventies at Ninewells Hospital and medical school, Dundee, andWelsh School of Medicine, Cardiff noted significant reduction in pain,tenderness, and lumpiness during EPO ingestion among women withcyclical breast symptoms. An increased effect was also found if vitaminC (750 mg.) was added to the regime. Non-cyclic breast symptomsshowed little change.27



Platelet Aggregation It has been shown that diets high in PUFAsinhibit platelet aggregation in both animals and humans.28 - 30 Linoleicacid was the fatty acid which provided the best results. Three studiesfound more consistent results can be obtained with EPO on dosages of 3gm. per day.31- -33 EPO also came out ahead in an experimental compari-son with corn oil.34

Vascular obstruction A PUFA-rich diet can arrest progression ofvascular obstruction, and has been shown to reverse the process,allowing the obstructions to clear.35,36,37 Increased exercise tolerance inindividuals with vascular obstruction has been reported 38. The pros-taglandin E1 from DGLA has been linked to dramatic improvements inpatients with vascular spasms, even relieving angina pectoris.39

Immunity and Inflammation Most of the anti-inflammatory drugscurrently used by allopathic doctors use one or more methods ofblocking AA to stop its possible cascade into leukotrienes. 40 - 44 Most ofthem, however, also block DGLA and therefore PGE1, a very strong anti-inflammatory. The administration of EPO and EPA will shunt the bio-chemical process away from AA, forming two of our own strong PG anti-inflammatories, while lowering AA and leukotrienes.

At the University of Connecticut and Pennsylvania, PGE1 has been shownto prevent adjuvant arthritis in rats, attenuate systemic lupus-likedisease in NZB/W mice and lower circulating lysosomal enzymes inrheumatic patients.45 As mentioned earlier, PGE1 raises cyclic AMP levels(an anti-inflammatory effect), inhibits AA, and activates T-lymphocytefunction.46,47 There is a very high concentration of PGE 1 in the thymussuggesting that it is the controlling chemical for T-suppressor cells. EPOis being studied in diseases that result from imbalances of T-cells 48,49 Weshould also remember the role of EPA in competing with AA triggering areduction in leukotrienes.

Other areas of EPO study Currently it is suggested that EPO can beeffective in the management of multiple sclerosis and in psychiatricproblems associated with neural transmissions and schizophrenia.50

More study is necessary in these areas.


Lipids

Plants containing EFAs

Borage Borage officinalis

Borage, a closely related plant to Evening Primrose, seems to have manyof the primrose’s medicinal properties but at a much reduced level.Borage has been useful in cases of Herpes simplex virus, arthritis,inflammation of the urinary passages, heart disease and edema.

Currants Ribes spp.

Currant oil is also now sold as a source of omega 3 and omega 6 oils.Again it should be emphasized that the use of simple omega three oromega six oil doesn’t guarantee the production of the prostaglandins.These oils have to get to the other side of the D-6-D “gateway”, a gatewhich is very fragile in people with particular illnesses.

Other important oils relating to EFAs are flax seed and safflower oil.Two other natural products that fit into the picture at this point are pearlpowder and feverfew. These medicinal items interact with the essentialfatty acid cycles though oils aren't found in either. Feverfew stops theinflammation triggered after AA in the biochemical pathway (Figure 6.8)and pearl powder seems to stimulate D-6-D.

Figure 6.13Currant

Ed



Feverfew Tanacetum parthenium

Feverfew has become rather popular over the last several years becauseof its ability to inhibit migraine headaches. Feverfew has been reportedto inhibit prostaglandin 2, inhibit platelet aggregation, inhibit phagocyticpotential, inhibit platelet deposition on collagen substrate, to haveantimicrobial activity and reduce human tumor cells.

How does feverfew have such a broad physiological impact? A group ofsesquiterpene lactones (parthenolides) in the plant inhibit inflammatoryprostaglandin and the production of AA on the surface of platelets . Thisof course inhibits the most inflammatory substance in the human body --leukotrienes. Consumption of these phytochemicals therefore reducesthe problems of migraines and arthritis. Even many allergy reactions,including asthma, can be affected. By stopping platelet aggregation andtheir deposition on collagen, atherosclerosis, arthritis, stroke and heartattack problems are indirectly influenced.51 - 55

Pearl Powder

Historically, pearl powder (a pearl found only in an oyster in Jin Thailake near Shanghai, China) has been used in cases of skin problems,asthma, arthritis and migraine. An ability to strengthen liver metabolismis also noted. Unpublished reports I received from the Materia MedicaCollege in Shanghai, during a visit in the late fall of 1988, reported thatpearl powder stimulates the body’s production of D-6-D. If true, it wouldmake it possible for the simpler, and more available, oils of the omega 3and 6 series to form into the proper prostaglandins, reducing inflamma-tion.

Atherosclerosis

Oil-related problems such as atherosclerosis are a major health cocernin Western society. For the next several pages we are going to discussthese problems, along with herbs that have positive therapeutic effects.

Atherosclerosis is the forming of atherosclerotic plaque, or atheroma, asan end product of a long term degenerate state. Thickening of thearterial wall and lowered blood flow are the results. This problem hasreached epidemic proportions in the Western world and is a major causeof death in United States. This plaquing can occur anywhere in the bodybut deaths related to the problem can be distinguished: myocardialinfarction (20% of all deaths in the U.S.), arteriosclerotic heart disease(accounts for 33% of all deaths) and cerebral vascular disease (the thirdmost common cause of death). Cost of health care due to atherosclero-sis is estimated at 56 billion dollars per year in the U.S.


Lipids

This health problem is a long term condition that develops over severalyears. It is often not diagnosed until serious, often lethal, clinical symp-toms appear. It is obvious that the only true cure for atherosclerosis isdietary and lifestyle change. Supplementation can help considerably butlifestyle changes must also be employed.

Overview of Lipoproteins

There seems to be two major factors related to the role of lipids in thepathogenesis of arteriosclerosis:

1. The particular form of the lipoproteins (usually the critical factor isdensity).

2. Genetic variation in the formation of lipoproteins.

The lipids (e.g., cholesterol, triglyceride, and phospholipid) can beclassified according to the density of the carrying particle (i.e., thelipoproteins). These carrying particles consist of a combination ofproteins, cholesterol esters, triglycerides, phospholipids and freecholesterol. There are five classifications according to density.

1. Chylomicrons (CM)2. Very Low Density Lipoproteins (VLDL)3. Low Density Lipoproteins (LDL)4. Intermediate Density Lipoproteins (IDL)5. High Density Lipoproteins (HDL)

Figure 6.14Feverfew



CM and VLDL are the lowest density molecules and the richest intriglycerides (TG) but are actually the largest particles. In Table 6.3 wecan see the proportions of the five components of the five densities oflipids. The relative size of the lipids can be seen by the stippled circleassociated with each lipid.

The TG in chylomicrons is of dietary origin while that of VLDL is ofhepatic origin. As the Figure indicates, LDL is the major carrier ofcholesterol and it originates mainly from the metabolism of VLDL,mediated by a lipoprotein lipase (enzyme). The current view of lipopro-teins metabolism is summarized in Figure 6.5. The ratio of the differentlipids in the body is of major significance when constructing the patho-genesis of atherosclerosis.

There are many theories now used to explain the lipid ratios. We will bedealing with these in much more detail in later sections. One reason whywe have these ratios seems to be due to the form of protein (calledapoprotein) found in these lipoproteins. It seems that these apoproteinsplay a pivotal role in the fate of the fat particles. We have listed themajor apoproteins in Table 6.3 below each group and their function inTable 6.4. The apoprotein in LDL (apo B) is crucial for the interactionwith cell surface receptors that lead to the uptake of nutrients into thecell.56 In HDL the principle apoprotein is apo A-I which is necessary forthe “reverse transport” of cholesterol from the cells to the liver (Figure6.15).

The synthesis of all the apoproteins and the receptor sites for LDL, andpossibly VLDL and HDL, is genetically controlled. This is one of thereasons that cholesterol problems often follow family lines. Another

Table 6.3Composition of Serum

Major Apolipoproteins

HDL LDL VLDLIDL Chylomicrons

apo A-Iapo A-II

apo B - 100 apo B - 100apo E

C proteinsapo B - 100

C proteins,apo A- I, apo B - 48apo E, others

The composition ofthe 5 major serumlipoproteins. Shadedareas indicate relativesize of lipoproteins.

Pro

tein

sC

hole

ster

yl E

ster

sTr

igly

ceri

des

Pho

spho

lipid

sFr

ee c

hole

ster

ol

100%

80%

60%

40%

20%


Lipids

reason, of course, is that dietary habits are often passed from a parent tothe offspring. There are several lines of evidence that point to plasmaLDL-cholesterol as playing a major role in coronary atherosclerosis:

1. Lack of LDL receptors, which can be controlled by individual geneticstructure, causes a rise of cholesterol in plasma. LDL receptors alsodecrease with age and with high fat intake.

2. There is a direct relation between increased blood cholesterol (morespecifically LDL-cholesterol) and coronary atherosclerosis.

3. Epidemiological studies show a graded and independent relationshipbetween plasma cholesterol over 220 mg/dl and coronary atherosis.

Cholesterol

Cholesterol is a hard, waxy lipid substance with a melting point of 149oC.Cholesterol is not required in our food supply but it is essential for life. Itcan be manufactured from double carbon acetate which is derived fromthe breakdown of sugar, fats and (to a minor degree) protein (Figure6.16). Because of this, the more sugar and fat (especially saturated andnon-essential fatty acid) we eat, the more cholesterol is formed. A personcan consume very small amounts of cholesterol yet still produce lots ofcholesterol if they have a high intake of other fats and sugars.

Humans can only absorb 2 - 4 mg. of cholesterol per day per kilogram.57

This fact can be very significant when looking at the some animalresearch data. Canines have 35 times the cholesterol absorption rate ofhumans. Rodents have 50 times the human rate. Absorption studies

Figure 6.15Lipoprotein Metabolism

LDL

ExtrahepaticCapillary

Beds

LDL ReceptorPathway

ScavengerPathway

ExtrahepaticCells

ExtrahepaticCells

CholesterylEsters

HDLRemnantsFree Cholesterol& Phospholipids

Liver

Bile Acids&

Cholesterol

VLDLChylo-microns

↓

↓

↓

←←

←

←↑↑

↓↓

Free Cholesterol& Phospholipids

Intestine

←

←

←

←

←←



conducted with these animals would give misleading results for humanmedicine. Man produces 9 mg. of cholesterol per day per kilogram.58 Abit of simple math ((9-4)/9 -(9-2)/9) indicates that 55 - 78% of the choles-terol in our bodies is manufactured in our body and not absorbedthrough our diet. Again we can see animal studies have limited useful-ness in human situations. In rats, the liver accounts for 51% of thecholesterol produced, in man it is only one sixth this amount.59

Cholesterol is not always a “bad guy”. It is necessary for many functionsin the body. Cholesterol is an integral part of our cell membranes,firming them up. Essential fatty acid, in contrast, gives fluidity to the cellmembranes. Too much cholesterol makes the membrane stiff and brittle,too little and the membrane becomes very fluid and falls apart.

Since our daily intake of lipids varies considerably, we need a regulatorto compensate at a “local” cellular level -- a perfect role for cholesterol.In fact this role is so important that each cell has the ability to manufac-ture its own membrane cholesterol.

The following is a list of other major functions in which cholesterol playsan important role:

1. Formation of sex hormones2. Formation of adrenal corticosteroids3. The formation of Vitamin D from sunshine (and bacteria)4. Bile salts5. Secreted onto the skin as a protection agent

Apolipo- Concentration Major Known Defectsprotein in Plasma (mg/d) Function(s)

A-I

A-IIB

C-IC-IIC-IIID

E

160±60

30-5060-125

4-73-88-151-5

3-6

Reverse transport of chole-sterol, Activation of LCAT?inhibitor of LCATInteraction with B and B, Ereceptors? Activation of LCATActivation of LPL?inhibits LPL?cholesterol transfer-proteinInteraction with B, Ereceptors

Tangier's disease, AI-deficiency, AI-CIII deficiency

AbetalipoproteinemiaHyperapobetalipoproteinemia

CII deficiencyAI-CIII deficiency

E2/E2 phenotype associatedwith dysbetalipoproteinemia?E4 found more often inchylomicronemia

Table 6.4Major Apolipoproteins


Lipids

The other side of Cholesterol Over the last few decades cholesterolhas gotten lots of bad press because of its role in cardiovascular disease.The tidal wave of medical research on heart disease over the last twodecades has funded many a laboratory, felled many a forest, filled manya TV talk show and provided us with new theories faster than thetextbooks can be written. The following is a synopsis of some of thecurrent theories:

Injury Hypothesis The most accepted theory is that the arterial wallsare first damaged (most likely by free radicals in the bloodstream) andthen cholesterol, and platelets, are deposited in these locations as anattempt to repair the arterial damage. The area undergoes cell prolifera-tion. This forms a fibrous cap. Secondary lipoprotein, especially LDL,deposits at this site.60,61,62

Micronutrient Hypothesis Cholesterol is deposited on the arterialwall because of low levels of micronutrients which are necessary todestroy free radicals. This theory was first reported in 1948 by Rinehartand Greenberg and has been advanced since then. Often call theHomocysteine and Pyridoxine Deficiency Theory, it basically states thatthe lack of pyridoxine (vitamin B6) leads to the accumulation of homo-cysteine, which causes damage to the arterial walls.63 A copper-contain-ing enzyme is also necessary in this process, and therefore might be partof the problem.64 Pyridoxine also inhibits platelet aggregation.65

Monoclonal Hypothesis This theory says the problem starts from aneoplastic growth (unnaturally rapid division) of some of the cells in thearterial wall, similar to cancerous cell tumor formation. The plaquing ofLDL is the result. The cell mutation is attributed to free radicals andtoxic material.61, 66

HO

Figure 6.16Production of Cholesterol

Cholesterol

Squalene

Acetate

SugarFatty acids

(protein)

↓

↓

↓C C



Free radicals are finally becoming an acceptable candidate as one of thecausal factors in cholesterol plaquing. The oxidative derivatives ofcholesterol are potent peroxides which are free radicals themselves,quite capable of causing damage to arterial walls.67 Whatever the cause,it is agreed that plaquing on the walls of the arteries is dangerous. Abouttwo-thirds of North Americans suffer from atherosclerotic deposits tosome degree, narrowing the arteries and slowing blood flow.

Platelet Aggregation The story does not stop with arterial damage.High amounts of cholesterol, saturated or denatured fats cause theplatelets in the blood to become more sticky, causing them to aggregate,increasing the risk of blood clot formation. This narrowing of the arterialwalls, along any clotting, can block off a blood vessel. This cuts off thenutrient and oxygen supply to the downstream cells. The deprived cellsend up dying. The individual experiences strokes if the brain is deprived,coronaries if the heart is affected and gangrene if peripheral areas arestarved. This platelet activity also has another side. Once plateletsaggregate, they release a potent mitogenic polypeptide that induces DNAsynthesis and local cell proliferation.68 Saturated fats in general increaseplatelet aggregation.

Other organs affected Atherosclerotic deposits will also harden thearteries, reducing elasticity. This of course raises the blood pressure,putting more strain on the heart and the kidneys.

Sources of Cholesterol As we stated earlier, the body produces its owncholesterol. The cell produces cholesterol on demand. For example, if aperson drinks a fair amount of alcohol one night, this alcohol will makethe membranes more fluid. The cells will immediately start to producecholesterol in response, to firm up their membranes to the proper state.As the alcohol wears off, the cell membrane starts to harden up. Thecells respond by esterifying the cholesterol with linoleic acid and B6,shipping the results off to the liver. In the liver, the cholesterol ischanged into bile acids and dumped into the intestinal tract to aid in fatdigestion. Eventually it is passed out of the body as waste. To a certainextent, this whole process is dependent on sufficient fiber in the diet sothat the intestinal transit time is not too slow and the bile (cholesterol) isnot reabsorbed.

The cells are not the only place where cholesterol is made. Increasedproduction also occurs in the liver, intestines, adrenal glands and sexglands. The production of cholesterol (see Figure 6.16) is the groupingtogether of acetates. These 2-carbon molecules are hooked together end-to-end until 30 of them are chained together. Cyclization results in 3carbons being clipped off, forming a 27 carbon cholesterol molecule.The raw material comes from the breakdown of non-essential fats,carbohydrates, and to a lesser degree, proteins.


Lipids

Cholesterol and Our Diet As noted earlier, substantially morecholesterol is formed in the body than is absorbed from the food. In fact,it appears that high fat in general (even with very low cholesterol) intandem with high carbohydrate consumption can cause pressure on thebiochemical pathways, creating a tendency towards cholesterol for-mation. It is sensible not to aggravate the situation with high cholesterolfoods in our diet. A few rules on diet preparation should be observed.

Plants contain no cholesterol. Eggs, meat, dairy, fish and shellfish allcontain cholesterol.

one egg - 250 mg1/4 lb of butter - 250 mg

The average diet in North America contains 800 mg of cholesterol perday. On average we can categorize the sources as follows: about 45%from eggs, 35% from meat and 20% from dairy. Of this, usually less than50% is absorbed. The average human contains 150 gm. of cholesterol,mostly found in cell membranes, with about 7 gm. in the blood. The dailyturnover is 1100 mg., obviously more than found in our diet.

A scientific debate about dietary cholesterol has continued for years.Since we can absorb dietary cholesterol, some researchers proclaimthere is an “evolutionary advantage” to not wasting the energy produc-ing it ourselves. The more cholesterol we absorb, the less we need toproduce ourselves. Other scientists feel that we cannot use the dietarycholesterol as thoroughly as the sort created by our own body.

One school of researchers insists that dietary cholesterol is the type thatis deposited in the body. Since vegetarians have 1/4 the cardiovasculardisease death rate and much lower cholesterol levels, it is felt thatcholesterol consumption must lead to cardiovascular problems. Otherresearchers feel it is the lack of micro-nutrients in the body which is thekey issue. Adequate levels of nutrients such as Vitamin C, niacin, sele-nium, zinc, and chromium (not to mention fibre) also dramaticallylowers cholesterol levels. And once again, vegetarians naturally get moreof these substances than omnivores.

Does dietary intake of cholesterol repress cholesterol biosynthesis inthe human liver? It’s debatable. Varying dietary cholesterol in humans(and therefore plasma cholesterol levels) appears to affect liver produc-tion69 but more extensive research is needed. Animal studies (rats70,squirrel monkeys71) and human studies72,73 report that cholesterolfeeding markedly inhibits hepatic cholesterogenesis. In rats, the degreeof inhibition of cholesterogenesis is directly proportional to the chylomi-cron remnants and LDL concentration in the blood.74,75



Measuring Blood Cholesterol The most common way to measurecholesterol is to measure total blood cholesterol. This of course groupsthe “good” (HDL) and the “bad” (LDL) together. This is not a trueindicator of the risk of cardiovascular disease (CVD). If we have a lowtotal cholesterol count but a high LDL/low HDL ratio, we would have ahigher risk than indicated by the single measurement. It isn’t even theamount as much as the ratios between the two. A ratio of 3.4:1 or lower(LDL/HDL) indicates low risk.

Dr. W. Castelli, in the famous Framingham Heart Study, estimates thatcardiovascular disease can be prevented (with 98% percent effective-ness) 5 years before it occurs by measuring the cholesterol ratios andblood pressure, and changing the diet.

Researchers feel that an HDL level of 50 -75 mg/dl of blood indicates thatthe body is getting rid of excess cholesterol properly and preventingaccumulation. A high LDL level (above 120 mg/dl) indicates our body isoverloaded by cholesterol.

While these facts might seem overwhelming, a few facts still add anelement of mystery to the research. Cholesterol consumption hasremained constant over 80 years in North America, while cardiovasculardisease has sky-rocketed in the last two decades -- as has the consump-tion of sugars, oils, additives, trans-fatty acids and denatured fats.

Objectives in handling atherosclerosis Cholesterol, and the role itplays in atherosclerosis, highlight a number of influencing factors andsome practical objectives in controlling the problem:

Objectives1. Keep intake of cholesterol and foods that produce cholesterol

(sugars, non-essential and denatured fats) low.2. Regulate the liver’s synthesis and excretion of cholesterol.3. Dissolve plaquing on the arterial walls.4. Compensate for genetic problems.5. Reduce damage to arterial walls and thereby reduce plaquing.

Factors1. The LDL/HDL ratio.2. Cellular uptake and deposits of cholesterol.3. Excretion of cholesterol from body.4. Absorption of cholesterol and reabsorption of bile salts.5. Platelet aggregation.


Lipids

Herbs and other nutrients that lower choles-terol

We have included the following nutrients and herbs in this chapterbecause they promote the objectives listed above. They don’t necessar-ily contain the lipids described in this chapter.

Alfalfa: Medicago sativa’s saponins has been shown to dissolve choles-terol in atherosclerotic plaque in monkeys, rats, chickens, dogs, pigeons,pigs and rabbits. Consumption can apparently prevent increase inplasma cholesterol after eating high cholesterol foods.76,77,78 Thesaponins are similar to digitonin saponins, probably working onpathways which lower cholesterol absorption and increase bile output.79

Even though the saponin-cholesterol interaction is an important part ofthe hypocholesterolemia action of alfalfa, it has been shown that alfalfawith the saponin removed still increases the output of bile acids --apparently saponins are not the only substance in alfalfa whichinfluences cholesterol levels.80 Regression of atherosclerosis has beendocumented by sequential contrast arteriography in humans usingalfalfa.81

Ginger: Zingiber officinale has long been considered by herbalists as aregulator of vascular cholesterol and blood circulation. Lab findingsconfirm that ginger will lower cholesterol levels82 and inhibit plateletaggregation.83 Ginger’s ability to reduce platelet aggregation seems to bedue to three unnamed compounds that inhibit platelet cyclooxygenaseproducts. This gives ginger very acceptable antithrombotic properties.

Garlic: Allium sativa is known to have fibrinolytic activity, inhibitingplatelet aggregation through inhibiting prostaglandin E 2 and release offibrinogen degradation products.84,85 Garlic has also been shown tosignificantly lower total serum cholesterol and triglyceride, simulta-neously increasing HDL levels. The effect is enhanced throughsuppression of the biosynthesis of the LDL rather than inhibition ofabsorption.86

Other studies reported that garlic can also significantly lower choles-terol in rats that have consumed a high cholesterol diet87 (a significantdecrease in VLDL and an increase in HDL).88 Chi’s group found that theliver weight, total liver lipids and cholesterol was increased in rats byfeeding them a high cholesterol and lard diet but garlic supplementationlowered these levels by 30% by increasing bile output. The same resultswere obtained irrespective of the level of supplementation.

As we have stated earlier, relying on data from rat studies to generalizeabout the effect of human cholesterol might be a bit misleading. Humanstudies have tended to confirm the results of garlic supplementation.Garlic has been shown to lower serum cholesterol and triglycerides,

Ed

Sc2

Sc2

Mo2

Sc2

Mo2



while increasing HDL in both healthy individuals and patients of coro-nary heart disease.89

Cayenne: Capsicum spp. are known to be very strong local stimulants inthe circulatory system. Capsaicin, the major constituent of cayenne, hasbeen shown to significantly lower both plasma cholesterol and triglycer-ides in female rabbits. Even more important, it lowered the LDL-HDLratio. The mechanism for this is not understood but the authors felt itmight be attributed to decreased intestinal absorption of the lipids.90

Capsaicin has also been shown to decrease platelet aggregation.91 Themechanism for thinning the blood is different than models created foraspirin.92 The production of substance P by cayenne has the knowneffect of dilating the arteries thereby lowering blood pressure.

Niacin: Both the pharmaceutical and naturopathic research teams haveshown niacin to be one of the best substances for controlling ar-teriosclerosis. Niacin is used rarely in clinical settings because of anassociated transient skin flushing in humans and poor marketing. It isknown to lower both LDL and total cholesterol with a reduction as muchas 48% in high doses (3 gm./day). While dose dependent, even smalldoses have an effect. The underlying mechanism is a reduction of thelipoproteins by decreasing the precursors.93 Niacin also has a significanteffect -- lowering platelet aggregation.94 A good review of niacin use incholesterol cases was written by Cohen.95

Pyridoxine (Vitamin B6): As stated earlier, Rinehart and Greenbergshowed that B6 deficiency can cause atherosclerosis in studies con-ducted in the late forties. In summary, a pyridoxine-dependent enzyme isnecessary to convert homocysteine into methione. A deficiency of B6 willlead to a homocysteine buildup, in turn causing damage to endothelialcells and on to atherosclerosis 63. Pyridoxine is also necessary in thecross linking of arterial elastin and collagen. Damage in this area cancause locations for the LDL to build up on64. Pyridoxine has also beenshown to inhibit platelet aggregation65.

Copper: As with pyridoxine the cross linking of arterial elastin andcollagen is dependent on copper 64. In many fad weight loss diets (such asthose based on liquid collagen) copper deficiency has led to deaths fromcoronaries.

Selenium: A study done in Finland on 11,000 case-controlled pairsreported a direct association between low selenium levels and theincreased risk rate of ischemic heart disease.96 Low levels of seleniumwill reduce the level of glutathione peroxidase, thus increasingperoxidation of lipid, which in turn will lead to increased vascularendothelial damage. Selenium is also necessary in the metabolism ofprostaglandin and to decrease platelet aggregation. Selenium deficiencyin platelets will increase cyclo-oxygenase activity due to the lack ofglutathione peroxidase.97

Sc2

Mo2


Lipids

Chromium: Total cholesterol and serum triglyceride are reduced aftersupplementation of chromium chloride (200 mcg, daily). HDL levels areincreased along with glucose tolerance factor.98,99

Phospholipids and Cell Membranes

The second major group of lipids, after triglycerides, found in foods andin our bodies is phosphatide (phospholipid). Two fatty acids (usually 16-or 18- carbon chains) are attached to a glycerol, like triglyceride, withthe third location holding a phosphate group(see Figure 6.17).

CH2

CH

P

OC

O

O

O

C

O

Figure 6.17Structure of Phospholipids

O

where R = cholineinositolethanolamineserine

Phospholipids are water soluble, spreading out over a thin layer wherewater and oils meet. This characteristic makes the phospholipid aperfect molecule to form cell and organelle membranes. As we can see inFigure 6.18, the cell membrane contains a double line of phospholipids.The cell membranes also contain protein, and cholesterol. Depending onthe fatty acids contained by the phosphatides, it will cause the cellmembrane to be more or less fluid. Too fluid can be leaky. Too solid canbe rigid and not conduct nutrients and life across the membrane. Theoccurrence of cholesterol and proteins tempers this process. As de-scribed earlier in this chapter, much of the cholesterol in our body ismanufactured at the cellular level to temper the fluidity of the mem-brane.

CH2

O -O - R



Phosphatidyl Choline

A special form of phosphatide that is found in lecithin is phosphatidylcholine. Phosphatidyl choline helps devolve cholesterol, assists the liverin its detoxification function, plays a role in the thymus gland (andtherefore in immunity) and moderates the ratio between LDL and HDL.Clinically, one of the most useful roles of the substance is its ability totake the highs and lows out of manic depression.

Figure 6.18Structure of a Biological Membrane

18:3w3 18:1w9 18:0 18:1w9 18:3w318:2w6

P P P P

Phosphatide

Cholesterol

more fluid

Figure 6.19Biological Membrane Transformation

more solid

PP

P

P P

P P

P

P

P P

P P

P P

P

← →

protein


Lipids

Summary

In this chapter we looked at the basic chemistry of fixed oils, fattyacids and phospholipids. The process of manufacturing oils isimportant to understand to aid in the choosing of oils. The structureof fatty acids have both a methyl end (omega end, -CH3) and carboxyl(-COOH) group. The carbon chains can be saturated or unsaturated(with double bonds). Hydrogenation is a manufacturing technique ofplacing hydrogen in unsaturated oil to saturate it, giving the oil a solidform such as margarine. Fatty acids usually come in groups of three,called triglycerides. Many oils are used by herbalists as a base foremollients, cosmetics, ointments and salves. Essential fatty acids havespecial health applications. Related problems plus some non-lipidcontaining herbs that aid in essential fatty uses were covered. Thewhole area "Atherosclerosis and Cholesterol problems" was dealtwith, from a chemistry point of view, hypotheses of atherosclerosisproblems, platelet aggregation, as well as non-lipid containing herbsthat aid in treatment. The chapter finishes with a look at phospholip-ids and the cell membranes as well as utilization of phosphatidylcholine.

Figure 6.20Phosphatidyl Choline

O(actually bends)

choline

H

O C H

O C H

CH2OP OCH2CH2N+(CH3) 3

O

O

O



References 20 Horrobin, D.F.,(ed.), Clinical Uses ofEssential Fatty Acids, Eden Press,London, Eng., 1982.

21 Glen, I., Glen, E., MacDonell, L.,Possible pharmacological ap-proaches to prevention andtreatment of alcohol-related CNSimpairment: results of a double blindtrial of essential fatty acids.Presented march 29, 1983 at theInternational Conference on Pharm.Treatment of Alcoholism. Institute ofPsychiatry, U of London Eng.

22 Campell, A., MacEwen, C.G., Systemictreatment of Sjorgen’s syndrome andsicca syndrome with Efamol (EPO),vitamin C and pyridoxine, EdenPress, 1982.

23 Colquahom, I. and Bunday, S., A lackof essential fatty acids as a possiblecause of hyperactivity in children,Med. Hypotheses, 7:673-9, 1981.

24 Horrobin, D.F. and Maku, M.S. How dopolyunsaturates lower cholesterollevels?, Lipids 18: 558-62, 1983.

25 - 50 Horrobin, D.F.(ed.), Clinical Uses ofEssential Fatty Acids, Eden Press,London, Eng., 1982.

51 Voyno-Yasnetskaya et al., “Effect ofan extract of feverfew on endothelialcell integrity and on cAMP in rabbitaorta”, J.Pharm. Pharmacol., 40: 501-2, 1988.

52 Johnson, E.S., “Feverfew: a traditionalherbal remedy for migraine andarthritis”, London, Sheldon Press,1987.

53 Johnson, E.S. et al., Pharmaceuticalscontaining sesquiterpene lactones inextract from Tanacetum parthenium,European patent appl. EP 98041, Jan.1983, 93 pp.

54 Loshe, W., et al., Feverfew: AnAntithrombotic Drug? FoliaHaematol. Leipzig 115: 181-184.

55 Loshe, W., et. al, Inhibition of theBehavioural Human PolynuclearLeukocytes by an Extract ofChrysanthemum parthenium; PlantaMedica 54: 381-384, 1988.

56 Goldstein JL, Brown MS. The lowdensity lipoprotein pathway and itsrelation to atherosclerosis Ann. RevBiochem 46: 897 - 930, 1977.

57Rudney H and Sexton R, Regulation ofCholesterol Biosynthesis Ann. RevNutr. 6:245-272 1986.

58Ibid.

1Erasmus, U., Fats and Oils: the guide tofats and oils in Health and Nutrition;Alive Books, Vancouver, Canada,1986.

2Erasmus, U., ibid., p.101.3Bland, J., Your Health Under Siege:

Using Nutrition to Fight Back,Stephen Greene Press, Brattleboro,Vermont, p.75, 1981.

4Erasmus, U., ibid., p. 100.5 Mead, J.F. and Fulco, A.J., The

Saturated and Polysaturated FattyAcids in Health and Disease,Springfield, Ill., C.C. Thomas, 1976.

6 Horrobin, D.F., Gamma-Linolenic AcidsMedicine, 1984-85 Yearbook ofNutritional Medicine, Keats Pub.,New Canaan, Con, 1985.

7 Erasmus, U., ibid.8 Horrobin, D. F.(ed.), Clinical Uses of

Essential Fatty Acids, Eden Press,London, Eng., 1982.

9 Erasmus, U., ibid.10 Horrobin, D.F., ibid.11 Erasmus, U., ibid.12 Manku, M.S., Horrobin, D.F. and

Morse, N., Reduced levels ofprostaglandin precursors in blood ofatopic patients: defective delta-6-desaturate function as a biochemicalbasis for atopy. ProstaglandinsLeukotrienes, Med. 9: 615-28, 1982.

13 Wright, S. and Burton, J.F., OralEvening Primrose seed oil improvesatopic eczema, Lancet, 2:1120-22,1982.

14 Horrobin, D.F., The role of essentialfatty acids and prostaglandins inPremenstrual Syndrome, J. Reprod.Med, 28: 465-8, 1983.

15 Brush, M.G.; Efamol (EPO) intreatment of Pre-menstrual Syn-drome, in “Clinical Uses of EssentialFatty Acids”, Eden Press, 1982.

16 Erasmus, U., ibid.17 WHO/FAO. Dietary Fat and Oils in

Human Nutrition. Report of an ExpertConsultation. UN Food and Agricul-ture Organisation, Rome, 1977.

18 Horrobin, D.F. and Manku, M.S., Howdo polyunsaturates lower cholesterollevels?, Lipids 18: 558-62, 1983.

19 Erasmus, U., ibid.


Lipids

59Dietschy J. M. et al.; Measurement ofrates of cholesterol synthesis usingtritiated water; J. Lipid Res 25:1469-76.

60Petersdorf R Harrison’s Principles ofInternal Medicine 10 Ed McGraw-Hill,New York, NY 1983

61Robbins S.A. and Cotran R PathologicBasis of Disease; WB Saunders, NewYork, NY, 1974

62Kostner G,M, Zechner et al Theinteraction of human plasma lowdensity lipoproteins with glycosamino-glycans: Influence of the chemicalcomposition Lipids 21:24-8 1985

63McCully K.S. and Wilson R.B.;Homocysteine theory of arteriosclero-sis; Arteriosclerosis 22:215-27, 1975

64Levene C.I. and Murray J.C.;Theaetiological role of maternal B

6deficiency in the development ofatherosclerosis; Lancet 628-9 1977

65Lam S.C. et al.; Investigation of possiblemechanisms of pyridoxal 5'-phosphateinhibition of platelet reactionThrombosis Res 20:633-45, 1980

66Bendit E; The origin of atherosclerosis;Sci Am 236:74-85,1977

67Peng S.K. et al., Cholesterol oxidationderivatives and arterial endothelialdamage, Atherosclerosis 54:121-33,1985.

68Ross R. and Vogel A., The plateletderived growth factor, Cell 14: 203-10,1978.

69Turley S.D. and Dietschy J.M.,Cholesterol metabolism and excretion;The Liver: Biology and Pathobiologyed Arias I et al., Raven, New York pp.467-92 1982.

70Dietschy J.M. et al., Cholesterolsynthesis in the intestine of man:regional differences and controlmechanisms, J. Lipids Res. 8:97 1967.

71Dietschy J.M. et al., Cholesterolsynthesis in the squirrel monkey:relative rates of synthesis in varioustissues and mechanisms of control; J.Clin. Invest. 47:166-74 1968.

72Bhattathiry E.P. and Siperstein M.D.,Changes in plasma lipids andlipoproteins during isoretinoin therapyfor acne, N. Eng J. Med 313:981-851985.

73Dietschy, J.M. et al., Cholesterolsynthesis in the intestine of man:regional differences and controlmechanisms, J. Clin Invest. 50:872-80

74Lasser N.L. et al., Serum lipoprotein ofnormal and cholesterol fed rats, J.Lipid Res 14:1-8 1973.

75Weis H. J. et al., Failure of bile salts tocontrol hepatic cholesterogenesis:Evidence for endogenous cholesterolfeedback, J. Clin. Invest. 48:2398-24081969.

76Malinow, M.R., Alfalfa, Atherosclero-sis, 30:27-43 1973.

77Malinow et al., 2 Steroids 29:105, 1977.78Reddy B.S., Watanabe, K. et al., Effect

of dietary wheat bran, alfalfa andcarrageenan on cholesterol and fecalbile and neutral sterol excretion in rats,J Nutr 110:6 1247-54, 1980.

79Malinow M.R., Effects of syntheticglycosides on cholesterol absorption,Ann. New York Acad. Sci., Vol 454 23-27, 1985.

80Story, J.A., LePage, S.L. et al.,Interaction of alfalfa plants and sproutswith cholesterol in vitro and incholesterol-fed rats, Am. J. ClinicNutrition 39:6 917-29, 1984.

81Malinow M.R., Experimental models ofatherosclerosis regression, Atheroscle-rosis 48:2 105-18, 1983.

82Gujarak S, Bhumra et al., Effect ofginger (Zingiber officinale roscoe)oleoresin on serum and hepaticcholesterol levels in cholesterol fedrats, Nutr Rep Int 17:183 - 9, 1978.

83Srivastava K.C., Effects of aqueous ofonion, garlic and ginger on plateletaggregation and metabolism ofarachidonic acid in the blood vascularsystem: In vitro study, ProstaglandinsMed. 13:227-35, 1984.

84Nowell D.Y and Tarr R.S., Garlic,vampires and CHD Osteopath Ann 12:276-80, 1984

85Bordia A.K., Josh H.K. and SanadhyaY.K., Effect of garlic oil on fibrinolyticactivity in patient with CHD, Athero-sclerosis 28:155-9, 1977.

86Qureshi A.A., Burger W.C., et al.,Suppression of Cholesterogenisis byplant constituents, Lipids 20:11 817-824, 1984.

87Sodimu, O., Joseph, P.K., et al., Certainbiochemical effects of garlic oil on ratsmaintained on high fat high cholesteroldiet, Experienta 40:1, 78 - 80, 1984.

88Chi M.S. and Koh E.T., et al., Effects ofgarlic on lipid metabolism in rats fedcholesterol or lard, J. Nutr 112:2 241-248, 1982.



89Bordia A., Effect of garlic on bloodlipids in patients with coronary heartdisease, Am. J. Clin. Nutr. 3410 2100-03, 1981.

90Negulesco, J.A. and Younge, R.M.,Capsaicin lowers plasma cholesteroland triglycerides of lagomorphs,Artery 12:5 301-311, 1985.

91Wang J.P. et al., Antiplatelet effect ofcapsaicin, Thromb-Res 36:6, 497-507,1984.

92Jih-Pyang-Wang, et al., Antihemostaticand antithrombotic effects of capsaicinin comparison with aspirin andindomethacin, Thromb-Res 37:6 669-679, 1985.

93Guraka A. et al., Levels of LipoproteinsLp(a) decline with neomycin andniacin treatment, Atherosclerosis57:2-3, 293-301, Nov. 1985.

94Nagakawa Y., Orimo H., et al., Theantiplatelet effect of niceritol inpatients with arteriosclerosis and therelationship of the lipid-lowering effectto the anti-platelet effect, Thromb. Res.40:4, 543-53, Nov. 15 1985.

95Cohen M., Antihyperlipidemicproperties of beta-pyridylcarbinol. Areview of preclinical studies, Life Sci.37:21, 1949-61, Nov. 25 1985.

96Salonen J.T., Association betweencardiovascular death and myocardialinfarction and serum selenium in amatched-pair longitudinal study,Lancet 2: 175-79, 1982.

97Schone N.W., Morris V.C., et al., Effectof selenium deficiency on aggregationand thromboxane formation in ratplatelets, Fed. Proc. 43:477, 1984.

98Riales, R. and Albrink, M.J., Effect ofchromium chloride supplementation onglucose tolerance and serum lipidsincluding high-density lipoproteins ofadult men, Am. J. Clin. Nutrition34:2670 - 78, 1981.

99Offenbacher, E.G. and Pi-Sun yer,Beneficial effect of chromium-richyeast on glucose tolerance and bloodlipids in elderly subjects, Diabetes29:919-25, 1980.


Volatile Oils

7

The complex chemistry of volatile oils is offset by one of the most exciting areas ofherbology. We start by looking at the extraction of, and use of, a great array offragrances. The methods of manufacturing volatile oils can be as simple as waterdistillation, as exotic as secret formulas or as high tech as hypercritical carbondioxide. The recent reintroduction of aromatherapy will also be briefly looked at.The division of volatile oils will done on a chemical basis, splitting them into eightgroups. A wide number of botanicals are examined for their volatile oil effects.

Synopsis:

Volatile Oils



Table of Contents

List of Tables and Charts

Figure 7.1 Steam Distillation ProcessFigure 7.2 Anatomy of the Olfactory ProcessTable 7.1 Essential Oil QualitiesTable 7.2 Odour Intensity IndexTable 7.3 Volatility IndexFigure 7.3 α - pineneFigure 7.4 α - limoneneFigure 7.5 Isoprene StructureFigure 7.6 Divisions of Volatile OilsFigure 7.7 Biosynthesis of α-pineneTable 7.4 General Effects of Terpenoid

CompoundsFigure 7.8 HopsFigure 7.9 HumeleneFigure 7.10 Alcohols & PhenolsFigure 7.11 PeppermintFigure 7.12 Interchange of Peppermint

TerpenesFigure 7.13 BorneolFigure 7.14 JuniperFigure 7.15 1 - terpinen - 4 - olFigure 7.16 AldehydesFigure 7.17 CinnamonFigure 7.18 CitronellalFigure 7.19 KetonesFigure 7.20 Biosynthesis of thujoneFigure 7.21 Camphor

Cinnamon Citronella

Ketone Volatile Oils Biosynthesis of Terpene Ketones Camphor Spearmint Caraway Buchu Absinthe or Wormwood

Phenol Volatile Oils Thyme

Phenylpropane Volatile Oils Cloves Aniseed Fennel seed Nutmeg Sassafras

Oxide Volatile Oils Chenopodium Eucalyptus

Ester Volatile Oils Lavender Rosemary Bergamot Wintergreen

Mini-Materia Medica - Volatile Oils

Introduction Methods of Obtaining Volatile Oils

Water Distillation Water and Steam Distillation Direct Steam Distillation

Other Methods Effleurage Maceration Expression Solvent Extraction Hypercritical Carbon Dioxide

The Modern Use of Aromatherapy Anatomy of Aromatherapy

Table of Aromatic Herbs Odour Intensity Index Volatility Index

Division of Volatile Oils Hydrocarbon Volatile Oils

Cubeb Humulus or Hops

Alcohol Volatile Oils Peppermint Cardamon seed Juniper

Aldehyde Volatile Oils

Figure 7.22 CarvoneFigure 7.23 BuchuFigure 7.24 WormwoodFigure 7.25 PhenolsFigure 7.26 ThymolFigure 7.27 Phenylpropane Volatile OilsTable 7.5 Properties of Phenylpropane

derived Essential Oil ConstituentsFigure 7.28 ClovesFigure 7.29 EugenolFigure 7.30 AniseedFigure 7.31 AnetholeFigure 7.32 FennelFigure 7.33 OxidesFigure 7.34 AscaridolFigure 7.35 EstersFigure 7.36 RosemaryFigure 7.37 Linalyl Acetate


Volatile Oils

olatile oils, also called essential oils, are among the most interest-ing subjects for study in herbology. The essential or volatile oilswhich are found in herbs, or which emanate from plants throughV

the action of oxygen, form the basis of what many call “The Breath ofLife” -- the essence of the plant.

Volatile oils have been used therapeutically since the time of ancientEgyptian civilization. Widely used in both India and China, they continueto be an active part of herbology today. Volatile oils are the vibrationessence which underlie Bach Flower Remedies, the basis of the field ofaromatherapy and are employed for the treatment of our more subtle‘bodies’.

Volatile oils are the odorous principles found in various plant parts.Because they evaporate when exposed to the air at ordinary tempera-tures, they are called volatile, essential or ethereal oils. These oils haveentirely different chemical and physical properties from fixed oils. Mostof the volatile oils are colourless with a few minor exceptions (e.g.chamomile has a blue volatile oil), and are usually lighter than water.Volatile oils may occur in specialized secretory structures. The specificlocation varies according to the particular plant family. Examplesinclude oil-tubes called vittae (Umbelliferae), glandular hairs (Labiatae),modified parenchyma cells (Piperaceae) and in lysigenous orschizogenous passages (Penaceae, Rutaceae). They are frequentlyassociated with fertilization or protection in plants, acting as hormones,regulators and catalysts.

The environmental protection provided by volatile oils can be dramaticwhen seen in extreme climates such as the Arabian desert. Both myrrh

Introduction



and frankincense produce a thin cloud of essential oil around the plantto protect it from the strong sun. By filtering out the harmful rays andfreshening the surrounding air, the oil clouds affect the plant’s micro-environment. Volatile oils are also emitted from plants roots and aerialparts as selective pesticides, inhibiting the growth of competing plantsand preventing attack by damaging insects.

There is little doubt that scent has a practical role in plants much thesame as pheromones in the animal kingdom. Peter Tompkin and Christo-pher Bird in their book “The Secret Life of Plants” say the following:

Flowers that remain unfertilized emit a strong fragrancefor as many as eight days or until the flower withers andfalls, yet once impregnated the flower ceases to exude itsfragrance, usually in less than half an hour.1

The complexity of the chemistry of volatile oils is almost overwhelming.What we might consider a simple scent is made up of many chemicals.One of the most dramatic examples of this is the volatile oil of banana,which contains at least 350 compounds.2 The components also varyduring the day, as well as throughout the year. Of course, the parts ofthe plant involved, the variation within species, the local soil (substrate),and the current climatic conditions can also cause variations. Identifyingand controlling these variations is the task of herbal harvesters andmanufacturers. Clinical implications fall to the herbalist for detailedexamination.

There are several points of differentiation between volatile oils and fixedoils. The volatile oils can be distilled from their natural sources. They donot consist of glyceryl esters of fatty acids hence they do not leave apermanent grease spot on paper and cannot be saponified with alkalies.Volatile oils do not become rancid as the fixed oils do. In contrast, onexposure to light and air, volatile oils will oxidize and resinify (thereason why they are kept in dark, sealed containers). Volatile oils aresoluble in ether, alcohol and most organic solvents.

While the volatile oils are in the plant, the essences are constantlychanging their chemical composition, and often move from one part ofthe plant to another according to the time of the day or the season.When picking plants destined for oil extraction, the timing and weatherconditions are of great importance. The amount of volatile oil in a plantis often very small, varying from 0.005% to 10% of the plant. To obtainone pound of essential oil it takes 50 pounds of eucalyptus or lavandin,150 pounds of lavender and 500 pounds of sage, thyme, or rosemary. Ittakes two to three thousand pounds of rose petals to produce one poundof rose oil!


Volatile Oils

Figure 7.1The Steam Distillation Process

Methods of obtaining volatile oils

Volatile oils are usually obtained by distillation of the plant parts con-taining the oils. There are three major methods of distillation:

1. Water Distillation2. Water and steam3. Direct steam

A few other methods will be briefly discussed after distillation.

Water Distillation

This method is used with herbs that contain volatile oils which areprimarily terpenic. The dried material is put into a distilling chamberand heated until all volatile matter (both oil and water), is condensed inthe condensing chamber. These oils are not affected by heat.

Water and Steam Distillation

This is the method employed when the oil can be injured by boiling. Thedried or fresh herb is covered with a layer of water and steam is passedthrough the macerated mixture. The steam is generated in other cham-bers to ensure the water temperature does not rise to the boiling point.The oil floats to the surface and is separated, often undergoing furtherprocessing.

vaporizedwater &essential oils

CondensationChamber

FlotationChamber

Floral waters

EssentialOils

Steam

Water Plantmaterial



Direct Steam Distillation

The method is applicable to fresh plants (peppermint, spearmint). Theplants are taken directly to the distilling chamber where they aresuspended on a grid (a wire basket or similar container).

Since the plant material is still green and contains considerable mois-ture, no maceration is necessary. The steam is forced through the freshherb carrying the oil droplets to the condensing chamber.

Other Methods

Other common methods employed in the preparation or extraction ofthe volatile oils are:

1. Effleurage2. Maceration3. Expression4. Solvent Extraction5. Hypercritical carbon dioxide

Effleurage: Both effleurage and maceration depend on the physical factthat fat will absorb essential oils. Animal fat is specially prepared(usually by a secret method). The cold fat is used with plants thatcontinue to generate volatile oils after they have been harvested (e.g.jasmine). The herb is soaked in the fat, the volatile oils are absorbed intothe prepared fat oil, then a new layer of herb is introduced until as muchas possible is absorbed. The mixture is then agitated and mixed withalcohol with the volatile oil transferring to the alcohol. The alcohol isthen evaporated.

Maceration: In this method the plants are plunged into hot fat immedi-ately after harvest. The flower parts are then separated by centrifuge orby straining. This process is repeated until saturation is obtained. Thenthe same alcohol method is employed as in effleurage.

Expression: The oils of the citrus family are extracted this way. The oilglands are punctured by a series of sharp projections on rollers and theoil is then squeezed out of the rind.

Solvent Extraction: The solvents usually employed are petroleum,ether, benzene or acetone. The plant material and solvent are heatedand the volatile oils are transferred to the solvent. The impregnatedsolvent is then filtered, leaving a paste behind containing the volatile oiland wax. This is further agitated in alcohol to cause the volatile oil totransfer to the alcohol. When the alcohol evaporates the volatile oil


Volatile Oils

remains. This technique is not used for aromatherapy because somesolvents are left behind, which is not acceptable for the subtle purposesinvolved in this medical discipline.

Hypercritical carbon dioxide: This very new method is likely to havegreat promise in the future. It is first important to understand whathypercritical carbon dioxide is. Substances usually can exist in one ofthree states: gas, liquid or solid, depending on temperature and pres-sure. Water can be ice, a liquid or steam. Some substances can reach ahypercritical state -- in which they are neither liquid nor gas, but behaveas both. Hypercritical substances have solvent properties (see Chapter12 on Herbal Manufacturing).

Carbon dioxide (a relatively inert gas found in the air we breathe) canbecome hypercritical at 330C (slightly above room temperature) whenunder high pressure. Hypercritical carbon dioxide acts as a greatsolvent of volatile oils. This relatively low temperature operationabsorbs volatile oils in only a few minutes but doesn’t change thechemistry of the volatile oil. To remove the solvent all that is necessaryis to remove the pressure, so no residue is left behind. The wholeprocess takes place in a closed chamber in which nothing is lost. Thisgives the purest fragrances yet known.

The major drawback is the extreme pressure, 200 times atmosphericpressure. This, in turn, means very strong and expensive stainless steelcontainers and a high level of technical sophistication during theprocess.

The Modern use of Aromatherapy

Before we go through many of the medicinal, chemical and industrialuses of the various volatile oils, we should mention a bit about some ofthe revolutionary ways they are presently being used.

Aromatherapy employs the various scents that are obtained from thevolatile oils externally (in massage oils, bath water, humidifiers, vaporiz-ers, diffusors, etc.). Each of the various scents has different healingattributes. The healing is said to be done by the scent, which works onour ‘higher’ bodies realigning them with the forces of nature. By puttingthe person in a natural equilibrium through scent, problems in thephysical tissue are ameliorated.

Aromatherapy often includes internal uses also. Some of the mostspecific actions of aromas are said to be on the mind. A great deal ofevidence in this area, both physiological as well as empirical, is begin-ning to appear.



Anatomy of Aromatherapy

The sense of smell has long been known to have links to the subcon-scious, capable of triggering memories and powerful emotions. Theolfactory nerves are connected directly to one of the most primitiveparts of the brain, the limbic system, also called the reptilian brain. Wemight say that the sense of smell is a direct extension of the brain itself.This is the most open gateway to the brain. The limbic system regulatesthe sensomotor activities dealing with sex, hunger and thirst. Stimulationof the olfactory bulb sends signals directly to the limbic system affectingdigestion, sexual and emotional behavior. It is interesting to note that thebrain’s electrical response to odour is the same as its response toemotions.

It is well established that a person exposed to an odour over a period oftime will stop observing it or become “blind” to the smell. The electricalresponse of the brain still continues to register it at the same levelhowever. This gives the impression that these scents are being regis-tered at an other-than-conscious level only. This effect has been shownto affect hormone levels. According to D. M. Stoddart in Perfumery: ThePsychology and Biology of Fragrance:3

“The hypothalamic region is a major receiver of olfactoryneurones, and releases a variety of hormones which passto the anterior pituitary via the hypophyseal portalsystem, and induces the pituitary to secrete the suite ofhormones which governs and controls the mammaliansexual cycles.”

The validity of this information can be seen in many ordinary physiologi-cal functions. An example is the series of experiments developed tounderstand the synchronization of menstrual periods in girls’ boardingschools. Apparently it is caused by unconscious scent messengers calledpheromones. The unconscious scent of other women’s estrous cycle,stimulate a synchronicity. Similarly, it has also been shown that kinder-garten children can accurately find their own mother’s dirty T-shirtamong many, in a very short time. Researchers propose that thispheromone signal is one of the mother-child bonding mechanisms.

We can, of course, find many other more dramatic examples of thisamong other mammals. Most researchers feel that pheromones are themajor form of communication among lower mammals.

It is not the purpose of this book to investigate aromatherapy since thereare a range of books and courses which offer greater detail and clinicalapplications. Nonetheless, the role of the volatile oils is likely to havegreater impact on the modern natural healing arts in the next decadethan virtually any other category of phytochemical.


Volatile Oils

There are many different approaches to aromatherapy now developing. Ihave included one approach for interest’s sake, that of Robert Tisserandand his followers. Tisserand applies the volatile oils often based on theyin-yang qualities, astrological rules (from Culpepper’s famous herbal),the index of evaporation (between 1 - 100; 1 very high, 100 very low) andthe odour intensity (developed by Louis Appell) between 1-10 (4 beinglow intensity, 7 medium, 10 very intense). I have included a few charts sothat you can see the different attributes of the most commonly used oilsin aromatherapy.

If you have an interest in the subject, The Art of Aromatherapy4 by RobertTisserand, Aromatherapy: an A-Z5 by Patricia Davis or The Handbook ofAromatherapy6 by Marcel Lavabre will give you an excellent overview. Ifyou need greater detail about specific plants and their volatile oils, onecan’t go wrong with the “tough-to-find” Perfume and Flavor Material ofNatural Origin7 by Steffen Arctander.

Figure 7.2Anatomy of the Olfactory Process

Olfactory Bulb

OlfactoryMucosa

Supporting cells

Receptor cells

Mucosal microvilliCilia

Basal cells

To Limbic System,hypothalamus and

pituitary

To Olfactive cortex,thalamus and neocortex

↑↑



Odour Evaporation RulingEssential Oil Intensity Rate Quality Planet

Basil 7 78 Yang MarsBenzoin 4 100 ? Yang SunBergamot 4 55 Yang SunBlack pepper 7 60 Yang MarsCamomile 9 47 Yin MoonCamphor 5 ? Yin SaturnCardamon 9 68 Yang MercuryCedarwood 4 97 Yang JupiterClary sage 5 82 Yang MercuryCypress 4 30 Yin SaturnEucalyptus 8 5 Yin SaturnFennel 6 85 Yang MercuryFrankincense 7 75 Yang SunGeranium 6 87 Yin VenusHyssop 6 65 Yang JupiterJasmine 7 95 Yang JupiterJuniper 5 30 Yang JupiterLavender 4 85 Yang MercuryMarjoram 5 40 Yang MercuryMelissa 4 ? 17 Yang JupiterMyrrh 7 100 ? Yang SunNeroli 5 79 Yang SunPatchouli 5 100 Yang SunPennyroyal 7 86 Yang MercuryPeppermint 7 70 Yang MercuryRose 7 99 Yin VenusRosemary 6 18 Yang SunSandalwood 5 100 ? Yang UranusYlang-Ylang 6 91 Yin Venus

Table 7.1Essential Oil Qualities

For the purposes of our inquiries, the volatile oils which are used byaromatherapy can be subdivided according to the biochemical struc-ture. Once again, approaching the substances from this perspective canprovide the herbalist with a clearer perception of their nature.

Source: Tisserand, Art of Aromatherapy


Volatile Oils

ODOUR INTENSITY INDEX

4 Benzoin 7 BasilBergamot Black pepperCedarwood FrankincenseCypress JasmineLavender MyrrhMelissa ? Pennyroyal

PeppermintRose

5 CamphorClary sageJuniper 8 EucalyptusMarjoramNeroli 9 CamomilePatchouli CardamonSandalwood

6 Fennel RosemaryGeranium Ylang-YlangHyssop

Table 7.2Odour Intensity Index

Volatility Index

5 Eucalyptus 82 Clary sage18 Rosemary 85 Fennel30 Cypress 85 Lavender30 Juniper 86 Pennyroyal40 Marjoram 87 Geranium47 Camomile 91 Ylang-Ylang55 Bergamot 95 Jasmine60 Black pepper 97 Cedarwood65 Hyssop 99 Rose68 Cardamon 100 Patchouli70 Peppermint 100 Benzoin ?75 Frankincense 100 Myrrh ?78 Basil 100 Sandalwood ?79 Neroli

? - presumed value

Table 7.3Volatility Index

Source: Tisserand, Artof Aromatherapy

Source: Tisserand, Artof Aromatherapy



Division Of Volatile Oils

The largest group of components found in volatile oils are terpenes andterpenoids. Monoterpenes are isomeric hydrocarbons having themolecular formula of C 10H16. Two closely related compounds are sesquit-erpenes C 15H24 and diterpenes C 20H32. The two most common terpenesare limonene and pinene. Limonene is the most widely distributedmonocyclic terpene.

As can be seen, in Figure 7.5 the carbons in terpenes are in multiples of5. This is called the isoprene structure and is very functional as abuilding unit of many essential oils, sterols, alkaloids, pigments, cardiacglycosides, etc. It should be noted though that these structures are the“skeleton” only and that often the functional groups give the individualproperties, both in living plant physiology and in therapeutic use. Theactive ingredient of a volatile oil often isn’t the most common by weightor volume. The most active functional group or often the most uniquegroup of ingredients can have the biggest impact.

The isoprene or isopentanes often arrange themselves in a head-to-tailconfiguration although there are exception to the rules. There areterpenoids with higher numbers of isoprene units than two - four. These30 and 40 carbon units are much too heavy to make up components of avolatile oils though. Some of these same constituents were discussedunder saponins in Chapter 4, while others will be discussed in Chapter 8(Resins) and Chapter 9 under steroidal compounds.

Both cyclic and open-chain compounds can be found amongst thevolatile oils, almost every possible arrangement it seems. With oxygen-ation of terpene hydrocarbons we get the presence of the functionalgroups. The word “terpene” is usually used for specific hydrocarboncompounds, while the word “terpinoid” is used for any compound that ismade up of isoprene units, regardless of the functional groups present.The properties of the essential oil is determined partly by the structure(mono-, sesqui-, diterpene) and mostly by the functional group.

Figure 7.3α− pinene

Figure 7.4α - limonene

↑

↑


Volatile Oils

O

C O

H

C

O

C O

Ketones

Aldehydes

Esters

Alcohols &phenols Ethers Oxides

As stated earlier, volatile oils are very complex mixtures of manycomponents, often made up of many types of functional groups in thesame compound. In our discussion of volatile oils we will, where pos-sible, place most volatile oils in one of the following groups:

1. hydrocarbon 5. phenol2. alcohol 6. phenolic ester3. aldehyde 7. oxide4. ketone 8. ester

Hydrocarbon volatile oils

These unoxygenated terpene hydrocarbons occur in practically allvolatile oils, and can be found in the monoterpenes, sesquiterpene andditerpenene structures. Limonene, as stated earlier, is the most commonin this group, found in citrus fruits as well as caraway. Other importantmonocyclic terpenes are terpinolene (coriander), α-terpinene (corian-der, origanum and cardamom oil), phellandrene (fennel and eucalyptusoil). Dicyclic (still monoterpenes) are pinene (conifers), sabinene (savin

CH2

CH2 CH CH2 CH2

Figure 7.5Isoprene Structure

Figure 7.6The Divisions of Volatile Oils

C O C C O CC OH



oil) and thujone. Typical sesquiterpenes are cadinene (cubeb oil),selinene (celery oil) and zingiberene (ginger oil).

The biosynthesis, of most volatile oils is not known. One of the hydrocar-bons, alpha-pinene (from pines) is understood (Figure. 7.7) It is assumedthat this same pathway, involving geranyl pyrophosphate and a monocy-clic intermediate, (responsible for the production of α-pinene) is similarto compounds in many plants.

Pinene has an interesting attribute. It is felt by many that the lowermonoterpenoids have stronger “ecological” effects than purely physi-ological. Many mono-terpenoids inhibit the growth of other competingplants and have insecticidal or toxic effects on higher animals. TheDouglas Fir beetle (Dendroctonus pseudotsugae) is attracted to α-pinenebut repelled by β-pinene.

Even though many consider the hydrocarbon terpenes rather insignifi-cant, definite medicinal activity is found in this group. Some, like pine oil,have been shown to be externally antiseptic once aged (and thusoxidized). Others have been thought to be skin or mucous membraneirritants. Limonene, α-sabinene and γ-terpinene reportedly possessantiviral properties.

Limonene can be found in 90% of citrus oils, bergamot and turpentine.Pinenes can be found in black pepper, pine oil (and other conifer oils),turpentine, nutmeg, mastrick and angelica. Table 7.4 gives the activity ofmono-, sesqui- and diterpenes.

Figure 7.7Biosynthesis of α - pinene

CH2 O PP

α - pineneGeranylpyrophosphate

Intermediate

↑

↑

↑↑


Volatile Oils

General Effects of Terpenoid Compounds

Activity Monoterpenes Sesquiterpenes Diterpenes

Anesthetic +Analeptic + +Analgesic +Anthelmintic + +Antiarrythmic +

Antibiotic (bact/fungi/viral) + + +Antiepileptic +Antihistamine +Antiinflammatory/Antiphlogistic + +Antirheumatic +

Antitumour + + +Choleretic/Cholagogue +Diuretic +Expectorant + +Hypotensive + + +

Insecticidal + +Irritant + +Juvenile hormone +Pherome + +Phytohormone +

Purgative + +Sedative + +Spasmolytic + +Toxic + +Vitamin +

Table 7.4General Effects of Terpenoid Compounds

When we move into the larger sesquiterpenes we find that sheer gravityof the shape and structure seems to have quite an effect, compensatingfor the lack of functional groups. Current research suggests that theimmune-stimulating properties of sesquiterpenes are detectable. Therehas been relatively little research into the physiological properties andmodes of action of sesquiterpenes considering that over 2000 types havebeen isolated.

Source: Lavabre, Aromatherapy Workbook



Some botanicals that are composed chiefly of hydrocarbon volatile oilsare cubeb, black pepper, pine (turpentine) and humulus.

Cubeb Piper cubeba

Cubeb or cubeb berries are the dried, nearly full-grown, unripe fruit ofPiper cubeba. They contain 18% volatile oil which yields di-sabinene,carene, cineol, terpene alcohols, cadinene and other sesquiterpenes.8

The plant also contains 1-3.5% cubebic acid. It is used as a stimulant,carminative, expectorant and diuretic. Cubebic acid causes stimulationof the kidneys, increasing urination. Cubeb has long been considered aremedy for gonorrhea.9

Humulus / Hops Humulus lupulus

The herb is the dried strobile of Humulus lupulus. This perennial herba-ceous climbing plant can be found in most parts of the world growingwild. It is also cultivated for its use in the brewing of beer. 10 - 16 Hops’major constituents are .03-1% humulene (a sesquiterpene volatile oil),lupulinic acid and 10% lupulon (lupulin).17- 20

Hops is used medicinally as a tonic, nervine, diuretic and anodyne. Thevolatile oils in hops seem to have little physiological effect but lupulinacts as a sedative. This is why hops is considered such a good nervine.Hops is also often used in stomach tonics, calming down the stomachand reducing acidity, especially in the duodenum. Lupulin can inducesleep without headache.

Figure 7.8Hops

Figure 7.9Humulene

Sc2

Mo2


Volatile Oils

Alcohol volatile oils

This terpenoid category occurs when an oxygen attaches itself to aterpene through the single bond of an hydroxyl group (-O-H, usuallyfrom water). Some of the most important alcohol terpinoids are lanalol,menthol, citronellol, borneol, santalol, geraniol and nerol. These alcoholterpenoids are some of the most active volatile oils and are especiallyused in aromatherapy. Alcohol terpenoids are reported to be generallyantiseptic, with a scent that is considered to be positively energizing.

Chemical Found In

Linalol Lavender, rosewood, petitgrain, neroli and coriander oils.

Citronellol Rose, geranium oils.Geraniol Palmarosa oil.α-terpineol Eucalyptus and niaouli.Terpineol-4 Tea tree, garden marjoram, juniper oils.

Some other important botanicals which contain this family of volatile oilsare peppermint, cardamon, coriander, sandalwood, rose, orange flowers,juniper and pine.

Peppermint Mentha piperita

This is one of the best known of the alcohol volatile oils. The volatile oilcomes from Mentha piperita. Mentha is from the Greek Mentha, the nameof a mythical nymph who metamorphosed into this plant, piperita isLatin for pepper, alluding to the aromatic and pungent taste of pepper-mint.

The perennial herb is indigenous to Europe and has naturalized in thenorthern United States and Canada. The main constituents of pepper-mint are: 0.7-1.5% volatile oil and 6-12% tannin. The volatile oil is mainlymade up of menthol (50-60%), menthyl acetate, menthyl isovaleranalmenthane and several other terpene volatile oils. Figure 7-2 shows howmany of the terpenes in peppermint change into each other.

Figure 7.10Alcohols & Phenols

C OH

Sc2

Mo2



Because of menthol’s (C10H19OH) importance, it is usually purified fromthe mint plant. Japanese mint (Mentha arvensis) contains a higherproportion of menthol (70-90% of the volatile oil) and is therefore mostoften used commercially. The volatile oil is refrigerated to -22.2 degreesC at which point menthol crystallizes. The rest of the oils are poured offas a liquid. The menthol is then repurified.21,22

The therapeutic properties of peppermint include carminative, stimu-lant, nervine, antiseptic, antispasmodic, diaphoretic and antibacterial.The oil and menthol are used for headache, rheumatism, neuralgia,toothache, earache and laryngitis. Topically, menthol has been used asan antipruritic on skin or mucous membranes, as a counterirritant, anantiseptic and a stimulant. It has also been used internally as a depres-sant for the heart.

The particular tannin in peppermint has been used to suppress theactivity of influenza virus. It has been shown experimentally to suppressviral action when injected into eggs and has been successful in defeatingHerpes simplex virus. These experiments performed at the Mayo Clinicresulted in the conclusion that peppermint was “a potent inhibitor ofdisease viruses” and manifested strong antiviral activity.

In aromatherapy, peppermint is recommended for asthma, bronchitis,cleansing, decongesting, insect repellent, migraine, sinusitis, brainstimulation and mental fatigue.

Figure 7.11Peppermint


Volatile Oils

O

peritenone

OO

Piperitone Menthone

OH

Menthol

O

O C CH2

Menthyl acetate

OO

Figure 7.12Interchange of Peppermint Terpenes

Figure 7.13Borneol

Menthofuranpulegone

Cardamon Seed Ellettaria cardamomum

The herb is the dried, ripe seed of Ellettaria cardamomum. Elettaria is thenative name of the plant in Malabar, cardamomum is the ancient classicalname for the spice.

The seed contains 2-8% volatile oils; 10% fixed oils, potassium salts,nitrogenous mucilage, acrid resin and starch. The volatile oil containsthe terpene alcohol borneol, plus limonene, cineole, d-alpha terpineoland terpinyl acetate. Cardamon is used as a carminative, stimulant, andaromatic but is rarely used alone. The seed is helpful for indigestion,flatulence and colic. The volatile oil is also a mild membrane irritantwhich makes it useful as a carminative.23 In aromatherapy the plant isused as an antiseptic, stimulant, to remove the smell of garlic and topromote digestion.

H3C C CH3

OH

CH3

↑↑

↑

↑

↑ ↑

↑



Juniper Juniperus communis

This botanical comes mainly from the berries of Juniperus communis .The constituents of the dried fruit contain 0.5-2% volatile oil and about10% resin, 33% sugar, tannin and a flavone glycoside. The highestcontent of volatile oil is found in the fully grown but not fully ripe berry(it takes two years to ripen). When the fruit ripens the volatile oil(obtained by steam distillation) contains 1-terpinen-4-ol, α-pinene,camphene and cadinene. The oil of juniper is given as a diuretic, sto-machic and carminative in indigestion, flatulence and diseases of thekidney and bladder. Large doses of oil of juniper can be an irritant tokidneys especially if they are inflamed. The berry as a whole does nothave the effect and is considered an excellent diuretic and antiseptic,helping to dissolve kidney stones and soothing the kidney. Marshmallowroot usually accompanies juniper berries in herbal formulas for thekidneys because of its demulcent properties.

In aromatherapy, the uses are dermatitis, eczema, acne, detoxification,poor memory, nerve tonic and fatigue.

Aldehyde volatile oils

Aldehyde terpenoids, as can be seen in figure 7.16 , have a double-bonded oxygen and a hydrogen attached to a carbon. This of coursemeans that the carbon cannot be in the middle of a chain but must be anend carbon. Some common aldehydes terpenoids are citral, citronellal,neral and geranial. We can find monoterpenoids in the oil of melissa(Melissa officinales), lemongrass, citronella, lemon verbena (Lippiacitriodora) and eucalyptus. Other herbs that contain aldehyde terpe-

OH

Figure 7.151 - terpinen -4 -ol

Figure 7.14Juniper

Ed

Sc2

Mo2


Volatile Oils

H

C

O

Aldehydes

noids are cinnamon, sweet orange peels, bitter orange peels, lemonpeels and bitter almond oil. Biosynthesis of aromatic aldehydes such asbenzaldehyde and vanillin starts with phenylpropanoid precursors,which were discussed in Chapter 4 (Glycosides).

Research on citronellal in Eucalyptus citriodora indicates that the terpenealdehydes derive from acetate metabolism. Most aldehyde volatile oilshave sedative activity. Citral has strong antiseptic properties.

Cinnamon Cinnamomum spp.

This herb comes from the dried bark of the Cinnamomum species,particularly C. loureirii, C. zeylanicum and C. cassia. We can find cinna-mon in literature, used for its medicinal properties as early as 2700 B.C.in Chinese herbals and in the book of Moses, by ancient Greeks. It hasbeen cultivated in Ceylon (Sri Lanka) since 1200 A.D.

C. Loureirii (Saigon Cinnamon) yields 2-6% volatile oils. C zeylanicum

Figure 7.16Aldehydes

Figure 7.17Cinnamon

(Ceylon Cinnamon) contains 0.5-1% ofvolatile oils. C. cassia (Cassia cinna-mon) yields 0.5-1% volatile oils. Otherconstituents include tannin (3-5%) andmannitol (which gives its sweet taste).

In Oil of Cinnamon, the major compo-nent is 80-95% cinnamic aldehyde(C7H8O), the remainder consists ofterpene and other compounds. Cin-namic aldehyde will oxidize into a resinand cinnamic acid (C9H8O2). Furtheroxidation changes it to benzoic acid.The oil should therefore be stored in awell-filled, tight, light-resistant con-tainer in a cool place.

The therapeutic properties of thesimple bark are carminative, sto-machic, stimulant, astringent, hemo-static, aromatic, antispasmodic,

Sc2



antiseptic, germicide and parturient. The oil has the same medicinalvalues but is much more powerful in all respects except that it has noastringent value. As a stimulant it works more as a local stimulant thansystemic. It is most often used in digestive problems. Cases of nausea,vomiting (especially during pregnancy) and excessive flatulence alsocall for this herb. As a parturient it is often combined with dolomite toaid in delivery and to stop hemorrhage of the womb.

In aromatherapy, it is used for coughs and irritation of respiratory tractand snake bites.

Figure 7.18Citronellal

CHO

Citronella Andropogon nardus

Andropogon nardus, the major variety, is widely cultivated in Sri Lanka,Indonesia, Florida and Central America.

Citronella Oil’s major constituent can also be obtained from Eucalyptuscitriodora. It is a yellowish green volatile oil containing chiefly d-citronel-lal and geraniol. It is quite valuable when applied to exposed areas andclothing as a protective agent against mosquitoes, black flies, “no see-ems” and similar insects. The volatile oils seem to act as an irritant ininsect stomata, dissuading them from landing on the plant.

Although oil of citronella is effective because it is so volatile, it is betterused in some sort of suspension. The best generally used is pine tar(also protective against insects) with the oil of pennyroyal. This mixtureis effective against even the strongest attack of mosquitoes. Citronella isalso quite effective as a “yard pesticide” by adding it to the wax in themaking of candles and burning them when mosquitoes are around.


Volatile Oils

Ketone volatile oils

Ketone terpenoids occur when oxygen atoms attach themselves to acarbon (Figure 7.19) in a carbon chain. This is called a carboxyl group.We can divide ketones occurring in volatile oils into:

(a) monocyclic terpene ketones - examples are menthone (pennyroyal,peppermint); carvone (spearmint, caraway); piperitone (eucalyptus);pulegone (hedeoma) and diosphenol (a crystalline ketone in buchu).

(b) dicyclic ketones - including 2-camphenone (camphor) and thujone(thuja, tansy, wormwood and sage).

(c) non-terpene ketones such as irone (violet, orris root).

C O

Figure 7.19Ketones

Figure 7.20Biosynthesis of Thujone

HOOC

HOOC

Mevalonate - 2- 14C

O O

Intermediate Thujone

Biosynthesis of terpene ketones

Thujone has been shown to be derived from mevalonate or acetate. Themost important botanicals in this group are camphor, spearmint, cara-way, buchu, absinthe, American pennyroyal, orris root and tansy. Inaromatherapy, ketones have been used extensively to ease and increaseflow of mucus and in skin care preparations (cytophylactic). Manyketones are neurotoxic when taken internally. This is true of pulegone inpennyroyal, and thujone in mugwort, sage and thuja.

ThujoneAcetate - 1 - 14C

CH3COOH↑ ↑ ↑ ↑



Camphor Cinnamomum camphora

Camphor (2-Bornanone) is a ketone obtained from Cinnamomumcamphora. Camphora is from the Arabic kafur, meaning chalk. The largeevergreen tree is indigenous to eastern Asia and naturalized in theMediterranean, Sri Lanka, Egypt, South Africa, Brazil, Jamaica, Floridaand California. Natural camphor is usually substituted with syntheticcamphor on the North American market.

The purified camphor found on the market consists entirely of thesaturated ketone, C10H16O. As you might remember, borneol, found incardamon seeds is very similar.

Camphor is used topically as an antipruritic and antiseptic. It is oftenmixed with other herbs as an aromatic decongestant.

Spearmint Mentha spicata

Mentha spicata or M. viridis. Spicata refers to the flower which forms inspikes. Spearmint closely resembles peppermint but the stems areusually more purple, the leaves sessile, the inflorescence a spike. Themajor constituent of spearmint is a volatile oil containing carvone. Themedicinal uses of spearmint are similar to peppermint but much milder.It is therefore often used as a remedy in children’s ailments.

CH3

Figure 7.21Camphor

O

Figure 7.22Carvone

O

H3C

H3C C CH3

CH3

CCH2

Mo2


Volatile Oils

Spearmint oil contains not less than 55%, by volume, of carvone(C10H14O). It also contains alcohols, esters and terpenes, chiefly l-li-monene, l-phellandrene and l-pinene. The carvone present is l-carvoneand is optically isomeric with d-carvone forms in caraway and oil of dill.The oil is also used as a carminative, stimulant and antispasmodic.

Caraway Carum carvi

This botanical comes from the dried, ripe fruit of Carum carvi. It contains5-7% volatile oils; 20% fixed oils; protein and calcium oxalate. These

Figure 7.23Buchu

Figure 7.24Wormwood

seeds can be used as an aromatic,mild stimulant and carminative. Thevolatile oil is 50-60% d-carvone and 40-50% d-limonene. The oil at one timewas used quite extensively as carmi-native, a tonic stomachic and fordyspepsia.

Buchu Barosma betulina

Buchu, Barosma betulina, is indig-enous to South Africa. Buchu containsa volatile oil with about 30%diosphenol (buchu camphor). It alsocontains a glycoside called diosmin,which is closely related to hesperidin,a bitter extractive, resin, tenthane andmucilage. Buchu acts as a diuretic andurinary antiseptic (diosphenol givingit antiseptic action). Buchu also isknown to dissolve excess uric acidcrystals, thereby reducing bladderand urinary tract irritation. Buchu isalso a specific for prostate infection.

Absinthe or WormwoodArtemisia absinthium

Artemisia absinthium contains l-thujone and d-isothujone, both knownto be toxic. Wormwood also containsthujol alcohol and phellandrene. InWest Germany, Glatzel andHackenbery have shown that worm-wood is a good digestive aid, inspiringgastric secretion along with bilesecretions. Herbalists have used

Sc2

Mo2

Ed

Sc2

Mo2



wormwood for centuries as a vermifuge, tonic and haemostatic. Asmentioned earlier, pennyroyal, orris root and tansy contain this group ofvolatile oils.

OH

Figure 7.25Phenols

Phenol volatile oils

When an alcohol hydroxyl group attaches to a benzene ring, it is called aphenol. The most important volatile oils in this group are eugenol,thymol and carvacrol. Eugenol occurs in clove oil, allspice oil and a fewother oils. Thymol and carvacrol occur in thyme oil and monarda oil.Some other important herbs in this group are myrica oil, birch tar,creosote pine tar and juniper tar.

These chemicals are strongly electropositive resulting in a very activechemistry. This gives some phenols, like thymol or carvacrol, strongantibacterial properties. This same property can also make these oilsirritant so they should be used in low concentrations.

Thyme Thymus vulgaris

The dried leaves and flower tops of Thymus vulgaris yield the highestquantity of volatile oil. Thymus comes from the ancient Greek meaning tosacrifice, alluding to its sweet odor, vulgaris is Latin for common. Thissmall evergreen shrub is indigenous to Spain and Italy and is presentlybeing extensively cultivated in Germany, France and England and to alesser degree in the United States. Thyme contains 1-2.6% volatile oil,resin, tannin and gum. It is used mostly as a flavoring and carminative.

Thyme oil largely contains thymol with small quantities of carvacrol.The oil can be used as an antiseptic, antispasmodic and carminative likemost volatile oils.

Thymol is obtained from thyme oil or often from oils of Monarda punctata(horsemint oil). It is obtained by freezing and crystallizing the oil.Thymol is antifungal and antibacterial in nature and is used in somelotions and ointments for this reason. The ointment usually contains 0.1-1% thymol.

In aromatherapy, thyme is used as a general stimulant, for pulmonarydisease, arthritis, hair loss, brain stimulation, for neurasthenia, depres-sion and fatigue.


Volatile Oils

Phenylpropane volatile oils

Phenylpropanes are made up of “aromatic” phenyl rings with a propane(three carbon) side chain (Figure 7.27). Some of the most pharmacologi-cally active molecules have a double bond in the side chain, causing a pi-electron interaction with the aromatic ring. The biosynthesis is differentfrom the terpenoids. These oils are often strongly antiseptic, with skinirritating qualities. Eugenol, from cloves is antiseptic and fungicidal,showing local anesthetic qualities and because of this is still used indental treatment.

Some other important phenylpropanes are anethole from anise andfennel, safrole from sassafras, camphor oil, myristicin from nutmeg andparsley, apiol from parsley and East Indian dill. (see Table 7.5).

Cloves Eugenia caryophyllus

Cloves are obtained from the dried flower bud of Eugenia caryophyllus.Eugenia from Latin and caryophyllus from Greek, combinging to mean“nut-leaf” and refering to the nutlike flower bud. The word cloves itselfcomes from the Latin clavis, a nail, refers to the shape of the whole spice.

Figure 7.26Thymol

OH

O

O

CH2 CH CH2

O

O

CH2 CH CH2

O

O

CH2 CH CH2

Figure 7.27Phenylpropane Volatile Oils

H3COH3CO

OCH3

Mo2

ApioleMyristicinSafrole



Phenylpropane Activity Property Source

Eugenol Antiseptic ClovesCinnamic aldehyde Stimulant Cinnamon

skin irritantsAnethol Increase

secretion AniseedMethylchavicol Expectorant Basil, TarragonSafrole, myristicin,

apiole Diuretic Saffron, Nutmeg,Spasmolytic Parsley.Abortive (apiole)CNS stimulantHallucinogenic (myristicin)

Table 7.5Properties of Phenylpropane Derived

Essential Oil Constituents

Cloves grow on trees fifteen meters in height, are indigenous to theMolucca Islands, but are presently being cultivated on the islands ofPenang, Ambon, Pemba, Zanzibar, Sumatra and Madagascar as well as inthe West Indies. Cloves are ground and mixed with tobacco and smoked.Sixty-five percent of the world’s crop is consumed this way, mostly inIndonesia.

The major constituents are 14-20% volatile oil, gallotannic acid (10-13%),oleanolic acid, vanillin and the chromone, eugenin. Cloves are consid-ered to be the most stimulating and carminative of all aromatics. Cloveoil is the volatile oil distilled with steam from the dried flower buds. Itcontains 85% by volume phenolic substances, chiefly eugenol. It iscarminative and antiseptic, but its major use is on toothaches, where it isapplied topically to the dental cavity to relieve pain.

Figure 7.28Cloves


Volatile Oils

Aniseed Pimpinella anisum

Pimpinella anisum is the source of anise. Pimpinella is Latin meaning two-winged, referring to the bipinnate leaves, anisum is the old Arabic namefor anise. Anise is one of the oldest known medicines to the Westernworld. It was mentioned by Theophrastus, Dioscorides and Pliny in theirwritings. Anise contains 1-3% of volatile oil, consisting of about 80-90% ofanethole; fixed oils (up to 30%), proteins and sugars. This botanical isused mostly as a flavoring agent but also has a role as a carminative.

Anise oil comes from Pimpinella anisum or Illicium verum (Chinese StarAnise Oil). This oil, 80-90% anethole, is used as a flavoring agent, carmi-native and pectoral. It is used often for a hard, dry cough where expecto-ration is difficult. Star Anise oil is also slightly diuretic.

It should be noted here that Japanese Star Anise (Illicium religiosum) isextremely poisonous and looks very similar to Chinese star anise. Thetaste is extremely pungent.

Figure 7.29Eugenol

CH2 CH CH2

OCH3

OH

Eugenol (4-Allyl-2-methoxyphenol) is classed as a dental analgesic,applied topically and as a dental protective. Eugenol is also consideredone of the most powerful germicides known (even more powerful thanbichloride of mercury). In aromatherapy, clove is considered antisepticand is used for impotency, gas, poor memory and intellectual clarity.

Figure 7.30Anise



In aromatherapy, anise is used as a respiratory decongestant, forasthma, colic, impotency, insufficient milk, migraines, painful periodsand heart palpitations.

Fennel Seed Foeniculum vulgare

This is the dried, ripe fruit of cultivated Foeniculum vulgare. Fennelcontains 2-6% volatile oil and 12% fixed oil. The volatile oil contains 50-60% anethole, 20% d-fenchone. Methyl chavicol, anisic aldehyde, anisicacid, d-alpha-pinene and dipentene are also present. Fennel is aromaticand carminative, and often used to allay any griping caused by otherherbs.

In aromatherapy, fennel is used as an antispasmodic, for bronchitis, gas,irregular menstrual cycles, whooping cough and worms.

Nutmeg Myristica fragrans

The dried ripe seed of Myristica fragrans contains 29-40% fixed oils (solidat room temperature), 8-15% volatile oils containing myristicin, safroleand elemicin. This herb has been used as an intoxicant because itcontains hallucinogenic agents. Roughly 15 grams must be ingested toget the desired effects, somewhat less if smoked. Intoxication alsoproduces flushing of the skin and absence of salivation. The activeingredient is thought to be elemicin. Nerve damage and death haveoccurred by overconsumption.

Figure 7.32Fennel

Figure 7.31Anethole

OCH3

CH CH CH3

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Volatile Oils

In aromatherapy, nutmeg is recommended for rheumatism, diarrhea, gasand as a biliary.

Sassafras Sassafras albidum

This botanical is obtained from the dried bark of the roots of Sassafrasalbidum. This tree (sometimes shrub) is indigenous to eastern NorthAmerica. Most of the supply comes from Virginia, Tennessee andKentucky. It contains 5-9% volatile oil, 6% tannin, resin and starch.Sassafras is used as an aromatic, stimulant, diaphoretic, and alterativeand is often used for rheumatism, syphilis and skin diseases.

The volatile oil is distilled with steam from the entire root (not just rootbark). It consists of 80% safrole with small amounts of α-pinene,phellandrene, d-camphor, eugenol and a sesquiterpene. The UnitedStates FDA banned the use of sassafras oil in 1960 because of a reportstating that safrole was carcinogenic. It has been shown that extendeduse of large quantities of safrole (above 2 drams) can produce a narcoticpoisoning with widespread fat degeneration, especially in the heart, liverand kidney.

In single very large doses, paralysis of respiration was produced in rats.Because of the high amount of safrole in the volatile oil of sassafras, theherb has been put on the herbal “hit list” in the United States and takenoff the market. Since the oil is 5-9% of herb content, one would have toconsume very large quantities for a poisonous effect from the herb.

Sassafras oil was used as a flavouring agent in root beer until 1960 in theUnited States. In aromatherapy, sassafras is recommended for insectbites, rheumatism, dermatitis, fatigue, gout and menstrual problems.

Figure 7.33Oxides

Oxide volatile oils

Consisting of an oxygen that bonds to two carbons, this group has a fewactive volatile oils.

C O C

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Chenopodium Oil Chenopodium ambrosioides

This oil is distilled with steam from the fresh above-ground part of theflowering and fruiting part of Chenopodium ambrosioides. The volatile oilis 1-2% and contains 60-80% ascaridole, 20% p-cymene, some l-limoneneand d-camphol. Ascaridol, the active principle, is an organic peroxide,liable to explode when heated. Don’t play with this one in your lab! It isalso a very good anthelmintic, especially for roundworm, hookworm andintestinal amoebae. The usual dose is 1 ml given in a single dose foradults.

Figure 7.34Ascaridol

CH3

O

O

Eucalyptus Eucalyptus globulus

This herb comes from the dried, scythe-shaped leaf of Eucalyptusglobulus. It contains 3-6% volatile oil, several resins and tannic acid. Thevolatile oil is distilled from the fresh leaves with steam and contains noless than 70% eucalyptol (C10H18O). It is used as an antiseptic, dia-phoretic, expectorant and stimulant.

In aromatherapy, eucalyptus oil is described as invigorating, balancing,useful as an expectorant, antiseptic, for colds, sinusitis, burns, as aninsect repellent and for rheumatism.

O

C O

Figure 7.35Esters

CH

H3C CH3


Volatile Oils

Ester volatile oils

Esters occur in many volatile oils. Some of the most common are terpin-eol, borneol and geraniol. It is often the practice to age perfumes topermit esterification to take place and thus improve the bouquet. Otherexamples of esters in volatile oils are allyl isothiocyanate in mustard oiland methyl salicylate in wintergreen oil.

Among the most common botanical oils in this group are lavender oil,rosemary oil, Dwarf pine needle oil, bergamot oil, mustard oil andwintergreen (Gaultheria) oil.

Lavender (Lavandula angustifolia)

This oil is obtained from the dried flower of Lavandula angustifolia bysteam distillation. It contains not less than 35% of linalyl acetate(C12H20O2). The flowers contain 0.8-2.8% of the volatile oil. Althoughlavender oil is a carminative and mild nervine, it is mostly used inperfumes.

In aromatherapy, lavender oil is regarded as calming, antiseptic, healing,able to rejuvenate oily skin, useful for acne, eczema, scars, soothing,appeasing and energy balancing.

Figure 7.36Rosemary

Rosemary Rosmarinus officinalis

Rosmarinus officinalis contains 2-6% of thevolatile oil bornyl acetate. It is used mostlyas a flavoring agent and a perfume but it isalso useful as a liniment and rubefacient.

In aromatherapy, it is a liver gallbladderstimulant, a cardiotonic, useful for dryskin, rejuvenating, hair loss, mentalfatigue, poor memory and sadness.

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Bergamot Citrus bergamia

Citrus bergamia (the volatile oil) yields 35-45% linalyl acetate(CH3COO.C10H17), 20-30% l-linalool. It also contains d-limonene, bergaptenand dihydrocuminyl alcohol. Medicinally, bergamot oil is used externallyas a mild stimulant and antiseptic for irritable skin. It is also considereda very good hair tonic.

In aromatherapy, it is used as a digestive, antispasmodic, tonic, brainstimulant, for mental fatigue and depression.

Wintergreen Gaultheria procumbens

This botanical comes from the dried leaves of Gaultheria procumbens, alow shrublike perennial. Methyl salicylate (similar to aspirin) can beobtained by steam distillation of the leaves (also from the bark of Betulalenta). This volatile oil contains no less than 98% C8H8O3. It is used as alocal irritant, antiseptic and antirheumatic. It should not be ingested inlarge doses. Ten ml can cause severe sickness and even death in chil-dren. Symptoms of poisoning include nausea, vomiting, pulmonaryedema and convulsions.

OAc

Figure 7.37Linalyl acetate


Volatile Oils

Looking at the exciting area of volatile oils has taken us from the some-what esoteric area of aromatherapy to specific scientific applicationssuch as antibiotics. These complex and specific chemical groups act asecological and metabolic storage mechanisms for the plant. Methods ofobtaining these scents vary greatly from water distillation, secret familyrecipes to high tech hypercritical carbon dioxide methods.

Modern use of aromatherapy has a somewhat esoteric feel but doeshave some solid basis in neuro-physiology. Dividing volatile oils intoeight groups, based on chemistry, can also direct us to some similaritiesin therapeutic application. Hydrocarbons have some ecological featuresas well as having antiseptic, antiviral and, occasionally, immune stimulat-ing properties.

The major botanicals containing hydrocarbon volatile oils which welooked at were: Cubeb and Hops. Alcohol volatile oils are present inmany important herbs including Peppermint, Cardamon Seeds, andJuniper. Some common actions of alcohol volatile oils are antisepsis,energizing, antibiotic, anti-viral and carminative. Aldehyde volatile oilscan be found in Cinnamon and Citronella and can be antiseptic, carmina-tive and have a insect repellent quality. In the ketone volatile oils welooked at Camphor, Spearmint, Caraway, Buchu and Absinthe. Althoughsome of the ketone volatile oils have neurotoxic qualities when takeninternally, many increase mucus flow, are used for skin care, antisepsisand are carminative.

Some phenylpropane volatile oils are contained in Cloves, Aniseed,Fennel Seed, Nutmeg and Sassafras. Phenylpropane oils can be antisep-tic, fungicidal, local anesthetics, carminative and antispasmodic. Oxidevolatile oils can be anthelmintic, expectorant, antiseptic, insect repellentand antirheumatic. We looked at chenopodium oil and eucalyptus asexamples of oxide volatile oils. Ester volatile oils include Lavender oils,Rosemary oil, Bergamot oil and Wintergreen oil. Ester volatile oils canbe carminative, mildly nervine, soothing and antiseptic.

Summary



Mini-Materia Medica -- Volatile oils.

Angelica (Angelica archangelica)Constituents: volatile oils make up 1% of constituents including

phellandrene, pinene, limonene, caryophyllene, linalool andborneol.

Therapeutic action: Carminative, diaphoretic, emmenagogue,stimulant, alternative, expectorant and tonic.

Anise ( Pimpinella anisum )Constituents: 2 - 6% volatile oil containing, anethole (up to 90%),

estragol (methyl-chavicol) and others.Therapeutic action: Carminative, expectorant, abortifacient,

anodyne, antiseptic, antispasmodic, aperient, aphrodisiac,diaphoretic, diuretic, stimulant and tonic.

Arnica ( Arnica montanum )Constituents: essential oils contain alcohol triterpene, arnidiol,

faradiol.Therapeutic action: Nervine, local stimulant, antibacterial, dia-

phoretic, emollient, diuretic, expectorant and vulnerary.Basil ( Ocimum basilicum )

Constituents: the main components of the volatile oil are linalool,lineol, and camphor.

Therapeutic action: gastric antispasmodic, stomach tonic, carmina-tive, galactogenic.

Burdock ( Arctium lappa )Constituents: volatile oils, inulin.Therapeutic action: diaphoretic, alterative, diuretic, antiscorbutic,

antimicrobial, antipyretic, stomachic, sudorific.Catnip ( Nepeta cataria )

Constituents: alpha- and β- citral, nepetalactone, limonene, geraniol,dipentene, citronella and nerol are all part of its volatile oil.

Therapeutic action: carminative, nervine, stimulant, tonic, dia-phoretic, emmenagogue, antispasmodic, aphrodisiac (cats).

Celery ( Apium graveolens )Constituents: leaves and seeds are high in essential oils, flavonoids,

and furanocoumarin (bergapten).Therapeutic action: diuretic, stimulating uterine contractent.

Chamomile ( Anthemis nobilis )Constituents: the volatile oils contains chamazulene, farnesene,

α-bisabolol oxide.Therapeutic action: stomachic, antispasmodic, tonic, stimulant,

carminative, nervine, emmenagogue and sedative.Coriander ( Coriandrum sativum )

Constituents: the volatile oil contains coroandrol (60-70%), geraniol,borneol and terpenes.

Therapeutic action: stimulate digestion, antispasmodic, carmina-tive, aphrodisiac and rheumatic pain.

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Volatile Oils

Elecampane ( Inula helenium )Constituents: essential oils with three lactones, alantolactone,

heline, among others. There is also an abundance of inulin.Therapeutic action: Tonic, diuretic and cholagogic.

Fennel ( Foeniculum vulgare )Constituents: the volatile oil contain 50-60% anethole, 20% d-

fenchone, among many others including pinene.Therapeutic action: Aromatic, carminative, pectoral and stomachic.

Feverfew ( Tanacetum parthenium )Constituents: the essential oils contain camphor, terpene, borneol

and esters.Therapeutic action: nervine for migraines and to interact with oil

metabolism.Hyssop ( Hyssopus officinales )

Constituents: 0.3 - 2% volatile oil containing pinocamphone,isopinocamphone and terpinenes, among many other ingredients.

Therapeutic action: expectorant, diaphoretic, stimulant, pectoral,carminative and cathartic.

Juniper ( Juniperus communis )Constituents: 0.5 - 2.0% volatile oil with about 50% l-terpinen-4-ol,

alpha-pinene, camphene and cadinene.Therapeutic action: diuretic, urinary antiseptic, antiseptic, carmina-

tive, emmenagogue.Lavender ( Lavendula angustifolia )

Constituents: volatile oils containing hydroxycoumarin, linalylacetate and herniarin.

Therapeutic action: stimulant, antispasmodic, tonic, carminative,stomachic, diuretic, and sedative.

Lovage ( Levisticum officinale )Constituents: essential oils with butyl-phthalidine, umbelliferone

and bergapten, various acids, resins and sugar.Therapeutic action: diuretic.

Marigold ( Calendula officinalis )Constituents: volatile oils with carotene, calenduline and lycopene,

with resins, saponins and a bitter compound.Therapeutic action: antiphlogistic, increases wound healing,

choleretic.Marjoram ( Marjorana hortensis )

Constituents: volatile oils of which 40% terpenes (terpinene, terpin-eol and borneol) and tannins.

Therapeutic action: expectorant, aromatic, digestive and carmina-tive.

Melissa ( Melissa officinalis )Constituents: essential oils containing linalool, geraniol, citronellal,

citral and aldehydes.Therapeutic action: stomachic, carminative, diaphoretic, sedative

and antispasmodic.

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Mugwort ( Artemis vulgaris )Constituents: rich in essential oil especially cineol.Therapeutic action: choleretic, vermifuge, regulates menstruation,

digestive tonic, used for moxabustion.Peppermint ( Mentha piperita )

Constituents: volatile oil containing 29 - 48% menthol, 20 - 31%menthone, 3 - 10% menthyl acetate, 1 - 7% menthofuran with smallamounts of limonene, pulegone and others including flavonoids,phytol, tocopherol, carotenoids, betaine, choline and tannins.

Therapeutic action: aromatic, carminative, diaphoretic,antispasmodic, and stomachic.

Pine ( Pinus silvestris )Constituents: pinene, carene, limonene, and bornyl as components

of the volatile oil with various glycosides also present.Therapeutic action: linament for rheumatism, sciatica, bronchitis,

coughs, pneumonia and nephritis, applied topically.Rosemary ( Rosmarinus officinalis )

Constituents: 0.5% volatile oil made up of d-pinene, camphene,cineole and borneol, with flavonoids, phenolic acids,rosemaricine, isorosemaricine and triterpenic acids.

Therapeutic action: tonic, aromatic, astringent, diaphoretic, stimu-lant and mild analgesic. It aids in stimulating bile flow.

Saffron ( Crocus sativus )Constituents: a glycoside that volatilizes to produce picrocrocrine

later forming safranol with carotenoids and crocin.Therapeutic action: stimulate appetite, emmenagogic and sedative.

Sage ( Salvia officinalis )Constituents: 1 -2.8% volatile oil contains terpene, thujone (35%),

camphor (28%), pinene (3%), humulene (4.4%), sabinol (4%) andsalvene, other components are picrosalvin, carnosol, salvin,carnosic acid, flavonoids, phenolic acid, salviatannin amongothers.

Therapeutic action: stimulant, antispasmodic, astringent,anthelmintic and lactation inhibitor.

Tansy ( Tanacetum vulgare )Constituents: 0.12-0.18% volatile oil with thujone(95%), camphor

and borneol present contains three resins and a bitter principle.Therapeutic action: anthelminthic, tonic, stimulant, nervine tonic

and abortifacient.Tarragon ( Artemisia dracunculus )

Constituents: a volatile oil containing phellandrene, ocimene andmethyl chavicol, with heriarin and hydroxycoumarin present.

Therapeutic action: stimulates appetite and a digestive aid.Thyme ( Thymus vulgaris )

Constituents: 2.5% volatile oils consisting of thymol (40%), carva-crol, borneol, linalool with tannins.

Therapeutic action: used for anorexia, dyspepsia, chronic gastritisand lax colon. Also known to stimulate the immune system.

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Volatile Oils

Turmeric ( Curcuma longa )Constituents: essential oils containing a ketone turmerone with a

yellow pigment, curcumine and resin.Therapeutic action: digestive aid, emollient, diuretic. Externally

used to treat colds and pain.Valerian ( Valeriana officinalis )

Constituents: volatile oils consisting of bornyl acetate, isovalerate,camphene, and pinene with tannins, and alkaloids, valerianineand chatarine.

Therapeutic action: antispasmodic, stimulant, tonic, nervine andcarminative.

Yarrow ( Achillea millefolium )Constituents: 0.1 - 1.4% volatile oils containing 0 - 51% azulene, 16%

pinene, 17% camphor, 12% sabinene and 9% cinole, with severallactones (achillin, millefin, deacethymatricarine) rutin, tanninscoumarins, saponins, sterol salicylic acid and others.

Therapeutic action: diaphoretic, astringent, hemostatic, stimulantand mildly analgesic.

1Tompkins P., Bird C., The Secret Lifeof Plants; Harper & Row, N.Y., 1973.

2Tressel R, Drawert F, Heiman et al., Z.Naturforch 24b p 781-83, 1969.

3Toller SV, Dodd G. Perfumery: ThePsychology and Biology of Fragrance,Chapman & Hall, New York, 1988.

4Tisserand R.B., The Art ofAromatherapy: the healing andbeautifying properties of essentialoils of flowers and herbs, DestinyBooks, Rochester, VT, 1977.

5Davis, P., Aromatherapy An A-Z, C.W.Daniel Company Ltd., SaffronWalden, Essex England, 1988.

6Lavabre, M., The Handbook ofAromatherapy, self publishedCulver City, CA, 1986.

7Arctander, S., Perfume and FlavorMaterials of Natural Origin, SteffenArctander Publication, Elizabeth,N.J., 1960.


9 Tyler, V., Brady, L., Robbers, J.,Pharmacognosy, (7th ed.), Lea &Febiger, Phila., PA, 1976. ibid..


11 Spoerke, D.G., Herbal Medications,Woodbridge Press Publ. Co., SantaBarbara CA, 1980. p.88.

12 The Merck Index 5th ed., Merck & Co.Inc., Rahway NJ, 1940. p.324.

13Gathercoal, E.N. and Wirth, E.H.,Pharmacognosy, Lea & Febiger,Phila. PA, 1936, p.226.

14 Wallis, T.E., Textbook ofPharmacognosy, J & H Churchill,London, 1967. pp.27, 281.


16 Duke, J.A., Handbook of MedicinalHerbs, CRC Press Inc., Boca RatonFL, 1985. p.234.


18Wohlfart, R., et al., An investigation ofsedative-hypnotic principles in hops,Part 3, Planta Med. 45:224, 1982.

19Wohlfart, et al., Nachweis sedativehypnotischer principle wirstoffe inhofen 4; Planta Medica 48 120-231983.

References

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20Haensel, R., et al., Versuche, sedativehypnotische wirkstoffe in hopfennachzuweisen, II, ZhurnalNaturforschung 35c, 1096-97, 1980.

21 Schauenberg, P., Paris, F., Guide toMedicinal Plants, Keats Publ., NewCanaan, Conn., 1977, p.245.




Resins

8Resins

Resins have often been considered dense volatile oils, having similar but heavierchemical structures, though often associated with volatile oils. We will split resinsinto four groups. The botanicals covered in this chapter are Mandrake, Kava kava,Cannabis, Male Fern, Ginger, Poplar Buds, Myrrh, Asafetida and Balsam.

Synopsis:



Introduction Resin Acids Resin Alcohols Resenes Glycoresins

Methods of Collecting Resins Resins

Mandrake Kava Kava Cannabis

Oleoresins Male Fern Cayenne Ginger Poplar Buds

Gum-Resins and Oleo-Gum-Resins Myrrh Asafetida Balsams

Peruvian Balsam Benzoin

Summary


Figure 8.1 MandrakeFigure 8.2 Biosynthesis of podophyllotoxinFigure 8.3 DihydromethysticinFigure 8.4 ∆ - 9 - THCFigure 8.5 CayenneFigure 8.6 CapsaicinFigure 8.7 GingerFigure 8.8 ZingeroneFigure 8.9 Poplar BudsFigure 8.10 Protocatechuic AcidFigure 8.11 Umbelliferone

Table of Contents


Resins

Introduction

esins cannot be sharply defined. They are without a common formand are all products of a complex chemical nature. They areusually hard, transparent or translucent and brittle. On heatingR

they often soften and finally melt. All resins are heavier than water.Chemically, they are a complex mixture of resin acids, resin alcohols,resinotannols, esters and resenes. Resins are insoluble in water andrarely soluble in light petroleum. They are generally soluble in alcohol,ether, acetone, chloroform, carbon disulphide, solutions of chloralhydrate, fixed oils and volatile oils.

Resins are often found in association with volatile oils and are thusknown as oleoresins. Some natural oleoresins are turpentine, CanadaBalsam and copaiba. Oleoresins can be derived from aspidium, cubeband Capsicum.

Some researchers feel that volatile oils and resins should be dealt withtogether, as resins often seem to be a more concentrated, heavier formof volatile oil. This is most true of the oleo-gum-resins. As we pointed outin Chapter 7 on volatile oils, many volatile oils are terpenoids (terpenes[C10H16], sesquiterpenes [C15H24] and a few diterpenes [C20 H32]). Manyresins are diterpenoid. With the extra carbons, diterpenoids are heavierand therefore have higher boiling temperatures. In turn, this makesmany resins essentially volatile oils with high boiling points. Often resinsare left behind after distilling essential oils. This is true of the rosinremaining after distilling pine turpentine. We can also often findtriterpenes (C30, also discussed under glycoside saponins), as parts ofresins. Besides being associated with saponins, the triterpenes are veryclosely associated with steroidal compounds (discussed in Chapter 9).



Gum-resins are resins that occur in mixtures with gums. These mixturescan be separated very easily since gums (being carbohydrates) arewater-soluble, leaving the resins behind. Some gum-resins are: asafetida,gamboge and myrrh.

Balsams are resinous mixtures that contain cinnamic or benzoic acid orboth, or the ester of these acids. Confusion surrounds the term “balsam”because it has sometimes in the past been associated with oleoresinsand other resins. Some of the real balsams are: benzoin, Peru Balsam,Tolu Balsam and styrax.

Resins can also be found associated in glucosidal combinations and arecalled glucoresins or more properly glycoresins. We can find these inipomea, jalap and Podophyllum. The preceding classifications are, atbest, artificial because of the complexity and the mixture of the com-pounds. Most gum-resins have a certain amount of volatile oil presentand most oleoresins have small amounts of gums in them.

Resins are considered by many authorities to be the end product indestructive metabolism. Some are believed to be the results of oxidationof terpenes. Although resins are complex mixtures their principal con-stituents may be classified as follows:

1. Resin Acids2. Resin Alcohols3. Resenes4. Glycoresins

Resin Acids

Resin acids usually contain a large proportion of oxyacids, often combi-nations of carboxylic acids and phenols. They can be found in free statesand as esters. They are soluble in aqueous solutions of alkalies, usuallyforming soap-like solutions or colloidal suspensions. Their metallic saltsare known as resinates. These resinates are used in the manufacturing ofcheaper soaps and varnishes. Some examples include abietic acid inrosin or colophony (Pinus sp.), copaivic and oxycopaivic acid in copaiba(Copaifera sp.), guaiaconic acid in guaiac, pimaric (pimarinic) acid inBurgundy pitch and frankincense, sandaracolic (sandarcinolic) acid insandarac (Tetraclinis articulata), aleuritic acid in shellac andcommiphoric acid in myrrh.


Resins

Resin Alcohols

There are two types:1. resinotannols are complex alcohols that produce a tannin reaction

with iron.2. resinols give no such reaction.

These resin alcohols exist in free states and as esters, often in associa-tion with simple aromatic acids. Known resinotannols include aloe-resinotannol from aloe, ammoresinotannol and galbaresinotannol fromammoniac, peruresinotannol from balsam of Peru, siaresinotannol andsummaresinotannol from balsam of Tolu. The following are examples ofresinols: benzoresinol from benzoin, storesinol from styrax andguaiacresinol from guaiac resin.

Resenes

This is a group of neutral substances devoid of characteristic chemicalproperties. They do not form salts or esters. They can be found in guttapercha as alban and fluavil, from dammar as dammaresene, fromdragon’s blood (a Chinese herb) as dracoresene and from olibanum asolibanoresene.

Glycoresins

These are complex structures that yield sugars and resin acids onhydrolysis. The resins in jalap and scammony are in this class.

Methods of collecting resins There are five basic ways in which resinsare obtained:

1. extracting the resin from the plant with alcohol and precipitatingthe resin in water (e.g., jalap, scammony, ipomea and podophyllin).

2. separating the oil from oleoresin by distillation (copaiba).3. heating the plant part (e.g., guaiac resins from guaiac wood).4. collecting natural resin that has been exuded or induced through

artificial punctures (e.g., Burgundy pitch, mastic sandarac).5. collecting fossil resins such as copal, kauri, and dammar.



Resins

Mandrake Podophyllum peltatum

Also called podophyllum or Mayapple, this botanical is the dried rhi-zome and roots of Podophyllum peltatum. Podophyllum is Greek andmeans footlike leaf, peltatum means sheathlike. This perennial herb haslong jointed rhizomes.

Mandrake is indigenous to the eastern United States and Canada. It isobtained chiefly from plants growing wild in Virginia, North Carolina,Kentucky, Indiana and Tennessee. The rhizomes are collected in the fall,washed free from soil, cut into lengths of about 10 cm, and carefullydried. The slender adventitious roots are often removed.

The active constituent of Mandrake is primarily a resin 3.5-6%, the activeprinciples of which are lignanous glycosides. These include podo-phyllotoxin (20%), α-(10%) and β-(5%) peltanin. Synthetic manufacture ofpodophyllotoxin is not economic. The plant creates the resin from twocinnamic acids (see Figure 8.2). There are a number of other lignanspresent but they are essentially inactive.1,2 In the pharmaceutical indus-try this plant is normally used in the resin form as a concentrate. Theresin is obtained by making an alcohol extract of the rhizome and thendiluting it with water. The resin precipitates out.

Podophyllotoxin, the most active ingredient, is an intestinal irritant. Insmall doses it is toning to the small intestine, especially to the duodenumwhere it increases the bile secretion. Mandrake also is a very strong andeven drastic cathartic causing intense griping, but very slow in action.Catharsis normally occurs 23-36 hours after consumption.

Figure 8.1Mandrake

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Resins

Podophyllotoxin also has antimitotic properties and can therefore stopcell division. Of course this is not normally desired but the feature hasbeen used very beneficially in the treatment of different types of cancer.The St. Jude Children’s Residential Hospital in Memphis, Tennesseeconducted a study and concluded that it “may be effective against acuteleukemia” but does have the side effects of nausea, vomiting, diarrheaand fever.3

Externally it has been successfully used to treat scalp infection (tineacapitis). The resin has also been used successfully in treating venerealwarts. Internally, as stated above, mandrake rhizomes are a very strongcathartic. Usage for this purpose is to be avoided if possible. It can bequite useful if taken in small quantities, preferably mixed with manyother herbs.

Toxicity, though a nuisance, is low enough that mandrake seldom causesfatality unless extremely large doses are taken. The antimitotic andpurgative properties of podophyllotoxin are based upon a lactone ring inthe trans configuration. Treatment with a milk alkali produces anepimerization with the formation of the stable cis-isomers which arephysiologically inactive. Picropodophyllin is an inactive cis isomerproduced in this way from the active trans podophyllotoxin.

An allied plant, Podophyllum emodi (Indian Podophyllum) grows on thelower slopes of the Himalayas and has a much higher (11.4-12%) yield ofresin, roughly twice as much podophyllotoxin as P. peltatum. It is notoften used because of the high podophyllotoxin content. It can be easilydistinguished from American Mandrake by adding copper acetate to thefilter alcohol extract of each. The American variety will turn brightgreen, the Indian variety yields a brown precipitate.

COOH

COOHO

O

OH

O

O

OCH3

OCH3

CH3O

Podophyllotoxin2 Cinnamic acid

Figure 8.2Biosynthesis of podophyllotoxin

+

↑



It should be further noted that these mandrakes have no relation to themandrake (also called Satan’s Apple) Mandragora officanarum whichproduces a hallucinatory poison, similar to belladonna.

Kava Kava Piper methysticum

This botanical is the dried rhizome and root of Piper methysticum. Theplant is a large shrub widely cultivated in Oceania where the natives usethe root to produce an intoxicating beverage. The major constituent ofthis botanical is 5-10% resin from which six closely related lactonesknown as pyrones have been isolated: yangonin, desmethoxyyangonin,kavain, dihydrokavain, methysticine and dihydromethysticin.4,5

These chemicals have a distinct relaxing effect, notably on skeletalmuscles. Kava kava can also be used as an antipyretic, working toreduce fevers and for its local anesthetic properties. The pyrones’ maineffect is on the reticular formation of the brain stem, with endo-anaesthetic effect on the gastric mucosa and the bladder mucosa. KavaKava is an antagonist to strychnine poisoning and tetanus. A 20% oil ofKava resin, in oil of sandalwood, called gonosan, is used internally forgonorrhea, but also produces an aphrodisiac effect. Kava Kava has mildantibacterial action but strong antifungal action, though not againstCandida sp. Up to 6 grams can be taken a day without any problems, butextended use of large amounts may cause skin discoloration and evenskin lesions.

Cannabis Cannabis sativa

This herb, popularly called marijuana or pot, consists of the leaves, butpreferably the dried flowering female tops of Cannabis sativa. This plantis an annual herb, indigenous to central and western Asia, but because ofits popularity as a drug it is now cultivated or naturalized circumpolar.There are two major varieties: one used for its intoxicant effect and oneused for the making of rope (hemp). In North America the general useand selling of marijuana is illegal but at one time Cannabis was usedextensively by the medical profession and industry.

O

O

H2CO

OCH3

O

Figure 8.3Dihydromethysticin

Sc2


Resins

The active ingredient is ∆-trans-tetrahydrocannabinol, commonlyreferred to as ∆9-THC. Other isolated constituents include cannabinol,cannabidiol, cannabigerolic acid, cannabichromene, cannabigerol. Thecannabichromene and cannabidiol usually produce a sedation whereasTHC produces euphoric activity. In the past Cannabis was used foreasing pain, to induce sleep (although in some it has the opposite effect)and to soothe the nervous system. It has been used in neuralgia, gout,rheumatism, delirium tremens, insanity, infantile convulsion and insom-nia, all successfully.6,7

The tincture was used to aid parturition, for gonorrhea, menorrhagia,chronic cystitis and painful urination. An infusion of Cannabis seeds isuseful for afterbirth pains and prolapsus uteri. This botanical wasofficially recognized in the B.P. and U.S.P. until the late 1930’s.

The following is said to be a sure cure for gonorrhea:

Take equal parts of the tops of male and female Cannabisblossoms, bruise in mortar, express the juice and add anequal portion of alcohol. Take 1-3 drops every two-threehours.

Recent studies on this controversial botanical have shown that althoughsmall, infrequent consumption of Cannabis is not harmful, long termchronic use can have strong deleterious effects. Long term use has beenshown to create a definite psychological addiction (similar to ciga-rettes), cause early senility and lung congestion (in some cases respon-sible for emphysema). THC, being a fat-soluble (not water-soluble)compound, collects in fat tissue (especially the brain and nervoussystem), remaining there 10 months after the cessation of chronicconsumption. Consumption during pregnancy results in large amounts ofTHC detectable in the amniotic fluid. THC activates the adrenal glandand is therefore very stressful on people who have weak adrenal glands.This problem is compounded because many users consume marijuanato relax after a stressful day. It is similarly very deleterious for peoplewith low blood sugar syndrome.

O

OH

C5H11

Figure 8.4∆9 - Tetrahydrocannabinol



Oleoresins

As we have stated earlier, oleoresins are compounds with a monogenousmixture of resin and volatile oil. Since there is no sharp line of demarca-tion between different types of resins we might find up to 10% gum in theresin as in guaiac resin and still not consider it a gum resin. Somecommon oleoresins are turpentine, Oregon balsam, Canada Balsam,Burgundy pitch, hemlock pitch, male fern root, Capsicum, ginger, poplarbuds, white pine bark and copaiba.

Male Fern Dryopteris filix-mas

This botanical is the rhizome of Dryopteris filix-mas also known asAspidium or European Aspidium. American Aspidium is Dryopterismarginalis . Dryopteris is Greek for “growing on oak”, filix-mas means“male fern” in reference to its asexual reproduction; marginalis refers tothe marginal position of the sori (reproductive organ) in this species. D.filix-mas is indigenous to Europe, Asia, west of the Rocky Mountains inNorth America and in the South American Andes. D. marginalis can befound in eastern North America from Prince Edward Island south intothe central United States.

Male fern root consists of 6.5-15% oleoresin which contains a number ofactive phloroglucinol derivatives. The major constituents are filmaroneand filicic acid. Other constituents of the oleoresin include aspidinol,albaspidine, paraaspidin, deaspidin and lignins. The root also containsvolatile oils, sugar, starch, several resins, wax and tannins. The fluidextract is considered one of the best remedies available for ridding thebody of worms, especially tapeworms. The worms are killed directlyand/or expelled alive. The encapsulated herb, though useful and morepleasant to use, is not quite as effective. Male fern has a very offensivetaste.8,9,10

It is recommended that one take male fern at night before bed, afterfasting since noon. Normal dosage levels (up to 5g) are not consideredtoxic, but if consumed with castor oil, male fern is toxic. Castor oilincreases the absorption of the filicins (considered muscle poisons) intothe bloodstream. Aspidinol is known to have a phenolic (wound healing)action.

Cayenne Capsicum frutescens

Capsicum or Cayenne Pepper is the dried, ripe fruit of Capsicumfrutescens (African Cayenne) or related Capsicum species. The Africanvariety is considered the best from a medicinal point of view. The majorchemical in capsicum is capsaicin (0.02%), a phenol.

Sc2

Mo2

Sc2

Mo2


Resins

The most important constituents of Capsicum are pungent phenolcompounds (0.05 - 1.5 %). As stated, the most prominent is capsaicin(C18H27NO3) the vanillyl amide of isodecenoic acid.11 Besides capsaicin(69% or 10 - 800 mg of the phenol compound), the pungent principalcontains dihydrocapsaicin (22%), nordihydrocapsaicin (7%), homo-capsaicin (1%), and homodihydrocapsaicin (1%).12,13 There is also aminute quantity of a liquid alkaloid, a saponin capsicidin, a fixed oil,carotene and a red pigment capsanthin.14--17 Capsicum also contains up to0.2% ascorbic acid.18

The vitamin and mineral content (per 100gm of dried herb) includescalcium (29mg), phosphorus (78mg), iron (1.2mg), potassium (374mg)Beta-carotene (12,960 I.U.), thiamine (0.22 mg), riboflavin (0.36mg),niacin (4.4mg).

Cayenne is a stimulant of the strongest nature, able to equalize bloodpressure and stop bleeding. Cayenne also stimulates the mucous liningof the stomach and intestinal tract. As a rubefacient it has been used as aliniment for muscle pain and rheumatism. Cayenne increases circulation,warming up the body. It is also considered a very good alterative,cleansing the lifeline of the body. Cayenne is also a good heart tonic. It

Figure 8.6Capsaicin

Figure 8.5Cayenne

OH

OCH3

(CH3)2CH - CH = CH - (CH2)4 - CO - NH - CH2



also lowers cholesterol, specifically the LDL-HDL ratio, decreasesplatelet aggregation and produces substance P, thereby dilating arter-ies.19 Capsicum and capsaicin both significantly prevent the increase inliver cholesterol levels in rats while enhancing fecal cholesterol excre-tion via bile. Capsaicin has also been shown to decrease platelet aggre-gation. Its reduction of thromboxane B 2 formation and erythrocytehemolysis suggests a membrane stabilizing property that interferes withthe activation of phospholipase A2.20 The mechanism for thinning theblood is different than models created for aspirin.21

The production of substance P by cayenne has the known effect ofdilating the arteries, in turn reducing blood pressure. It can regulatenerve response and work as a cardiotonic. Capsaicin has been studiedextensively in recent times. All kinds of information has been uncoveredrelating to the botanical’s influence on bronchiole function, cAMP andcardiac function.22 There is even some speculation that capsaicin mighthave some anti-carcinogenic effects.23

Ginger Zingiber officinale

Zingiber officinale is used as a dried rhizome and is commercially knownas Jamaican Ginger.

Ginger’s characteristic aroma is due to 0.25-3% volatile oil content,principally sesquiterpenes, beta-phellandrene, zingiberine, camphene,cineol, citral, borneol and zingiberol. The pungency of the botanicalcomes from the oleoresin which contains the two ketones zingerone andshogaol. Ginger also contains large amounts of starch (more than50%).24 - 30 The oil of ginger primarily contains the sesquiterpene hydro-carbons, zingiberene and traces of bisabolene. Ginger oleoresin containsmainly gingerols and shogaols as well as some zingerone. Shogaols andzingerone are dehydration products of gingerol.31

Ginger is a carminative, diffuse stimulant and irritant. It has specificeffect on the liver, both toning and cleansing it. Ginger is also considereda specific for abdominal cramping, due to its gingerol content. It alsolowers both hepatic and serum cholesterol, inhibits platelet aggregationand kills vaginal trichomonads.32 Herbalists have considered Zingiberofficinale a regulator of vascular cholesterol and blood circulation for along time. Lab reports support such a view. Ginger will apparently lowercholesterol levels33 and inhibit platelet aggregation.34 In the latter case,three unnamed compounds in ginger inhibit platelet cyclooxygenaseproducts, resulting in very acceptable antithrombotic properties.35 Theextract of ginger has been shown to stimulate vasomotor and respiratorycenters in anesthetized cats as well as acting as a direct heart stimu-lant.36

Sc2

Mo2


Resins

Figure 8.7Ginger

OH

OCH3

CH2 - CH2 - CO - CH3

Figure 8.8Zingerone

Poplar buds Populus spp. especially P. balsamifera

This herb is actually the winter bud of the poplar (a term which includesmany species). The best species from a medicinal perspective is Populusbalsamifera. The bud contains an oleoresin (whose major component ishumulene), gallic acid, malic acid, mannite, chrysin, tectochrysin, a fixedoil and two glycosides, salicin and populin (populin is salicin ben-zoate).40 - 43

The salicin and populin give poplar bud (often called Balm of Gilead) anantipyretic, antirheumatic and analgesic action. Made into an oil it isused externally as a mild counterirritant for muscle strain and rheuma-tism. The buds have antioxidant properties that prevent the oil from

In China, fresh ginger has been shown to bea clinically effective treatment for rheuma-tism, acute bacterial dysentery, malaria andorchitis (inflammation of the testicles).37

Ginger’s beneficial effect on colic andflatulence has been well known for centu-ries.

Ginger oil has been shown to increasecapillary permeability and to inducephagocytic activity of capillary endotheliumsimilar to histamine.38,39 This product isused extensively in Third World countriesto prevent colds.

Ed

Sc2

Mo2



going rancid. The oil or buds used externally are very soothing andhealing to wounds, stopping associated pain almost immediately. Thebud, when chewed, can be used as an analgesic for dental extraction inrural emergencies. Internally, the oil is a stimulant expectorant used forcoughs due to cold or bronchitis. It is also a useful cathartic and willlower cholesterol.44 - 49

Gum-resins and Oleo-gum-resin

By definition gum-resins consist of a mixture of resin and gum. The gumis normally a glucosidal substance. There are a few true gum-resins butmost have some volatile oil, making them an oleo-gum-resin. One truegum-resin is Gamboge (Garcinia hanburyi), a drastic purgative. Oleo-gum-resins have gum, volatile oils and resin in a mixture. The principal oleo-gum-resins are myrrh and asafetida.

Myrrh Commiphora molmol

Commiphora molmol and Commiphora abyssinica are the two majorsources of the substance, although other Commiphora species are used.The name myrrh is from the Arabic murr, meaning bitter, Commiphora isfrom Greek, meaning gum-bearing, molmol is the native Somali name,and abyssinica refers to the habitat of the plant. This tree, attaining aheight of 10 meters, is found growing on the Arabian peninsula, inEthiopia and Somalia. The gum is naturally exuded from the bark but isoften encouraged by artificial incision.

Figure 8.9Poplar buds

Mo2


Resins

Figure 8.10Protocatechuic acid

Myrrh contains a yellow to yellow-green, rather thick volatile oil (2.5-8%)having the characteristic odor of myrrh. The resin (25-40%) is composedof different commiphoric acids, resenes, and phenolic compounds, oneof which yields protocatechuic acid and pyrocatechin. A gum is present,about 60% being of an acacia type.50,51

The oleoresins act as a local stimulant and as a light peristaltic. Myrrh isvery astringent to mucous membranes and is considered an excellentantiseptic. It is also used as a carminative and often as an antisepticprotective.

Asafetida Ferula assafoetida

This botanical is the oleo-gum-resin of Ferula assafoetida , F. rubricaulisand F. foetida. The oleo-gum-resin is obtained by incising the livingrhizomes and root. Another common name for asafetida is Devil’s Dung.Its major constituents are 4-20% volatile oil, 40-60% resin and about 25%gum. The oil contains isobutylpropanyl disulfide along with many otherdisulfides. The resin contains asaresinotannol along with umbelli-ferone.52,53,54

The volatile oil acts as a carminative, has expectorant properties and isused for flatulence and bronchitis. The lungs will eliminate these particu-lar volatile oils causing an expectorant action. This herb has also beenused for chronic colic. Asafetida is used in a 2% solution as a flavoringagent in Worcestershire sauce.

OH

OH

COOH



Balsams

These are resinous mixtures which contain large proportions of benzoicor cinnamic acid or both, or the ester of these acids. The medicinalbalsams include Tolu balsam, Peru balsam, styrax and benzoin.

Peruvian balsam Myroxylon pereirae

This balsam comes from Myroxylon pereirae, Myroxylon is Greek frommyron, meaning ointment, xylon meaning wood, and pereirae is in honourof Jonathan Pereina (1804-1853), an English pharmacognosist. Thebalsam is formed by injury to the tree. It contains 60% cinnamein (avolatile oil) consisting of benzyl cinnamate and some benzyl benzoate.The resin esters are composed of 30-38% peruresinotannol cinnamicacid, peruviol benzoate and vanillin.

Peru Balsam is used as a local protectant, antiseptic, vulnerary,rubefacient and has parasiticidical activity for certain skin disorders. InCuba, a tincture is used as a rub to alleviate headaches and rheumatism.Internally, it is a stimulating expectorant. It is rarely used internally. Perubalsam has been used extensively for incense.55,56,57

Benzoin Styrax benzoin

This balsamic gum is obtained from “wounded” Styrax benzoin, a small-medium size tree (up to 20m in height) growing in tropical Asia. Itcontains 60-80% coniferyl cinnamate, cinnamyl cinnamate (styracin),benzoate plus 10% free benzoic acid, triterpene siaresinol (6%) andtraces of vanillin. Benzoin possesses antiseptic, stimulant, expectorant,carminative, deodorant and diuretic properties.58,59,60

Compound Benzoin Tincture is often used as a topical protectant. Itcontains Tincture of Benzoin, aloe, styrax and Tolu balsam and is oftenused in vaporizers as an expectorant. The tincture was applied tocracked nipples by Malayans. Benzoic Acid is often used as a commer-cial preservative and medicinally as an antifungal agent. It is often usedas a base for incense. GRAS 172.510.

HO O O

Figure 8.11Umbelliferone


Resins

Summary

This chemically complex group have often been categorized as dense,volatile oils. We found the resin acids contain large proportions ofoxyacids, found in free states and as esters. Resin alcohols are com-plexes of resins and alcohols (also in free states and as esters). Resenesare neutral substances, not forming salts or esters. Glycoresins yieldsugar and resin acids on hydrolysis. Resins we looked at were Mandrake(known for its very strong cathartic action), Kava kava (known for itsmuscle relaxing effect) and Cannabis (known as a street drug). Botani-cals listed with oleoresins are Male Fern (a known anthelmintic), Cay-enne (a strong stimulant), Ginger (a moderate stimulant), Poplar Buds(an antirheumatic and analgesic). Gum-resins and oleo-gum-resinsdiscussed were Myrrh (antiseptic and local stimulant), Asafetida (carmi-native, expectorant), Peruvian balsam (antiseptic, antirheumatic) andBenzoin (antiseptic, stimulant).



3Heinerman, J., The Science of HerbalMedicine, Bi-world Publisher, Orem,Utah, 1979, p. 136.



6 Hsu, H.Y., Chen, Y.P., Hong, M., TheChemical Constituentsof OrientalHerbs (Vol. 1), Oriental Healing ArtsInstitute, Los Angeles, CA, 1982, p.96.





11Gathercoal, E.N. and Wirth, E.H.,Pharmacognosy, Lea & Febiger,Phila. PA, 1936,p.647.

12Trease, G.E. and Evans, W.C.,Pharmacognosy 11 ed., BailliereTindall, London, 1978. p.364.

13Leung, A.Y., Encyclopedia of commonnatural ingredients used in food,drugs, and cosmetics, John Wiley &Sons Inc., New York, 1980.p.86.

14Wallis, T.E., Textbook ofPharmacognosy, J & H Churchill,London, 1967.p.266.


16Martindale: The Extra Pharmacopeia,The Pharmaceutical Press, London,1941.p.360

17The British Pharmaceutical Codex1934. The Pharmaceutical Press,London, 1934.p.276.

18Tyler, V.E. et al., Pharmacognosy (7thed.), Lea & Febiger, Phila. PA, 1976.p.188.

19Negulesco J.A. and Younge R.M,Capsaicin lowers plasma cholesteroland triglycerides of lagomorphs,Artery 12:5 301-311 1985.

20Wang J.P. et al., Antiplatelet effect ofcapsaicin, Thromb. Res. 36:6 497-5071984.

References



21Jih-Pyang-Wang et al., Antihemostaticand antithrombotic effects ofcapsiacin in comparison with aspirinand indomethacin, Thromb. Res. 37:6669-679 1985.

22Gamese R et al., Bronchial, cardiovas-cular and secretory responses aftercentral administration of capsaicin inguinea-pig, Archives of Pharm.333:59-69 1986.

23Modly CE et al., Capsain as an in vitroinhibitor of Benzo(a)pyrenemetabolism and its DNA binding inHuman and Murine keratinocytes,Ann. Soc. Pharm. and Ex. Ther. 14 (4)413-416 1986.

24 The British Pharmaceutical Codex1934. The Pharmaceutical Press,London, 1934. p.1130.



27 Textbook of Pharmacognosy, J. & A.Churchill Ltd., Rahway, N.J., 1976.(citation not confirmed) p.392. andGathercoal, E.N. and Wirth, E.H.,Pharmacognosy, Lea & Febiger,Phila. PA, 1936. p.170.

28Trease, G.E. and Evans, W.C.,Pharmacognosy 11 ed., BailliereTindall, London, 1978. p.452.

29 Sai, H.M. (ed.) HamdardPharmacopeia of Eastern Medicine,Pharmaceutical Advisory Council ofHamdard, The Times Press, SadarKarachi, 1969, p.416

30Herbert, B.E. and Ellery, K.W.,Textbook of PracticalPharmacognosy, Bailliere, Tindalland Cox, London, 1948. p.95.

31Leung, A.Y., Ibid.32Leung, A.Y., Ibid.33Gujarak, S., Bhumra, et al., Effect of

ginger (Zingiber officinale roscoe)oleoresin on serum and hepaticcholesterol levels in cholesterol-fedrats, Nutr. Rep. Int. 17:183 -189, 1978.

34Srivastava K.C., Effects of aqueous ofonion, garlic and ginger on plateletaggregation and metabolism ofarachidonic acid in the bloodvascular system: In vitro study,Prostaglandins Med 13:227-35, 1984.

35Srivastava, K.C., Ibid.36Leung, A.Y., Ibid.37Leung, A.Y., Ibid.38Gozsy, B., et al., Effect of phagocytic

stimulation on experimentaltuberculosis of guinea pigs, Amer.Rev. of Tuberculosis, 73(3) 442-43.1956.

39Suzi, Y. et al., Pharmacological studieson Zingiber mioga. GeneralPharmocologial effect of waterextracts, Folia Pharm. J. 75: 669-682,1979.

40 Tyler, V.E. et al., Pharmacognosy (7thed.), Lea & Febiger, Phila. PA, 1976.p.189.



43Felter, H.W., Eclectic Materia Medica,Pharmacology and Therapeutics,Eclectic Medical Publ., Portland OR,1922 (1983). pp.612,561.

44The British Pharmaceutical Codex1934. The Pharmaceutical Press, London, 1934. p.918.

45Tyler, V.E. et al., Pharmacognosy (7thed.), Ibid.


Ibid.48British Herbal Pharmacopeia Section

1, British Herbal Medicine Associa-tion, London, 1971.

49Felter, H.W., Eclectic Materia Medica,Pharmacology and Therapeutics,Ibid.






Resins











Terpenoids, Sterols, Etc.

9

In this chapter, we are going to look at some of the more evolved terpenoids. Thesewill include steroidal compounds, cardiac glycosides and tetraterpenoids (β-caro-tene). We conclude the chapter with a look at porphyrins -- both chlorophyll andheme compounds.

Synopsis:

Terpenoids,Sterols,CardiacGlycosidesandPorphyrins



Introduction Terpenoids Sterols

Ergosterol Sitosterol

Cardiac Glycosides Digitalis Squill Lily of the Valley Black Indian Hemp, Dogbane

Tetraterpenoids Beta-Carotene

Porphyrins Chlorophyll and Related Compounds Heme and related compounds

Conclusion Materia Medica - Terpenoids, Etc.


Figure 9.1 LanosterolFigure 9.2 Terpenoid Notational SystemFigure 9.3 ErgosterolFigure 9.4 Stigmasterol, SitosterolFigure 9.5 DigitoxinFigure 9.6 DigitoxigeninFigure 9.7 ScillareninFigure 9.8 Glucoconvallasaponin AFigure 9.9 Beta-caroteneFigure 9.10 Antioxidant Mechanism of Beta-caroteneFigure 9.11 PorphyrinsFigure 9.12 Chlorophyll

Table of Contents



erpenoids are very active substances, as we have already seen. Inthe more advanced terpenoids, we discover steroidal compounds,cardiac glycosides and tetraterpenoids (like beta-carotene). Por-

Introduction

Tphyrins are added to this chapter to complete a review of the majorpigments in plant material.

Terpenoids

Terpenoids were discussed earlier under saponins in Chapter 4 (Glyco-sides), and in Chapters 7 (Volatile oils) and 8 (Resins). To briefly review,terpenoids are made up of isopentane units, usually in “head-to-tail”arrangement. They often form in cyclic configurations. The lowernumber carbon chains are often considered volatile oils. The diter-penoids and triterpenoids are resins and saponins. These higher terpe-

Figure 9.1Lanosterol

HO



noids are usually cyclic and both resemble and probably have bioge-netic relationships with steroids. Some of the triterpenoids were at onetime considered steroids -- reflected in the name lanosterol. In Figure 9.2,we can see the general shape and numbering system.

Sterols

Steroid nuclei are very similar to lanosterol and other tetracyclictriterpenoids. The significant difference is that there are only two methylgroups at position 10 and 13. The nomenclature of steroids is verycomplicated. It is based on the parent ring structure as well as the sidechain structure. The basic configuration can be found in cholesterol(discussed in Chapter 6 -- Lipids). The carbons are numbered and therings are lettered. If one or more of the carbon atoms is not present, itdoes not affect the number of the higher carbons. If we consider thestructure as a plane projected onto paper, an atom or group attached tothe ring below the plane is termed alpha a (α) and is denoted withbroken lines (- - - -). If it is above the plane, it is called beta β and shownas a heavy solid line ( ).

Sterols are alcohols and, as one would guess, have -OH in their configu-rations. Other notable sterols are ergosterol (found in many fungi),sitosterol (found in seed oils) and stigmasterol (found in soybean oil andcalabar beans).

Ergosterol

This chemical becomes Vitamin D2 upon exposure to ultraviolet light. Wecan find it in many fungi: Pachyma hoelen, Lobaria pulmonaria, Morusalba, Elvinga applanata, Phellinus igniarius and Ganoderma lucidum.1Although the constituents of these fungi are complex, most are known tobe active against tumor systems. An ability to lower blood

Figure 9.2Triterpenoid Notational System

12

34

5

10

67

8

19

11

914

12

13

18

15

16

2021 22

23

24

26

27

2517

A B

C D

E



Figure 9.4Stigmasterol and β-Sitosterol

HO

CH3

CH3

H3C

CH3

CH3

H3C

Figure 9.3Ergosterol

HO

CH3

CH3

H3C

CH3

CH3

CH3

HO

CH3

CH3

H3C

CH3

CH3

H3C

lipids and blood pressure has also been reported. We cannot conclude,however, that the steroidal compounds have caused these effects. Morestudy is needed.

Sitosterol

Beta-sitosterol is abundant in many plants such as: chaparral, coltsfoot,Hyssopus officinalis, pipsissewa, red clover, sarsaparilla and grain germoils. It has been shown to inhibit tumor growth2,3 and is used in treatment

Stigmasterol

β- sitosterol



Figure 9.5Digitoxin

HO

OH

O

of atherosclerosis. Sitosterol is poorly absorbed but competes withcholesterol for absorption, thus reducing blood cholesterol.

Cardiac Glycosides

These steroidal-like glycosides have specific, powerful effects on theheart. Some of the chemicals are very poisonous and aren’t often usedby herbalists. This brings up an important concept -- Therapeutic Index.

A Therapeutic Index (TI), as defined by L. Goodman,4 is the median lethaldose (LD50) divided by median effective dose. (LD50/ED50). A median is thenumber which will split the group in half, ie., 50% of the population willdie at the LD50 range, while 50% of the population have an effectivedosage at ED50. For example, if the median lethal dose is 5 g/Kg and theeffective dose is 1 g/Kg the Therapeutic Index is 5.

This is a very useful parameter by which herbalists can determine thesafety of a herb. The higher the TI, the greater the herb’s safety. Herbswith low TIs are not recommended, especially for junior or inexperi-enced practitioners. A good list of LD50 ratings can be found in Duke’sCRC Handbook of Medicinal Herbs.5 Herbs containing cardiac glycosidesgenerally have very low Therapeutic Indexes. The TI for a cardiacglycoside (digitoxin) found in digitalis is 0.4 - 0.5. A herb like comfrey,now considered toxic by the F.D.A., has a calculated TI of 150, whilecoffee is 15 - 30.5

Most cardiac glycosides (e.g., digitalis) are used because of their abilityto increase the force of systolic contraction. This, of course, increasesthe emptying of the ventricles, shortening the length of systole, givingthe heart more time to relax. In turn, there is increased renal outputwhich relieves the edema often associated with heart failure. This herbal“solution” seems to be very attractive, and indeed is sometimes neces-sary for life support, but the method is much like whipping a tired horse.

O



Digitalis Digitalis purpurea

Digitalis purpurea from the Latin digitus, meaning finger, because of thefinger-shaped corolla, purpurea, Latin referring to the purple color. It canbe found in Europe, United States and Canada. It has been used medici-nally since 1640, but most extensively since 1776. The constituents areseveral glycosides (digitalein, digitalin, digitin, digitoxigenin, digitoninand digitoxin). It also contains choline, acetylcholine, coumaric acid,caffeic acid, ferrulic acid, chlorogenic acid and mucilage.6,7

Digitalis is considered a cardiac tonic, stimulant and diuretic. It is verytoxic and therefore is not used internally by modern herbalists. Exter-nally, an ointment has been used to soften hardened tissue, especiallylumps in the breast and indolent tumors. Digitoxin has shown antitumouractivity against KB tumor systems. It has also been used for epilepsy,asthma, edema, fevers, insanity, nephrosis, neuralgia and for palpita-tion.8 Death has resulted from drinking a cup of digitalis tea.

Squill Urginea maritima

This herb is from the inner scales of the bulbs of Urginea maritima. Scillais Greek for skilla meaning split, referring to the separating scales.Urginea is from Latin urgere referring to the compressed seed, maritimafrom the Latin, ‘the habitat on the Mediterranean coast’. The constitutionof squill is made up of a group of glycosides, glucoscillaren A (scillarenin+ rhamnose + 2 glucose), scillaren A (scillarenin + rhamnose + glucose),proscillaridin A (scillarenin + rhamnose), scillaridin A, scilliglaucoside,scilliphaecoside, glucoscilliphaeoside, amongst others.9,10

Squill is considered an expectorant, emetic, cardiotonic and diuretic.This herb is used extensively as a rat, mouse and rodent poison. It rarelycauses a toxic effect in humans, due to it emetic effect. Humans vomitthe herb before a toxic level is consumed. Rats cannot vomit and

HO

OH

O

Figure 9.6Digitoxigenin

O



therefore they can consume toxic levels. This herb was used as a folkremedy for cancer and tumors. Scilliglaucosidin has shown activity in KBcancer systems. It has been used for asthma, bronchitis, catarrh, croupand whooping cough. Even though many researchers feel squill isrelatively safe, others consider it a toxic plant. The main reason for thecontroversy seems to be the accumulation rate. Unlike digitalis, squilldoes not remain in the body long and therefore has less chance ofaccumulation . This herb can be specific to heart problems associatedwith renal problems.11,12,13

OCH3

CH3

Figure 9.7Scillarenin bis-L-rhamnoside

OOHO

OH

O

OHOH HOHO

HO OH

HOO

Figure 9.8Glucoconvallasaponin A

O

OH

HOH2C

O O O

O

O

HOHO



Lily of the Valley Convallaria majalis

The active portion of Lily of the Valley is the dried rhizome and roots ofConvallaria majalis. The chief constituents of this plant are two glyco-sides, convallarin and convallamarin. Convallaria is ten times moreactive than digitalis. One-tenth of a gram of Convallaria is equal to 12digitalis units. Lily of the Valley has little cumulative effect and is there-fore not considered as dangerous as digitalis. It is considered diureticand has also been used for convulsions, dropsy, epilepsy, palsy andvertigo. The fruit is considered extremely poisonous.14,15,16

Indian Hemp, Dogbane Apocynum cannabinum

The rhizome and roots of Apocynum cannabinum are the key parts usedfor medicinal purposes. They contain the cardiac glycoside cymarin,apocannoside, cynocannoside, K-strophanthin, tannin and resins. Thisplant is considered extremely toxic. It has been used as a cardiac tonic,cathartic, diaphoretic, diuretic, expectorant, febrifuge, hydragogue,laxative, tonic and emetic. The Amerindians used it extensively. 17,18

Tetraterpenoids

The most familiar of the tetraterpenoids are the carotenoids (yellow tored). Over 400 distinct kinds have been identified. These compoundsoften have cyclization at one or both ends, with a central carbon chain.Two of the important tetraterpenes are beta-carotene and lutein, foundin the leaves of many plants. Another common form is capsanthin, foundin Capsicum annuum.

Beta-Carotene

Because beta-carotene is also known as pro-vitamin A, people feel thatits major use is to stimulate Vitamin A activity. This is not true. There aremany uses above and beyond this. Even though beta-carotene can bebroken into two vitamin A molecules, the human body will only do this ifit needs vitamin A. The beta-carotene is the preferred state, as it is moreactive and less toxic. Its most important action is probably its very

Figure 9.9β - Carotene

Sc2



potent ability to quench singlet oxygen free radicals. In this role, it ismany time more potent than Vitamin E.19 Carotenoids are superiorantioxidants. It is felt that some of the other carotenoids might even bemore potent than the beta-carotenoids.

Beta-carotene is associated with a reduced rate of cancer involvingepithelial cells (lung, skin, uterus, cervix, respiratory, GI tract, etc.).20,21,22

Beta-carotene potentiates interferon’s action while inhibiting interferon’ssuppressor systems.23,24,25 Beta-carotene also increases immune cellproliferation (something that is inhibited by vitamin A), making itseffects on the immune system much more comprehensive than vitaminA.26,27

Beta-carotene and vitamin A reportedly have a role in thymo-protection,preventing stress-induced thymic problems and promoting thymusgrowth.28,29 Beta-carotene significantly increases (by approximately 30%)the T-lymphocyte helper cells within 7 days and all types of T- lympho-cyte cells within 14 days. This will, of course, increase the immunesystem’s capability, making it a very useful clinical approach in treatingimmune diseases such as AIDS and Chronic Fatigue Syndrome. Beta-carotene, of course, acts as an excellent prophylactic, protecting thehost from all kinds of viruses, bacteria and fungi.30

Oral use of beta-carotene is known to boost antitumour immunity incancer patients. Beta-carotene has therefore been described as increas-ing longevity. It has the capacity to increase “maximal life-span poten-tial” (MLSP) for mammals, including humans, better than any substanceso far studied.31

It is important to note that even though vitamin A has a relatively lowtoxicity, beta-carotene’s toxicity is so low that it is effectively unknown.Even though a person’s skin might turn yellow or orange with high intakeof carotenoids, the substance itself is not toxic.32 It appears that Nature

Figure 9.10Antioxidant Mechanism of β-carotene

O * O2

2. The beta-caroteneswitches to retrogradeform.

1. A beta-carotene drawsnear to a singlet oxygen.

3. Beta-carotene extracts energyfrom the singlet oxygen and releasesan oxygen molecule.

4. Oxygenscombine into O2.

O

O *↑

↑ ↑

O

↑



intended us to use beta-carotene as our source of vitamin A. Once againit should be noted that significant evidence suggests that many of thecarotenoids have biological activity, possibly even stronger than beta-carotene.

Porphyrins

The other major group of pigments in plants includes chlorophyll andrelated pigments. It is classified as a porphyrin (as is hemoglobin invertebrates). Porphyrins are widespread throughout the plant andanimal kingdoms. They have a role in oxygen transport and storagesystems in vertebrates, in respiratory chains in most cells, and as themajor component of the solar collector in plants, chlorophyll.

CH

HN

CH

N

CH

CH

NH

Figure 9.11Porphyrin

The basic shape of the parent nucleus is a cyclic tetrapyrrol (see Figure9.11). The numbering system consists of numbers, Roman numerals andGreek symbols (indicating side).

Chlorophyll and Related Compounds

Chlorophyll A and B are the only green pigments found in all plants moreevolved than algae. The ratio of chlorophyll A and B is usually 3:1. Theyare not interconvertible. The herb with the highest level of chlorophyll ischlorella (also discussed in Chapter 3 -- Carbohydrates).

When chlorophyll has been injected into test animals, porphyrin derivedfrom the chlorophyll protected local tissue while destroying tumors.33

This information is presently under investigation by a researcher called

N

I II

IIIIV

α

β

χ

δ



N

N

NCH2CH3

CH3CH

CH2

CH3

CH3

H

CH2

CH2

C

OC20H39

CO

OCH3O

N

Mg

Dupont for possible anti-cancer applications.34 Tumors saturated withporphyrin are exposed to light, causing the release of singlet oxygen andresulting in destruction of the tumor. Chlorophyll has been shown toincrease wound healing by 24.9%, treat pancreatitis, deodorize badsmells, and have antibacterial properties.35

Heme and related compounds

Hematin (or iron porphyrin) pigments are well known in animal tissue(e.g. hemoglobin) but can also be found in plant tissue. Even thoughhemoglobin has been found in plant tissue (legume roots), the majorhematin compounds are cytochrome respiratory pigments, which play amajor rolein cellular respiration. These hematins transport electronsalong a chain in human aerobic tissue as follows:

cytochrome b 557 ----> cytochrome b 560 ----> cytochrome c549 ----> cyto-chrome c547 ---> cytochrome a ----> cytochrome a3 (cytochrome oxidase) ----> O2

The heme P-450, important in hormone metabolism in animals at acellular level, is also found in plant tissue.

Figure 9.12Chlorophyll A

O




12 Tyler, V., Brady, L., Robbers, J.,Pharmacognosy, (7th ed.), Lea &Febiger, Phila., PA, 1976. ibid..





17 Duke, J., CRC Handbook of MedicinalHerbs, CRC Press, Boca Raton, FL,1985, p.49-50.

18 Moerman, D., Medicinal Plants ofNative America, Univ. of MichiganMus. of Anthrop. Tech Rep No. 19,Ann Arbor, 1986.

19Burton G., Ingold, K., Beta-carotene:an unusual type of antioxidant,Science 224:569-73, 1984.

20Peto, R., Doll, R., et al., Can dietarybeta-carotene materially reducehuman cancer rate?, Nature 290:201-8, 1981.

21Creasey, W.A., Diet and Cancer, Lea &Febiger, Phil. PA, 1985.

Summary

As we have seen, the advanced terpenoids covered in this chapter arevery active medicinally. Some steroidal compounds have cancer-relatedclaims and blood lipid and pressure lowering qualities. Cardiac glyco-sides are also steroidal in nature. Even though these glycosides are veryactive, they have a low therapeutic index and are therefore not usedinternally very often. We looked at digitalis, squill, Lily of the Valley andIndian Hemp under these categories. The major tetraterpenoid welooked at was beta-carotene, with its antioxidant, anticancer and im-mune-enhancing qualities. The group of porphyrins include chlorophylland hemoglobin. They are particularly important for their energytransfer and respiration mechanism.

References

1 Hsu, H.Y., Chen, Y.P., Hong, M., TheChemical Constituents of OrientalHerbs (Vol. 1), Oriental Healing ArtsInstitute, Los Angeles, CA, 1982,p.1029.

2Jonathan L. Hartwell et al.,Antineoplastic Principle in Plants,Advanced in pharm and Chemo-therapy 7: 117-209, 1969.

3Raicht, R. et al., Protective Effects ofPlants Sterols Against ChemicallyInduced Colon Tumors in Rats,Cancer Research 40: 403-04, 1980.

4 Goodman, L., Gilman, A., ThePharmacological Basis of Therapeu-tics (4th ed.), Collier-MacmillanCanada Ltd., Toronto, 1970, p.22.



7 Tyler, V., Brady, L., Robbers, J.,Pharmacognosy, (7th ed.), Lea &Febiger, Phila., PA, 1976. p.205-212.






22National Research Council: Diet,Nutrition and Cancer, National Acad.Press, Wash., D.C., 1982.

23Retura, G., Stratford, F., et al.,Prophylactic and therapeutic actionof supplemental beta-carotene inmice innoculated with C3HBAadenocarcinoma cells: Lack oftherapeutic action of supplementalascorbic acid, JNCI 69:73-7, 1982.

24Rhodes, J., Human interferon action:Reciprocal regulation by retinoicacid and beta-carotene, JNCI 70:833-7, 1983.

25Rhode, J., Strokes, P., et al., Humonetumor-induced inhibition ofinterferon action in vitro: Reversal ofinhibition by beta-carotene, CancerImun. Immunother 16:189-92 1984.

26Rhodes, ibid.27Rhode, Strokes, et al., ibid.28Cohen, B.E., Gill, G., et al., Reversal of

postoperative immunosuppressionin man by vitamin A, SurgeryGynecol Obstet 149:658-52, 1979.

29Burton, G., Beta-carotene: An unusualtype of lipid antioxidant, Science224:569-73; 1984.

30Alexander, M., Newmark, et al., Oralbeta-carotene can increase the [] ofOKT4+ cells in humans blood,Immunol Letters 9:221-4., 1985.

31Culter, R.G., Carotenoids and retinols:Their possible importance indetermining longevity of primatespecies, Proc. Natl. Acad. Sci 81:7627-31, 1984.

32Peto, R., The marked differencebetween carotenoids and retinoids:methodological implication forbiochemical epidemiology, CancerSurv. 2:327-40, 1983.

33Figge, F.H.J., et al., Cancer detectionand therapy. Affinity of neoplastic,embryonic, and traumatized tissuefor porphyrins and metallo-porphyrins; Proc. Soc. Exp. Biol &Med 68:640, 1948.

34Dupont, R. et Duhamel, G., Chloro-phyll et Cancer Bull. []

35Steenblock, D., Chlorella: NaturalMedicinal Algae, Aging ResearchInstitute, El Toro, CA, pp.45, 1987.


Alkaloids

10Alkaloids

Synopsis:

This very large and diverse group of chemicals includes analgesics, narcotics,central nervous system stimulants, can cause pupil dilation or contraction,increase blood pressure or lower blood pressure. We can divide alkaloids into ninegroups. We will be looking at seven in some detail.



Table of ContentsIntroduction Physiological Effects Alkaloid Groups Pyridine - piperidine

Tobacco Areca Lobelia Pomegranate

Tropane Alkaloids Bella Donna Stramonium Cocaine

Quinoline Alkaloids Cinchona

Isoquinoline Alkaloids Ipecac Goldenseal Barberry Opium

Indole Alkaloids Ergot Alkaloids Imidazole Alkaloids Steroidal Alkaloids Lupinane Alkaloids

Broom Alkaloidal Amines

Ma Huang Colchicum Peyote

Purine Alkaloids Kola Coffee

Summary Mini-Materia Medica - Alkaloids


Figure 10.1 Representative AlkaloidsFigure 10.2 Pyridine - PiperidineFigure 10.3 NicotineFigure 10.4 Arecholine HydrobromideFigure 10.5 LobeliaFigure 10.6 LobelineFigure 10.7 Synthesis of Tropane AlkaloidsFigure 10.8 AtropineFigure 10.9 Scopolaminefigure 10.10 CocaineFigure 10.11 QuinolineFigure 10.12 Quinine

Figure 10.13 IsoquinolineFigure 10.14 Emetine HydrochlorideFigure 10.15 HydrastineFigure 10.16 GoldensealFigure 10.17 BerberineFigure 10.18 CodeineFigure 10.19 MorphineFigure 10.20 SparteineFigure 10.21 Biosynthesis of ephedrineFigure 10.22 ColchicineFigure 10.23 PeyoteFigure 10.24 Biosynthesis of mescalineFigure 10.25 Purine


Alkaloids

lkaloids are one of the largest, most diverse and complex groupsof chemicals represented in the plant world. Alkaloids are ex-tremely difficult to define. They aren’t a homogeneous group ofA

compounds, from a chemical, physiological or biochemical point of view.

We will define an alkaloid as a substance with nitrogen in the molecule,connected to at least two carbon atoms. The molecule must have at leastone ring, but it is not necessarily heterocyclic. The compound cannot be astructural unit of macromolecular cellular substances and cannot serve as avitamin or hormone.

Most alkaloids are well defined crystalline substances and contain theelements carbon, hydrogen, nitrogen and oxygen in their molecules.There are a few, such as coniine from hemlock and nicotine from to-bacco, which are liquid and oxygen-free. Alkaloids are normally white, arare exception is berberine, which is yellow and the copper-red salt ofsanguinarine. For a plant to be acknowledged as having alkaloids,minimum content must be 0.01%.

In the early 1800’s, the German pharmacist Serthurmer succeeded incrystallizing the alkaloid morphine. In 1803, Derosne published themethod of extracting this alkaloid. The word alkaloid dates back to theGerman pharmacist Meisner (1792-1853). Derosne and Serthurmerreferred to them as “plant alkalis”.1

The scientific search for alkaloids has been intense because of theirestablished physiological action. In 1968 there were 800 known alkaloids.Ten years later, there were 6000 identified compounds with alkaloid-like

Introduction



properties. With the nebulous definition of “alkaloid”, debate continuesover whether particular chemicals are alkaloids. Some would not includemescaline or ephedrine as alkaloids because the nitrogen in thesesubstances are in open chains (aliphatic). Others would not considercaffeine as an alkaloid in the true sense, merely a purine base. Forpurposes of discussion, the first definition allows us to include these“questionable” alkaloids.

Alkaloids appear throughout the plant kingdom. Amongst the angio-sperms, the Leguminosae, Papaveraceae, Ranunculaceae, Solanaceae,Rubraceae and Berberidaceae have a very high number of alkaloid-yielding plants. The Labiatae and Rosaceae are almost free of alkaloidsas are the gymnosperms. For many years it was thought that only plantscontained alkaloids, but a few species of both vertebrates and inverte-brates have also been found to contain alkaloids.

Alkaloids can be found in various parts of the plant:

in the seeds (nux vomicae, areca),in the fruit (black pepper, conium),in the leaves (belladonna leaf, hyoscyamus),in underground stems (sanguinaria, corydates),in the roots (aconite, belladonna root),in the rhizomes (ipecac, hydrastis)and bark (cinchona, pomegranate).

Alkaloids generally remain active through the drying process but can beaffected by ethylene oxide gases (used to control micro-organisms).Some alkaloids affect the heart, raising or lowering blood pressurethrough their influence on the central nervous system. Some of thealkaloids work on the autonomic nervous system. The action can beantispasmodic, mydriatic (pupil dilating), analgesic, narcotic or as localanaesthetic. Some alkaloids, especially tropical ones such as quinine, areantiparasitics or chemotherapeutics. Alkaloids are usually extremelybitter.

As indicated above, the physiological action of alkaloid-containingbotanicals on humans and other mammals, varies widely. The followingare some examples:

1. analgesic and narcotic: morphine and codeine.2. central nervous system stimulant: brucine, strychnine.3. mydriatic (causing pupil dilation): atropine, homatropine.4. myotic (contracts the pupils): physostigmine, pilocarpine.5. to increase blood pressure: ephedrine.6. to lower blood pressure: reserpine.


Alkaloids

Many alkaloids are derived from the aromatic amino acids phenylalanineand tyrosine. This can be seen in simple phenylethylamines such asmescaline. The names for alkaloids are obtained in a variety of ways:

1. From the generic name of the first plant it was found in(hydrastine, atropine).

2. From the specific name of the plant (cocaine, belladonnine).3. From the common name of the botanical yielding them

(ergotamine).4. From the physiological action of the alkaloid (emetine,

morphine).5. There are a few named after the discoverer (pelletierine).

By now the observant reader will have noticed that alkaloids should endin “ine” by chemical rules. Sometimes a prefix or suffix is added to theprincipal alkaloid name to designate similiar alkaloids (guanine, guani-dine, hydroguanine).

Most alkaloids contain one nitrogen, although some contain manyradicals:

1. Primary amine (RNH2)2. secondary amine (R2NH)3. tertiary amine (R3N)

We can group many of the alkaloids together according to their basicchemical structure. Many of these structures can be seen in Figure 10.1.

1. Pyridine and Piperidine: arecoline, pelletierine, lobeline,coniine and nicotine.

2. Tropane (which is a condensation product of pyrrolidine andpiperine): atropine, hyoscyamine and hyoscine.

3. Quinoline (contains cinchona alkaloids): guanine, guanidine,cinchonine and cinchonidine.

4. Isoquinoline: hydrastine, d-tubocurarine, emetine and certainopium alkaloids.

5. Indole Ring: ergonovine, reserpine, strychnine.6. Imidazole Ring: pilocarpine.7. Purine: theobromine.8. Phenanthrene: morphine, codeine.9. Steroidal: aconitine and protoveratrine.



N NH

NN

NH

H2C C CH2

N CH3 CH2

H2C C CH2

H

H N

N

N

N

HN

Figure 10.1Alkaloids

TropanePyrrolidine Indole Imidazole

CyclopentanohydrophenanthrenePhenanthrenePurine

Benzene Pyridine Piperidine Quinoline Isoquinoline

The function of the alkaloids within plants is debatable. Some of thepossibilities are as follows:

1. To protect the plant through their poisonous effects oninsects and herbivores. Though there are cases of this in theliterature, it is felt that this theory is overworked and isprobably an anthropocentric concept.

2. As an end product of metabolic pathways, locking up toxiccompounds, like urea and uric acid as in animals.

3. Growth regulator. Alkaloids in lupine act as germinationinhibitors. In rice we can find a growth stimulator and incorn we have growth inhibiting quinoline alkaloid struc-tures.

4. As nitrogen storage reservoirs.

N

N


Alkaloids

For the purposes of an advanced herbology we will look at the followingalkaloids, grouped according to the ring structure or nucleus of the chiefalkaloid group:

1. pyridine - piperidine2. tropane3. quinoline4. isoquinoline5. indole6. imidazole7. steroid8. lupinane9. alkaloidal amine10. purine

Pyridine - Piperidine

These two are considered together because as we can see (in Figure10.2) the tertiary based pyridine is easily reduced to the secondarybased piperidine.

Some of the important alkaloids in this group are arecoline, hydro-bromide, lobeline, pelletierine, coniine, piperine and nicotine.

Tobacco (Nicotine) Nicotiana tobacum

Nicotine is the major alkaloid obtained from Nicotiana tobacum andNicotiana rustica, commonly known as tobacco. It was used as a majorreligious herb by Amerindians long before Europeans were introducedto it in the 15th century. Nicotine was first isolated by Posselt andReiman from N. tobacum. Nicotine (1-menthyl-2 (3-pyridyl) pyrrolidine) isbiosynthesized from ornithine and quinolinic acid. It can be found inconcentration of 2 - 8% combined with citric and malic acids.2

Nicotine’s action is varied, both stimulating and depressing the CNS. Itinitially acts on the ganglia as a nerve stimulant followed by persistentand protracted depolarization, thereby stopping proper nerve impulses.

Figure 10.2Pyridine -- Piperidine

N NHPyridine Piperidine



During the brief stimulatory phase there is nausea, increased intestinalactivity, arteriole and capillary constriction. This progresses to pallor,sweating and increased blood pressure. Nicotine liberates catecholamines from the adrenal medulla resulting in pronounced vasoconstric-tion. Nicotine is passed on to the breast milk at a rate of about 0.5 mg perliter.3

Smoking is associated with lung cancer, coronary heart disease, emphy-sema. Chewing tobacco is associated with oral and esophageal cancer.Fatal doses as low as 2 - 3 cigarettes are recorded for infants. Tobaccohas long been know as a folk remedy for bronchial disorders, as apoultice for topical uses and as a ritual herb among many cultures.

Areca Areca catechu

Areca nut or Betel nut is the dried seed of Areca catechu. Areca is fromthe Spanish name of betel nut, catechu is East Indian for astringentextract or juice.

This tall, beautiful palm is extensively cultivated in East India, SouthernAsia and East Africa. The nut and sometimes the leaves of this plant arechewed to stimulate saliva secretion and as a digestive aid after largemeals. In some Indian restaurants you can find a “dessert” item calledpaan (pronounced Pone), that is eaten as the final item of a feast. Betelnut is also an excellent vermifuge, specifically taenifuge (tapeworms). Itis often used in veterinary medicine.4

Areca contains several alkaloids which are reduced pyridines. The mostprominent ones are arecoline (arecaidine methyl ester), arecaidine (N-methyl guvacine), guvacine and guvacoline. The alkaloid content isusually 0.45%. Arecoline is the most abundant and most physiologicallyactive of these alkaloids. Free tyrosine and phenylalanine and combinedarginine are also noted.5,6

Arecoline hydrobromide is obtained from this plant and is used as aveterinary anthelmintic for dogs at 1.5 mg. per Kg of body weight. Poul-tices and juice of the leaf has been mixed with bland oil and appliedtopically for lumbago. The nut is considered laxative, carminative,

Figure 10.3Nicotine

N

N CH3


Alkaloids

aphrodisiac and is used as a nervine in India.7 Dosages range as follows:powder - 1 - 2 grams, extract - 1 - 2 ml, tincture- 5 - 10 ml.

Lobelia Lobelia inflata

The herb Lobelia or Indian Tobacco is actually the dried leaves and topsof Lobelia inflata. The name Lobelia is in honour of Matthias de L’Obel aFlemish botanist (1538-1616), inflata describes the hollow fruit which isinflated upon ripening. This plant is native to Eastern and Central U.S.A.and Canada. It is commercially picked and grown in North Carolina,Virginia and Tennessee. The best picking time is when the fruit capsuleis inflated.

CO OCH3

CH3H

Br -

Figure 10.4Arecholine Hydrobromide

This herb has had a varied history, alternately described as one of thegreatest herbs available and as a poison not to be used. There arefourteen alkaloids (representing 0.13 - 2.5%) in this herb, the major onebeing lobeline.8 Lobelia contains lesser amounts of the pyridine alka-loids, lobelanine and lobelanidine, many minor alkaloids, resin, gum,chelidonic acid9,10 and a pungent volatile oil.11 The minor alkaloids aresimilar in action but milder than lobeline.12

Figure 10.5Lobelia

N+

Sc2

Mo2



OH

H5C 6

O

Figure 10.6Lobeline

In small amounts this herb is a depressant, diaphoretic, diuretic, expec-torant and short term respiratory stimulant. Lobelia is popular as ananti-smoking agent because it binds up the receptor site for nicotine,reducing the desire to smoke. The activity of the lobeline alkaloids issimilar to nicotine but much milder. The herb is also used in many lung,bronchial and asthmatic formulas due to its antispasmodic quality -dilating bronchioles by relaxing the muscles. In the digestive tract,lobelia is both inhibitory and stimulatory. Lobelia has also been shownto be an adrenal stimulant, a platelet aggregation inhibitor and has amoderate antibiotic action on Gram-positive and Gram-negative bacteria.

Pomegranate Punica granatum

The roots and stems are derived from Punica granatum. Found in North-western India originally, the plant is now cultivated in subtropical zonesthroughout the world, primarily for the edible fruit. The whole plant isastringent because of the high concentration of tannins (20% in the driedroot). This plant is vermifugal (again specifically a taeniafuge) due to thealkaloids pelletierine (C8H18ON) and methylisopelletierine (C9H17N).13

Tropane Alkaloids

These dicyclic compounds are formed by condensation of a pyrrolidineprecursor (ornithine) with three acetate derived carbon atoms. Botani-cals and alkaloids important in this group are: belladonna leaf,Hyoscyamus, Stramonium, atropine, hyoscyamine, scopolamine, cocoaand cocaine.

Belladonna Atropa belladonna

Deadly nightshade or Belladonna is the dried leaves and flowers orfruiting tops of Atropa belladonna. Atropa comes from the Greek wordatropas meaning to cut the thread, alluding to its poisonous properties.Belladonna comes from the Italian bella meaning beautiful, donna

C6H5N

CH3


Alkaloids

COOH

NH2

NH2

Ornithine 2 14C

COOH

CH3

COOH

CH3

2 Acetates

(Methionine)

CH2

N .(CH3)CHOH

CH2

Tropine

C

CH2OHC

H

O

H

NCH3

Figure 10.8Atropine

meaning lady. The juice of the berries was at one time dropped into eyesof women to dilate the pupil and increase the beauty of the eyes.

This perennial herb is native to southern Europe and Asia Minor and iscultivated in England, U.S.A., Germany and India. It has been officiallyrecognized both in the United States and England as an anodyne, relax-ant, sedative, antigalactagogue, antidiuretic and for limiting otherglandular secretions. It was also used as an antiasthmatic for Parkinson’sdisease, epilepsy, whooping cough, spermatorrhea, night sweats, gastriculcers, kidney stones and gallstones.

Recovery from toxicity is usually complete in forty-eight hours. A majoralkaloid in modern pharmacy is atropine (C 17H23NO3) which is used as ananticholinergic (a cholinergic blocking agent which impedes parasympa-thetic nerve impulses).14,15

Figure 10.7Synthesis of Tropane Alkaloids

∆

∆

∆

∆

↑

↑

↑

O



Coca (Cocaine) Erythroxylon coca

Coca leaves come from the dried leaves of Erythroxylon coca and closelyrelated species. Erythroxylon is Greek meaning red wood, alluding to thecolour of the plant, coca is the Spanish name of the tree. The alkaloids ofthis plant range from 0.4-2.5%, the main alkaloids are cocaine (derivativeof ecgonine) C 17H21NO4, cinnamylcocaine and truxilline.16,17

The production of cocaine has expanded into a multibillion dollarindustry because of a high priced underground market and extensiveuse as an illicit drug. Cocaine is a local anesthetic and cerebral stimu-lant (considered narcotic in large doses). It is absorbed easily by themucous membranes and becomes physically addictive, destroyingmucous membranes with extended use.

Cocaine is an alkaloid that is not particularly stable. It will easily convertto a more stable hydrochloride salt. This salt is not volatile, thoughcocaine itself is. Since smoking has been shown to give a more intense

Stramonium / Jimson weed Datura stramonium

Stramonium or Jimson weed is the dried leaf and flowering or fruiting topof Datura stramonium. This plant was available in most North Americandrug stores across the counter as an asthma herb until 1968 when it wasplaced on prescription lists because of “thrill seekers” who started usingit as an hallucinogen. This plant is considered a very strong ritual plantby some Native American groups and is said to enable its user to gainextraordinary powers. It is also very poisonous and can kill its users.

The chief alkaloids (0.25 - 0.7%) are hyoscine, hyoscyamine, atropineand scopolamine. It has mostly been used for its antispasmodic action inasthma and for Parkinson’s disease because it is an antagonist toacetylcholine. Atropine has been shown to paralyze the vagus nerveendings, relieving bronchial spasms.

C

CH2OHC

H

O

H

NCH3

Figure 10.9Scopolamine

O

Sc2

O


Alkaloids

"high", "free basing" has been developed. By taking the street drug(mostly in salt form), and mixing it with sodium bicarbonate (bakingsoda), an extraction of the alkaloid in ether will yield a "free base"cocaine. There is usually still some bicarbonate left over, resulting in thecocaine chunking (called "Rocks" on the street). When the material isburnt in a pipe, the bicarbonate causes a crackling sound, hence thestreet name "crack". Crack is much more addictive than cocaine ab-sorbed by other methods because larger proportions of the purealkaloid are absorbed.

H2C C CH COOCH3

N CH3 C O C

H2C C CH2 O

Figure 10.10Cocaine

N

Figure 10.11Quinoline

Quinoline alkaloids

These alkaloids contain quinoline as their basic nucleus. Some of themajor botanicals containing these alkaloids include cinchona (quinine,quinidine, cinchonine and cinchonidine), Acronychia baueri (acronycine)and Penicillium viridicatum (viridicatin). Cinchona is the only botanicalof this group that has therapeutic value.

Cinchona Cinchona succirubra

Cinchona or Peruvian Bark is the dried bark of the stem and root ofCinchona succirubra (sometimes one of the related species or hybrids).Cinchona was named in honour of Countess of Cinchona, wife of theViceroy of Peru. Succiruba is Latin meaning “red juice”.

Trees whose bark is shaded and are 6-9 years old produce the maximumamount of the key alkaloid. Cinchona contains some 25 closely relatedalkaloids of which guanine is the most important. The yield of thealkaloids is between 6-16%, half to two-thirds of which is quinine in theyellow bark. Cinchonidine is highest in the red bark.18,19,20

Mo2



Peruvian bark has been used for the treatment of malaria fever forcenturies throughout the world. Overdose of Peruvian bark can causetemporary loss of hearing and ringing in the ears. This is much morecommon in synthetic guanine than from the bark itself. Death hasoccurred in adults after consumption 8 gms of quinine. Quinine is alsoused in the preparation of tonic water.

Isoquinoline Alkaloids

This structure occurs in a rather wide number of plants. The mostimportant botanicals in this group are ipecac (emetine), Hydrastis(hydrastine), Sanguinaria (curare, tubocurarine), Berberis (berberine),opium and its alkaloids.

The opium alkaloids (morphine, codeine, thebaine) have a phenanthrenenucleus, but the majority of its alkaloids do have an isoquinoline ringstructure, the basis for placing opium in this group.

Ipecac Cephaelis ipecacuanha

Ipecac is the dried rhizome and root of Cephaelis ipecacuanha. Cephaeliscomes from the Greek words “head” and “to collect or roll up” referringto the inflorescence. Ipecacuanha is Portuguese meaning “a creepingplant that causes vomiting”.

There are five alkaloids (1.8-4%) in this plant. The three most importantones are emetine, cephaeline and psychotrine. Approximately two-thirdsof the alkaloid content is emetine and one third cephaeline.21,22 Ipecac isemetic in large doses, diaphoretic and expectorant in smaller doses andin still smaller doses, stimulating to the stomach, intestine and liver.

N

Figure 10.12Quinine

HO

H

H

N

C

C

H3CO

CH2CH2

CH2

Sc2


Alkaloids

Figure 10.11Isoquinoline

One quarter - two grains is used for expectorant action and 15-30 grainstriggers emesis. Ipecac syrup is included in many poison antidote kitsbecause of its emetic properties. Ipecac is well known for its beneficialaction on amoebic dysentery but it is often needed in doses that causevomiting. The major alkaloid emetine is sometimes injected producingrapid cure for amoebic problems.

Goldenseal Hydrastis canadensis

Goldenseal or Hydrastis is the dried rhizome and roots of Hydrastiscanadensis . Hydrastis comes from Greek “to accomplish or act withwater” referring to its habitat. It previously grew in the eastern U.S.A.and Canada but is almost extinct due to its high economic value. It ispresently cultivated in Oregon, Washington, North Carolina, Tennessee,Michigan and Wisconsin. Most commercial goldenseal comes fromArkansas and the Blue Ridge Mountains.

Figure 10.14Emetine Hydrochloride

CH20

CH20NH

CH2CH3

N

OCH2

OCH2

2HCl. 4H20

There are three alkaloids which have been isolated from this plant:hydrastine (1.5-4%), berberine (0.5-6%), berberastine (2-3%), withcanadine, candaline and others also making an appearance.23,24,25

Goldenseal is a tonic, alterative, astringent and mild laxative. It isconsidered the “King of the mucous membranes” and is used by herbal-ists in many mucus-related problems. The expense of goldenseal root isrising rapidly and this is reducing the clinical application of the botani-

N

Sc2

Mo2



cal. Goldenseal root is often mixed with the leaves, diluting the strengthand usefulness. Goldenseal helps build up a natural immunity and has anantibiotic effect on a large range of micro-organisms.

Berberine has been found active against a wide range of microbes. As animmunostimulator it increases blood supply to the spleen,26 activatesmacrophages,27 and has tumor inhibitory action.28 Hydrastine has beenemployed to stop hemorrhaging in the uterus and to stimulate the heartmuscle.

Berberine sulfate has shown activity against B1, KB and PS tumorsystems. Folklore suggests it is effective against uterine cancer. Onemight expect some limited success in this area.29 Goldenseal has beenemployed for inflammation, chronic catarrh, gastritis, enteritis, for aninflamed uterus, vagina and bladder, as well as hemorrhoids and analfissures. Goldenseal root uses high amounts of B-complex vitamins whentaken in large doses over a period of time.30 - 35

Externally, Goldenseal is valuable for chronic inflammation of mucousmembranes, cracks and fissures of the nipples, indolent ulcer, and as alotion to stop profuse sweating.38 Goldenseal or its alkaloids are useful asan eyewash.39

Barberry Berberis vulgaris

Berberis, Oregon Grape root and Barberry are common names forBerberis vulgaris . Berberine is the major alkaloid, but the plant alsocontains oxyacanthine, berbamine and a little tannin.40 - 43

C OO

OCH3

OCH3

Figure 10.15Hydrastine

O

ON CH3

Ed

Sc2

Mo2


Alkaloids

Figure 10.16Goldenseal

OCH3

OCH3

OH

Figure 10.17Berberine

Berberine is recognized as a internal treatment for malarial, typhoid,scarlet and Rocky Mountain spotted fevers. Berberine can increasemuscle tone, lower blood pressure and increase the volume of blood inthe spleen. Herbalists uses barberry as a tonic, hepatic, purgative andantiseptic.

O

ON



Figure 10.18Codeine

N CH3

H3CO

Figure 10.19Morphine

N CH3

Opium Papaver somniferum

Opium comes from the air-dried milky exudate obtained by incising theunripe capsule of Papaver somniferum. Opium is from the Greek wordopion meaning poppy juice. Papaver is Latin for poppy, somniferum isLatin for sleep.

The three major varieties are Turkish Opium, Indian Opium and ChineseOpium. The production and export of Chinese opium has not been fullydocumented since the Communist party took control of mainland Chinain the late 40’s. Approximately 300,000 kg of opium is imported into theU.S.A. yearly for the pharmaceutical market. The amount imported onthe black market for illicit use probably equals this amount, typically inthe form of heroin.

Opium contains morphine (4-21%), codeine (0.8-2.5), noscapine (for-merly narcotine, 4-8%), papaverine (0.5-2.5%) and theobaine (0.5-2%).Other alkaloids include protopine, narceine, laudanine, codamine,cryptopine, tanthopine and neconidine.44,45 Opium is a narcotic thatworks mostly on the central nervous system, acting as a stimulantinitially and then depressing nerve response. It is employed as ananalgesic and hypnotic, checking peristalsis and contracting the pupil ofthe eye.

O OH

O OHHO


Alkaloids

Morphine is a narcotic analgesic which is strongly hypnotic. It inducesnausea, vomiting and constipation, and is very habit forming. Heroin, amuch more addictive substance, is formed by acetylization of morphine.Codeine is also a narcotic analgesic and antitussive. It is often found incough remedies and Tylenol®. Codeine is less toxic and habit formingthan morphine.

Indole Alkaloids

The most important botanicals and alkaloids in this group are: Rauwolfia(reserpine), Catharanthus (Vinca) (vinblastine, vincristine), Nux Vomica(strychnine, brucine), Physostigma (physostignine) and Ergot (ergota-mine and ergonovine).

Although alkaloids in this group have great significance to allopathicmedical practices, they have relatively little value to a herbalist. Theallopaths, after finding active alkaloids in these botanicals, syntheticallyderived variations with more powerful effects. Most of the indole alka-loids have tryptophan as a precursor.

Ergot Alkaloids

This group includes hallucinogens such as LSD and also have little valuein an advanced herbology practice.

Imidazole Alkaloids

This group contains one herb that is sometimes still used -- Pilocarpus,whose major alkaloid is pilocarpine. The crude botanical is rarely used.Pilocarpine is antagonistic to atropine, stimulating the nerve endingsparalyzed by that drug.46

Steroidal Alkaloids

Some of the prominent botanicals and alkaloids that fit into this groupare Veratrum (protoveratrine), aconite (aconitine) and Larkspur. Helle-bore (Veratrum), monkshood (Aconite) and Larkspur (Delphinium) areall poisonous and therefore not used internally by herbalists.



Lupinane Alkaloids

The major medicinal botanical in this group is broom.

Broom Cytisus scoparius

Broom is the dried top of Cytisus scoparius. This plant grows in Europe,western Asia and has naturalized in the United States. The major alkaloidis sparteine (1.5%) with two minor ones, sarothamnine and genisteine. Italso contains flavone, scoparin, tannins and volatile oils.47,48

It is used as a diuretic and cathartic. Large doses are considered nar-cotic because of the sparteine (Figure 10.20). Broom is also consideredan oxytocic -- inducing labor, stimulating uterine contractions. It was saidto be used by King Henry VIII for gout. Broom is a cardiac depressant.This plant is considered unsafe for internal consumption by the UnitedStates Food and Drug Administration.

Alkaloidal Amines

Botanicals and alkaloids in this group include Ephedra (ephedrine), col-chicum (seed and corms) (colchicine), khat and peyote.

N

N

Figure 10.20Sparteine

COOH CHO

Figure 10.21Biosynthesis of Ephedrine

Phenylalanine-3-14C Ephedrine

NH2

OH

NHCH3

Benzalaldehydeequivalent

↑ ↑


Alkaloids

Ma Huang Ephedra sinica

Ephedra or Ma Huang is the entire plant, above ground, of Ephedrasinica. In Chinese it is called “Ma” meaning astringent and “Huang”means yellow. This low, dioecious plant is a practically leafless shrub,60-90 cm high, growing in China, Northwestern India and Pakistan.

Ma Huang contains between 0.44 - 2.56% alkaloid content varyingbetween species and picking time. The highest alkaloid content is foundin plants in September. The alkaloid content is mostly l-ephedrine (ca.85%) with the rest being d-pseudoephedrine (which readily convertsinto ephedrine). There are also small amounts of other related alkaloidspresent. Apparently, biosynthesis in the plant moves from phenylalanineand methionine to ephedrine. There is also small amounts of saponins,catechin, tannins. 49 - 54

Ephedrine is very similar to epinephrine in action but has the advantageof oral administration. It is absorbed and not altered by the liver. It isvery useful for dilating the bronchial tubes in cases of allergies, bronchi-tis and asthma. It stimulates the cardiac muscles often causing a rise inblood pressure. It has also been used to contract the uterus and as adiuretic. Other Ephedra species such as Brigham or Mormon tea alsocontain ephedrine, but in much smaller quantities.

Colchicum Colchicum automnale

Colchicum (also called meadow saffron) comes from the corm or seed ofColchicum automnale. The alkaloid significant from this is up to 0.8%colchicine (C22H25NO6). It also contains colchiceine and six other alka-loids. Colchicum has been used successfully as a suppressant for gout. Ithas also been found to be antirheumatic, cathartic and emetic. Largedoses have violent purging action and can even cause poisoning. Thedosage is 2-5 grains of powdered root, 1-10 drops fluid extract, 5-15drops of tincture.55,56

Figure 10.22Colchicine

NH CO CH3

OCH3

OH3CO

H3CO

H3CO

Sc2

Mo2



NH2

Figure 10.24Biosynthesis of Mescaline

Peyote or Mescal Button Lophophora williamsii

This botanical consists of the dried tops of Lophophora williamsii, usedas a ceremonial plant by many Native American tribes. Many hallucino-genic drug users have adopted this plant and its alkaloids as an alterna-tive to LSD. Effects are similar but milder.

The major alkaloid is mescaline but the plant also contains ankalanine,ankalamine and ankalidine. Mescaline can also be found in other cactisuch as Trichocereus sp. Mescaline is similar in structure and action topsilocybin found in a mushroom Psilocybe mexicana. These chemicalshave proven useful in experimental psychiatry but are also often sold asstreet drugs.

Figure 10.23Peyote

OCH3

Mescaline

OH

HO

HO

Dopamine

HO

CH3O

NH2

CH3O

NH2HO

NH2

CH3O

HO

OCH3

NH2CH3O

CH3O

↑

↑

↑

↑


Alkaloids

Purine Bases

These purine alkaloids consist of the six membered pyrimidine ringfused to the five-membered imidazole ring. Purine does not occur innature but many derivatives of it do. The botanicals that fit into thisgroup are: coffee, guarana, kola, maté, tea and coca.

Kola Cola nitida

Kola, Cola or Kolanuts is one of the most important derivatives of thisgroup. The dried cotyledon of Cola nitida and many other of the Colaspecies is the flavour underlying the cola drinks. The fresh nuts arechewed as a stimulant in tropical countries where it grows. It is culti-vated in West Africa, Sri Lanka, Indonesia, Brazil and the West Indies.Jamaica is the chief commercial supplier to North America. The colaplants contain caffeine (1-3.5%) and theobromine (1%). The caffeine isformed mostly in the drying process.

Coffee Coffea spp.

Coffee is the dried and roasted seeds of Coffea arabica or Coffea liberica.Coffee contains 1-2% caffeine, about 1.25% trigonelline, 3.5% tannin, 15%glucose and dextrin, 10-13% fatty oil (mostly olein and palmitin).57

N

Figure 10.25Purine

N

Figure 10.26Caffeine

N

N

HN

N

CH3

N

N

H3CO

O

CH3



In the roasting process the caffeine is liberated from its inactive combi-nation with chlorogenic acid. The aroma associated with coffee is knownas caffeol which is 50% furfurol with traces of valerianic acid, phenol andpyridine (all of which are often considered responsible for the undesir-able hangover effects experienced by some people).

Coffee is a stimulant with direct effect on the central nervous system,kidneys, muscles, heart and adrenals. Coffee also works as a catharticwhen used infrequently but is constipating after continuous use. There isapproximately 100 mg of caffeine in a usual cup of coffee (1/15 of esti-mated maximal daily dose).

In decaffeinized coffee, some of the caffeine, often up to 90%, is removedthrough the application of chemicals or less harsh “water” methods.Guarana and tea are considered briefly under tannic acids, but couldalso be included in this group.

Summary

This diverse group of chemicals has many active herbs and has gener-ated a great deal of scientific research. Of the nine groups of alkaloids,we review seven in depth. Pyridine-piperidine-containing alkaloidsinclude tobacco (both stimulating and depressing to the CNS), Areca,(laxative, nervine, aphrodisiac) and Lobelia (nervine, diaphoretic,diuretic and expectorant) and pomegranate (vermifuge). Tropanealkaloids include belladonna (poison, anodyne, relaxant), stramonium(poison, antiasthmatic) and coca (street drug, anesthetic). Quinolinealkaloids include cinchona (antimalarial, tonic). Isoquinoline alkaloidsinclude ipecac (emetic, diaphoretic, expectorant), goldenseal (tonic,alterative, astringent), barberry (similar to goldenseal) and opium(narcotic, analgesic, hypnotic). Lupinane alkaloids were representedBroom (diuretic, cathartic). Alkaloidal amines include ephedra (bron-chial dilator), colchicum (gout suppresant, antirheumatic) and peyote(hallucinogenic). Purine-based alkaloids include kola (CNS stimulant),coffee beans (CNS stimulant), guarana and tea.

Materia Medica -- Alkaloids

Barberry (Berberis vulgaris)Constituents: seven alkaloids, the major being berberine, oxyacan-

thine, berbamine, palmitin, jatrorrhizine, hydrastine and tannins.Therapeutic action: inflammation, antibiotic, works on liver, gall-

bladder, digestive and spleen problems. Ed

Sc2

Mo2


Alkaloids

Belladonna (Atropa belladonna)Constituents: hyoscyamine (converting to atropine), scopolamine.Therapeutic action: used mostly by allopaths to dilate pupils,

antispasmodic (especially for smooth muscles), nephritic, colic,for Parkinson’s disease and as an antidote.

Bryony (Bryonia sp.)Constituents: alkaloid (bryonicine), resin (bryoresin), glycoside

(bryonine).Therapeutic action: drastic purgative and for laryngitis, tracheitis,

bronchitis, pneumonia, pleurisy, muscular rheumatism, poly-arthritis and sciatica. Often used externally as a counterirritant.

Cayenne (Capsicum annum)Constituents: capsaicin, capsaicine, fixed oil, carotene, ascorbic

acid.Therapeutic action: stimulant for circulation, for cholesterol, anti-

platelet aggregation, production of substance P, diaphoretic,rubefacient.

Fumaria (Fumaria officinalis)Constituents: seven alkaloids, the most important being fumarine.Therapeutic action: used for eczema, dermatitis, as well as being

stomachic, laxative and diuretic.Goat’s Rue (Galega officinalis)

Constituents: the main alkaloid is galegine, a glucoside (galuteoline),saponins, tannin and glucoquinine.

Therapeutic action: galactogenic, antidiabetic, diuretic, diaphoretic.Henbane (Hyoscyamus niger)

Constituents: poisonous alkaloids (hyoscyamine, atropine andscopolamine).

Therapeutic action: not used often because of ease of overdosing.Oil of leaf used in eye disorders and rheumatism. Used in thepast by sorcerers as an aphrodisiac in many types of lovepotions.

Houndstongue (Cynoglossum officinale)Constituents: alkaloids (cynoglossine, consolidine), volatile oils, and

tannins.Therapeutic action: antidiarrhetic, toxic to cold blooded animals.

Jimson Weed (Datura stramonium)Constituents: hyoscyamine, atropine and scopolamine.Therapeutic action: this toxic plant is used as an antispasmodic and

for coughs, asthma and laryngitis.Lobelia (Lobelia inflata)

Constituents: 14 alkaloids, the major one is lobeline.Therapeutic action: depressant, diaphoretic, nervine, diuretic,

expectorant and respiratory stimulant.Ma Huang (Ephedra sinica)

Constituents: ephedrine, pseudoephedrine and small amounts ofsaponins, catechin and tannins.

Sc2

Mo2

Sc2

Mo2

Sc2

Mo2

Sc2



Therapeutic action: bronchodilator, excites sympathetic nervoussystem, depressing smooth muscle and cardiac muscle action,similar to epinephrine but does not change in the GI, raise bloodpressure and dilate pupils.

Mistletoe (Viscum album)Constituents: viscotoxin, viscols A & B.Therapeutic action: diuretic, cardiotonic, hypotensive. Acts as a

peripheral vasodilator, used heavily in Europe as an anti-cancerdrug. Large doses are toxic.

Monkshood (Aconitum napellus)Constituents: major alkaloids (napelline, aconitine), flavonoids,

luteolin and apigenin.Therapeutic action: poisonous. used for neuralgia (sciatica),

anaesthetic and febrifuge.Motherwort (Leonurus cardiaca)

Constituents: alkaloids (leonurinine), bitter compound (leonurine),tannin, essential oil and glucosides.

Therapeutic action: angina pectoris, amenorrhea, dysmenorrhea,anti-diarrhea and anemia.

Narcissus (Narcissus exsertus)Constituents: two alkaloids (lycorine, lycoremine).Therapeutic action: emetic.

Nuphar (Nuphar lutea)Constituents: alkaloids (nupharine, thiobinupharidine,

desoxynupharidine).Therapeutic action: hypotensive, antispasmodic, astringent, used

for skin, impotency, vaginal problems and diarrhea.Poppy (opium) (Papaver somniferum)

Constituents: 25 alkaloids (including morphine, narcotine andcodeine)

Therapeutic action: narcotic.Ragwort, Groundsel (Senecio vulgaris)

Constituents: alkaloids (senecionine, and others), glycoside,quercetol.

Therapeutic action: ranges from irritant to poisonous to the liver,amenorrhea, dysmenorrhea, for nose bleeding.

Sedum (Sedum acre)Constituents: alkaloid (semadine), rutin, tannins and several acids.Therapeutic action: hypertension.

Snow drop (Galanthus nivalis)Constituents: alkaloids (tazettine, lycorine and galanthamines)Therapeutic action: emetic, used for poliomyelitis.

Yew (Taxus baccata)Constituents: toxic alkaloid (taxine), other alkaloids (milossine,

ephedrine) and glycoside (taxicatin).Therapeutic action: used mostly by homeopaths, rheumatism and

for arthritis, liver and urinary problems. Used on arrow tips as anerve poison by Celts.

Sc2

Sc2

Mo2

Ed

Ed


Alkaloids

1 Schauenberg, P., Paris, F., Guide toMedicinal Plants, Keats Publ., NewCanaan, Conn., 1977, p.21.

2 Marderosian, A.D., Liberti, L., NaturalProduct Medicine, George F. StickleyCo., Phila. PA, 1988, p.31.

3 ibid.4 Tyler, V., Brady, L., Robbers, J.,

Pharmacognosy, (7th ed.), Lea &Febiger, Phila., PA, 1976. p.232.


6 Kapoor, L.D., CRC Handbook ofAyurvedic Medicinal Plants, CRCPress, Boca Raton, FL, 1990, p.46.

7 Kapoor, L.D., CRC Handbook ofAyurvedic Medicinal Plants, CRCPress, Boca Raton, FL, 1990, p.46.

8 Wood, H.C. and Osol, A., Dispensatoryof the United States of America 23rded.,J.B. Lippincott, Montreal, P.Q.,1943. p.652.



11 Tyler, V.E. et al., Pharmacognosy (7thed.), Lea & Febiger, Phila. PA, 1976.p.233.

12Goodman, L.S. and Gilman, A., ThePharmacological Basis of Therapeu-tics (4th ed.), The MacMillan Co.,New York, 1970. p.587.












24 Leung, A.Y., Encyclopedia ofCommon Natural Ingredients, AWiley-Interscience Pub., Toronto,ON, 1980, p.189.


26 Sabir, and Bhide, N., Study of somepharmacologic action of berberine,Ind. J. Pharm. 15:111-32, 1971.

27 Kumazawa, Y., et al., Activation ofperitoneal macrophage by berberinealkaloid in terms of induction ofcytostatic activity, Int. J.Immunopharm. 6:587-92, 1984.

28 Duke, J.A., Ibid., p.287-288.29 Duke, J.A., Ibid.30 Martindale: The Extra Pharmacopeia,

The Pharmaceutical Press, London,1941.

31 Veninga, L. and Zaricor, B.R.,Goldenseal/Etc.: A Pharmacognosy ofWild Herbs, Ruka Publ., Santa Cruz,1976.

32 Youngken, H.W., Textbook ofPharmacognosy, Blakiston, Toronto,1950, p.318.

33 Veninga, L. and Zaricor, B.R.,Goldenseal/Etc.: A Pharmacognosy ofWild Herbs, Ibid.

34 Trease, G.E. and Evans, W.C.,Pharmacognosy 11, Ibid.

35 Youngken, H.W., Textbook ofPharmacognosy, Ibid.

36 Veninga, L. and Zaricor, B.R.,Goldenseal/Etc.: A Pharmacognosy ofWild Herbs, Ibid.

References



37 Martindale: The Extra Pharmacopeia,Ibid.

38 Martindale: The Extra Pharmacopeia,Ibid.

39 Morton, J.F., Major Medicinal Plants:Botany, Culture and Uses, Charles C.Thomas Inc, Springfield IL, 1977.p.42.

40 Wren, R.C., Potter’s New Cyclopaediaof Botanical Drugs and Preparations,Health Science Press, Rustington,Sussex, U.K., 1975. p.28.

41 The Merck Index 5th ed., Merck & Co.Inc., Rahway NJ, 1940. p.79.

42 The British Pharmaceutical Codex1934. The Pharmaceutical Press,London, 1934. p.204.







49 The British Pharmaceutical Codex1934, Pharmaceutical Press, London,1934, p.409.

50 The Merck Index, 5th ed., Merck & Co.Inc., Rahway, N.J., 1940, p.213.

51 Trease, G.E., and Evans, W.C.,Pharmacognosy (11th ed.), BailliereTindall, London, 1978, p.566.

52 Remington’s Pharmaceutical Sciences,Philadelphia College of Pharmacyand Science, Mack Publishing Co.,Easton, Penn., 1980, p.822.

53 Chen, K.K., and Schmidt, C.F.,Ephedrine and Related Substances,Williams and Wilkins Co., Baltimore,Md., 1930, p.7-15.

54 Duke, J.A., Handbook of MedicinalHerbs, CRC Press Inc., Boca Raton,FL, 1985, p.176





Herbal Product Assessment

11HerbalProductAssessment

To know a herb matches its description is the least a herbalist can ask. This isn'talways true. In industry, herbs are not always properly or honested labeled.Techniques to assure identification include botanical identification,macromorphology, micromorphology, taste and smell, chemical reagency andchromatography. We will finish off the chapter with a brief discussion of stan-dardization.

Synopsis:



Table of Contents

Introduction Establishing Herbal Identity

Botanical Identification Macromorphology Micromorphology Taste and Smell Chemical Reagency Chromatography

Quantitative Methods, Standardization and the Nature of Quality Summary


Figure 11.1 Sample Microscopy DescriptionFigure 11.2 First Chromatography ExperimentFigure 11.3 Chromatography ApparatusFigure 11.4 Hypothetical separationFigure 11.5 Chromatogram of hypothetical separationFigure 11.6 Essential components of HPLC



orrect dosage is of utmost importance to the clinical herbalist.Herbalists should be able to rely on the content and nature of theproducts they recommend. The problem is that this concernC

doesn’t seem to carry over to the manufacturing companies workingwith botanicals around the world. This chapter attempts to provide abrief introduction to the methods used to assess and validate botanicalmaterials.

Most large North American manufacturing companies don’t have staff(or the techniques available to them) to do a proper analysis of theirown products. Manufacturers rely on the people “upstream” -- thebrokers, growers and harvesters -- to know what they are doing. Manu-facturers are always looking for the lowest price for their raw materials.Products with lowest prices, however, often don’t have the best qualitycontrol associated with them. There have been many practical examplesover the years but a dramatic one occurred just months before this bookwent to press.

A medium-sized American herb broker listed Siberian Ginseng(Eleuthrococcus sp.) for a very good price. Several manufacturers boughtthe raw material, produced products and, of course, sold them. Some-time later, a few consumers had health problems. After investigation byDr. D. Awang of the Canadian Health Protection Branch (similar to theU.S. F.D.A.) the product was found to contain Periploca sepium (silk vine)which has known cardioactive glycosides. Eleuthrococcus was nowhereto be found.

Introduction



Tracing the same botanical shipment to its source, it was further discov-ered that some American producers were selling this material as Panaxginseng. Obviously the manufacturing and brokering companies didn’teven know the difference between Eleuthrococcus sp. and Panax sp., letalone analyse what they were selling (Periploca sp).1

Nothing is gained by unnecessarily alarming people but these examplesindicate the need for improvement. The modern botanical productindustry must return to a state of competence seen, unfortunately, onlyin the previous century and the early part of this one. Fortunately, theNorth American industry is starting to get more concerned about itsstandards.

Members of the American Herbal Product Association (AHPA) havemade a great strides in increasing responsible manufacturing. Unfortu-nately, all manufacturers are not members of this association. On theother end of the economic scale, many small “cottage industry” produc-ers create tinctures by collecting their own plants and are very accuratein their preparations. But their accuracy is not 100%, either. It is impor-tant to know the background, qualifications and commitment of suppli-ers.

Establishing Herbal Identity

The minium requirement for manufacturers should be a guarantee of thespecies or genus of the botanical components of products they sell. Thisis not demanded by law and it is, therefore, often not established. Herbsoften look similar to a consumer when ground into a powder. Let’s lookat some methods for identification that modern herbalists can begin toinsist on when they deal with manufacturers and herbal brokers.

There are several ways to identify a plant substance. One or more of thefollowing should be employed up to the point of creation of the finalmanufactured, labelled product. Other techniques might be used, butdefinite identification is the necessary first step.

1. Botanical identification (either wildcrafted or cultivated). This canbe undertaken in the field or by the broker when the botanicalmaterials are still in very raw form.

2. Macromorphology. Identification by large pieces, up to a tea cut,with up to 10 power magnification.

3. Micromorphology. Identification at a cellular level throughmicroscopes.

4. Taste and smell. Trained individuals can both taste and smelldifferences in botanical products.



5. Chemical analysis. Certain reagents will cause reactions tomaterial found in the product, giving a pretty clear indication ifthe product is what it claims to be.

6. Chromatography, most specifically, HPLC (high performanceliquid chromatography). A very advanced and increasinglyeffective means of validating botanical content.

Botanical Identification

Easy identification of herbal materials can began with the wildcrafter orperson sowing seeds for cultivation. The easiest and most cost effectiveplace to identify the plant is in the field where such information requiresa minimum of equipment (though not necessarily a minimum of skill).

Wildcrafters are people who roam uncultivated land, collecting wildplants which are destined for herbal processing. By and large they areoutstanding, sometimes with generations of their family active inwildcrafting. Unfortunately, in some parts of the world, the wildcraftingtradition has been re-established by well-meaning people who aren’tparticularly skilled or who have no adequate supervision. It’s importantfor wildcrafters to progress in their art, much as a herbalist will.

Junior practitioners should collect plants which are easily identifiableand which do not have poisonous or useless “lookalikes”. Such peopleshould also do their collecting at a time of year when identification isvirtually foolproof. As the wildcrafter works more with botanists andherbalists, they can begin to expand their collecting to a broader rangeof species and a greater range of seasons.

One point should be strongly emphasized here. The ecology of medicinalplants is not especially different from the rest of the plant kingdom. Foreconomic reasons, or simple ignorance, wildcrafters can permanentlyremove medicinal plants from large areas of uncultivated land byoverharvesting or poor harvesting techniques. With very careful atten-tion to collecting methods, however, plants will return a “crop”, yearafter year. Collecting aboveground plant parts after the ripening of fruit,or after first frost, may be less financially rewarding but it may allow fora sustainable crop. Letting particular areas “rest” during some yearsmay allow the subtle conditions required for optimum to growth return.Avoiding the collection of endangered specie is critical. An extremelyhigh ethical standard is required of wildcrafters, especially when theylive in a culture which rewards them little for their lifestyle and whichvalues money above all.



Figure 11.1Sample Microscopy Description (from Jackson & Snowdon, 1990)



Figure 11.1Sample Microscopy Description (from Jackson & Snowdon, 1990)



It would be tragic indeed if the burgeoning interest in herbs in theindustrialized world accomplished nothing more than the rapid deple-tion of herbal resources, both abroad and at home. Herbalists need tothink of themselves as a link in a sophisticated chain of biology andhuman industry. Our medicinal products always come from “some-where”. Wholistic health products for human beings should not rely ongreedy and unbalanced industrial practices.

If a species can be cultivated, it should be. This is not only more ecologi-cally sound, it provides a greater degree of control over production andquality. It’s also something humans have been doing for five thousandyears. We should be able to get it right. Many of the plants discussed inthis book are extensively cultivated. With growing concern over the useof pesticides and agricultural chemicals, and with the global appearanceof pollution (even radioactive fallout), cultivation alone will not ensuresafe or useful botanical products. Fortunately, quality control at everystep is now becoming a “selling feature” for harvesting and manufactur-ing companies. Ultimately the consumer, whether practitioner or ailingpatient, will have the greatest ability to improve the nature of medicinalherb cultivation.

If each broker has trained buyers and each plant retains certificates ofidentification right through to the manufactured product, it should beenough to ensure consistent herbal products. The details of plantidentification were covered in the TextBook of Modern Herbology. Thereare many books available on the subject in university and public librar-ies. When in doubt, a herbarium or standardized specimen may benecessary to put questionable material in its place.

Botanical identification is one area in which any herbalist can increasetheir skills and awareness. Use of raw or semi-processed medicinalherbs varies greatly between practitioners. Some rural practitionerscollect all their own herbs and sell them directly to people along withtheir clinical assistance. Some practitioners will combine the use offormulas with activities designed to involve patients in their health -- thepreparation of ginger, onion or yarrow in the kitchen. Whichever style ofpractice the herbalist prefers, the responsibility to provide useful andsafe substances is paramount.



Macromorphology

Beyond the identification of a plant in the forest or field, processedherbal material also can have its unique features -- its macromorphology(macro - “large”, morphology “the study of shape or structure"). Aperson has to be versed in structural botany and have access to appro-priate documents to properly undertake macromorphological assess-ment. It is useful to have a certified specimen to compare with. This typeof identification can be done with parts as small as "tea cut", using amagnifying instrument.

In this type of analysis the examiner is looking for identification featureslike fracture types (i.e., does the bark break even, or jagged, long orshort?). Do the leaves have hairs, no hairs (pubescent, ciliate)? What isthe color of both sides of the leaf? What is the twig diameter, seed color,shape? This type of verification or identification has to be made bymatching up several characteristics of a known specimen.

Macromorphological analysis is something which brokerage companiesdealing with herbs should undertake unless they are 100% confident inany field identification. Even in such cases, spot checking at themacromorphological level can catch inadvertent labelling mistakes.

Micromorphology

As the name implies, micromorphological analysis requires great skilland more expensive equipment. It uses identification with 500 powermagnification. It is used heavily by forensic science and is the standardfor authenticating raw material. Usually the product is observed, smelledand tasted (if it is not thought to be poisonous). The product is thenprepared for the microscope glass slide using specific reagents (13standard ones) and observed. The resulting microscopic view is com-pared to an standardized visual atlas of plant material. The most com-monly used atlas in the English speaking world is Atlas of Microscopy ofMedicinal Plants, Culinary Herbs and Spices by B. Jackson and D. W.Snowdon.2

It also suggests other plants that have similar structure, in this case arelated species Frangula (Rhamnus frangula) (see Figure 11.1).

Taste and smell

Taste and smell may seem to be cruder techniques than micromorpho-logy but a trained person can often determine the nature of a substanceby taste and smell with tremendous subtlety. Many plant materials havecharacteristic smell and taste. Often the aftertaste is just as important asthe taste. I have given a herbal formula (with eight herbs) in tablet form



to a trained Chinese herbalist and they have been able to identifyseveral of the contents within 10% of their actual representation in theformula. Some contents were not Chinese and therefore were notfamiliar to the herbalist. There are many reputable herb buyers thatmake their final judgements on the merits of taste and smell.

Chemical reagency

Though not often used in present times, this method can determine if aspecific ingredient is in a herb or to quickly spot a known adulterant in alarge shipment of botanical materials. Certain chemicals have specificreactions with others, often changing colour when in the presence ofother chemicals. An example of this is lapacho (Tabebuia avellanedae).Small yellow flakes on the surface of the bark will turn red-brown with afive percent (5%) solution of NaOH (sodium hydroxide). This tells us thatthere is above 1.0% lapachol in the herb, the result of a litmus typereaction.

A test for senna involves: boiling 0.5 g of a herb for twominutes with an alcoholic solution of potassium hydroxide(1 in 10) 10cc. Add water (10cc), acidify filtrate with HCl,shake with ether. Then shake etherial layer with ammoniaT.S. 5 cc -- later a pinkish-, bluish-red color appears.3 Thisproves the presence of emodin and/or chrysophanic acid.Of course other plants might pass this test but would haveto have very similar properties without appreciableamounts of contradictory chemicals.

If the description of the test above seems confusing, take heart. Very fewherbalists actively test their materials in this way. If you have a chanceto examine the materia medicas and pharmacopaeias of the early part ofthe 20th century, however, many of the morphological and reagent testsfor determining authenticity were provided. Taking a brief look at themwill convince you of the importance that herbalists placed on accurateidentification in the past. Some good examples are Felter and Lloyd,King’s American Dispensatory and Culbreth’s A Manual of Materia Medicaand Pharmacology.

Chromatography

Chromatography is the general name given to the method by which twoor more compounds in a mixture physically separate themselves,helping to determine the type and amount of constituents. The methodwas first discovered in 1906 by a Russian botanist, Michael Tswett andhe coined the term chromatography -- “color writing”. He performedexperiments to separate out the various pigments in a leaf. He separatedtwo chlorophylls (green), carotin (red) and xanthophyll (yellow) bypassing a solution of leaf in petroleum ether through a column of calcium



carbonate (chalk). The different pigments flowed at different rates andformed different coloured bands at different levels (see Figure 11.2).

This technique is not restricted to coloured substances as long as thereis a technique to determine the separation of the components. Anexample is the mixing of colour producing reagents to the solution and/or measurement in various spectrum (e.g. ultraviolet). From this meth-odology, paper chromatography (PC) was developed. In this “planar”technique, separation is achieved on sheets of filter paper. Paperchromatography lead to thin-layer chromatography (TLC) in which a

Figure 11.2First Chromatography Experiment by Tswett

(adapted from Walton & Reyes, ModernChemical Analyses, 1973.)

SolventSolvent

Chlorophyll

Chlorophyll

Xanthophyll

Xanthophyll

Carotin

Figure 11.3Chromatography Apparatus

To Detector

To Detector

CB

To Detector

A

A - large particu-late packingliquidchromatography

B - HPLC withpellicularpacking

C - HPLC withmicroparticulatepacking.



thin layer of absorbent material supported on a plate of glass or otherrigid material was used for separation. To aid and enhance separation anelectrical field was applied to the paper or plate resulting in paper orthin-layer electrophoresis.

Gas chromatography uses gas as the moving phase. The sample iscarried as vapour in a stream of an inert gas like helium or nitrogen. HighPerformance Liquid Chromatography (HPLC) is an analog of gas chroma-tography and is the major modern technique used to determine theidentity of a wide range of materials.

All forms of chromatography depend on the difference in partitioning ordistribution of the different substrates between the two phases (standing

Figure 11.5Chromatogram of Hypothetical Separation

Figure 11.4Hypothetical Separation of a Three Component MIxture

Sequence, left to right, ofchromatographicseparation of a substancewith three components.The shaded arearepresents the originalsolvent displaced overtime by the components.Component A:Component B:Component C:

Time

Det

ecto

r R

espo

nse

Time, Min or Volume

Chromatogram of threecomponents in Figure11.4. t

o=time for solvent

to traverse the column,trb=retention time of

substance B, twb

= peakbase width of substanceB, h = peak height. Unitscan also be given interms of volume ratherthan time: Vo, Vrb, Vwb,etc.

0 2 4 6 8 10 12 14 16 18 20 22 24

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and mobile). In liquid chromatography a small amount of a solution to beanalysed is injected at the column inlet (Figure 11.3). The mobile solvent(under pressure) moves the substance along the column. Each compo-nent has a different affinity to the column packing material. This meansthat some components will move faster or slower through the column.The slower ones spend more time in the stationary phase, the fast onesspend less time in the stationary stage. We can see a distribution inFigures 11.4. By measuring the concentration of each component as itexits from the column and plot it as a function of the volume of themobile phase passed through the column, a chromatogram results (Fig11.5 ).

High-performance liquid chromatography (HPLC) is one of the majoranalytical techniques used in the pharmaceutical industry. Its ability toanalyze practically all pharmaceutical substances adequately with highspeed, accuracy, and precision is the reason. A typical setup can be seenin Figure 11.6. By matching up specific parameters of solvents, flow rate,column temperature, column size and detector, a “signature” of achemical can be obtained.

With computer technology this information can be checked against adatabase library to identify a chemical or group of chemicals. Forbotanical substances this will point to the signature of the plant thesample is derived from. This technique separates different chemicals aswell as their isomers.

Though complex, chromatography offers the herbal industry the finalmeans of absolutely determining the nature of the products it offers forsale. The creation of “signature” databases for the plant kingdom will

Figure 11.6Essential Components of HPLC (adapted from Knox, J.H, HPLC , 1978.)

Eluentreservoir

Filter

Pump

PressureGauge

Syringe

Injectionhead withseptum

column

Thermostat

Detector

Detectorcell

Recorder



take many years and the will to apply rigourous testing and identificationare not yet evident in the Western world but we can all hope that thiswill change. Each practitioner can slowly and steadily add their voice tothe chorus calling for safer, cleaner, dependable botanical products.

Quantitative Methods, Standardizationand the Nature of Quality

Through techniques like high performance liquid chromatography, thequantity of a specific chemical can be determined. Some herbalistsprefer to use this information as a criterion of quality.

Specific herbs could be required to contain above “X” percentage ofglycosides, or a specific chemical, before being considered “good”.Other practitioners feel that a specific chemical or group of chemicalsshould be an exact percentage to give them greater clinical control. Thiscan be accomplished by concentrating the product or “spiking” theproduct to produce a specific amount.

Even though standardization of product might sound great, it is notwithout its drawbacks. This mechanical, pharmaceutical view of herbsmight be necessary for modern ginkgo products (for example) but itdoes not really fit into the concept of holistic health. It biases theimportance of one chemical against others. It is as if we say a symphonyorchestra has an oboe player as its definition of quality. Of course thereare many parts to a symphony orchestra. Sixteen oboe players (and onlysixteen oboe players) do not make a typical symphony orchestra. It isuseful to have analytical techniques but locking the profession intoquantitative models steps away from the subtle elements of herbologywhich we discussed in the early chapters of this book.

Summary

To know that a product is what it purports to be is one of the basicpremises of herbology. Identification should be the reponsibility initiallyof wildcrafters, growers and manufacturers. It is important that manufac-turers especially live up to their responsibility and that herbalists holdthem to it. Some techniques to identify herbal products are botanicalidentification, macromorphology, micromorphology, taste, smell,chemical analysis and HPLC. For some products, the amount of a specificchemical is as important as the identification of the particular species.



References

1Awang, D., Open Letter of June 4, 1991,Banting Building, Health ProtectionBranch, Canadian Federal Govern-ment.

2Jackson, B.P., Snowdon, D.W., Atlas ofMicroscopy of Medicinal plants,Culinary Herbs and Spices, CRCPress, Boca Raton, Florida, 1990.

3 Culbreth, D., A manual of MateriaMedica and Pharmacology, EclecticMedical Pub, Portland, Oregon, 18??reprint 1983, p. 293.




Herbal Product Manufacture

HerbalProductManufacture

Synopsis:

In this chapter, we will look at the manufacture of herbal products from thesimplest tea to complex techniques of large scale manufacturing of specializedextracts. Manufacturing depends on the final dosage form. There are manyproblems that creep up in large scale production of botanical material. We willexamine some of the pitfalls as well as some of the machinery used.

12



Table of Contents

Introduction Manufacturing

Desired Final Form Herbal Teas (aqueous extracts)

Infusion (Infusa) Decoction (Decocta)

Tinctures (Tincturae) Fluid Extracts (Extracta fluida) Spagyric extracts

Problems with Liquid Extracts Dry Extract (Extracta sicca) Oily drug extract (Olea medicata) Volatile Oils Capsulated Herbs Tablets

Starting Materials Drying Process Problems associated with producing plant products based on Pharmacopoeia

quality standards Wildcrafting vs. cultivation

Pest control Antibacterial agents

Quality Control Processing

Processing leaves and herbs Processing roots and bark Processing seeds, fruits and flowers

Extraction Methods of extraction Purification of Micellae Bacterial counts and pasteurization Concentration of micellae

Capsules and Tablets Standardization during manufacture Summary


Table 12.1 Parts of Drug PlantsTable 12.2 Methods of Grinding vs. Material CharacteristicsFigure 12.1 Stages of Shredded Infusion MaterialTable 12.3 Principal Machinery Used in Plant ProcessingFigure 12.2 Processes of ExtractionFigure 12.3 Schematic of electrocharge extraction processFigure 12.4 Supercritical point of carbon dioxide



Introduction

n the last chapter, the methods for identifying herbal material werebriefly reviewed. Now we move on to the methods of processingonce we know which plant we are dealing with. Preparing herbalI

products for your clients can be very rewarding, from both a creativeand a financial point of view. A pharmacy or small production area canoften mean the difference between success and failure to a herbalpractice.

Production on a small level and production at a large marketing level canbe quite different. Many herbalist/wildcrafters distribute their ownproducts by giving their patients herbal teas. Perhaps they maketinctures or offer powdered herbs that can be capsulated either by handor simple machinery. Manufacturing products on a small commerciallevel can be very simple -- from packaging bulk herbs to making gallonbatches of tincture. Usually it’s a “cottage” industry with very little todistinguish between the quality of one operation and another.

Herbalists tend to get busier and busier and often don’t have time toproduce their own formulas or tinctures. This means one must rely moreand more on others to provide medicinal products.

There is often a relationship between the cottage manufacturers and thepractising herbalist. It is important to feel confident in the quality of theproducts you are using. It doesn’t take long before some of the good“little” producers start to increase in size. As soon as the manufacturingreaches a certain level, herbal production takes on a whole new mean-ing. The products cease to be simple teas or tinctures. Producing atincture is so simple at a personal or cottage level that the herbalistoften imagines the same conditions exist at a commercial industrial level



-- only bigger. But with the growth of the production level, all kinds oftechnical problems arise. Apart from the normal headaches of anybusiness -- paperwork, delivery, personnel, taxation -- large scale opera-tions must employ different techniques to make their operation profit-able. Storing fifty pounds of yarrow is one thing, storing ten tons isanother. Keeping vermin and insects out of your garage or workroom isone thing. Maintaining hygenic conditions in a warehouse the size of anOlympic swimming pool is a different proposition.

This chapter focuses primarily on the commercial manufacturing level ofherbal production. The sheer volume of that production means thatmost people in the industrialized world use herbal products createdcommercially. Many books review how to make a tincture in yourkitchen but it is important for the practising herbalist to also understandthe processes a herbal product undergoes during industrial production.

Manufacturing

From living plant to final dose, many processes that a herb goes throughduring manufacture remain a mystery for the average consumer, per-haps even to the average herbalist.

Production of herbal materials in large quantities requires an elaboratesystem, from Quality Control (QC), to final packaging the dose form ofthe product. This process is called Phytopharmaceutical Technology inEurope.

Strangely enough, the place to begin is the final step -- dosage form.Deciding on the final form determines the preceding steps of manufac-ture. Producing some special volatile oils requires planning before theharvest stage. The perfect stage of the plant growth and even the time ofthe day and the weather all are important. A simple powdered, encapsu-lated herb can be a far more simple task. The manufacturer might justbuy the herb, pre-ground from the cheapest wholesale source andmerely encapsulate it themselves. Let’s start our discussion with dosageform and some of the pros and cons of the various forms.

Desired Final Form

Crude Herb: It is very rare for a herb to be consumed in its natural form.It is usually ground or powdered and put into a tea, extract, capsulatedor tablet form.

Cut and Powdered Herb: There are several grades of cutting, powder-ing or pulverizing a botanical. If the processed particles are approxi-mately 4 mm along any axis they are considered coarsely shredded, 3



mm is moderately fine shredded, 2mm is finely shredded. Powders startwith a coarse powder (0.75 mm), 0.30 mm for moderately fine powders,0.15 mm as finely powdered.

Herbal teas (Aqueous extracts)

Infusions (Infusa)1: are usually prepared from the soft part of thebotanical such as leaves, whole herb or flowers. The herb or botanicalformula is simply steeped or macerated (soaked). Control of micro-organisms occurs during the drying process.

It is important to understand where the active chemicals of a particularbotanical reside. Most of the hydrophillic active substances will justswell and maybe act as roughage. If you need active ingredients at thecellulose level that is not water soluble, you won't get them with infu-sions.

Decoctions (Decocta): are usually prepared from the hard parts -- barks,root, twigs and the like. The herb is boiled or heated to at least 90oC for 5- 30 min.

From a manufacturing point of view, aqueous end products are notappropriate because of micro-organism spoiling and reduced shelf life.An aqueous extract provides just too perfect an environment for organ-isms to grow in. The product will usually spoil before it gets to market.Notable exceptions to this prohibition are the times when the aqueousextraction is only one step in the manufacturing process. Furtherprocessing ensures a longer shelf life. If the product is put into airtightvials or ampoules immediately after manufacturing, it can also have along shelf life. Some Oriental and European products use this hermeticseal method to maintain aqueous extracts.

Aqueous products which also have a water menstruum (extractionagent) only contain constituents that are soluble in water.

Tinctures (Tincturae): are prepared by soaking the herb or botanicalformula in ethanol (alcohol) of varying concentrations. The menstruumfor 1 part of herb varies from 2 - 10 parts of alcohol. The concentrationshould be declared 1:5 (1 part herb : 5 parts alcohol) or 1:10. Thepreparation method can either be maceration or percolation with anapparatus like a Sohxlet or Lloyd extractor.

Fluid extracts (Extracta fluida): are very similar to tinctures but moreconcentrated. Here the liquids can be at most 1:2, usually 1:1. Strictdefinitions vary between the official pharmacopoeias.



Spagyric extracts

With the aqueous solution of infusions and decoctions as well as thealcohol solutions of tinctures and fluid extracts, only the soluble ingredi-ents are passed on in the product. None of the herbal residue, called themarc remains. In a special alchemical process called spagyric thematerial left over after production of the tincture is burned to an ash andreintroduced to the tincture as a soluble substance. Chapter 14 providesmore details on alchemical concepts and manufacturing.

Problems associated with liquid herbal products All of the liquidproducts are easily absorbed by the human body but they are lessconvenient for many people. The old axiom, “the worse the taste, thebetter the medicine”, is not widely accepted in the Western world! Manyconsumers, though not all, have been spoiled and want their botanicalproducts both convenient and either tasteless or good tasting. Often theherbalist’s attitude can be passed on to patients -- if the practitionerdoesn’t mind liquid products, their customers won’t mind them either.

Dry extract (Extracta sicca) The fluid extract or tincture is prepared andthe liquid is removed through some sort of evaporation. Techniquessuch as sublimation (freeze-drying) can often accomplish this in a waythat doesn’t affect the active ingredient. These substances are veryhygroscopic (attracting moisture) and therefore need to be ground andstored in situations where there is no moisture.

Oily drug extract (Olea medicata) The herb or botanical formula ismacerated in oils (almond, olive, peanut, apricot or others). Activeingredients that are soluble in oils will be extracted. This form is notoften used because the resulting product is not very stable. It is onlyused if the product is meant for fairly immediate consumption afteropening, as an initial step in a more complex manufacturing process or ifit is destined for encapsulation in soft gel capsules. Once again we onlyget the ingredients that are soluble in the oil.

Volatile Oils: Processing techniques for volatile oils were discussed inChapter 7. Volatile oils are often distilled macerate or extracted byhypercritical carbon dioxide. Storage is important because the sub-stances are volatile. They have to be stored in airtight containers assoon as manufactured. Many products are sensitive to light, which mustbe considered when selecting storage methods. Volatile oils do not gorancid like other oils -- one less worry.

Capsulated Herbs: The herb or botanical formula is dried, powderedand inserted into two-piece hard gelatin capsules. This manufacturingprocess is very common in the North American market and the equip-ment necessary is almost laughably simple. Capsules are convenient,easy to swallow and have great consumer acceptance.



Encapsulation does have some drawbacks. The public is getting increas-ingly concerned about capsules that can be tampered with. Incidents likethe U.S. Tylenol® scare, where tampered products caused illness anddeath, resulted in great distress to the consumer. Simple hard gelatinencapsulation may be outlawed soon for commercial products in the U.S.because of these tampering concerns.

Capsulated herbs can have a reduced herbal activity level after inges-tion. The enclosed herbs are simply dried, powdered and encapsulated.This form of herbal product is not easily assimilated by the body. Hotwater consumed with the capsulated product can help. The capsulesthemselves are often full of all kinds of preservatives and sometimescolouring agents. They are usually made of animal products, obviouslynot acceptable to some vegetarian consumers. The preservative andcolouring agents have been reduced in recent years by improvedmanufacturing. To make good vegetable-source capsules, however hasbeen a problem. In high speed encapsulating machinery, such capsulesoften break too easily.

Tablet: The powdered form of the herb, or botanical formula, is mixedwith flowing agents, binding agents and disintegration agents andpressed into the desired form. In the past the most common form was asimple round, flat tablet. There are now many shapes. The most pre-ferred shape these days is the “caplet” shape, oblong and similar inappearance to a capsule. Consumers are most familiar with this shapebecause mass market advertising of pharmaceutical products (such aspain killers) have popularized them. Another popular shape is the“football” with torpedoe-shaped ends. Both of these shapes are easier toswallow than the old round version.

This convenient dosage form has great public acceptance. It is a familiardrug dosage, easy to swallow and convenient to package and for theconsumer to transport. A few tablets fit well in a purse, pill holder orpocket. Unless special processing is undertaken, the herb is a simplepowdered product, pressed into a tablet. This reduces the assimilationof active ingredients. The herb also is mixed with adulterants -- thebinding agents, etc. Generally, these are very safe ingredients but eventheir presence increases the possibility of allergies in some sensitivepeople. Specially prepared tablets using the Quadgyric method reducesallergy problems to some degree. In that specific process the botanicalsare soaked in an alcohol/water solution creating a mild extract. Theliquid is then evaporated, the marc is granulated, ground and tableted.This process makes the product more easily assimilated.



Starting Materials

Identification: The proper identification of the plant in the field is ofgreat importance. Reliability is greatest at that point. Plants are some-times wildcrafted and sometimes cultivated. Cultivated plants areusually well identified because the seedstock is known. Wildcraftedplants often contain adulterants or even completely wrong species. Thisshould be avoided. Suppliers often make mistakes, knowingly or not.Ideally, verification of the plant material needs to be confirmed “inhouse”. Chapter 11 deals with this step in more detail. Some botanicalsuppliers provide pharmaceutical names in price lists and on packaging(see Table 12.1).

Drying Process

In most of the temperate parts of the world (and in cases where plantsare sent to the temperate parts of the world) plants are dried for storageand shipping. In some areas of the world a continuous growing seasonallows usage of fresh herbs. Some manufacturers use techniques thatinvolve the production of tinctures and extracts from fresh plant mate-rial. For the most part, herbs are dried before they are processed. Thedrying process brings up two interesting points.

Plant part Meaning Example

Balsamum Balsam Balsam ToluBulbus Bulb Bulbus ScillaeCortex Bark Cortex CascaraeFlos Flower Flores MalvaeFolium Leaf Folium hydrangeaeFolliculus Pod (follicle) Folliculi SennaeFructus Fruit Fructus Piperis NigriGemma Bud Gemmae PopuliGlandula Gland Glandulae LupuliGummi Gum Gummi arabicumHerba Herb Herba LobeliaLegumen Capsule, pod Legumina PhaseoliLignum Wood Lignum SappanNux Nut Nux vomicaPercarpium Fruit skin Percarpium ArecaePix Tar Pix betulinaPulpa Fruit pulp Pulpa tamarindorumRadix Root Radix GinsengResina Resin Resina JalapaeRhizoma Rootstock Rhizoma BistortaeSemen Seed Semen PlantaginisSiliqua Pod, husk Siliqua dulcisStigma Stigma, spot Stigamata CrociStipes Stem Stipites DulcamaraeStrobilus Cone Storbili LupuliSummitates Twigs Summitates SabinaeTuber Tuber Tubera SalepTurio Shoot Turiones Pini

Table 12.1Parts of Drug Plants (adapted from List, 1989)



1. What happens to the chemical constituents of the plants in thedrying process.

2. Micro-organism control during the drying process.

Most of the hydrophillic active substances such as alkaloids, glycosidesand tannins are stored in the aqueous cell fluids. The notable exceptionto this is cellulose which makes up the cell membranes themselves. Thelipophilic substances such as volatile oils, balsams and resins are rarelyassociated with the aqueous plasma but are usually found in separatecavities with little or no water present. These substances mix during thedrying process, often producing reactions. Little is known about whathappens during this process, even though most drugs in the worldthroughout our history have been subject to these effects. Research isunderway on the subject at the Vegetable Husbandry program of theMunich Technical College.

Enormous changes go on in the botanical material during water loss. Thegel state of the plasma is changed, active principles are partially precipi-tated and enzymes, usually segregated, come into contact with theactive substances. This often leads to hydrolysis, oxidation (especiallywhen air is present), polymerization and other changes. This can mostdramatically be seen in mustard, where we get the myrosin and sinigrinreaction noted in previous chapters.

During the drying process, the plant can and will rot if proper proce-dures are not followed. Many enzymes are meant to digest the plantmaterial to make it ready for the microorganism kingdom in the natural“recycling” process. The most significant enzymes are oxidase andperoxidase that will oxidize phenols, unsaturated fatty acids, terpenesand so on. Hydrolase will cleave esters and glycosides and break downpolysaccharides. Isomerase, will isomerize some alkaloids (e.g. theergots). Because of the action of these enzymes it is important tostabilize the situation as fast as possible -- drying the plant as fast aspossible. In some cases the enzymes are purposely denatured. Enzy-matic action is sometimes very advisable, even creating the activeprinciples themselves. Some aromatic substances undergo changesduring this process creating a desirable end product. Cascara sagrada isa good example of a herb that undergoes changes after picking thatmakes the plant more useful.

Since most of the traditional uses developed for plants were based onmaterials put through the drying process, it is probably the mostacceptable form of delivery when used in a traditional way. This is not tosay that fresh plant tinctures are not useful. It is accurate to say thatfresh plant tinctures may have slightly different properties than stated inoriginal folklore literature. Some products have traditionally been freshplant extracts. Arnica is a good example. Homeopathic "mothers" areoften made from fresh plant extracts.



Problems associated with producing plant-based products ofpharmacopoeia quality

To produce high quality products has always been a challenge. As theconsumption of the products increase, as has been the case over the lastfew years, the quality issue become even more important and more of aproblem. The following are problems adapted from a list by Schilcher 2:

1. Inadvertent or deliberate substitution or adulterations.2. The plant part is different than stated in the monograph or

Pharmacopoeia.3. Foreign matter limits are exceeded.4. The maximum values of sulphate ash have been exceeded.5. The minimum content of a desired constituent is not present,

either because of poor raw material, growing season fluctuation,etc.

6. The herbs are not suitable due to infestation or microbial spoil-age.

7. Micro-organism contamination is too high.8. Pesticide or preservative residues exceed permitted levels.9. Heavy metal content exceeds limits.10. Sociological, political or economic problems make supply

unreliable, due to many factors.11. Legal regulation on import/export of wild plant material as well

as possible outdated legal restrictions on botanical prepara-tions.

Cultivation vs. wildcrafted materials The two major ways of obtain-ing plant material are wildcrafting and cultivation. Wildcrafted botani-cals have the advantage of very low pesticide levels (although loggingand related spraying operations can affect huge areas of forested land)and can usually be considered “organic”. On the other hand there is anincreased risk of the product containing adulterants. Confusion ormixing of species and poor initial drying and storing procedures aremore common. Chapter 11 reviewed some of the ongoing ecological andproduction concerns about wildcrafting.

Cultivated herbs often are grown in conditions where the grower usedpesticides to increase the yield. Even though there is a movementtowards “certified organic” products, most products available are grownunder pesticide regimes.

A third method of producing raw botanical material is tissue culture.Here specific plant tissue is grown in laboratory conditions. These, oftengenetical manipulated cultures, can produce specific raw materials --increasing or decreasing specific constituents. Even though this hasgreat potential for pharmaceutical type “natural” products, my personalfeeling is that this kind of research has “Frankenstein-like” implications,



at odds with much of the “wholistic” health movement’s use of naturalproducts. Not being connected to Gaia or Earth, these substances arenot likely to exude much “green” energy.

Pest control

Pest control is of utmost importance in the commercial cultivation ofbotanical products. Pest control can be maintained by either biological,physical or chemical agents. The last is most objectionable but unfortu-nately most common.

Biological pest control employs natural enemies of a specific pest. Thiscan be as simple as the farm cat controlling rodent damage, to specificinsects that eat other insects, perhaps even sterile insects reproducingwith fertile insects, thus keeping populations down. Physical means ofpest control are as common as weeding, by hand or mechanically.

Chemical pest control can have undesirable side-effects. Resistantstrains of a pest can be created. Chemicals sometimes influence theconstituents of the plant. Most alarming of all is the presence of residueof pesticide or metabolites on harvested material.

The kinds of pesticide used are: fungicides, herbicides, insecticides,acaricides, nematocides, rodenticides, antibacterials as well as deter-rents to mollusks and birds. One or a combination may be used, from thegrowing process through to the manufactured product. The range ofchemical pest control substances is not only large, it is ever increasing.Little is known about the ultimate effects on the end consumer. In light ofthe endless combinations and permutations of these chemicals whichhave been used around the globe, scientists are whistling in the darkwhen they say they understand the full implications. This has lead manyconsumers and manufacturers to seek out “certified organic” materialwhen possible for medicinal herbs.

The range of pesticides are so large that it takes several tests andtherefore great expense for the conscientious manufacturers to test forresidues on raw material before further manufacturing. In most parts ofthe world there is no legal requirement to test for pesticide residue. Soit’s not done. This raises a great concern for herbalists.

Antibacterial agents

Usually the raw material destined for herbal manufacture does notsatisfy even the most liberal food restrictions on bacterial content inNorth America. It is mandatory in many countries that raw materialscontain less than 10-4/g of pathogenic bacteria, with final product to



contain less than 10-3/g. The usually indicator organisms are Escherichiacoli, Salmonella, Shigella, Pseudomonas aeringosa and Staphylococcusaureus. Presence of these organisms in large quantities can be disastrousto the consumer.

The most common methods of dealing with such organisms are ethyleneoxide gassing and/or radiation. Toxicity of ethylene oxide makes itnecessary for the botanicals to be tested before further manufacturing.Ethylene oxide acts on proteins, killing microorganisms, but also leadingto reactions with primary, secondary and even tertiary amino-groups.Alkaloid-containing plants are therefore at some risk of alteration duringthe process. Testing for alteration of alkaloids or other amino acidcomponents should be conducted after ethylene oxide gassing.

Even though no radiation is left over after radiation process, there isgreat public resistance to radiating herbs or foodstuffs. Possible alter-ation of some chemical structures during this process has consumersunderstandably hesitant.

Quality Control

When raw material first comes to the manufacturing premise, it shouldimmediately be put into quarantine. Release from quarantine should beabsolutely forbidden until suitable tests are conducted. If the incomingmaterial is wet, it should of course be dried. Cross contamination mustbe avoided. The following is a check list of procedures the raw materialshould go through.

1. Macro- and Microscopic examination for identification.2. Possible thin-layer chromatographic examination for identifica-

tion.3. Examination for foreign organic and inorganic impurities.4. Determination of water content.5. Determine ash.6. Determine crude fibre.7. Determine extractable component if applicable.8. Determine active component.9. Determine microbial contamination levels.10. Examination of pesticide residue.

The proper sampling techniques need to be applied as well as theprescribed testing methods that can been found in several sourcesincluding Phytopharmaceutical Technology by List and Schmidt (CRCPress, 1989).



Processing

To outline the processing stage, as indicated earlier, one has to firstdecide what kind of final dosage form is required. The first stage isusually the fragmentation of the raw material into smaller particles,typically through some kind of mechanical process. This is calledpulverization or comminution. Determining the right machinery toaccomplish this process is based on the hardness, end product size andthe type of material pulverized. Table 12.2 gives ratings on methods forgrinding relative to the characteristics of the material.

The coarseness of the process is determined by the need. For any kindof infusion or extraction one needs the product to be as dust free aspossible. Dust will clog up percolators and cause clarity problems in thefinal product. Extreme differences in the size of particles will add to theextraction time. The removal of sand and dust are important. Theseparation of any material that is already the right size avoids undueprocessing that might decrease volatile compounds during the process-ing stage. This is usually accomplished by some type of elaboratesieving. After shredding, any new dust is removed. Figure 12.1 highlightsthe general flow of the products.

Notsuitable

Limitedsuitability

Verysuitable

Proper ty

(Structure)

H a m m e r

Act ion

Pressure Fr i c t i on Impact C u t t i n g

Hard (abrasive)

Medium hard

S o f t

Br i t t l e

R e s i l i e n t

T o u g h

F i b r o u s

Poor thermal

s t a b i l i t y

Table 12.2Methods of Grinding vs. Material Characteristics (adapted from List)



The varying sizes of fine, semi-fine and coarsely shredded productwould be separated and used for different processes -- capsulation,tableting, teabags, extracting or percolation.

Processing leaves and herb

There can be many problems associated with the pulverization of theraw material. Twigs, stems, barks, roots, soft leaves and brittle leaves allhave different applications and different resistance to processingmachinery. The following list indicates some of these differences.

1. Easily friable medicinal leavesBelladonnaDigitalisMelissaSenna

2. Strong but friable medicinal leavesUvae UrsiEucalypti

3. Soft, fibrous medicinal leavesAlthaeaMalvaSalvia

Figure 12.1Stages of Shredded Infusion Material

Bales or sacks of raw drug

Opening Operation

Removal of metal and sand

First Sieve

Cutting or shredding

Second sieve

Preparation of fine cut

Third sieve

Dust Fine Cut Semifine cut Coarse cut

Burner Storage container Storage container Storage container

↓

↓

↓

↓

↓

↓

↓

↓ ↓ ↓ ↓

←

←←

← ←

← → →

→ →

→ →



4. Medicinal Herbs with high stem/stack contentHypericiThymi

5. Medicinal herbs containing fat/resinsBetulaBoldo

6. Very hard and very brittle medicinal herbsEphedraeEquisetiMaté

A difference in the type of machinery or the blades used to grind orpowder the herb is clearly required. Shredding mills are very commonlyused and are effective for both stems, stalks, and for soft, fibrousmaterial. They produce a coarse end product useful for teas and ex-tracts.

Hammer mills are used for easily friable and resinous herbs, grindingcoarse to fine powders. Pin mills are used for herbs with high fat orvolatile oil content that are to be ground finely. Both of these machinesproduce heat while grinding. For this reason a fluted roller grinder hasbeen developed to work on products that have highly volatile sub-stances.

Toothed disc Friction 5-16 Dried extracts,freeze-mill and dried materials, fruits

shearing and seeds.

Knife or cutter Cutting 5-18 leaves, herbage and roots,mill used for percolation

Hammer mills Impact 40-50 Coarse grind of brittle(100) herbs, friable substances

especially roots.

Machine System Milling Rotation Botanical milledaction speed (m/sec)

Pin Mill Impact 80-100 Dried extract, ergot, someseeds

Blower Mill Impact 40-110 Pulverization of leaves,(micronizer) bark and roots.

Cross beater Impact 50-70 Leaves, bark and roots.(disintegrator) and

shearing

Hammer basket Impact 70-90 Tobacco, leaves, roots and millherbage.

Table 12.3Principal Machinery Used in Plant Processing



Processing Roots and barks

These substances are usually moderately hard or hard but also varygreatly in nature. They are often sent through cutters and shredders firstto get a coarse material, and then a hammer mill later if finer material isdesired.

Processing Seeds, fruits, and flowers

High concentrations of fats and volatile oils in these items explain whythey are frequently sent through rollers and fluted rollers, but hammermills are also used. A special cold grinder has been developed, in whichthe grinder is cooled with liquid nitrogen, lowering volatilization andstopping plant material from sticking to the parts of the machinery.

Extraction

The important terms to know for extraction are:

Menstruum = solvent or mixture of solvents used for extractionMiscella = solution containing the extracted substanceRinsing = dissolution of extractive substance out of

dis-integrated cellsLiviation = extraction with water solvent.

A threefold process is involved in extraction:

- penetration of the solvent into the plant cells and swelling of the cell.- dissolution of the extractive substances.- diffusion of the dissolved extractive substance out of the plant cell.

All of the following affect the amount of the extracted material:

1. Mixture ratio of solvent to herb. Decreasing with increased solventand increasing with increasing herb.

2. Dissolution from disintegrated cell. The more the cell is brokendown, the more the yield.

3. Steeping and swelling of drug plant material. More diffusion occurswith dilated cells. This is not true with heavy mucilaginous cells,excessive swelling can inhibit diffusion.

4. Diffusion ratio between the inside of the cell and the outside of thecell.

5. Temperature often increases the rate of extraction but may destroysome volatile or delicate substances.

6. pH value will often influence the extraction.



The following are some of the common methods of extraction:

1. Maceration. The herbal material just sits in the solvent at roomtemperature for several days with the odd shaking or stirring.

2. Kinetic maceration is also at room temperature but materials arekept constantly in motion. Many types of machinery are used. Thefollowing are examples:

a) Apparatus without stirrersCube mixersGyro mixersBall extractorsTumbler mixersSiphon mixersTurbomixers

b) Apparatus with stirrersPloughshare mixersPlanetary mixersBucket mixersIntensive MixersMasticators

Figure 12.2Processes of Extraction

DiffusionRinsing,Washing out

↑

↑↑



3. In exhaustive extraction slightly different techniques are used,taking advantage more of temperature and pressure.

1. Percolation is a process that can be as simple as percolatingcoffee. On an industrial level fancier apparatus such as theSohxlet extractor described in Chapter 14 (Alchemy) or acountercurrent extraction apparatus are used.

2. Supercritical Gas extraction, mentioned in Chapter 7 (Vola-tile Oils), is an up-and-coming method where the specialproperties of a gas at a hypercritical state are used.

Limitations on the type of method usually comes down to cost. Straightmaceration can be done on small quantities, at very little cost. As thecomplexity of the apparatus increases, so does cost. Methods aretherefore directly related to the relative cost of both raw material andend product of the herb. With more expensive herbs that have high

Figure 12.3Schematic of electrocharge extraction process

ResistorDischarge gap

ExtractionvesselHT source v Capacitor ( F )

c) Ultrasound extraction increases extraction by sending sound wavesthrough the solution above the frequency of 20,000 Hz. This isusually done with magnetostrictive or piezoelectric ultrasonictransmitters.

d) Electro extraction by using an electrical field. An electromagneticfield and electrical discharge will accelerate extraction yields.

In all of the above, the solution is separated from the marc andthen it is expressed to obtain more miscella.

↑

↑



demand, it is more expedient to used more elaborate apparatuses.Another critical factor is the relative fragility of the micellae. Are thereimportant volatile ingredients that will be destroyed by heat or can asimple closed system keep them present in the micellae? Will themucilaginous qualities of the mixture cause clogging up of the apparatus,thus slowing down production? What is the cleaning time of the appara-tus? Can it be used 24 hours a day, twelve months a year, for how manyyears? All of these are considered when using various apparatus.

Purification of Micellae After the extract is made and the marc, if any,is expressed, purification is still required. Simple separation, decanting,filtration, pressure or centrifugal force can do the job. If specific con-stituents are sought, specific methods are used for separation.

Bacterial counts and pasteurization Material has to be retested formicro-organisms and often goes through a pasteurization process tostabilize the product so it has an acceptable shelf life.

Concentration of micellae Concentration procedures range fromsimple evaporation of the solvent with heat to special pressurizedvaporizing chambers. To produce a dry extract, even more elaborateprocedures must be taken. Some techniques that are employed aresublimation drying where the solids fall out of solution, convectiondrying where hot gas transfers heat to the material being dried, contactdrying where the material is placed on hot sheets, freeze drying or

Figure 12.4Supercritical point of Carbon Dioxide

Pres

sure

Volume

Temperature

Solid(Dry Ice)

Solid/gaseous

LiquidGaseous

Criticalpoint

Liquid/gaseous

↑

↑

↑

↑

↑



spray drying where the substance is sprayed into a chamber and finallymicrowave drying.

Capsules and Tablets

The initial procedures are applicable here. The product still needs to gothrough quality control for identification and bacterial counts. It stillneeds to be ground, usually into a powder in a hammer mill in the finalstages.

For capsulization, the fine powder is either passed through a encapsulat-ing machine (slow to extremely high speed) that encapsulates theproduct with two-part hard gel capsules. In some of the very fast ma-chines, a flowing agent is often required to properly feed some productsto the caps. Even though vegetarian, non-preservative capsules areavailable, shelf life and the fragility of these capsules in high speedmachines reduce their viability at a commercial level. This is bound tochange. There are very few colouring agents that are acceptable tonatural health practitioners, therefore most capsules are clear. Several“natural” coloured capsules have started to enter the marketplace.Colour coding makes it easier to distinguish one product from another.Because of tampering, there has been a move to this process.

Tablets, on the surface, are very similar to capsules. The starting pointcan be simple powders of the botanicals, solid extracts or their combina-tions. From here the product has a binding agent added. The mostcommon additives are:

1. binding agents2. flowing agents3. disintegration agents4. filling agents

Binding agents help keep the product together. The nature of botanicalmaterial makes it less complicated to process than chemical pharmaceu-ticals because the botanicals are often already sticky. Many naturalgums and agents (acacia gum) can accomplish binding.

Flowing agents help the material flow through the machinery. Botanicalscan be sticky (often even a bit wet) when they go through severalmanufacturing techniques and may contain a binding agent. A commonsubstance to encourage flowing is a vegetable sterol.

Disintegrating agents make sure that the tablet disintegrates within somany minutes once it is in a person’s digestive system. There are many“explosive” cellulose compounds and substances (like whey) that willmake the tablet disintegrate after perhaps fifteen minutes in an aqueous



system such as our digestive tract. Some mechanisms rely on the pH ofthe stomach but are therefore less reliable.

Filling agents are designed to make the physical size of the tabletprecisely right for the die and punch that determines the end productshape. Tableting is usually done on high speed machinery. As statedearlier in this chapter, special techniques can increase the viability ofthe end product, such as soaking the herbal formula in an alcohol/watermixture and doing a wet granulation of the product to make the constitu-ents more bioavailable (similar to extracts).

Because of the shape, smell and taste, often the tablet is coated eitherwith a thin clear vegetable shellac, a colour code dye substance, or asugar coat (all to common in Oriental and European products).

Standardization during manufacture

In Chapter 11, we briefly discussed the industrial trend towards stan-dardized botanical products and how some practitioners are quiteconvinced that this is key to increasing the popularity of herbal medi-cine. Just as the identification, cultivation and harvesting of botanicalshas been a focus for standardization, manufacturing processes havebeen examined to standardize results.

Some manufacturers want end products that have specific amounts of aconstituent. In theory it sounds good but after reading this chapter youmight guess that it is not as easy as it sounds. Different raw materials,growing conditions, and so on, make it almost impossible. Minimumstandards are the best compromise.

Product literature should state that it has no less than x percent or xmilligrams of specific constituent y. This can be done by adding concen-trate to the final product form, to top it up if necessary. Standardizationoften shortens the shelf life of the product. And the whole argumentabout which constituents are most important keeps herbalists chattingaway for hours. At the moment, there has been no North Americanagreement on what “standardization” is. Even if a product say it is“standardized”, the processes involved might be quite different fromanother similar product.

Summary

At a personal or cottage industry level, the production of botanicalproducts is seems quite simple. Whatever artistry or skill involved ismultiplied and elaborated even more at a commercial level. As the field



of herbology increases in size, we can expect the appearance of moreand more sophisticated manufacturing techniques. We will also probablysee more small cottage type manufacturers appearing. Almost likecommunity pub/breweries making small lots, local or regional manufac-turers can provide custom quality service making products for a specificgroup of herbalists and stores. Since the procedures can become verycomplex, it behooves the herbalist to look in detail at the most commonproducts they use and be comfortable with the techniques used duringmanufacture.

After all, if you don’t feel the need to be comfortable with the productsyou recommend -- why choose herbology at all?

References1 consult Table 12.1 for a chart of

standard pharmaceutical terms.2 Schilcher, H., Pharm. Ztg. 126, 2119

(1981).3 List, P.H., and Schmidt, P.C., Phyto-

pharmaceutical Technology, CRCPress, Boca Raton, FL, 1989.


Herbology and Pharmacological Research

13

HerbologyandPharmacologicalResearch

Synopsis:

In this chapter, the various resources for getting up to date information on herbsare reviewed. Our first stop will be institutions like the Herb Research Founda-tion and Lloyd library. Next, the chapter lists valuable books and bibliographiesfor herbal researchers. Computerized information services are more and morecommon and several contain information on medicinal plants.



Table of Contents

IntroductionHerb Research FoundationLibrariesBooks

Pharmacognosy, Chemistry and related booksMateria Medicas, Botanical and related booksOlder Herbal ClassicsBibliographies

Primary PublicationsSecondary and Tertiary Publications

Abstracting ServicesComputerized Databases

CA SearchBiosisExcerpta MedicaWPIComputerized Information on Chinese Medicinal MaterialMapisNAPRALERTDatabase On Thailand Medicinal PlantsGlobalHerbIbis

Patent InformationSummary

List of Figures and Tables

Table 13.1 Significant Journals Reporting Research on Medicinal Plants



esearch is one of the most important tasks facing a herbalist. Aresearch question can be as simple as a client wanting someinformation on herb “X” for health problem “Y” but it can also be

Introduction

Rmuch more complex. The average herbalist can rely on experience or apersonal library. But occasionally research goes much deeper, perhapsfor a thesis or a corporate client. How does one acquire the most up todate information on botanical medicine?

There are over 600 scientific periodicals published worldwide that coverbotanical medicine. Where do you begin in the huge mountain of mate-rial? You might want to start with a local college or university library.Librarians are typically quite helpful when they have the time to help.Chapter 13 will give both you and your librarian some “leads” on track-ing down the information you need. At first you may find very little andperhaps be overly disappointed. “With over 600 journals out there, whycan’t I find anything?” It is a common comment I hear. But over theyears, I have often found little gold mines of information in the strangestplaces. And like many adventures, the main thing is to never give up!

Herb Research Foundation

For years, I’ve suggested to students that they supplement their ownprimary literature searches with a professional service. One that wehighly recommend is the Herb Research Foundation (HRF) based inBoulder, Colorado in the United States(1007 Pearl St. Suite 200, BoulderCo 80302 USA Ph# 303 449-2265, Fax 303 449-7849). To quote Olayiwola



Akerele, M.D. Director of Traditional Medicine Program of the WorldHealth Organization, “The Herb Research Foundation is one of the mostreliable sources of accurate botanical information available. It has thepotential for becoming a major catalyst in revitalising and influencingthe serious scientific study of medicinal plants in the U.S. and interna-tionally”.

To start off with, HRF has a large list of botanicals with completedliterature searches. There is a good probability that the information youare researching has already been gathered. If it is, for a small fee (on aper page basis) you get a pretty strong trail on the botanical you arelooking for, at a substantially reduced price. This material is usually just“raw data” and might or might not come with an overview. There mightbe a few papers on the subject, but most important is a list of abstracts.An abstract is a small synopsis of the material covered in a paper. Anabstract will usually include title, author(s), key words (major topiccovered), a short description of the paper, language the paper is writtenin, journal, volume and page number(s), date and a location codenumber.

Read through the abstract, and if the information is what you are lookingfor, and it is in a language that you can read, obtain the paper. Chancesare you can get the paper from your local university if it is in a popularjournal. A phone call can answer that question. If not, HRF might haveinformation on where to get the paper, have copy themselves or canobtain it for you. Richard Schaffenberg of Herb Research Foundation willdo a complete literature search for you if you desire.

By becoming a member of HRF you receive their quarterly journal,HerbalGram. Dr. Varro Tyler, Executive V.P. for Academic Affairs atPurdue University and author of a major pharmacognosy text says, “There is no question in my mind that [Herbalgram] is the best of its kindin the entire nation”.

Unless you are research orientated, the paper trail can beoverwhelming. Over the past few years there has been a dramaticincrease in the interest in research on medicinal plants worldwide. Thisis due in part to the United Nation’s World Health Organisation (WHO).An WHO declaration on health care by the year 2000 lists the goal ofhaving medicinal plants serving a primary role. Dr. Holfdan Moher,Director General of WHO, stated; “there is no doubt that the judicioususes of such herbs, flower and other plants for palliative purpose inprimary health care can make a major contribution towards reducingthe developing countries’ drug bill”. This has encouraged manycountries to intensify research into new and traditional botanicalmedicines. Towards that goal, WHO has compiled an inventory of 21,000medicinal plant species based on the literature from 91 countries by theyear 1980.1



Libraries

A good knowledge of the local public and college/university library canbe a great help in research. If your local academic library doesn’t havethe information you need, it can usually be obtained by interlibrary loanfor a fee. Consult your librarian for particular loan policies and chooseyour loans carefully. Most major libraries will have indexes or abstractswhich will narrow your search.

For very special sources, one place to consider is Lloyd Library andMuseum, 917 Plum Street, Cincinnati, Ohio 45202. The Lloyd Library isdedicated to the field of pharmacognosy and related natural sciences.The library boasts three floors of books representing herbal and botani-cal studies from the last six hundred years. Established by the Lloydbrothers over one hundred years ago, the library is a precious resourcefor herbalists from around the world. North American Eclectic medicineis particularly well represented.

Books

A list of all the useful references for botanical medicine would be muchtoo long to include. The following are favourite research books, includ-ing many used to create this text and the Wild Rose Scientific Herbal. Wewill also look at some bibliographies that provide very inclusive lists.

1. Pharmacognosy, Chemistry and related books

Tyler, V., Brady, L., Robbers, J., Pharmacognosy, (7th ed.), Lea & Febiger,Phila., PA, 1976. This was a primary reference in generating thematerial in this book. It lists material in more or less the same orderas Advanced Herbology. It has gone through many editions and isused as a primary text in pharmacognosy.

Trease, G.E., Evans, W.C., Pharmacognosy (11th ed.), Bailliere, Tindall,London, Eng., 1978. Another very popular older text ofpharmacognosy.

Robinson, T., The Organic Constituents of Higher Plants (4th ed.),Cordus Press, North Amherst, Mass., 1980. Notes used by theDepartment of Biochemistry, Unversity of Massachusetts, Amherst,Mass. for pharmacognosy classes.

Hsu, H.Y., Chen, Y.P., Hong, M., The Chemical Constituents of OrientalHerbs (Vol. 1), Oriental Healing Arts Institute, Los Angeles, CA, 1982.Chemical diagrams and details of Chinese Herbs. 1546pp



Hsu, H.Y., Chen, Y.P., Hong, M., The Chemical Constituents of OrientalHerbs (Vol. 2), Oriental Healing Arts Institute, Los Angeles, CA, 1985.A continuation of the previous book. 829pp

Goodman, L., Gilman, A., The Pharmacological Basis of Therapeutics (4thed.), Collier-Macmillan Canada Ltd., Toronto, 1970. The basic text onpharmacy employed by most universities. 1794pp

Martindale, The Extra Pharmacopeia, The Pharmaceutical Press, Lon-don, Eng., 1941. An extra pharmacopeia listing many botanicalremedies.

2. Materia Medica, Botanical and related books

Duke, J., CRC Handbook of Medicinal Herbs, CRC Press, Boca Raton, FL,1985. A very thorough list of some 365 herbs with scientific, folklore,chemical and nutritional information, with line drawings. Extensiveappendices and tables. 677pp

Leung, A.Y., Encyclopedia of Common Natural Ingredients, A Wiley-Interscience Pub., Toronto, ON, 1980. A listing of many commonlyused herbs with chemical, pharmacological and biological informa-tion, along with food and folk medicine uses and commercial prepa-rations. 409pp

Kapoor, L.D., CRC Handbook of Ayurvedic Medicinal Plants, CRC Press,Boca Raton, FL, 1990. An Ayurvedic materia medica which liststraditional uses, Ayurvedic energetics, chemical constituents,pharmacological action, medicinal properties and line drawings.416pp

Hsu, H.Y., Oriental Materia Medica: a concise guide, Oriental Healing ArtsInstitute, Los Angeles, CA, 1986. A very useful and complete materiamedica of Oriental herbs with energetics, traditional uses, chemicalconstituents, pharmacology, some chemical diagrams and many linedrawings. 932pp

Bensky, D., Gamble, S., Chinese Herbal Medicine - Materia Medica,Eastland Press, Seattle, WA, 1986. Another very excellent OrientalMateria Medica with energetics, functions, major combinations,cautions and contraindications, doses, major constituents, pharma-cological and clinical research, line drawings. 723pp.

Grieve, M., A Modern Herbal, Jonathan Cape, London, 1931. An older butuseful materia medica covering medicinal, culinary, cosmetic,cultivation and folklore of many hundreds of botanical products.912pp.



Spoerke, D., Herbal Medications, Woodbridge Press Publ. Co., SantaBarbara, CA, 1980. Brief, often usesful information on over 200plants, specializing in chemical and toxic information along withmodes of action and “alleged uses”. 192pp

Tierra, M., Planetary Herbology, Lotus Press, Santa Fe, New Mexico.Lists herbs according to therapeutic uses, including energetics,useful plants parts, active constituents, properties, uses and dos-ages. 485pp.

Important Bibliographies For Herbalist

A Bibliography on Herbs, Herbal Medicine, “Natural” Foods, and Uncon-ventional Medical Treatment by Theodora Andrews. LibrariesUnlimited, Littleton, Colorado, 1982. 339 pp. This book is a bit oldbut does has a good annotated bibliography of 749 titles, split into21 headings.

Herbs: An Index Bibliography 1971-1980. The Scientific Literature onSelected Herbs, and Aromatic and Medicinal Plants of the TemperateZone by James Simon, Alena Chadwick and Lyle Cracker. ArchonBooks. The Shoe String Press, Inc, Hamden, Connecticut 06514; 1984;770pp. This book deals with 70 herbs including over 10,000 refer-ences.

Alternative Medicine: A bibliography of books in English by Ruth Westand Joanna Trevelyan, Mansell Pulishing Ltd., London, New York,1985. 210pp. This book lists 2189 books in various fields of naturalhealing.

Old Classic books on Herbals

The Eclectic Materia Medica, Pharmacogy and Therapeutics by Felter,reprint 1922. 743 pp. The materia medica was one of the mostcomplete works for the early part of this century.

American Materia Medica, Therapeutic and Pharmacognosy, FinleyEllingwood MD 1898; 564pp. Again, a very scholarly reference of thebotanical uses in the era by medical doctors.

A Manual of Materia and Pharmacology, David Culbreth, M.D. 18??.650pp. This book gives detailed botanical descriptions, includingmacromorpholgical and micromorphological features of medicinalplants. It also includes chemical assays of several herbs and adulter-ants.



Specific Medicines, 15th ed., J. Scudder, M.D., 1903. 432pp. This was oneof the most popular Materia Medica of the era.

Kings’s American Dispensatory, Felter and Lloyd, 1898. 2172pp. This twovolume set is extremely useful. It is being probably the most exten-sive reference and is available in reprinted form.

United States Dispensatory, 23rd (1943) and 24th (1947) editions,Lippincott, 1881. pp & 1927pp. These two dispensatories are the lastof the long series to include herbs to any extent.

The British Pharmaceutical Codex, London, Eng., 1934. 1768pp. Includesmany botanical medicines.

Eclectic Medical Journals. mid 1800’s - 1906. The medical journal of thetime that has an ongoing discussion of medical theories and the useof botanical medicines.

Primary Publications

As stated earlier, there are over 600 periodicals published worldwidewhich cover the field of medicinal plants.2 Many of these journals arerelatively new and come out of China and India. Table 13.1 includessome of the more useful journals. A few major journals are dedicatedexclusively to botanical medicines and they are: Journal of NaturalProducts (Lloydia), Planta Medica, Plantes Medicinale et Phytotherapie,Fitoterapia, Farmatsiya, Zeitschrift fur Phytotherapie, PhytotherapyResearch, Journal of Ethnopharmacology, and Journal of ScientificResearch on Plants Medicine. As you can see, there are several journalsthat are not written in English. Articles written in other languages oftendo include an English abstract. I have included this list for interest’s sakeand for people that can speak more than English or who have access totranslators. On occasion, custom translation of particular scientificpapers is crucial to a thorough research project.

Secondary and Tertiary Publications

These publications include newsletters, journals of societies, encyclope-dias, abstracting journals and the like. Some of these serial publicationsare more dedicated to complementary medicine, others are morescientifically oriented abstracting services.

By far the most useful complementary medicine journal is: HerbalGram(the journal of the American Botanical Council and the Herb Research



1. Act Chimica Sinica (Beijing, China)2. Acta Pharmaceutical Sinica (Beijing, China)3 African Journal of Pharmacy and Pharmaceutical Sciences (Apapa, Nigeria)4. Agents and action (Basel, Switzerland)5. Agricultural and Biological chemistry (Tokyo, Japan)6. American Journal of Clinical Nutrition (Bethesda, MD,USA)7. Ancient Science of Life (Coimbatore, India)8. Annales Pharmaceutiques Francaise (Paris, France)9. Archiv der Pharmazie (Weinheim, Germany)10. Archives of Internationales de Pharmacodynamie et de Therapie (Ghent, Belgium)11. Archives of Pharmacal Research (Seoul, Korea)12. Arzneimittel Forschung (Aulendorf, Germany)13. Atherosclerosis (Amsterdam, Netherlands)14. Biochemical Pharmacology (Oxford, England)15. Bollettino Chimico Farmaceutica (Milan, Italy)16. British Medical Journal (London, England)17. Bulletin of Faculty of Pharmacy Cairo University (Cairo, Egypt)18. Bulletin of Medico-Ethnobotanical Research (New Delhi, India)19. Carbohydrate Research (Amsterdam, Netherlands)20. Chemical and Pharmaceutical Bulletins (Tokyo, Japan)21. Chemical and Druggist (London, England)22. Chemistry Letter (Tokyo, Japan)23. Chinese Journal of Integrated Traditional and Western Medicine (Beijing, China)24. Chinese Medical Journal (Beijing, China)25. Clinical Pharmacology and Therapeutics (St. Louis, MO, USA)26. Clinical Toxicology (New York, USA)27. Contraception (California, USA)28. Current Medical Practice (Bombay, India)29. Deutsche Apotheker Zeitung (Stuttgart, Germany)30. Drugs and Cosmetics Industry (New York, USA)31. Drug information Bulletin (Maple Glen, USA)32. Economic Botany (New York, USA)33. Egyptian Journal of Pharmaceutical Sciences (Cairo, Egypt)34. Ethomedizin (Hamburg, Germany)35. Farmacia (Bucharest, Romania)36. Farmaco (Pavia, Italy)37. General Pharmacology (Oxford, England)38. Herba Hungarica (Budapest, Hungary)39. Herba Polonica (Warsaw, Poland)40. Indian Drugs (Bombay, India)41. Indian perfumer (Jammu, India)42. International Journal of Crude Drug Research (Lisse, Netherlands)

Table 13.1Significant Journals Reporting Research on Medicinal Plants



43. Japanese Journal of Pharmacology (Kyoto, Japan)44. Journal of African Medicinal Plants (Cairo, Egypt)45. Journal of Agriculture and Food Chemistry (Washington D.C., USA)46. Journal of Chromatography (Amsterdam, Netherlands)47. Journal of Economic and Taxonomic Botany (Jodhur, India)48. Journal of Ethnopharmacology (Lausanne, Switzerland)49. Journal of Food Sciences (Illinois, USA)50. Journal of Natural Products (Lloydia)(Cincinnati Ohio, USA)51. Journal of Pharmaceutical Science (Washington D.C. USA)52. Journal of Pharmacy and Pharmacology (London, England)53. Journal of Research in Ayurveda and Siddha (New Delhi, India)54. Journal of Science Food and Agriculture (London, England)55. Journal of Scientific Research in Plants and Medicine (Hardwar, India)56. Journal of Tropical Forestry (Jabalpur, India)57. Lancet (London, England)58. Lawrence Review of Natural Products (Collegeville, PA, USA)59. Medicinal Traditional (Mexico City, Mexico)60. Lipid (Champaign, IL, USA)61. Naturwissenschaften (Heidelberg, Germany)62. Naunyn-Schmiedeberg’s Archives of Pharmacology (Heidelberg, Germany)63. Nippon Nogeikagaku Kaishi (Tokyo, Japan)64. Pakistan Journal of Forestry (Peshawar, India)65. Parfumerie und Kosmetik (Heidelberg, Germany)66. Perfumer and Flavorist (Illinois, USA)67. Parfums, Cosmetiques, Aromes (Paris, France)68. Pharmacology (Basel, Switzerland)69. Phytochemistry (Oxford, England)70. Plant Science Letter (Limerick, Ireland)71. Planta Medica (Stuttgart, Germany)72. Plantes Medicinales et Phytotherapie (Angers, France)73. Sachitra ayurved (Patna, India)74. Taxon (Utrecht, Netherlands)75. Zeitschrift Naturforschungs Wissenschaftliche (Tubingen, Germany)76. Zeitschrift fur Phytotherapie (Munich, Germany)

Table 13.1 (Continued)Significant Journals Reporting Research on Medicinal Plants



Foundation), P.O. Box 201660, Austin Texas 78720 (512 331-8868). It iswritten in a popular format with a impressive advisory board. Thearticles include research reviews, legal and regulatory issues, herbal“blurbs”, a media watch, review articles, book reviews, etc.

Others include:

The Bu$iness of Herbs, Northwind Farm, Rt. 2, Box 246(G), Shevlin MN56676.

Foster’s Botanical and Herb Reviews, P.O. Box 106, Eureka Springs, AR72632 (501 253-7309).

American Herb Association Quarterly Newsletter, P.O. Box 353, RescueCA 95672.

The Canadian Journal of Herbalism (the Quarterly of the Ontario Herbal-ist Association) an excellent presentation. 7 Alpine Ave, Toronto,Ont., Canada M6P 3R6 (416 536-3835)

Australian Journal of Medical Herbalism, P.O. Box 65, Kingsgrove, NSW,2208 Australia.

Important abstracting and indexing journals for medical plants include:

Biological Abstracts (Philadelphia USA) SemimonthlyBulletin Signaletique (Paris France) MonthlyChem Abstracts (Columbus OH USA) WeeklyCurrent Advances in Plant Science (Oxford England) MonthlyCurrent Contents (Philadelphia USA) WeeklyCurrent Research on Medicinal and Aromatic Plants

(Lucknow, India) QuarterlyExcerpta Medica (Amsterdam Netherlands) MonthlyHorticultural Abstracts (Slough England)Index Medicus (Bethesda MD USA) MonthlyInternational Pharmaceutical Abstracts (Washington D.C. USA)

BimonthlyMedicinal and Aromatic Plants Abstract - MAPA

(New Delhi, India) BimonthlyPharmaceutical Abstracts (Austin Texas) QuarterlyRingdoc Abstract Journal (London England) Weekly

Most of these publications can be found in “hard” copy or via electronicmedia and database services.

Abstracting services typically deal with a much broader area thanbotanicals, but in electronic form, they become very easy and useful tosearch. We will discuss this in more detail in the computerized databasesection.



Computerized Databases

There are several forms of computer databases that can assist theresearcher at any level of expertise.

Two of the biggest access methods are DIALOG and the commercial on-line services. Abstracting services available through these systemsprovide a kind of “one stop shopping” mall for information. Usually theservices have technical people on-line or available by phone to help youfind information. We will note these as we review the services.

DIALOG is essentially an academic clearinghouse for scientific informa-tion. Many public and academic libraries have information on how toaccess DIALOG for an hourly fee.

Compuserve, Delphi, America OnLine, Genie and Prodigy are on-lineservices for personal computer users. Like Topsy, they have grown andgrown to the point that over 5,000,000 people around the world use themregularly. Though focused primarily on computer issues, such servicesalso have special interest electronic forums. For example, herbalists willbe interested in the Herbal section of the HOLISTIC forum (GOHOLISTIC) on Compuserve where they can access library files and postmessages to other herbalists. The major on-line services have e-mail anddatabase gateways to many medical and scientific resources.

In the early 90's, the "Internet", an international network of networks,exploded with activity. Specialized herbal discussion groups and filearchives relating to herbalism appear with increasing frequency there.Because the Internet allows communication between people on most ofthe on-line services, it will likely become the common electronic meetingground and library of herbalists around the world.

CA Search - Chemical Abstract Service draws on 12,000 scientific andtechnical journals published in 140 nations and 50 languages. It grows byabout half a million articles a year. It has been computerized since 1967.It in available on DIALOG.

Biosis - Reviews 9,000 serials from more than 100 countries. It is growingby 300 - 500,000 items per year. It can be accessed from DIALOG.

Excerpta Medica inputs information from over 35,000 biomedical serials,books, Congress proceedings, symposia and other relevant literature. Itcontained three million items in 1984, growing at a rate of 250,000 itemsper year and can be accessed from DIALOG.



WPI - World Patent Index covering 6 million patents growing at a rate of300,000 patent a year. It can be accessed through dialog

MEDLINE - A centralized database for medical doctors in the UnitedStates. The system is growing very rapidly as a central means of access-ing health and pharmaceutical information. Users receive custompersonal computer software to access the system.

The above database are all pretty general but can be used very easily forour purposes. The following computerized databases are more specificto botanical medicine.

Computerized information on Chinese Medicinal Material - Originatingfrom the Chinese University of Hong Kong it provides on-line informationon 1860 of the most common Chinese medicinal plants. It includesbotanical, chemical, pharmacological, and clinical reports. It has majorarticles translated into English. It is updated from 64 Chinese periodicals.This database is only available on campus, but this may soon change.

Mapis - New Delhi, India. It covers data on medicinal and aromatic plantsfrom MAPA, with 600 journals from 50 countries in 22 languages

NAPRALERT - College of Pharmacy University, University of Illinois,Chicago. NAPRALERT (Natural Product Alert). It include reports onfolkloric, ethnomedical or traditional uses of plants along with chemistryand pharmacology of natural product in 4500 genera. It primarilyincludes the years 1975-1984 culled from 70,000 articles.

Database On Thailand Medicinal Plants - can be found in CA Searchfrom DIALOG. It includes 1750 Thai plants and information from 1967 to1982. It was compiled from a 42 volume work called Austrian-ThaiScientific Cooperation: The Chemistry of Medicinal Herbs in Thailand.

There are a few programs that can be bought and run on a PC

1. A group of programs called GlobalHerb, PlanetHerb, ProHerb andHomeHerb have been written by Steve Blake for both IBM and Macenvironments. These programs are fancy computerized indexes thatcross-reference many books on herbal medicine. P.O. Box 873, BenLomond, CA 95005, USA. Ph# 408 336-2442.

2.IBIS- Interactive BodyMind Information System for Mac or IBM environ-ments. It contains nutritional information, botanicals, Chinese herbs andacupuncture, homeopathy, physical, vibrational and psychospiritualmedicine with indications for 282 medical conditions.



Patent Information

If a patent is held on a medical derivative you can often find informationin the bigger databases (like DIALOG) or your country’s National Patentoffice. The most exhaustive service for this kind of information is offeredby Derwent Publication Ltd., London, England, offering World PatentIndex (WPI, see Computerized data).

Summary

If you are seriously gathering information on a particular herb, your firststop should be the Herb Research Foundation, either for current orcustom searches. Your local librarian can assist you in general searchesthrough abstracts and indexes. Interlibrary loan is a crucial service forpeople not located in a major city. “Books in Print”, available at anybookstore, will help you track down particular books for purchase.

If your librarian is stumped and can’t find a source for a particular book,try Lloyd library in Cincinnati. We looked at a few books useful for herbresearch, a list of primary, secondary and tertiary publications, a briefsurvey of computerized databases and review information on patentmaterial.

References

1Penso G, WHO Inventory of MedicinalPlants Used in Different Countries,World Health Organisation, Geneva1980.

2Chadha Y, Singh G; Information onMedicinal Plants, The Medicinal PlantIndustry Ed Wijesekera; CRC PressBoca Raton Florda p 237, 1991.


Alchemy and Herbs

14

One of the richest and most advanced forms of Western herbology comes from thestudy of alchemy. This ancient science and art, the basis of most modern science,is usually cloaked in mystery. In this chapter, we attempt to demystify some basicconcepts of plant alchemy. Alchemists divide the plant into its pure body, soul andspirit and then recombine them to produce a very high quality botanical productcalled the "little works"or a "plant stone". During the process, we will visitastrology, the Kabbala and laboratory procedure, to see how some of the greatestminds of the past used herbs.

Synopsis:

AlchemyAndHerbs



Introduction Background Different bodies of a Plant Alchemy Astrology Planetary Rulers of Some Plants

Sun Moon Mercury Venus Mars Jupiter Saturn

Kabbala (QBL) Finding One's Path or Simple Numerology

Laboratory Procedure Summary


Table 14.1 Astrological Influence on PlantsFigure 14.1 The Kabbalistic Tree of LifeFigure 14.2 Kabbalistic Pathway MeaningsFigure 14.3 Star of DavidFigure 14.4 Soxhlet Extractor

Table of Contents


Alchemy and Herbs

ost modern herbalists, like the general public, associate alchemywith “the quest for gold”, the transmutation of base substancesinto precious metals. While this view of alchemy has someM

Introduction

historical basis, the alchemists of past centuries were very much awareof the plant kingdom. Alchemy was a broad philosophical and medicaltradition which underlay much of literature and scientific research fromearliest times through to the Renaissance. It included many famousdoctors and scientists among its ranks.

Because this is a text on advanced herbology, it’s appropriate to con-clude this book the way we began. Chapter 1 introduced the traditionalChinese, Ayurvedic and North American Indian advanced herbologies.We’ve reviewed all the phytochemical branches of the plant world of keysignificance to a herbalist. Now it’s time to, once again, reflect on themysterious and subtle side of an advanced herbology. Our studywouldn’t be complete without at least a glance at the principles whichunderlay the most subtle and sophisticated use of herbal materials inEuropean, Hebrew and Arabic tradition. That tradition has never totallydisappeared and now better books and skilled practitioners are oncemore appearing in public life. Perhaps alchemy will once again play acentral part in the future practice of herbology.

European alchemists consider the most potent form of herbal medicineto be the making of a “plant stone”, referred to as the “Little Works”.Plant stones are reputedly so powerful that a single herb or botanicalformula placed beside the stone will become much more effective. Plantstones represent the spiritual and energetic essence of particular plantstransformed to indestructible objects.



Alchemy is a system of physical transmutation, found in almost allancient civilizations including those of the Middle and Far East. Westernalchemy has had a significant role to play in the history of Europe andwas the intellectual tradition most concerned with De Rerum Naturae,“The Nature of Things”, before chemistry and physics became promi-nent. Alchemical research was at the centre of medieval and Renais-sance scientific inquiry. Most astrology of the time was conducted foralchemical reasons and of course it was astrology which spurred thedevelopment of astronomy, calculus and celestial physics. Isaac Newtonhimself was active in alchemical studies.

Let’s look at this traditional view of plants and herbal formulas, keepingin mind that alchemy represents the seeds of both modern allopathicmedicine and modern herbology.

Western alchemy’s roots are linked to the oldest philosophical traditionsof the Mediterranean region. The QBL or Kabbala of Jewish origin set thestructure of the relationship of numbers and universal elements which isfundamental to alchemy. Alchemists had a specific perception of theplant kingdom. Each plant is associated with particular times, days of theweek, numbers and celestial bodies. These associations led alchemiststo collect, process and finally prescribe the use of herbs in very specificways. The potency of the preparations or techniques is greatly refinedby these considerations according to alchemical theory.

Most importantly for the purposes of this text, alchemists developedmost of the techniques for processing plants and volatile oils whichcontinue to our day. With tools we might consider quaint or crude, theywere able to prepare elaborate and subtle extracts and formulas. Thiswas especially true in the creation of tinctures and essences. Plants werepicked and stored according to specific instructions and then infused orextracted according to the equipment available and the purpose in-tended.

With our emphasis on huge industrial processes and public discussion ofall facts, we miss the significance of the alchemical herbalists working insecret to discover the rules of herbal preparation and application. Theyare our intellectual and spiritual ancestors.

Background

Wholistic healing attempts to reconcile all elements of a health condi-tion. Many of the herbalists of the past knew nothing of ‘scientific’elements of botanicals but were, nonetheless, very effective. Traditionalhealers from around the world talk of the same healing properties of thebotanicals. These people didn’t have our communication systems and


Alchemy and Herbs

our printing presses. They couldn’t communicate their findings witheach other easily but many of the plants were used for the same ail-ments.

One of the things that was common to most of these healers was anappreciation of energies that plants contain. This energy was describedby many names. Prana in India, qi or chi in the Orient, vital energies inEurope, and totem or good medicine by many of the North Americannative people.

Many of you have seen pictures of a North American Indian totem pole.This totem pole is made up of many figures, (often animal) piled on topof each other, representing specific energies and powers. A person orgroup of people with many totems (protective energies) would constructa pole of these protections to show others.

Plants in the past were not regarded much differently. They all havevarious degrees of energy associated with them. Many of the traditionalhealers used their knowledge of these subtle energies to heal sickindividuals. They didn’t know that the pain in the back was really akidney problem. They certainly did not know that the arbutin in the uvaursi would change into hydroquinone to work as a local antiseptic to thekidney. What they determined through focused awareness was the linksbetween certain human conditions and particular plants.

The systems that these healers used were very sophisticated. To be-come a medicine person in the various societies took a great deal ofeducation, lasting many years. In Chapter 1 we looked at several ad-vanced herbologies and their theoretical foundations. The foundationsfor Western alchemy will be immediately familiar to those brought up inthe West.

Different bodies of a Plant

In wholistic healing we recognize that a “person” is not just a physicalbody alone. We have a physical body that takes up three dimensions,can be weighed, measured, touched and analyzed. We have emotionsand mental concepts, too. While not as easy to measure with physicaltools they do exist. We can say that emotion and mind take up negativespace, with a positive time. Western science has struggled with theinsubstantiality of emotions, thoughts and feelings for hundreds of years.It is only with the appearance of the powerful paradoxes of quantumphysics that the boundary between the physical and the mental causesscientists less anxiety.



Many of the healers that have gone on before us feel that plants alsohave different non-physical bodies, another source of the most impor-tant healing properties. Many books that are written on this subject andyou may wish to review them every so often:

The Pattern of Health by Aubrey Westlake MD1

The Secret Life of Plants by P. Tompkins and C. Bird.2

Practical Handbook of Plant Alchemy by M. Junius.The Alchemist of the Rocky Mountains by Frater AlbertusThe Alchemist's Handbook by Frater Albertus

Alchemy

A lexicon of alchemy3 defines it as “the separation of the impure from thepure substance”. The idea of alchemy is to purify a substance’s energies.If a person can purify the energies of a base metal (thus fully understand-ing its energies) they may at some level be able to manipulate theseenergies and create an enhanced physical substance -- whether aprofoundly powerful herbal remedy or a metal turned into gold. Metal-work is often called the ‘Great Works’ or philosopher’s gold. One caneasily see that a person who accomplished transmutation would not bedoing it for mere financial reward. The philosopher’s gold is thought tobe much more valuable to its owner than the financial value. Making goldis not the purpose of this text!

In the long process of developing alchemical “sensitivities”, the first stepis the ‘Little Works’ of the plant kingdom. This involves making a‘philosopher’s stone’ out of plants. The physical methods of doing thisare relatively simple but it takes much more than lab procedure tocomplete the job. It is said that the alchemist must purify their own bodyin the process of purifying the plant material.

The ‘Little Works’ are said to be the most potent form of a herb in theherbal kingdom. Let’s say that we make a stone out of mint. Thephilosopher’s stone would not only be the most potent form of that mint,but is said to stimulate other herbs to their most potent state. As apractical step, the alchemical herbalist would take their stone and put itin a herbal infusion or decoction as they were making it for a person.This would make the tea much more potent (irrespective of the originalcontents). As the stone would not dissolve or diminish in quality, it canbe retrieved after the preparation of the tea, to be used again and again.It seems to act like a magnet, drawing out the power of other herbs foruse in medicinal circumstances. Sounds useful! It is not as easy as itseems, however.


Alchemy and Herbs

Alchemy is made up of three different disciplines:

1. Astrology 2. Kabbala (QBL) 3. Lab work

Astrology and Kabbala have been slandered over the centuries much thesame as alchemy. While these disciplines have come in conflict with theestablished churches over the years, there is nothing intrinsically evil orSatanic associated with them nor with the goal of developing advancedplant products. The objective is to bring the purest essence out of theplant, to leave behind all the impurities.

Astrology

The astrology of alchemy is much the same as modern day astrology butit deals primarily with the inner seven planets, the planets well known tothe medieval world. Astrological knowledge is meant to help healersunderstand cycles of energy -- their own, those of the planet and those ofthe patient. Does this concern with energetic “context” seem familiar?

Many of the old herbalists, like Culpepper, classified all of their plants byastrological principles. A particular formula was given to a person asmuch for its astrological significance as for any particular physiologicalproperty. Herbalists proved that the potency of a plant varied accordingto the season, time and conditions under which it was harvested.Modern science confirms that plants circulate their constituents farmore dynamically that we might suppose. To the ancient herbalists,

Table 14.1Astrological Influence on Plants

DAY Su Mo Tu We Th Fr Sa

1st g c f b e a d

2nd a d g c f b e

3rd b e a d g c f

4th c f b e a d g

5th d g c f b e a

6th e a d g c f b

7th f b e a d g c

The energies of the planets

a = aggressive = su = Sunb = relaxing = ve = Venusc = mental = me = Mercuryd = change = mo = Moone = disruptive = sa = Saturnf = fortunate = ju = Jupiterg = impulsive = ma = Mars



operating under an astrological perspective of nature, the plants seemedto follow cosmic principles of behaviour. Without a nearby HPLC labora-tory to depend on, herbalists used their own senses to distinguishbetween particular plants!

Table 14.1 demonstrates simply how astrological influences on plantswere calculated. Each time of the day is split into seven parts (a cycle ofseven, within a weekly cycle of seven), representing approximately 3hours and 24 minutes per section. The second part of each day (i.e.approximately 3:30 a.m. - 7:00 a.m.) corresponds with the planet repre-senting the day (i.e. Sun for Sunday, Moon for Monday, etc.). The daysgot their names from this energetic influence. The most powerful time ofany day is the “second part” (sunrise).

The best time to pick a plant is also in the second part of the day,especially on days or times ruled by the planet that represents the plant.Chamomile is ruled by the Sun. The most potent time to pick chamomilewould be Sunday around sunrise. In turn, chamomile is most potent as amedicine during the part of each day in the time sector represented byan ‘a’ (ruled by the Sun). Chamomile taken on a Thursday, for example,would be most potent in the fourth part of the day or 10:15 a.m. - 1:30p.m. The whole system seems elaborate but it focuses both patient andpractitioner on the broader cycles of nature in which plants and humanslive.

Before beginning work on a project like a philosopher’s stone, analchemist would purify himself or herself for a year. This puts one in asgood a physical, emotional and mental state as possible. After determin-ing their own personal health needs, often by astrological andKabbalistic means, practitioners would dmatch their weaknesses withappropriate medicines. The steps to purification (as determined byastrological perspectives) would be as follows:

1. Determine which herb would be the best for the practitioner, foreach of the planets.

2. Pick the herb at the appropriate time (i.e. sunrise of the day inwhich the planet ruled).

3. Make a tincture of the herb (4 oz of herb to 26 oz of alcohol)letting it set for 14 days (or Soxhlet extraction method discussedbelow).

4. Strain the herb, burn the herb and add the ash back to the tinc-ture (spagyric tincture).

5. Take one tablespoon of the herbal spagyric tincture representingthe planet for that day, each morning in the second sector of theday.

6. Repeat for a whole year. Seven herbal spagyric tinctures, in acycle of seven, for a year!


Alchemy and Herbs

Many books provide lists of astrological rulers of particular herbs.Notable examples include ‘Culpepper’s Herbal’ and ‘The Alchemist’sHandbook’.4

Planetary Rulers of Some Herbs

Just to give students something to ponder, here is a brief list of plantsruled by the seven “inner” planets. Astrological herbology is a specializa-tion in itself. If at all possible, reading and study should be supplementedby apprenticeship to a herbalist skilled in astrological analysis.

Sun

Angelica, ash tree, bergamot, black mustard, burnet, calamus ,celandine, (small) centuary, chamomile, cinnamon, cinquefoil,cloves, dittany, elecampane, eyebright, gentian, ginger, grapevine, ground ivy, juniper, laurel, lemon balm, lemon tree, lovage,marigold, marshmallow, mistletoe, mustard (white), olive tree,orange tree, passion flower, pepper, peony, pimpernel, plantain,rice, rosemary, rue, saffron, St. John’s wort, strawberries (wild),sundew, sunflower, tormentil, turnsole, vine viper’s bugloss,walnut tree, zedoary.

Moon

Acanthus, arrach, atriplex, brankursine, cabbages, chickweed,clary, cleaver, colewort, coralwort, cucumber, daisies, duck-weed, fluellein, galiums, hawkweed, hyssop, iris, lady’s smock,lettuce, lilies (white, water), lime tree, monk pepper, moonwort,mouse-eared chickweed, myrtle, moneywort, nutmeg, orpine,papaya, privet, poppies, periwinkle, pumpkin, rattle-grass,saxifrage, sedum, speedwell, stonecrop, tumeric, wallflower,water chestnut, watercress, willows.

Mercury

Acacia, anise, bryony, bittersweet, buckbean, calamint, carrot(wild), caraway, celery, chicory, clover, coltsfoot, digitalis, dill,elecampane, endives, fennel, germander, hazelnut, hedge-mustard, honeysuckle, horehound, houndtongue, lavender,licorice, lily of the valley, mandrake, marjoram, mercury, mints,mulberry, myrtle, nailwort, nux vomica, oats, oregano, parsley,parsnips, pellitory, pepper (cubeb), savory, scabius, smallage,southernwood, valerian.



Venus

Alkanet, alder, alehoof (ground ivy), apples, arrach (wild),artichoke, archangel bean, blackberry, birch, bishops weed,bramble, bugle weed, burdock, catnip, cherry tree, chestnuts,chickpeas, columbine, coltsfoot, cotyledon, cudweed, cowslip,crab’s claw, crosswort, daisy, devils bit, digitalis, dyer’s alkanet,elders, eringo, featherfern, figwort, geraniums, goldenrod,gromel, gooseberry, gromwell, groundsel, kidneywort, ladiesmantle, marshmallow, mercury (french), mint, moneywort,motherwort, mugwort, orchids, parsnip, pennyroyal, peach,pears, periwinkle, plantain, plums, poppies, purslane, primose,privet, queen of the meadow, ragwort, roses, rye, sanicle, selfheal, soapwort, sorrel, sow-thistle, spicknel, strawberry, tansy,teasel, thyme, vervain, wheat, wormwood, yarrow.

Mars

All-heal, aloes, anemone, barberry, basil, bryony, benedictus,blessed thistle, box, capsicum, catnip, cedar (red), coriander,crowsfoot, cuckoopint, daisy, dovesfoot, dogrose, elder, figwort,flax, garlic, gentian, geranium, hawthorn, hedge-hyssop, honey-suckle, hop, horseradish, madder, master-wort, mezereon,mustards, nettle, nux vomica, oak, onion, pepperwort, pine-apple, pine, plantain, radishes, restharrow, rhubarb, savine,sarsaparilla, senna, spurge-laurel, squill, star thistle, tobacco,tormentilla, wormwood.

Jupiter

Agrimony, alexander, almonds, apple, apricots, anise, arnica,ash, asparagus, basil, balm, beet (white), bilberry, borage,carnations, centaury, celandine, chicory, chervil, chestnut,cinquefoil, coltsfoot, comfrey, costmary, couch grass, dandelion,dock, dog’s grass, dog rose, elecampane, endive, fennel, figs,flax, fumitory, flowering ash, gentian, ginseng, grapevine, hart’stongue, hedge-nettle, henbane, horse chestnut, house-leek,hyssop, Irish moss, jasmine, juniper, laurel, lavender, licorice,lime tree, liverwort, lungwort, madder, marshmallow, mapletree, masterwort, melilot, mistletoe, mullein, myrrh, nutmeg, oak,oats, olives, peppermint, pimpernel (scarlet), polypody, poplars,raspberries, roses, sage, samphire, sandalwood, scurvy grass,sorrels, sugar cane, lady’s thistle, tansy, tomatoes.


Alchemy and Herbs

Saturn

Aconite, aloes, amaranths, ashweed, barley, belladonna, buck-thorn, burdock, cannabis, caraway, centuary, corn, corn flower,cowbane, beets (red), beech tree, bifoil, birdsfoot, blue bottle,buck’s horn plantain, chickweed, cockle weed, comfrey, digi-talis, dodder, elder, elm tree, fenugreek, fireweed, flax, fleawort,flux weed, fumitory, henbane, gladwind, goutwort, heart’s ease,hawthorn, hawkweed, hemlock, henbane, hellebore, horsetail,holly, iris, ivy, jew’s ear, knapweed, knotgrass, malefern, man-drake, medlar tree, mosses, mullein, nightshades, onions, pansy,pines, periwinkle, plantain, plums, polygonum, poplars, poppies,quince tree, royal fern, rye, senna, service tree, solomon’s seal,shepherd’s purse, spleen-wort, squill, tamarind, tamarisk tree,melancholy thistle, blackthorn, thorough wax, tutsan woad,twayblade, Solomon’s seal, willow herb, wintergreen, yew tree.

As you might have noticed, some of the herbs are ruled by more thanone planet. Herbalists apparently felt that the nature of particular plantsreflected the influence of more than one planet. I can not verify theselists from personal experience. In fact, I cannot even confirm the Latinnames of many. The lists are a collation from several herbal alchemybooks and are meant to peak your interest.5,6,7

KABBALA (QBL)

At first glance, the Kabbala seems to be even less useful to the modernherbalist than astrology. Based primarily in a very old Hebrew intellec-tual tradition, the Kabbala deals with the significance and power ofnumbers. It extends mathematics into the realm of daily human exist-ence, discovering relationships between the universe and humans whichconform to mathematical law. Once of the most common symbols ofKabbalistic knowledge is a tree.

This symbol is often called the Tree of Life. Many of the stations (calledSephera) have astrological signs associated with them. The sephera isassociated with a digit that represents its location in the path. The tenlocations match the ten numbers of our decimal system. The sepheracan represent many levels (i.e. yesod (9) can represent 9, 19, 109, 1239etc.). This system is a constantly evolving cycle, on the base ten. Eachsephera has a meaning noted in Figure 14.2.



Figure 14.1The Kabbalistic Tree of Life

1KETHER

3BINAH

9YESOD

2CHOCKMAH

5GEBURAH

4CHESED

6TIPHERETH

8HOD

7NETZACH

12 11

17 1518 16

23 2122 20

26 24

25

27

30 28

2931

19

13

14

32

The pathways also have meaning as follows:

11. scintillating (sparkle)12. transparent13. uniting14. illuminating15. constituting16. eternal or triumphal17. disposing18. house influence

^_

`a

10MALKUTH


Alchemy and Herbs

19. all spiritual being (cross 3other paths -- plant, mineral,animal)

20. will21. conciliation22. faithful23. stable24. imaginative25. tentative (probation)26. renovation

27. exciting28. natural29. corporeal30. collective31. perpetual32. administrated

Figure 14.2Kabbalistic Pathway Meanings

1CROWN

9FOUNDA-

TION

2WISDOM

5SEVERITY

4MERCY

6BEAUTY

8SPLENDOR

7VICTORY

12 11

17 1518 16

23 2122 20

26 24

25

27

30 28

2931

19

13

14

32

3UNDER-

STANDING

b

c

d

ef

g

hi

10KINGDOM



The alchemist uses the Tree of Life to interpret his own location andpath upon the chart, where his destination is, and an appropriatemethod of purification (by travelling those paths).

Finding One’s Path or Simple Numerology

Finding one’s path the alchemical way through use of the Kabbala is asimple form of numerology. Take a person’s birthdate (let’s say 05-05-1911), add the numerals up and we get 22. This represents the 22nd pathor Lamed. The destiny is found by adding these again (2+2=4) to get four,or the goal of the life. There are two simple ways to get to 4 (Chesed)from 22, though 5 (Geburah) and along 19 (teth), or through 6 (tiphereth,beauty) and along 20 (jod). One could decide by their own astrologicalconfiguration and the influences of the path, which would be best.

If we start with a date like 09-09-1899 we get 45 a more complex example.This number is above 32, so we subtract 10 (45-10=35), this is still above32 so we do it again to get 25. Twenty-five (25) with the goal of 9 (4+5=9)from our original number.8 Here the person starts at 25 (tentative) goingto Yesod (foundation).

Laboratory Procedure

We started off this chapter defining alchemy as the process ofseparating the impure from the pure. The lab procedures for plantprocessing are the basis for purification. An alchemist believes that allthings, including plants, can be separated into three parts:

body = Salt =

soul = Sulphur =

spirit = Mercury =

The job of an alchemist in the lab is quite a simple -- to separate, purify,and cohabitate. We need to separate the plant into its three bodies (orparts). This can only be done using the four ancient natural elements:

AirFireWaterEarth

Combining these symbols we get the Star of David, long considered animportant spiritual symbol. There is also a fifth non-descript elementcalled Quinta Essentia or Quintessence. It is the permeating energy ofthe whole creation. It is everything but nothing at all. It binds the four


Alchemy and Herbs

elements together. Remember our previous review of Qi, Prana, Ki andvital energy. Personal evolution for the alchemist mimics his own lab-oratory procedures -- an alchemist must transmute their own nature.There is no other way. Practical lab techniques cannot by themselvescreate a true ‘philosopher’s stone’.

Spirit in the plant kingdom is represented by plant alcohols. We refer tospirits (wine) for just this reason. The soul of a plant is its essential oil.The body is the purified ash that is left behind. Alchemists feel that thepurified spirit of the plant kingdom is unified. One hundred percentalcohol is the spirit of the entire plant kingdom. When we drink of spiritswe get intoxicated by the energies of the plant kingdom. Too much is notgood. At one time, spirits were used only for important rituals. Wine isstill employed by the Roman Catholic Church today. From the alchemi-cal perspective, the alcohol can be fermented from the plant in questionor from any other plant source.

To separate the body from the soul and spirit, we simply make a tinc-ture. We can make the tincture in the traditional way -- simple macera-tion, letting it set in alcohol for fourteen days. A more expedient andmore complete method uses a Soxhlet extractor (see Figure 14.4).

The Soxhlet extractor has three parts: the condenser, extractor and theflask. Pure alcohol is placed in the bottom flask, crushed botanicals areput into a filter paper thimble in the extractor. Heat is applied to boil thealcohol. It evaporates up into the condenser, condenses and drips downthrough the herb in the thimble. When the thimble is full, it will automati-cally drain into the flask hermetically and the whole process repeats.

After several circulations the fluid draining from the thimble will becompletely clear. This signals that all of the soul and spirit is taken fromthe herb. We then take the herb and light it on fire. It will turn black. Wecan then put the ashes in a crucible and further calcinate the herb byplacing it over a Bunsen burner for many hours. At first the ashes willturn grey. With much patience it will turn pure white.

Figure 14.3Star of David



The next step requires obtaining the pure essence or volatile oil of thesame plant. Now we have a pure body (ash), a pure soul (the essentialoil) and a pure spirit (pure alcohol). We then combine them in propor-tion to form a solid stone, that will not dissolve in water or alcohol. This"plant stone" is one of the highest quality botanical products known.

Alchemy is much more than the concept making gold out of base metal.Philosopher's gold is made in somewhat the same way as a plant stone.The metal has to be separated into pure body, soul and spirit and thenbrought back together again. This "philosopher's gold" is worth muchmore than the pure material value. If it is nothing else it is a metaphor forwhat the alchemist is trying to do personally.

Alchemy is not only a Western tradition, it was heavily used in China.One of the major endeavours of the Taoist alchemist was the search forthe elixir of longevity. I have talked briefly about this in one of my otherbooks (Reishi Mushroom: Herb of Spiritual Potency and Medical Wonder).Many elixirs were tried. Some may have worked but many causeddeath. The Chinese were also interested in the creation of alchemicalgold. Though these same alchemists deplored material wealth, and felt itbarred immortality and extended longevity, they nonetheless sought outthe principles of making gold. A mysterious compulsion when earninggold was an easier matter for any skilled healer.The answer, obviously,lies in the perception that "philosopher's gold" had profoundly differentattributes when compared to gold which was mined.

Figure 14.4Sohxlet Extraction

Heat is applied to the beaker (A), causing hotalcohol vapour to rise through a tube(E) andup to a cooling chamber (C) (which has coldwater flowing through it.

The hot condensing alcohol drips through afilter paper thimble (B) in which herbalmaterial is placed. Volatile oils and constitu-ents are leached out. When sufficient fluid isextracted and enters tube G, the siphon (F)pulls the liquid back into the beaker. Theprocess continues until all constituents areleached from the herbal material.

Water←

←


Alchemy and Herbs

Summary

The "Little Works" or the plant stone, was the first step in the Europeanprocess of learning how to make gold. Some call it a training lesson.Nevertheless, plant stones remain the most potent herbal products andare central to the creation of other less exotic herbal products.

Alchemy is a mysterious science, a scientific art, which combinesfeatures of laboratory science, astrology, Kabbala and alchemical rules.Its history lists a "who's who" of the greatest thinkers in the Westerntradition. Herbalists like Culpepper, commonly thought of as the fatherof English herbalism, used alchemical principles at the core of theirdiagnostic and prescriptive theories.

Perhaps alchemy will once again come from out of the shadows todominate the intellectual traditions of Western herbalism.

References

1Westlake, A., The Pattern of Health,Shambhala, Berkeley, CA, 1973.

2Tompkins, P. and Bird, C., The SecretLife of Plants, Harper & Row, NewYork, 1973.

3Rudland, M., translated by Waite, A.E.,A Lexicon of Alchemy, Samuel WeiserInc., York Beach, Maine, p. 20 reprintin 1893 of a 1612 book.

4Junius, M. Practical Handbook of PlantAlchemy, Inner Traditions Interna-tional Ltd., New York, NY, 1985.

5Junius, ibid., pp. 101-122.6Culpepper, Complete Herbal and

English physician, Gleave and Son,Deasgate; Manchester, England, 1826.

7Muir, A., The Healing Herbs of theZodiac, Llewellyn Publ., St. Paul,Minn., 1974.

Coudert, Allison, Alchemy - ThePhilosopher's Stone, WildwoodHouse, London, 1980.

Albertus, Frater, The Alchemist of theRocky Mountains, ParacelsusResearch Society, Salt Lake City, UT,1976.

Albertus, Frater, The Alchemist'sHandbook (3rd printing), SamuelWeiser, New York, 1978.

8Albertus Frater; What Is A Path In TheQ.B.L.?, Parachemy; Journal ofHermetic Arts and Sciences, Salt LakeCity; Autum 1973.




Appendices

Appendices

Seeking GRAS InformationPeriodic Table of the Elements



GRAS Information

Botanicals Generally Recognized As Safe

provided by Rob McCaleb of the Herb Research Foundation,updated as of July, 1989.(see Chapter 13 for Foundation address)

This list is a compilation of all botanicals which appear on the FDA’sGRAS list, a list of food additives which are Generally Recognized As Safeby a consensus of scientific opinion. You will note that most items listedcarry notations or restrictions like “flavorings for use in alcoholicbeverages”. Many herbs are listed by the FDA because of their use inliqueurs and as components of natural flavorings prior to 1958, when thefood additive regulations were written. However, alternative uses of theplant, such as flavoring water in an herbal tea, are presumably also safe,and the FDA has taken no action against any product on their list.

Many herbal products fall into a “grey area” of regulation. Around half ofthe herbs sold by the herb industry are not on the GRAS list, but arewidely imported and sold for food use. Their omission from the list doesnot imply that they are not safe (for instance barley and arrowroot arenot GRAS food additives).

This list is excerpted from the Code of Federal Regulations (CFR) Title 21Parts 172, 182, 184, and 186. It is a complete listing of botanicals ac-cepted by the FDA for food additive use, but does not include all plantderivatives; for instance some plant gums, waxes and resins have notbeen included. All substances used for flavoring use are included. Thefollowing is an explanation of the abbreviations used in the list. In manycases species other than those listed are also used, and share the samecommon name. Our thanks to Dr. James Duke for his invaluable help inreviewing the taxonomic classifications on the list.

Abbreviations used on the list:

Ext ExtractsFla FlavoringsOil OilsOlr Oleoresins (total fat-soluble extract - oils, waxes, resins, volatile

and fixed oils).Pr Less than 25 ppm prussic acid - a natural toxinSeas SeasoningsSp SpiceSF Safrole-free (a carcinogenic natural toxin)TF Thujone-free (another natural toxin)Herb Research Foundation


Appendices

COMMON NAME BOTANICAL NAME NOTATIONS

Acacia (Gum Arabic) Acacia vera (A. spp.) Fla; EmulsifierAlfalfa Medicago sativa L. Sp; FlaAlgae: Red and brown Sp; Sea; Fla;

Flavor enhancerSpecies approved: and adjuvant.BROWN ALGAE: Analipus japonicus,Eisenia bicyclis, Hizikiafusiforme, Kjellmaniella gyrata,Laminatia spp., Macrocystispyrifera, Petalonia fascia,Scytosiphon lomentaria, Undariapinnatifida.

RED ALGAE: Gloiopeltis furcata,Porphyra spp., Rhodymenia spp.

Allspice Pimenta officinalis Lindl. Sp; Olr; Oil;(P. dioica (L.) Merr. Ext

Almond, bitter Prunus amygdalus Batsch, Oil; Olr; ExtP. armeniaca (apricot), Free of prussic acidP. persica (L.) Batsch (peach)

Aloe Aloe barbadensis Mill. or spp. FlaAlthaea (root, flowers) Althaea officinalis L. FlaAmbrette seed Hibiscus abelmoschus L. Sp; Seas; Fla;

= H. moschatus Moench Oil; Olr; Ext(Abelmoschus moschatus Moench)

Amyris Amyris balsamifera L. FlaAngelica Angelica archangelica or spp. Sp; Seas; Fla (root, seed, stem) Oil; Olr; ExtAngola weed Rocella fuciformis Fla*Angostura Galipea officinalis Hancock Sp; Seas; Fla; Oil; (Cusparia bark) Ext; OlrAnise Pimpinella anisum L. Sp; Seas; Fla; Oil; Ext; OlrAnise, Star Illicium verum Hook.f. Sp; FlaApricot kernel Prunus armeniaca L. Ext used with Sp; Seas; FlaArtemisia (wormwood) Artemisia spp. Fla; TFArtichoke leaves Cynara scolymus Fla*Asafetida Ferula assa-foetida L., Oil; Ext; Olr

F. Spp.Balm (Lemon Balm) Melissa officinalis L. Oil; Sp; Fla; OlrBalsam, fir Abies balsamea (L.) Mill FlaBalsam of Peru Myroxylon pereirae Klotzsch. Oil; Ext; OlrBasil, bush Ocimum minimum L. Sp; FlaBasil, sweet Ocimum basilicum L. Oil; Ext; Sp; Fla; OlrBay Laurus nobilis L. Oil; Ext; Sp; Fla;OlrBenzoin resin Styrax spp. Fla*Bergamot Citrus aurantium L. Oil; Ext; Olr (Bergamot Orange) subsp bergamia Wright et Arn.Blackberry bark (Rubus fruticosus L.) & all Fla

Rubus species in subgenus EubatusBois de Rose Aniba rosaeodora Ducke. Oil; Ext; OlrBoldus (Boldo) leaves Peumus boldus Mol Fla*Boronia flowers Boronia megastigma Nees. FlaBryonia root Bryonia alba L & Fla*

B. dioica Jacq.Buchu leaves Barosma betulina Bartl. Fla

et Wendl.B. crenulata (L.) Hook,B. serratifolea Willd.

Buckbean leaves Menyanthes trifoliata L. Fla*Cacao Theobroma cacao L. Oil; Ext; OlrCajeput Melaleuca leucadendron L. & spp. FlaCalendula Calendula officinalis L. Sp; Fla; Seas

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Calumba root Jateorhiza palmata (Lam.) Meirs Fla*Camphor tree Cinnamomum camphora (L.) Fla; SF

J.S.PreslCananga Cananga odorata Hook.f. Oil; Ext; Olr

et Thoms.Capers Capparis spinosa L. Sp; Seas: FlaCapsicum Capsicum frutescens L or Oil; Ext; Olr;

C. annuum L. Sp; SeasCaraway Carum carvi L. Sp; Seas; Fla; Oil; Ext; OlrCaraway, black Nigella sativa L. Sp; Seas; Fla (black cumin)Cardamon (cardamom) Elettaria cardamomum Maton. Sp; Seas; Fla; Oil; Ext; OlrCarob bean Ceratonia siliqua L. Oil; Olr; ExtCarrot Daucus carota L. Oil; Ext; OlrCascara Sagrada Rhamnus purshiana DC FlaCascarilla bark Croton eluteria Benn. Oil; Ext; OlrCassia Cinnamomum cassia, Sp; Seas; Fla;

C. loureirii & C. burmanni Oil;Ext: OlrCassie flowers Acacia farnesiana (L.) Willd. FlaCastor oil Ricinus communis L. FlaCastoreum Castor fiber L. Sp; Seas; Fla;

and C. canadensis Kuhl. Oil;Ext; OlrCatechu, black Acacia catechu Willd. FlaCayenne pepper Capsicum frutescens L. Sp; Seas; Fla

C.annuumCedar, white Thuja occidentalis L. Fla; TF (leaves, twigs)Celery seed Apium graveolens L. Sp; Seas; Fla; Oil; Ext; OlrCentuary Centaurium umbellatum Gilib Fla*Chamomile (English or Roman) Anthemis nobilis L. Sp; Seas; Fla; Oil; Ext; Olr (German/Hungarian) Matricaria chamomilla L. Sp; Seas; FlaCherry, Wild, bark Prunus serotina Ehrh. Oil; Ext; OlrCherry pits Prunus avium L., Fla; Pr

P. cerasus L.Cherry - laurel leaves Prunus laurocerasus L. Fla; PrChervil Anthriscus cerefolium Sp; Seas; Fla;

(L.) Hoffm. Oil;Ext; OlrChestnut leaves Castanea dentata (Marsh.) Borkh FlaChicory Cichorium intybus L. Oil; Ext; OlrChirata Swertia chirata Buch. - Ham Fla*Chives Allium schoenoprasum L. Sp; Seas; FlaCinchona (red, yellow) Cinchona spp. Fla; 83 mcg alkaloidCinnamon Cinnamomum spp. Sp; Seas; Fla; Oil; Ext;OlrCitronella Cymbopogon nardus Rendle. Oil; Ext; OlrCitrus peels Citrus spp. Oil; Ext; OlrClary (Clary Sage) Salvia sclarea L. Sp; Seas; Fla; Oil;Ext; OlrClover Trifolium spp. Sp; Seas; Fla; Oil;Ext; OlrCloves Eugenia caryophyllata Thunb. Oil; Sp; Seas;

(Syzygium aromaticum (L.) Fla;Ext; Olr** Merr. & Perry)

Coca (decocainized) Erythroxylum coca Lam. & spp. Oil; Ext; OlrCoffee Coffea spp. Oil; Ext; OlrCola nut Cola spp. Oil; Ext; OlrCopaiba S.American spp. of Fla

Copaifera L.Cork oak Quercus suber occidentalis L.

or Q. occidentalis F. Gray or(Quercus suber L. ** Terrell) Fla*

Corn silk Zea mays L. Ext; Fla - 4-30 ppmCostmary Chrysanthemum balsamita L. Fla*Coriander Coriandrum sativum L. Sp; Seas; Fla; Oil; Ext; OlrCostus root Saussurea lappa Clarke. FlaCubeb Piper cubeba L.f. FlaCumin (Cummin) Cuminum cyminum L. Sp; Seas; Fla; Oil; Ext; Olr

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Appendices

Cumin, black Nigella sativa L. Sp; Seas; Fla (Black Caraway)Curacao (orange peel) Citrus aurantium L. Oil;Ext;OlrCurrant, black, Ribes nigrum L. Fla (buds & leaves)Cusparia bark Galipea officinalis Hancock Oil; Ext; OlrDamiana leaves Turnera diffusa Willd. FlaDandelion root Taraxacum officinale Weber Oil; Ext; Olr (and whole plant) & spp.Davana Artemisia pallens Wall. FlaDill Anethum graveolens L. Oil; Ext; OlrDill, Indian Anethum sowa Roxb. FlaDittany (fraxinella) Dictamnus albus L. Fla* (root)Dittany of Crete Origanum dictamnus L. FlaDog Grass (Quackgrass) Agropyron repens (L.) Beauv. Oil; Ext; OlrDragon’s Blood Daemonorops spp. Fla (dracorubin)Dulse Rhodymenia palmata Ext (see also Red algae)Elder tree leaves Sambucus niger L. Fla*; PrElder flowers Sambucus canadensis L. Sp; Seas; Fla

& S. niger L. Sp; Seas; FlaElecampane rhizome Inula helenium L. Fla* (and root)Elemi Canarium commune L. FlaErigeron Erigeron canadensis L. FlaEstragole or Estragon Artemisia dracunculus L. Sp; Seas; Fla; (Tarragon) Oil; Ext; OlrEucalyptus leaves Eucalyptus globulus Labill FlaFennel, common Foeniculum vulgare Mill. Sp; Seas; Fla; Oil; Ext; OlrSweet, finocchio F. vulgare var dulce (DC.) Sp; Seas; FlaFoenugreek Trigonella foenum-graecum L. Sp; Seas; Fla; Oil; Ext; OlrFir, “pine” Abies sibirica Lebed., Fla (needles & twigs) A. alba Mill, A. sachalinesis

Masters or A. mayriana Miyabeet Kudo.

Fir, balsam, needles Abies balsamea (L.) Mill Fla (and twigs)Galanga (Galangal) Alpinia officinarum Hance. Oil; Olr; Ext; Sp; Seas; FlaGalanga, greater Alpinia galanga Willd Fla*Gambir (Catechu, pale) Uncaria gambir Roxb. FlaGarlic Allium sativum L. Oil; Ext; OlrGenet flowers Spartium junceum L. FlaGentian rhizome, root Gentiana lutea L. FlaGentian, stemless Gentiana acaulis L. Fla*Geranium, fragrant Pelargonium spp. Sp; Seas; Fla; Oil; Ext; OlrGermander, chamaedrys Teucrium chamaedrys L. Fla*Germander, golden Teucrium polium L. Fla*Ginger Zingiber officinale Rosc. Sp; Seas; Fla; Oil; Ext; OlrGlycyrrhiza Glycyrrhiza glabra L., Sp; Seas; Fla;

G. spp. Oil; Ext; OlrGrains of Paradise Amomum melegueta Rosc. Sp; Seas; FlaGrapefruit Citrus paradisi Macf. Oil; Ext; OlrGuaiac Guaiacum spp. FlaGuarana Paullinia cupana HBK. FlaGuava Psidium spp. Oil; Ext; OlrGum ghatti Anogeissus latifolia Emulsifier

(Roxb.)Wall.Gum tragacanth Astragalus gummifier Emulsifier

Labillard.Haw, black, bark Viburnum prunifolium L. FlaHemlock needles, twigs Tsuga canadensis (L.) Carr. Fla

T. heterophylla (Raf.) Sarg.Hibiscus Hibiscus sabdariffa L. Fla* (Roselle)

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Hickory, bark Carya spp. Oil; Ext; OlrHops Humulus lupulus L. Oil; Ext; OlrHorehound Marrubium vulgare L. Sp; Seas; Fla; Oil; Ext; OlrHorsemint Monarda punctata L. Oil; Ext; OlrHorseradish Armoracia lapathifolia Gilib. Sp; Seas; Fla

(Armoracia rusticana **Gaertn., Mey., & Schreb.)

Hyacinth, flowers Hyacinthus orientalis L. FlaHyssop Hyssopus officinalis L. Sp; Seas; Fla; Oil; Ext; OlrIceland Moss Cetraria islandica Ach. Fla*Imperatoria Peucedanum ostruthium (L.)

Koch (Imperatoria ostruthium Fla(L.)**)

Immortelle Helichrysum augustifolium DC. Oil; Ext; OlrIva Achillea moschata Jacq. Fla*Jasmine Jasminum officinale L. Oil; Ext; Olr

& J. spp.Juniper Berries Juniperus communis L. Oil; Ext; OlrKaraya gum Sterculia spp.Kola nut Cola spp. Oil; Ext; OlrLabdanum Cistus spp. FlaLaurel berries, leaves Laurus nobilis L. Oil; Ext; OlrLavender Lavandula officinalis Chaix Sp; Seas; Fla; Oil; Ext; OlrLavender, spike Lavandula latifolia Vill. Oil; Ext; OlrLemon Balm Melissa officinalis L. Oil; Sp; Fla; (Balm) OlrLemon Grass Cymbopogon citratus DC. Oil; Ext; Olr

C. flexuosus Stapf.Lemon Peel, Fruit Citrus limon (L.) Burm. f. Oil; Ext; OlrLemon Verbena Lippia citriodora HBK Fla*

(Aloysia triphylla * *(L.’Her.) Britt.)

Licorice Glycyrrhiza glabra & G. spp. Sp; Seas; Fla; Oil; Ext; OlrLime Citrus aurantifolia Swingle. Oil; Ext; OlrLinaloe wood Bursera delpechiana Poiss.

& B. spp. FlaLinden flowers Tilia spp. Sp; Seas; Fla;

Oil; Ext; OlrLinden leaves Tilia spp. Fla*Locust Bean Ceratonia siliqua L. Oil; Olr; Ext (Carob)Lovage Levisticum officinale Koch. FlaLungwort Sticta pulmonacea Ach. FlaLupulin Humulus lupulus L. Oil; Ext; Olr (Hops)Mace Myristica fragrans Houtt. Oil; Ext; OlrMaidenhair Fern Adiantum capillus-veneris L. Fla*Malt (extract) Hordeum vulgare L., Oil; Ext; Olr

other grainsMandarin Citrus reticulata Blanco. Oil; Ext; OlrMaple, Mountain Acer spicatum Lam. FlaMarigold, pot Calendula officinalis L. Sp; Seas; FlaMarjoram, pot Majorana onites (L.) Benth; Sp; Seas; Fla

(Origanum onites (L.)**)Marjoram, sweet Majorana hortensis Moench. Sp; Seas;

(Origanum majorana L.**) Fla; Oil; Ext; OlrMaté (Matté) Ilex paraguariensis St. Hil. Oil; Ext; OlrMelissa Melissa officinalis L. Oil; Sp; Fla; (Balm) OlrMenthol Mentha piperita L. Sp; Seas; Fla; Oil; Ext; Olr (Peppermint)Mimosa flowers Acacia decurrens Willd. (Black Wattle) var. dealbata FlaMullein flowers Verbascum spp. Fla*

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Appendices

Mustard, black, brown Brassica nigra (L.) Koch. Sp; Seas; Fla; Oil; Ext; OlrMustard, white, yellow Brassica hirta Moench. Sp; Seas; Fla;

Oil; Ext; OlrMyrrh Commiphora spp. FlaMyrtle Myrtus communis L. Fla*Naringin Citrus paradisi Macf. Oil; Ext; Olr (Grapefruit)Neroli, bigarade Citrus aurantium L. Oil; Ext; OlrNutmeg Myristica fragrans Houtt. Sp; Seas; Fla; Oil; Ext; OlrOak, English, wood Quercus robur L. Fla*Oak, white, wood Quercus alba Fla*Oak moss Evernia spp. Fla; TFOlibanum Boswellia carteri, Fla

Birdw. B. spp.Onion Allium cepa L. Oil; Ext; OlrOpopanax Opopanax chironium Koch. FlaOrange, bitter Citrus aurantium L. Oil; Ext; Olr (flowers, peel)Orange, sweet Citrus sinensis (L.) Osbeck Oil; Ext; Olr (flowers, leaves, peel)Oregano Lippia spp. Sp; Seas; FlaOriganum Origanum spp. Oil; Ext; OlrOrris root Iris germanica L. Fla

& I. pallida Lam.Palmarosa Cymbopogon martini Stapf. Oil; Ext; OlrPansy Viola tricolor L. Fla*Paprika Capsicum annuum L. Sp; Seas; Fla; Oil, Ext; OlrParsley Petroselinum crispum Sp; Seas; Fla;

(Mill.) Mansf. Oil; Ext; OlrPassion Flower Passiflora incarnata L. FlaPatchouly Pogostemon cablin Benth. and Fla

P. heyneanus Benth.Peach kernel Prunus persica Sleb et Zuce. Ext used with sp; seas; flaPeach leaves Prunus persica (L.) Batsch Fla*; PrPeanut Arachis hypogaea L.Pennyroyal, American Hedeoma pulegioides (L.) Fla

Pers.Pennyroyal, European Mentha pulegium L. FlaPepper, black, white Piper nigrum L. Sp; Seas; Fla; Oil; Ext; OlrPepper, red Capsicum frutescens, Sp; Seas; Fla

C. annuumPeppermint Mentha piperita L. Sp; Seas; Fla;

Oil; Ext; OlrPeruvian Balsam Myroxylon pereirae Klotzsch Oil; Ext; OlrPetitgrain Citrus aurantium L. Oil; Ext; Olr (bitter orange)Pimenta Pimenta officinalis Lindl. Oil; Ext; OlrPine, needles, twigs Fla dwarf Pinus mugo Turra var. pumilio

(Haenke) Zenari Scotch P. sylvestris L.Pine bark, white Pinus strobus L. Fla*Pine oil, white Pinus palustris Mill., P. spp. Fla*Pipsissewa leaves Chimaphila umbellata Nutt. Oil; Ext; OlrPomegranate Punica granatum L. Oil; Ext; OlrPoplar buds Populus balsamifera, P. Fla*

candicans Ait., P. nigra L.Poppy Seed Papaver somniferum L. Sp; Seas; FlaPot Marigold Calendula officinalis L. Sp; Seas; Fla (see Marigold, pot)Pot Marjoram Majorana onites (L.) Benth; (see Marjoram, pot) (Origanum onites (L.)** Sp; Seas; FlaPrickly Ash bark Xanthoxylum americanum Mill. Oil; Ext; OlrQuassia Picrasma excelsa (Sw.) Planch, Fla

Quassia amara L.

Mo2

Sc2

Mo2 Sc2

Mo2Sc2

Mo2Sc2

Sc2

Sc2

Mo2Sc2

Mo2 Sc2

Ed

Sc2

Mo2 Sc2 Ed

Mo2 Sc2



Quebracho bark Aspidosperma quebracho Fla-blanco Schlecht,(Quebrachia lorentzii (Griseb).

Quillaia (Soapbark) Quillaja saponaria Mol FlaQuince seed Cydonia oblonga Miller. Ext used with Sp, Seas, FlaRed saunders Pterocarpus santalinus L. Fla*Rhatany root Krameria triandra Ruiz

et Pav, K. argentea Mart. FlaRhubarb root Rheum rhaponticum L. Fla*

R. officinale Baill. R. spp. FlaRose buds, flwrs., Rosa spp. Oil; Ext; Olrfruit (hips and leaves)Rose Geranium Pelargonium graveolens L’Her. Oil; Ext; OlrRoselle Hibiscus sabdariffa Fla*Rosemary Rosmarinus officinalis L. Sp; Seas; Fla; Oil; Ext; OlrRosin Pinus spp. Fla*Rue Ruta graveolens L., Fla not to

R. montana L.,R. bracteosa L. exceed 2 ppm.R. chalepensis L.

Rue oil Ditto Fla not to exceed 10 ppmSaffron Crocus sativus L. Sp; Seas; Fla; Oil; Ext; OlrSage Salvia officinalis L. Sp; Seas; Fla; Oil; Ext; OlrSage, Greek Salvia triloba L. Sp; Seas; Fla: Oil; Ext; OlrSt.John’s Bread Ceratonia siliqua L. Oil; Olr; Ext (carob)St.John’s Wort leaves Hypericum perforatum L. Fla* - Hypericin-freeSandalwood, white, Santalum album L. Fla (yellow, East Indian)Sandarac Tetraclinis articulata Fla*

(Vahl.), MastSarsaparilla Smilax aristolochiaefolia Fla*

Mill,S. regelii Killip e tMorton, S. febrifugaKunth, or S. spp.

Sassafras leaves Sassafras albidum (Nutt.) Nees Fla, Safrole-freeSavory, Summer, Winter Satureja spp. Sp; Seas; Fla; Oil; Ext; OlrSchinus molle Schinus molle L. Oil; Ext; OlrSenna, Alexandrian Cassia acutifolia Delile FlaSerpentaria (Virginia Aristolochia serpentaria L. Fla* Snakeroot)Sesame Sesamum indicum L. Sp; Seas; FlaSimaruba bark Simaruba amara Aubl Fla*Sloe Berries Prunus spinosa L. Oil; Ext; Olr (Blackthorn Berries)Snakeroot, Canadian Asarum canadense L. Fla (Wild Ginger)Snakeroot, Virginia Aristolochia serpentaria L. Fla* (Serpentaria )Spearmint Mentha spicata L. Sp; Seas; Fla; Oil; Ext; OlrSpruce needles, twigs Picea glauca (Moench) Voss, Fla

P. mariana (Mill.) BSP.Star Anise Illicium verum Hook. f. Sp; Fla (see Anise, Star)Styrax (Storax) Liquidambar orientalis Mill. Fla

or L. styraciflua L.Tagetes (marigold) Tagetes patula L., Fla - as oil

T. erecta L.,T. minuta L. only(T. glandulifera Schrank)

Tamarind Tamarindus indica L. Oil; Ext; OlrTangerine Citrus reticulata Blanco. Oil; Ext; Olr (mandarin)Tansy Tanacetum vulgare L. Fla*, TFTarragon Artemisia dracunculus L. Sp; Seas; Fla;

Oil; Ext; OlrTea Thea sinensis L.;

(Camellia sinensis L. Ktze.**) Oil; Ext; Olr

Mo2 Sc2

EdSc2

Sc2

Sc2

Sc2 EdSc2

Sc2

Mo2Sc2

Mo2

Mo2

Ed

Sc2

Sc2

Mo2Sc2


Appendices

Thistle, Blessed Cnicus benedictus L. Fla* (Holy Thistle)Thyme Thymus vulgaris L. Sp; Seas; Fla; Oil; Ext; OlrThyme, Wild or Thymus serpyllum L. Sp; Seas; Fla; Creeping Oil; Ext; OlrThymus capitatus Thymus capitatus Hoffmg. Fla (Spanish “origanum”) et LinkTolu Myroxylon balsamum (L.) Harms FlaTriticum Agropyron repens (L.) Beauv. Oil; Ext; Olr (Dog grass)Tuberose Polianthes tuberosa L. Oil; Ext; OlrTumeric; Turmeric Curcuma longa L.; Sp; Seas; Fla;

(Curcuma domestica Val.**) Oil; Ext; OlrTurpentine Pinus palustris Mill., Fla* (Pine oil) P. spp.Valerian rhizome, Valeriana officinalis L. FlaVanilla Vanilla planifolia Andr., Sp; Seas; Fla;

V. tahitensis J.W.Moore Oil; Ext; Olr Veronica Veronica officinalis L. Fla*Vervain, European Verbena officinalis L. Fla*Vetiver Vetiveria zizanioides Stapf. FlaViolet flowers, leaves Viola odorata L. Oil; Ext; OlrViolet, Swiss Viola calcarata L. FlaWalnut husks (hulls), Juglans nigra L., or Fla leaves and green nuts J. regia L.Wild Cherry Bark Prunus serotina Ehrh. Oil; Ext; OlrWoodruff, sweet Asperula odorata L. Fla*

(Galium odoratum (L.) Scop.)Wormwood (Artemisia) Artemisia spp. Fla; TFYarrow Achillea millefolium L. Fla*, TFYerba Santa Eriodictyon californicum Fla

(Hook. et Arn.) Torr.Ylang-Ylang Cananga odorata Hook.f. Oil; Ext; Olr

et Thoms.Yucca, Joshua-Tree Yucca brevifolia Engelm. FlaYucca, Mohave Yucca schidigera Roezl Fla

et Ortgies(Y. mohavensis Sarg.)Zedoary bark Curcuma zedoaria Rosc. Sp; Seas; Fla; Oil; Ext; Olr

Mo2Sc2

Mo2 Sc2 Ed

Ed

Mo2 Sc2 Ed

Mo2 Sc2 Ed

Sc2

Ed

5 8

C e

1 4 0 . 1

5 9

P r

1 4 0 . 9

6 0

N d

1 4 4 . 2

6 1

P m

( 1 4 5 )

6 2

S m

1 5 0 . 4

6 3

E u

1 5 2 . 0

6 4

G d

1 5 7 . 3

6 5

T b

1 5 8 . 9

6 6

D y

1 6 2 . 5

6 7

H o

1 6 4 . 9

6 8

E r

1 6 7 . 3

6 9

T m

1 6 8 . 9

7 0

Y b

1 7 3 . 0

7 1

L u

1 7 5 . 0

9 0

T h

2 3 2 . 0

9 1

P a

2 3 1 . 0

9 2

U

2 3 8 . 0

9 3

N p

2 3 7 . 0

9 4

P u

(244)

9 5

A m

(243)

9 6

C m

(247)

9 7

B k

(247)

9 8

C f

( 2 5 1 )

9 9

E s

(254 )

1 0 0

F m

(257)

1 0 1

M d

(258)

1 0 2

N o

(255)

1 0 3

L w

(260)

Periodic Chart of the Elements

1

H

1 . 0 0 8

2

H e

4 . 0 0 3

3

L i

6 . 9 4 1

4

B e

9 . 0 1 2

5

B

1 0 . 8 1

6

C

1 2 . 0 1

7

N

1 4 . 0 1

8

O

1 6 . 0 0

9

F

1 9 . 0 0

1 0

N e

2 0 . 1 8

1 1

N a

2 2 . 9 9

1 2

M g

2 4 . 3 1

1 3

Al

2 6 . 9 8

1 4

S i

2 8 . 0 9

1 5

P

3 0 . 9 7

1 6

S

3 2 . 0 6

1 7

C l

3 5 . 4 5

1 8

Ar

3 9 . 9 5

1 9

K

3 9 . 1 0

2 0

C a

4 0 . 0 8

2 1

S c

4 4 . 9 6

2 2

Ti

4 7 . 9 0

2 3

V

5 0 . 9 4

2 4

C r

5 2 . 0 0

2 5

M n

5 4 . 9 4

2 6

F e

5 5 . 8 5

2 7

C o

5 8 . 9 3

2 8

N i

5 8 . 7 0

2 9

C u

6 3 . 5 5

3 0

Z n

6 5 . 3 8

3 1

G a

6 9 . 7 2

3 2

G e

7 2 . 5 9

3 3

A s

7 4 . 9 2

3 4

S e

7 8 . 9 6

3 5

B r

7 9 . 9 0

3 6

Kr

8 3 . 8 0

3 7

R b

8 5 . 4 7

3 8

S r

8 7 . 6 2

3 9

Y

8 8 . 9 1

4 0

Z r

9 1 . 2 2

4 1

N b

9 2 . 9 1

4 2

M o

9 5 . 9 4

4 3

T c

9 8

4 4

R u

1 0 1 . 1

4 5

R h

1 0 2 . 9

4 6

P d

1 0 6 . 4

4 7

A g

1 0 7 . 9

4 8

C d

1 1 2 . 4

4 9

I n

1 1 4 . 8

5 0

S n

1 1 8 . 7

5 1

S b

1 2 1 . 8

5 2

T e

1 2 7 . 6

5 3

I

1 2 6 . 9

5 4

X e

1 3 1 . 3

5 5

C s

1 3 2 . 9

5 6

B a

1 3 7 . 3

5 7

L a

1 3 8 . 9

7 2

H f

1 7 8 . 5

7 3

T a

1 8 0 . 9

7 4

W

1 8 3 . 9

7 5

R e

1 8 6 . 2

7 6

O s

1 9 0 . 2

7 7

Ir

1 9 2 . 2

7 8

P t

1 9 5 . 1

7 9

A u

1 9 7 . 0

8 0

H g

2 0 0 . 6

8 1

Tl

2 0 4 . 4

8 2

P b

2 0 7 . 2

8 3

B i

2 0 9 . 0

8 4

P o

(209)

8 5

At

( 2 1 0 )

8 6

R n

(222)

8 7

F r

(223 )

8 8

R a

2 2 6 . 0

8 9

A c

2 2 7

1 0 4

?

( 2 6 1 )

1 0 5

?

(262 )

1 0 6

?

(263 )

Per

iod

s

1

2

3

4

5

6

7

LanthanideSeries

ActinideSeries

1A

2A

3B 4B 5B 6B 7B 8B 1B 2B

3A 5A4A 6A 7A

0

NobleGases

Atomic Number

Atomic Mass

1

H

1 . 0 0 8


Chemical Index

Indices

Chemical IndexGeneral Index



Chemical Index

(+)-boschniakine 761-Hydroxyanthraquinone 1141-menthyl-2 (3-pyridyl) pyrrolidine 2931-Methoxyanthraquinone 1141-terpinen-5-ol 2322-Acetoxymethylanthraquinone 1142-Bornanone 2362-camphenone 2352-Hydroxy-3-methylquinone 1142-Hydroxymethylanthraquinone 1142-Methylanthraquinone 1143-0-methyl-D-galactose 744-Allyl-2-methoxyphenol 2414-O-methyl-D-glucuronic acid 745-dehydroshikimic acid 166abietic acid 256acetate 104, 131, 202, 235acetone 218, 2552-Acetoxymethylanthraquinone 114acetylcholine 137, 149, 279acetylcholine antagonist 298acetyltannic acid 164achillin 251aconitine 291, 305, 312acronycine 299adenine 137, 171adenosine 137adrenal corticosteroids 200adrenalin 188aescine 148aglycones 111alantolactone 249alban 257albaspidine 173, 262albumin 131alcohol 225, 255alcohol triterpene 248aldehyde 55, 225aldehyde alcohols 69aldehyde terpenoids 232aldehydes 249aldobiuronic acid 76aleuritic acid 256aliphatic substances 290alkalies 216, 256alkaloidal amines 306alkaloids 164, 224, 339, 342allantoin 1414-Allyl-2-methoxyphenol 241allyl isothiocyanate 102, 131, 245aloe-emodin 109, 111, 147, 149aloe-emodin anthrone C-10 glucoside 107aloeresinotannol 257aloin 105

alpha-citral 248alpha-lapachone 114alpha-linolenic acid 188alpha-peltanin 258alpha-pinene 226, 232, 243, 249alpha-sabinene 226alpha-terpinene 225alpha-terpineol 229amines 61, 291amino acids 84amino-phenol 149ammoresinotannol 257amygdalin 127, 129, 137, 147amygdaline 147anabolic steroids 123anethole 239, 241, 242, 248, 249anisic acid 242anisic aldehyde 242ankalamine 308ankalanine 308ankalidine 308anthocyanidins 137anthocyanin 134anthracene related aglycones 103anthranol 103anthraquinone glycosides 102, 111anthraquinone-2-aldehyde 113anthraquinones 107, 113anthrone 103, 107apigenin 312apiine 147apiol 239apocannoside 281apoproteins 198arabane 172arabinose 125l-arabinose 74, 76arachidonic acid 186, 189arbutin 31, 101, 141, 147, 150, 168, 371arecaidine 294arecaidine methyl ester 294arecoline 291, 293, 294arecoline hydrobromide 294arginine 294arnidiol 248aromatic aldehydes 233As 125asaresinotannol 267ascaridole 244ascorbic acid 263, 311asiaticosides 116asparagine 93, 121, 147asperuloside 147


Chemical Index

aspidinol 173, 262asterosaponins 115astragalin 168atraol 147atropine 290, 291, 296-298, 305, 311aucubin 76aucuboside 93avicuroside 148azulene 251B-12 84balsams 339baptisin 141barbaloin 105, 107, 147belladonnine 291benzaldehyde 127, 129, 233benzene 163, 218, 238benzoate 268benzoic acid 233, 256, 268benzoin 256benzoresinol 257benzoylsalicin 139benzyl benzoate 268benzyl cinnamate 268berbamine 302, 310berberastine 301berberine 289, 300-302, 310berberine sulfate 302bergapten 246, 248, 249beta 1,3 glucan 82beta-carotene 84, 124, 263, 281beta-citral 248beta-lapachone 114beta-peltanin 258beta-phellandrene 264beta-pinene 226beta-sitosterol 76, 277betaine 250bichloride of mercury 241bioflavans 137bioflavonoids 132biotin 84, 125bisabolene 264bisabolol 2272-Bornanone 236borneol 231, 236, 245, 248-250, 264bornerol 229bornyl 250bornyl acetate 245, 251(+)-boschniakine 76botogenin 123brominated phenalic compound 75brucine 290, 305bryonicine 311bryonine 311bryresin 311butyl-phthalidine 249butyric acid 179

C-glycosides 105cadiene 237cadinene 226, 228, 232, 249caffeic acid 137, 163, 279caffeine 171, 172, 290, 309caffeol 310caffeotannic acid 172calcium 84, 263calcium oxalate 111, 140, 168, 237calcium salts 128calenduline 249callitannins 165cAMP 264campesterol 76camphene 232, 249-251, 2642-camphenone 235d-camphol 244camphor 248-251d-camphor 243canadine 301cannabichromene 261cannabidiol 261cannabigerol 261cannabigerolic acid 261cannabinol 261caoutchouc 93capaloin 107caprylic acid 177capsaicin 206, 262, 263, 311capsanthin 263, 281capsicidin 263carbon dioxide/hypercritical 218carbon disulphide 255carboxyl 163carboxyl group 235carboxylic acid 58, 59, 256cardiac glycosides 224, 278, 281, 317cardiotonic amines 137carene 228, 250carnosic acid 250carnosol 250carotene 249, 263, 311beta-carotene 84, 124, 263, 281carotenoids 94, 143, 250, 281carvacrol 238, 250carvone 235, 237d-carvone 237l-carvone 237caryophyllene 248cascarosides 105catechin 147, 307, 311catechol 164catechol amines 294cellulose 339cephaeline 300chamazulene 227, 248chatarine 251



chelidonic acid 295Chlorella Growth Factor 84chloroform 255chlorogenic acid 165, 279, 310chlorophyll 283chlorophyll A 84, 283chlorophyll B 84, 283cholesterol 187, 197, 199, 276, 278cholesterol esters 197cholesytokinin 81choline 125, 137, 149, 168, 171, 250, 279choralhydrate 255chromium 203, 207chromium chloride 207chromone 240chrysaloin 105chrysin 139, 265chrysophanic acid 106, 107chrysophanol 109, 111, 149chylomicrons 197cinchona alkaloids 291cinchonidine 291, 299cinchonine 291, 299cineole 143, 228, 231, 250, 264cinnamein 268cinnamic acid 139, 233, 256cinnamic aldehyde 233cinnamyl cinnamate 268cinnamylcocaine 298cinole 251cis-linoleic acid 188citral 232, 233, 249, 264alpha-citral 248beta-citral 248citric acid 125, 161, 293citronella 248citronellol 229, 232, 233, 249d-citronellol 234Co 125cobalt 84cocaine 291, 296, 298codamine 304codeine 290, 291, 300, 304, 312colchiceine 307colchicine 306, 307colloidal suspensions 256commiphoric acid 256, 267coniferyl cinnamate 268coniine 289, 291, 293conium 293consolidine 311convallamarin 281convallarin 281copaivic acid 256copper 84, 206copper acetate 259coroandrol 248

cortisone 115, 124cortisone precursors 123coumaric acid 163, 279coumarin 88, 148, 251crataegolic acid 137, 148crocetin 143crocin 250crocin-1,2, 3, 4 143crozetine 149cryptopine 304Cu 125cubebic acid 228curare 300curcumine 251cyclic tetrapyrrols 283cyclooxygenase products 264cyclopentadiene 9cymarin 281p-cymene 244cynocannoside 281cynoglossine 311cytochrome respiratory pigments 284d-alpha terpineol 231d-alpha-pinene 242d-camphol 244d-camphor 243d-carvone 237d-citronellal 234d-fenchone 242, 249D-galactose 74D-galacturonic acid 74D-glucose 139D-glucuronic acid 74d-isothujone 237d-limonene 237, 246D-mannose 74d-pinene 250d-pseudoephedrine 307d-trans-tetrahydrocannabinol 261d-tubocurarine 291D-xylose 74, 76dammarane-type triterpenoids 119dammaresene 257deacethymatricarine 251deaspidin 262dehydro-alpha-lapachone 1145-dehydroshikimic acid 166delta-6-desaturease 187deoxybarbaloin 105deoxylapachol 114desmethoxyyangonin 260desoxynupharidine 312dextrin 309dextrose 70, 129di-sabinene 228dietary fiber 84digitalein 279


Chemical Index

digitalin 279digitin 279digitonin 205, 279digitoxin 8, 278, 279dihomogamma-linoleic acid 189dihydrocapsaicin 263dihydrocuminyl alcohol 246dihydrokavain 260dihydromethysticin 260dimeric glycosides 111diosgenin 123diosinine 148diosmin 132, 149, 237diosphenol 235, 237dipentene 242, 248disaccharides 70disulfide 64diterpenes 224, 225, 255diterpenoids 275dracoresene 257ecgonine 298echinacin 85eicosapentaenoic acid 186, 189elemicin 242ellagic acid 164, 169ellagic tannin 141ellagitannins 165, 169emetine 291, 300emodin 102, 104, 105, 109emulsin 139enzymes 84ephedrine 290, 306, 307, 311, 312l-ephedrine 307epinephrine 311equisetin 148ergonovine 291, 305ergosterol 88, 276ergot alkaloids 305ergotamine 291, 305ergots 339ericinol 141ericolin 141esculoside 148essential oils 224ester volatile oils 245esters 225, 237, 249, 255, 339estradiol 120estrogen precursors 120estrone 120ether 218, 255ethylene oxide 290, 342eucalyptol 244eucalyptus oil 225eugenin 240eugenol 238, 239, 243faradiol 248farnesene 248

fats 177fatty acids 147, 177d-fenchone 242, 249fennel oil 225ferrulic acid 279ferulic acid 163fibrinogen degradation products 205filicic acid 262filicin 173filicinic acid 173filmarone 262fixed oils 177flavoglycosides 134flavones 147, 306flavonic derivatives 147flavonoids 94, 121, 132, 134, 148, 168, 248,250, 312Flavonol Glycosides 132fluavil 257fluorides 147folic acid 84free crocetin 143fructosan 70fructose 70, 143fumaric acid 52, 125fumarine 311furanocoumarin 248furfurol 310galactane 172galactosans 94galactose 70, 93d-galactose 74d-galacturonic acid 74galanthamines 312galbaresinotannol 257galegine 311gallic acid 128, 139, 162, 164, 168, 169, 265gallic tannin 141gallotannic acid 170, 240galuteoline 311gamma-linoleic acid 188gamma-terpinene 226gandelan A,B 88gaultherin 102, 149gelatin 164genisteine 306gensenin 125gentialutine 143gentianine 143gentianose 143gentiopicrin 143geranial 232geraniol 229, 234, 245, 248, 249geranyl pyrophosphate 226germanium 88gingerols 264ginkgo heterosides 134



ginsenosides 125, 148beta 1,3 glucan 82glucocorticoids 188gluconapin 130glucoquinine 311glucoresins 256glucosans 70glucoscillaren A 279glucoscilliphaeoside 279glucose 70, 188d-glucose 139glucuronic acid 120, 121d-glucuronic acid 74glutathione 136glutathione peroxidase 206glyceraldehyde 50glycerol 177glyceryl esters 216glycogen 70glycoresins 256, 257glycoside saponins 255glycosides 312, 339O-glycosides 105glycyrhhizine 149glycyrrhetic acid 120glycyrrhizic acid 120, 121, 149glycyrrhizin 120, 121GSH 136guaiac resins 257guaiaconic acid 256guaiacresinol 257guanidine 291guanine 137, 171, 291, 299guvacine 294guvacoline 294hamalin 168hamamelin 168hamamelitannins 168hamamelose 168hederacoside 148hederagenine 148heline 249hematin 284heme 284hemiacetal 58hemoglobin 283heriarin 250herniarin 249heroin 304hesperidin 132, 141, 148, 237heteroglycan 70hexosans 70hexose 70hexose sugar 168histamines 186holoside 94holothurins 115

homatropine 290homo-capsaicin 263homocysteine 206homodihydrocapsaicin 263homoglycan 70hormone 289humulene 139, 228, 250, 265hydrastine 291, 300, 301, 310hydrobromide 293hydrocarbon 225hydrocyanic acid 128, 129hydroguanine 291hydrolase 339hydroquinone 141, 371hydroquinone beta-glycoside 322-Hydroxy-3-methylquinone 1141-Hydroxyanthraquinone 114hydroxycoumarin 249, 2502-Hydroxymethylanthraquinone 114hydroxyl groups 56, 229hyoscine 291, 298hyoscyamine 291, 296, 298, 311hyperoside 148, 149hypoxanthine 171hyrodonic acid 86imidazole alkaloids 305imidazole ring 291indicainine 76indole alkaloids 305indole ring 291inositol 84insulin 193interferon 282inulin 85, 93, 248, 249iodine 75ipecacuanhic acid 165iridin 141iron 84, 128, 143, 257, 263iron porphyrin 284irone 235isobutylamine 137isobutylpropanyl disulfide 267isocitric acid 161isodecenoic acid 263isoleucine 51l-isoleucine 51isomerase 339isomeric hydrocarbons 224isopentanes 224, 275isophorone 143isopinocamphone 249isoprene 224isoquercetin 141, 142isoquercitrin 148isoquinoline 291, 300isorosemaricine 250isosarsapogenin 122


Chemical Index

isothiocyanate 131d-isothujone 237isovalerate 251jatrorrhizine 310K-strophanthin 281kaempferol 147, 148, 168kavain 260ketone 57, 225ketone alcohols 69ketone terpenoids 235ketone volatile oils 235l-arabinose 74, 76l-carvone 237l-ephedrine 307l-isoleucine 51l-limonene 237, 244l-linalool 246l-phellandrene 237l-pinene 237l-rhamnose 74l-terpinen-4-ol 249l-thujone 237lactone glycosides 102lactones 134, 249, 260lactose 70lactose glycosides 140laetrile 127, 128lanalol 229lanostan 88lanostane-type triterpenoids 119lanosterol 119, 276lapachol 113, 324alpha-lapachone 114beta-lapachone 114laudanine 304lecithin 208lentinan 90leonurine 312leonurinine 312leucoathocyanidins 148leukotrienes 186, 189ligins 262lignans 258lignin 77, 121lignous glycosides 258limonene 224-226, 231, 248, 250d-limonene 237, 246l-limonene 237, 244linalool 229, 248-250l-linalool 246linalyl acetate 245, 246, 249lineol 248linoleic acid 185, 191, 202alpha-linolenic acid 188lipophilic substances 339lipoproteins 187, 197, 206lobelanidine 295

lobelanine 295lobeline 291, 293, 295, 312LSD 305, 308lupinane alkaloids 306lupulin 228lupulinic acid 228lupulon 228lutein 281luteolin 148, 312lycopene 249lycoremine 312lycorine 312madelonitrile 127magnesium 84maleic acid 52, 125malic acid 106, 125, 139, 161, 172, 265, 293maltose 70manganese 84mannite 139, 265mannitol 233d-mannose 74menaquinone 113menthofuran 250menthol 229, 250menthone 235, 2501-menthyl-2 (3-pyridyl) pyrrolidine 293menthyl acetate 229, 250menthyl isovaleranal menthane 229mescaline 290, 291, 308metallic salts 256methione 206methionine 3071-Methoxyanthraquinone 114O-methoxyphenylethylamine 137methyl arbutin 147methyl chavicol 242, 2503-0-methyl-D-galactose 744-O-methyl-D-glucuronic acid 74methyl salicylate 102, 149, 245, 246methyl-chavicol 248methyl-glucoside 1012-Methylanthraquinone 114methylarbutin 141methylcellulose 75methylisopelletrierine 296methysticine 260mevalonate 235millefin 251milossine 312Mn 125monocarboxylic acids 60monocyclic terpene 224monocyclic terpenes 225monosaccharides 70monoterpene alkaloids 76monoterpenes 224, 225, 226, 232morphine 290, 291, 300, 304, 312



mucilage 76, 148, 171, 237, 279myosin 130, 131myricyl alcohol 111myristicin 239, 242N-methyl guvacine 294NAD+ 54NADH 54napelline 312naphthalene 143naphthoquinone 113narceine 304narcotine 304, 312naringen 132neconidine 304nepetalactone 248neral 232nerol 229, 248neutral saponins 116niacin 84, 203, 206, 263nicotine 148, 289, 291, 293nicotinic acid 125nitriles 127nitrogenous mucilage 231nordihydrocapsaicin 263noscapine 304nucleic acids 84nupharine 312O-glycosides 105O-methoxyphenylethylamine 137ocimene 250oleanolic acid 148, 240olein 309oleo-gum-resin 266oleonolic acid 137oleoresins 255, 257, 262, 264olibanoresene 257oligosaccharides 70omega 3 essential fatty acids 177omega 3, alpha-linolenic acid 186omega 6 essential fatty acids 177opium alkaloids 291, 300organic cyanides 127ornithine 293, 296oxalic acid 162, 173oxidase 339oxide 225oxide volatile oils 243oxyacanthine 302, 310oxyacids 256oxycopaivic acid 256oxysafranal 143p-cymene 244palmitin 309, 310panacen 125panaguillin 125panax acid 125panaxic acid 125

panaxin 125panaxosides 125pantothenic acid 84, 125papaverine 304paraaspidin 262parillin 122parminobenzoic acid 84parthenolides 196pectin 137, 172pelletierine 291, 293, 296alpha-peltanin 258beta-peltanin 258pentosans 94pentose 70, 93peroxidase 339peruresinotannol 257peruresinotannol cinnamic acid 268peruviol benzoate 268petroleum 218phellandrene 225, 237, 243, 248, 250beta-phellandrene 264l-phellandrene 237phenalic compound 75phenanthrene 291, 300phenethylamines 291phenol 225, 310phenol acid 163phenol compounds 263phenol glycoside 141phenol volatile oils 238phenolic acid 141, 250phenolic compounds 267phenolic ester 225phenols 256, 339phenylalanine 291, 294, 307phenylethylamine 137phenylpropane volatile oils 239phenylpropanoid precursors 233pheromones 220phlobatannins 165phlorapine 173phloridzin 141phloroglucinol derivatives 262phosphate group 207phosphatide 177, 207phosphatidyl choline 208phospholipase A2 264phospholipid 177, 197, 207phosphorus 84, 263physostigmine 290physostignine 305phytol 250phytosterbain mucilage 111phytosterols 93, 122picrocrocin 143picrocrocrine 250picropodophyllin 259


Chemical Index

picrosalvin 250pigments 224pilocarpine 290, 291, 305pimaric acid 256pimarinic acid 256pinene 9, 116, 143, 225, 226, 248-251alpha-pinene 226, 232, 243, 249d-alpha-pinene 242beta-pinene 226d-pinene 250l-pinene 237pinocamphone 249piperidine 291, 293piperine 293piperitone 235plant alkalis 289planteose 76ploy-B-keto-methylene acid 104podophyllotoxin 258pollinastanol 122polyhydric phenol 164polysaccharides 70, 339populin 139, 147, 265porphyrins 283potassium 84, 128, 143, 147, 263potassium hydroxide 324potassium myronate 131potassium oxalate 173potassium salts 231pro-vitamin A 281proanthocyandins 134proanthocyanidins 137procyanidins 137progesterone 123pronase 128properdin 86proscillaridin A 279prostaglandin 184, 196, 206prostaglandin E2 205protocatechuic acid 164, 267protopine 304protoveratrine 291, 305prunasin 128pseudoephedrine 311d-pseudoephedrine 307pseudotannins 171psilocybin 308psychotrine 300pulegone 235, 250purine 291purine base 290, 309purine derivatives 137pyridine 291, 293, 295, 310pyridines/reduced 294pyridoxine 84, 201, 206pyrocatechin 267pyrogallol 164

pyrogallol tannins 165, 169pyrones 260pyrrolidine 291quercetin 137, 141, 142, 168, 172quercetin-3-galactoside 137quercetol 312quercitannic acid 170quercitin 132, 143, 148quercitol 148quinidine 299quinine 290, 299quinoline 291quinoline alkaloids 299quinolinic acid 293quinones 103raffinose 70resenes 255, 257, 267reserpine 290, 291, 305resin acids 255, 256resin alcohols 255, 257resinates 256resinols 257resinoltannols 107resinotannols 255, 257resins 275, 281, 339rhamnose 279l-rhamnose 74rhaponticine 149rhein 111, 149rhein anthrones 109rhein dianthrone 111riboflavin 84, 263rosemaricine 250rosmarinic acid 163rutin 132, 148, 251, 312rutoside 147S 125sabinene 225, 251alpha-sabinene 226sabinol 250safranal 143safranol 250safrole 168, 239, 242, 243salicin 139, 150, 265salicin benzoate 139, 265salicortine 150salicyl alcohol 139salicylic acid 111, 139, 251salicylic aldehydes 149saligenin 139salvene 250salviatannin 250salvin 250sandaracolic acid 256sandarcinolic acid 256sanguinarine 289santalol 227, 229



sapogenin 116, 125saponin glycosides 125saponins 147, 148, 168, 205, 224, 249, 251,255, 275, 307, 311saponoside 149sarothamnine 306sarsaparilloside 122sarsapogenin 122, 149sarsasaponin 122scillaren A 279scillarenin 279scillaridin A 279scilligaucosidin 280scilliglaucoside 279scilliphaecoside 279scoparin 306scopolamine 296, 298, 311selenium 203, 206selinene 226semadine 312senecionine 312sennidin 111sennosides 111, 149serum cholesterol 205sesquiterpene hydrocarbons 264sesquiterpene lactones 196sesquiterpenes 224, 225, 227, 243, 255,264shogaol 264siaresinotannol 257silica 148silybin 135silychristine 135silydianin 135silymarin 135, 149sinalbin 130singlet oxygen free radicals 282sinigrin 102, 130, 131sitosterol 122, 276, 277beta-sitosterol 76, 277smilagen 122smilagenin 122smilasaponin 122socaloin 107sodium hydroxide 324sparteine 306spiraeoside 149spireine 149steroidal alkaloids 305steroidal compounds 224, 255steroidal sapogenins 115steroids 276sterols 224, 276stigmasterol 76, 122, 276storesinol 257strychnine 290, 291, 305styracin 268

substance P 206, 264sucrose 70sulphur 84summaresinotannol 257tabebulin 113tannates 164, 293tannic acid 106, 109, 168, 244tannins 121, 141, 142, 147, 148, 163, 169,171, 172, 249, 281, 296, 307, 310-312, 339tanthopine 304tartaric acids 125, 162, 172tartrates 172taxicatin 312taxine 312tazettine 312tectochrysin 139, 265tenthane 237terpene alcohols 228terpenes 134, 148, 224, 233, 237, 248, 249,250, 255, 339terpenoids 224, 255, 2751-terpinen-5-ol 232l-terpinen-4-ol 249terpinenes 249alpha-terpinene 225terpineol 245, 249alpha-terpineol 229d-alpha terpineol 231terpineol-4 229terpinolene 225terpinyl acetate 231testosterone 123tetracyclic triterpenoids 276d-trans-tetrahydrocannabinol 261tetraoxyflavonol 141tetraterpenoids 281tetrose 70thebaine 300, 304theobromines 171, 172, 291, 309theophylline 171, 172thiamine 84, 263thiobinupharidine 312thiols 64thromboxane B2 264thujone 226, 235, 250l-thujone 237thymol 238, 250tocopherol 250tormentol 150trehalose 70triglycerides 182, 197, 205, 207triglycerol 182trigonelline 309triterpene acids 137triterpene glycoside 121triterpene siaresinol 268triterpenes 88, 255


Chemical Index

triterpenic acids 250triterpenoids 275tropane 291, 296truxilline 298tubocurarine 300d-tubocurarine 291turmerone 251turpentine 255tussilagine 93tyramine 137, 149tyrosine 291, 294umbelliferone 249, 267uronic acid 74, 86, 93ursolic acid 137, 141, 142, 148urson 141ursone 141uvaol 141V 125valerianic acid 310valerianine 251vanillin 140, 233, 240, 268vanillyl amide 263vinblastine 305vincristine 305vinyl chloride 9violaquercetin 149viridicatin 299viscol A,B 312viscotoxin 312vitamin A 282Vitamin B1 125, 143Vitamin B2 125, 143vitamin B6 201, 202, 206Vitamin B12 125vitamin B17 127Vitamin C 84, 148, 203Vitamin D 200Vitamin D2 276Vitamin E 147, 282Vitamin K 84Vitamin P 132, 138vitexin 137vitexin-4-rhamnoside 137, 138vitexin-rhamnoside 148xanthine 171xanthones 143xanthophyll 93, 149D-xylose 74, 76yangonin 260zinc 84, 203zingerone 264zingiberene 226, 264zingiberine 264zingiberol 227, 264



General Index

A Manual of Materia Medica and Pharma-cology 324Abdominal cramping

ginger 264Abdominal pain

oak toxicity 171Abortifacient

anise 248saffron 144tansy 250

Absinthe 235, 237Acacia 74, 165, 350Acacia arabic 165Acanthus 375Acerola cherries 134Acetylcholine antagonist

jimson weed 298Achillea millefolium 251Achyrocline satureidoides 92Acne

juniper 232lavender 245

Aconite 290, 305, 377Aconitum napellus 312Acronychia baueri 299Acupuncture meridians 13Adaptogen 83, 118, 125

ginseng 148reishi 88

Adder Fern 93Addison’s disease 120Additives/food 193Adrenal cortex 125Adrenal glands 118, 202

lobelia 296nicotine 294THC 261

Adrenaline 118Aesculus hippocatanum 148Afterbirth pains

cannabis 261Agathis sp. 119Aging 117, 188

gingko 135Aglycone 101Agrimony 376AIDS 82, 113, 282

reishi 88shiitake 90

Akerele, Olayiwola, M.D. 356Alchemy 369, 372Alcohol 56, 188Alcohol glycosides 102Alcohol-damaged liver 137

Alcoholism 192Aldehyde 57Aldehyde glycosides 102, 140Alder 376Aldol condensation 58Alehoof 376Alexander 376Alexandria senna 111Alfalfa 205Algae 83, 283Algal polysaccharides 77Algonquin Indians 191Aliphatic 290Alkaline 60Alkaloid poisoning

tannins 164Alkaloids 289Alkanet 376All-heal 376Allergies 133

chlorella 85ephedra 307feverfew 196reishi 88rhinitis 188

Allium sativa 205Allspice oil 238Ally 28Almonds 147, 376Aloe 102, 107, 147, 257, 268, 376

anthracene-related aglycones 103Aloe barbadensis 107Aloe vera 107Aloes 377Alpha-particle 40Alterative

angelica 248bayberry 169burdock 248cayenne 263goldenseal 301sassafras 243

Althaea officinalis 93Amanita phalloides 136Amaranths 377Amenorrhea

motherwort 312ragwort 312

American Aspidium 262American Herbal Product Association 318American pennyroyal 235Amide formation 60Amines 61Ammoniac 257


General Index

Amoebic dysenteryipecac 301

Anal fissuresgoldenseal 302

Analgesic 115alkaloids 290codeine 290morphine 290opium 304poplar 140poplar buds 265rosemary 250wintergreen 102yarrow 251

Andropogon nardus 234Anemia 119

motherwort 312Anemone 376Anesthetic

alkaloids 290monkshood 312

Anesthetic (local)cocaine 298eugenol 239kava kava 260

Angelica 226, 248, 375Angelica archangelica 248Angina attack inhibition

hawthorn berry 138Angina pectoris 194

motherwort 312reishi 88

Angiotensin converting enzymehawthorn/inhibitor 138reishi 89

Anise 239, 241, 248, 375, 376Annelids 115Anodyne

anise 248belladonna 297hops 228

Anorexiathyme 250

Anthelminticadder fern 93chenopodium 244sage 250tansy 250

Anthelmintic /veterinaryarecoline hydrobromide 294

Anthemis nobilis 248Anthraquinone glycosides 102Anthriscus cerefolium 147Antiallergic 120

flavonoids 133Antiarthritic

black poplar 147

Antiasthmaticbelladonna 297

Antibacterialarnica 248chlorophyll 284coltsfoot 93kava kava 260peppermint 230phenols 238reishi 90thymol 238

Antibacterial agents 341Antibiotic

barberry 310echinacea 85goldenseal 302uva-ursi 142

Antibiotic (moderate)lobelia 296

Anticarcinogeniccayenne 264flavonoids 133mistletoe 312

Anticholinergicbelladonna 297

Antidiabeticgoat’s rue 311

Antidiarrheticcrab apples 172goldenrod 148houndstongue 311knotgrass 148motherwort 312pectin 77rhubarb 149silverweed 150

Antidiureticbelladonna 297

Antidotebelladonna 311

Antifungal 115benzoic acid 268coltsfoot 93kava kava 260thymol 238

Antigalactagoguebelladonna 297

Antihepatotoxicmilk thistle 149

Antiinflammatory 189echinacea 85flavonoids 133gentianine 143lapacho 114



Antimicrobialalmonds 147burdock 248feverfew 196oak 170

Antimitoticpodophyllotoxin 259

Antineoplasticechinacea 86

Antioxidantcarotenoids 282flavonoids 133poplar 140poplar buds 265reishi 89

Antiparasitic 113quinine 290

Antiphlogistichorse chestnut 148marigold 249

Antipruriticcamphor 236peppermint 230

Antipyreticburdock 248kava kava 260poplar 140poplar buds 265

Antiradiation treatment 133Antirheumatic

colchicum 307elder 148meadowsweet 149poplar 140poplar buds 265salicin 139white willow 150wintergreen 246

Antiscorbuticburdock 248

Antisepticalcohol terpenoids 229anise 248barberry 303benzoin 268bergamot 246camphor 236cardamon 231cinnamon 234citral 233cloves 240eucalyptus 244eugenol 239juniper 232, 249lavender 245myrrh 267peppermint 230

Peru Balsam 268phenylproprane volatile oils 239pine oil 226tannins 163thyme 238uva-ursi 142wintergreen 246

Antiseptic/urinarybuchu 237

Antismoking agentlobelia 296

Antispasmodic 117, 120, 124alkaloids 290anise 248belladonna 311bergamot 246catnip 248chamomile 248cinnamon 233coriander 248datura 311elder 148fennel 242ivy 148jimson weed 298lavender 249licorice 149lobelia 296melissa 249nuphar 312peppermint 230, 250sage 250silverweed 150spearmint 237thyme 238valerian 251

Antispasmodic sedativehawthorn 148

Antithromboticginger 205, 264

Antitumour 115, 117digitoxin 279feverfew 196quercitin 134sitosterol 277

Antitussivecodeine 305

Antiviralflavonoids 133oak 170peppermint 230shiitake 90terpinenes 226

Aorta arterywild cherry 129


General Index

Aperientanise 248

Aphrodisiacanise 248betel 295catnip (cats) 248coriander 248gonosan 260guarana 171henbane 311saffron 144vanilla 140

Apium graveolens 248Apocynum cannabinum 281Appell, Louis 221Appetite stimulant

saffron 250tarragon 250

Apples 161, 376Apricots 127, 376Arabic tradition 369ARC 82Archangel 376Archis hyprogaea 183Arctander, Steffen 221Arctium lappa 248Arctostaphylos uva-ursi 141, 147, 168Areca 165, 290, 294Areca catechu 294Armillaria mellea 90Arnica 248, 376Arnica montana 92Arnica montanum 248Aromatherapy 215, 219Aromatherapy: an A-Z 221Aromatic

caraway 237cardamon 231cinnamon 233fennel 242, 249marjoram 249peppermint 250rosemary 250sassafras 243

Aromatic compounds 50Aromatic decongestant

camphor 236Aromatic ring structures 50Arrach 375, 376Arrhythmias

hawthorn 148Artemis vulgaris 250Artemisia absinthium 237Artemisia dracunculus 250Artemisia sage 26Arterial elastin 206Arterial insufficiency 135

Arterial plaquing 187Arteriosclerosis 135, 206Arteriosclerotic heart disease 196Arthritic related disease 191Arthritis 16, 113, 122, 195, 196

chlorella 85goldenrod 148pearl powder 196thyme 238yew 312

Arthropods 115Artichoke 376Asafetida 256, 266, 267Ash tree 375, 376Ashweed 377Asparagus 376Asparagus Fern 147Asparagus officinalis 147Aspen 139Aspidium 255, 262Aspirin 139, 189, 246, 264Aspirin-induced asthma 189Asthma 188, 191

anise 242bronchial/aloe 107coltsfoot 93datura 311digitalis 279ephedra 307feverfew 196jimson weed 298pearl powder 196peppermint 230plantain 93saffron 144squill 280

Asthmatic formulaslobelia 296

Astragalus 82, 83, 91Astringent 106

bayberry 169cinnamon 233gallic acid 162goldenseal 301knotgrass 148malic acid 162myrrh 267nuphar 312oak 170pomegranate 296psyllium 76raspberry 173rosemary 250sage 250silverweed 150tannic acid 162tormentil 168



uva-ursi 142, 168wintergreen 150witch hazel 168yarrow 251

Astrological aromatherapy 221Astrology 370, 373Astronomy 370Atheroma 196Atherosclerosis 119, 196, 205, 206, 278

chlorella 85Atlas of Microscopy of Medicinal Plants,Culinary Herbs and Sp 323Atopic Eczema 191Atopy 188ATP synthesis/enhanced

ginkgo 134Atriplex 375Atropa belladonna 296, 311Atropine antagonist

pilocarpine 305Attention Deficit Disorder 193Auerbach plexus 106

Cascara sagrada 106Australian kinos 165Awang, Dr. D. 317Ayurvedic diagnosis 23Ayurvedic Medical Theory 17B-cells

chlorella 84Bach Flower Remedies 215Bacillus pneumonia

reishi 90Bacterial dysentery

ginger 265Balm 376Balm of Gilead 139, 140, 265Balsam of Peru 257Balsam of Tolu 257Balsams 256, 268Banana 216Baptisia tinctoria 92Barbaloin

griping/aloe 109Barberry 302, 310, 376Barley 93, 377Barosma betulina 237Basil 248, 376Bayberry 165, 169Bean 376Bearberry 31, 141, 147, 165, 168Bechic

elecampane 249Bedsores

oak 170Beech tree 377Beef fat 182Beer 228

Beet (white) 376Beets 377Belladonna 260, 290, 296, 311, 377Benedictus 376Benzene ring 47Benzoic acid 268Benzoin 256, 257, 268Berberidaceae 290Berberine sulfate

goldenseal 302Berberis 300, 302Berberis vulgaris 302, 310Bergamot 226, 375Bergamot oil 245, 246Bergman, Dr. R. 24Beryllium 41Beta vulgaris 71Beta-blockers 188Beta-glucosidase activity 128Betel nut 294Betula lenta 246Betula pendula 149Bichloride of mercury 241Bifoil 377Bilberry 376Bile acids 79Bile flow, mild 105Bile induction

milk thistle 149Bile salts 200Bile stimulant

rosemary 250Biliary

nutmeg 243Bilious colic 124Binder (food)

guar gum 77Binding agents 337, 350Biocatalyst 126Biochemical pathways 10Biogenesis 10Biological intelligence 1, 2Biomphalaria glabrata 142Biosis 364Birch 139, 376

tar 238Bird, Christopher 216Birdsfoot 377Bishops weed 376Bitter almond 127, 129, 233Bitter orange peels 233Bittersweet 375Black mustard 102, 130, 375Black pepper 226, 228, 290Black poplar 147Blackberries 161, 376Blackthorn 147, 377


General Index

Bladderjuniper 232

Bladder infectionsastragalus 91

Bladder inflammationgoldenseal 302

Bladder mucosa 260Bleeding (internal)

horsetail 148Blessed thistle 376Blond Psyllium 74Blood calcium

oxalic acid 163Blood circulation 205

ginger 264Blood lipids 276Blood pressure 193, 277

berberine 303contraindication/gentian 143ephedrine 290hawthorn 148psyllium 76reishi 89reserpine 290warning/licorice 121

Blood pressure reductionchervil 147cleaver 147hawthorn berry 138saffron 144

Blue bottle 377Boils 113

bayberry 169Borage 93, 195, 376Borage oil 185, 189Borago officinalis 93, 195Boron 41Botanical identification 318Bowel toxicity

chlorella 85Bradycardia

saffron 144Brain stem 260Brain stimulant

bergamot 246peppermint 230thyme 238

Bramble 376Bran 80Brankursine 375Brassica juncea 130Brassica nigra 130Breast cancer

kelp 75Breast feeding 191Breast lumps

digitalis 279

Breast milkCascara sagrada 106nicotine 294

Breasts/tender 193Breathing problems 191Breckhman, Dr. 83, 118Brigham tea

ephedrine 307British Pharmaceutical Codex 360Bronchial asthma 107

aloe 107reishi 88, 89

Bronchial catarrhplantain 93

Bronchial disorderstobacco 294

Bronchial irritationsmarshmallow 93

Bronchial spasmsatropine 298

Bronchiol function 264cayenne 264

Bronchitisasafetida 267black poplar 147bryony 311ephedra 307fennel 242peppermint 230pine 250plantain 93poplar bud 266squill 280

Bronchodilatorephedra 311

Broom 306Brucella sp. 113

kelp 75Bruising 133Bryonia sp. 311Bryony 311, 375, 376Buchu 235, 237Buchu camphor 237Buck’s horn plantain 377Buckbean 375Buckthorn 147, 377Bugle weed 376Bulking agents

hydrophilic/psyllium 76Burdock 122, 248, 376, 377Burgundy pitch 256, 257, 262Burkitt and Trowell 78Burnet 375Burns

aloe 147eucalyptus 244tannins 164



C-peptide excretiondiabetic study 80

CA Search 364Cabbages 375CABS neurotransmission 135Cacti 308Cadmium

chlorella 85Calabar beans 276Calamint 375Calcium flux/modulation

ginkgo 134Calculus 370Calendula officinalis 92, 249Calmus 375Calvin 71CAMP 264

cayenne 264Camphor 8, 235, 236Camphor oil 239Canada Balsam 255, 262Cancer 82, 113, 119, 259

beta-carotene 282breast/kelp 75Burkitt research 78chlorella 84reishi 88saffron 144shiitake 90squill 280

Candida sp. 260albicans 113

Cankersbayberry 169oak 170

Cannabis 260, 377sativa 260

Capella bursa-pastoris 149Capillary beds 132Capillary constriction

nicotine 294Capillary endothelium 265Capillary permeability 265

ginger oil 265Capsicum 255, 262, 376Capsicum annum 281, 311Capsicum frutescens 262Capsicum spp. 206Capsulated Herbs 336Capsules 350Caraway 225, 235, 237, 375, 377

d-carvone 237Carbohydrates 64Carbon 43Carbon chains 46Carbonyl group 57Carboxylic acids 59

Carbunclesbayberry 169

Carcinogenicsafrole 243

Cardamom oil 225Cardamon seeds 229, 231, 236Cardiac depressant

broom 306Cardiac muscle depressant 311Cardiac muscle stimulant

ephedra 307Cardioactive glycosides 102Cardiorenal conditions

grapes 172Cardiotonic

cayenne 264digitalis 279dogbane 281hawthorn 148milk vetch 91mistletoe 312rosemary 245squill 279

Cardiovascular problems 188, 204Caries 162Carminative

angelica 248anise 241, 248asafetida 267basil 248benzoin 268betel 294caraway 237cardamon 231catnip 248chamomile 248cinnamon 233cloves 240coriander 248cubeb 228fennel 242, 249ginger 264hyssop 249juniper 232, 249lavender 245, 249marjoram 249melissa 249myrrh 267peppermint 230, 250spearmint 237thyme 238valerian 251vanilla 140

Carnations 376Carnadines 376Carob bean powder 80


General Index

Carotid arterywild cherry 129

Carrot 375Carum carvi 237Cascara sagrada 102, 105, 339

anthracene-related aglycones 103Cassia acutifolia 111Cassia angustifolia 111, 149Castelli, W. 204Castor bean oil 183, 262Catalysts 215Catarrh

bayberry 169goldenseal /chronic 302squill 280

Catechin 165Catechol tannins 167Catharanthus 305Cathartic 103, 107

broom 306coffee 310colchicum 307dogbane 281hyssop 249poplar bud 266

Cathartic (drastic)mandrake 258

Cationic 61Catnip 248, 376Cayenne 206, 311Cedar (red) 376Celandine 375, 376Celery 248, 375

oil 226Celestial physics 370Cell membranes 207Cellulose 69Centaury 376, 377Centella asiatica 116Central nervous system (CNS) stimulant

brucine 290guarana 171strychnine 290

Cephaelis ipecacuanha 300Cerebral stimulant

cocaine 298Cerebral vascular disease 196CFS 82Chamomile 215, 248, 374, 375Chamomilla recutita 92Chaparral 277Charcoal 106Chemical analysis 319Chemical reagency 324Chemotherapeutic

quinine 290Chenopodium 244

Chenopodium ambrosioides 244Cherries 127Cherry Gum 74Cherry tree 376Chervil 147, 376Chestnut 165, 376Chi 13Chickpeas 376Chickweed 147, 375, 377Chicory 375, 376Chinese galls 165Chinese Medical Theory 13Chinese Opium 304Chinese Star Anise Oil 241Chlorella 82, 83, 283Chlorella Growth Factor (CGF) 83Chlorella pyrenoidosa 83Chlorellan 84Chlorophyll 83

chlorella 84Chlorosis 113Cholagogic

adder fern 93elecampane 249

Cholerabayberry 169

Cholereticgentian 143marigold 249mugwort 250

Cholesterogenesis 203Cholesterol 188, 192, 264, 278

cayenne 311chlorella 85reduction/kelp 75reishi 89shiitake 90

Cholinergicpsyllium 76

Chromatography 319, 324Chronic bronchial asthma 120Chronic Fatigue Syndrome 82, 113, 282Chronic hepatitis

reishi 88Cinchona 112, 165, 290, 299Cinchona succirubra 299Cinnamic acid 268Cinnamomum camphora 236Cinnamomum cassia 233Cinnamomum loureirii 233Cinnamomum spp. 233Cinnamomum zeylanicum 233Cinnamon 111, 233, 375

catechol 165Cinquefoil 375, 376Circulation

ginkgo 134



Circulatory stimulantcayenne 263

Cis 52Citronella 232, 234Citrus bergamia 246Citrus fruit 134, 225Citrus limonica 161Citrus oils 226Citrus plants 218Clary 375Cleanser

guar gum 77Cleansing

peppermint 230Cleaver 147, 375Clove oil 238Clover 375Cloves 111, 165, 239, 375CNS depressant

nicotine 293CNS stimulant

coffee 310nicotine 293

Coca 298, 309Cocaine 171

relation to guarana 171Cochlearia armoracia 131Cockle weed 377Cocoa 165, 296Coffea arabica 172Coffee 165, 171, 172, 278, 309Cola 309Colchicum 306, 307Colchicum automnale 307Cold

poplar bud 266Cold grinder 346Cold-pressed oil 177Colds

eucalyptus 244ginger 265turmeric 251

Colds/flushiitake 90

Colewort 375Colic

anise 242asafetida 267belladonna 311cardamon 231ginger 265

Colitis 113Collagen 138, 206Colon

melanin/Cascara sagrada 106Colon cancer

Burkitt research 78

Colon wall 105Colons/toxic

guar gum 77Colophony 256Coltsfoot 93, 277, 375, 376Columbine 376Comfrey 278, 376, 377Commiphora abyssinica 266Commiphora molmol 266Compound Benzoin Tincture 268Compuserve 364Conifer oils 226Conifers 225Conium 290Constipation 113

Burkitt research 78chlorella 85chronic/goldenseal 302morphine 305oak 171oak toxicity 171

Contact dermatitis 117reishi 89

Contact lenses 192Convallaria majalis 281Convulsions

Lily of the Valley 281wintergreen 246

Copaiba 255-257, 262Copaifera sp. 256Copal 257Copper

chlorella 85Coralwort 375Cordyceps 82, 90Coreolus versicolor 90Coriander 225, 229, 248, 376Coriandrum sativum 248Corn 377Corn flower 377Coronary atherosclerosis 199Coronary heart disease 79

reishi 88smoking 294

Corticosteroid/urineginseng 125

Cortisol 118Cortisone-like activity

echinacea 85Corydates 290Corynebacterium diphtheria

echinacea 86Cosmetic 107

aloe 147Cosmetics 183Costmary 376Cotyledon 376


General Index

Couch grass 376Cough

anise oil 241poplar 140

Cough remediescodeine 305

Cough syrupswild cherry 129

Coughsadder fern 93almonds 147cinnamon 234datura 311pine 250

Countercurrent extraction apparatus 348Counterirritant

bryony 311peppermint 230poplar buds 265

Covalent bonds 45Cowbane 377Cowslip 376Crab apples 172Crab’s claw 376Crack cocaine 299Cramping

Cascara sagrada 106Crataegus oxycantha 133, 137, 148CRC Handbook of Medicinal Herbs 278Creosote pine tar 238Crocus sativus 143, 250Crosswort 376Croup

squill 280Crowsfoot 376Crude botanicals 9Crude Herb 334Cubeb 228, 255, 375

oil 226Cuckoopint 376Cucumber 375Cudweed 376Culpepper 373Culpepper’s herbal 221, 375Curcuma longa 251Currants 195Cut and Powdered Herb 334Cyamopsis tetragonolobus 77Cyanophose glycosides 102, 127Cyclic AMP 194

formation 189Cyclical breast symptoms 193Cyclooxygenase 206

ginger 264pathway 189

Cynips tinctoria 170

Cystitis 113uva-ursi 168wintergreen 150

Cystitis (chronic)cannabis 261

Cytisus scoparius 306Cytomegalovirus 84

chlorella 84Cytophylactic

ketones 235Cytotoxic 115Dairy 203Daisies 375, 376Dammar 119, 257Dandelion 376Dardymov, I.V. 118Dark Stage 71Datura 311Datura stramonium 298, 311Davis, Patricia 221Dawning Men 30De Rerum Naturae 370Deadly nightshade 296Death Angel 136Deathcap 136Decocta 335Decoctions 335Decongestant

peppermint 230Decongestant/respiratory

anise 242Delirium tremens

cannabis 261Delphinium 305Demulcent 74

borage 93chickweed 147coltsfoot 93Karaya gum 75linseed oil 183marshmallow 93marshmallow root 232mullein 149olive oil 183

Dendroctonus pseudotsugae 226Dental adhesive

Karaya gum 75Dental analgesic

eugenol 241Dental caries 162Deodorant

benzoin 268chlorophyll 284

Depressantlobelia 296, 312



Depressionbergamot 246ginkgo 135thyme 238

Depressions/menstrualguarana 171

Depurgativechervil 147pansy 149

Dermatitisfumaria 311juniper 232sassafras 243

Derosne 289Detoxification

juniper 232Devil’s claw root 115Devil’s Dung 267Devils bit 376Diabetes 119, 133, 188, 193

Burkitt research 78reishi 88

Diabetic foodsoy bean 94

DIALOG 364Diaphoretic

angelica 248anise 248arnica 248bayberry 169black poplar 147burdock 248catnip 248cayenne 311dogbane 281elder 148eucalyptus 244goat’s rue 311hyssop 249ipecac 300lobelia 296, 312meadowsweet 149melissa 249peppermint 230, 250rosemary 250sassafras 243teas 27yarrow 251

Diarrhea 113bayberry 169caused by Cascara sagrada 106chronic/guarana 171gallic acid 162knotgrass 148nuphar 312nutmeg 243oak 170, 171

oak toxicity 171psyllium 76tormentil 168uva-ursi 168witch hazel 168wood sorrel toxicity 173

Diet aidspsyllium 76

Dietary fiber 77Digestive

barberry 310bergamot 246cardamon 231cinnamon 234marjoram 249mugwort 250tarragon 250turmeric 251wormwood 237

Digestive stimulantcoriander 248

Digestive system/infectionbarley 93

Digitalis 101, 278, 279, 375-377leaf 8

Digitalis purpurea 279Dill 375

d-carvone 237Dioscorea floribunda 123Dioscorea specalifora 123Diploccus pneumonia

astragalus 91Direct steam 217Disinfectant

bearberry 147wintergreen 150

Disintegration agents 337, 350Dissociation 60Distillation 217Dittany 375Diuretic 117

anise 248arnica 248asparagus fern 147bearberry 147benzoin 268black poplar 147blackthorn 147borage 93broom 306buchu 237buckthorn 147burdock 248celery 248chervil /mild 147citric acids 162cubeb 228


General Index

digitalis 279dogbane 281elecampane 249ephedra 307figwort 148fumaria 311goat’s rue 311goldenrod 148grapes 172hops 228horse chestnut 148horsetail 148juniper 232, 249knotgrass 148lavender 249licorice /mild 149Lily of the Valley 281lobelia 296, 312lovage 249meadowsweet 149mistletoe 312pansy 149plantain 93sarsaparilla 149silver birch 149squill 279Star Anise oil 241turmeric 251uva-ursi 142, 168

Diverticular diseaseBurkitt research 78

Dizzinessreishi 88

DNA 65Dock 376Dodder 377Dog rose 376Dog’s grass 376Dogbane 281Dolomite 106, 234Douglas Fir beetle 226Dovesfoot 376Dragon’s blood 257Drastics 104Dropsy

asparagus fern 147Lily of the Valley 281silver birch 149

Drug biosynthesis 10Dry extract 336Dry Eye Syndrome 192Dry skin

rosemary 245Drying 338Dryopteris filix-mas 173, 262Dryopteris marginalis 262Duckweed 375

Duke, J.A. 278, 358Duodenum 228, 258Dwarf pine needle oil 245Dyeing agents 103Dyer’s alkanet 376Dysentery 113

bayberry 169gallic acid 162knotgrass 148

Dysmenorrhoeamotherwort 312ragwort 312shepherd’s purse 149

Dyspepsiacaraway 237thyme 250

Echinacea colikelp 75uva-ursi 142

Earachepeppermint 230

Early senilitycannabis 261

East Indian dill 239Echinacea 82, 85Echinacea cannabinum 92Echinacea angustifolia 92Echinacea purpurea 92Echinodermata 115Eclectic medicine 357Eczema 188, 191

fumaria 311goldenrod 148juniper 232lavender 245

Edema 133, 195, 278digitalis 279licorice 121

Efamol Ltd. 191Effleurage 218Eggs 203Ehrich ascites

aloe 108Eight Principles 17Elastin 206Elder 148, 376, 377Elecampane 249, 375, 376Electro extraction 348Electrons 38Element 38Eleutherococcus senticosus 92, 116Eleuthrococcus sp. 317Elixir 117Ellettaria cardamomum 231Elm tree 377Elvinga applanata 276



Emeticblack mustard 131colchicum 307dogbane 281ipecac 300narcissus 312snow drop 312squill 279

Emmenagogueangelica 248catnip 248chamomile 248juniper 249saffron 250vanilla 140

Emollient 183aloe 147arnica 248borage 93chickweed 147karaya gum 75linseed oil 183marshmallow 93olive oil 183turmeric 251

Emphysemacannabis 261smoking 294

Emulsivealmonds 147

Endives 375, 376Endothelial cells 206Endotoxin binding 122Enol form 59Enteritis

goldenseal 302knotgrass 148

Enuresis 113Eosinophil cells 125Ephedra 306, 311Ephedra sinica 307, 311Epilepsy

belladonna 297digitalis 279Lily of the Valley 281

Epimedium 82Epstein-Barr virus 84

chlorella 84Equisetum arvense 148Ergot 305Eringo 376Erythrocyte hemolysis 264

cayenne 264Erythroxylon coca 298Escherichia coli 342Esophageal cancer

chewing tobacco 294

Essential fatty acids 184Essential oils 215Ester 56Ester bond 62Ester formation 60Estrogen 118Ethereal oils 215Ethers 101Ethylene oxide gassing 290, 342Eucalyptus 165, 216, 229, 232, 235, 244Eucalyptus citriodora 233, 234Eucalyptus globulus 244Eugenia caryophyllus 239Eupatorium perfoliatum 92European Aspidium 262Evaporation 336Evening primrose 191

oil 185, 191Excerpta Medica 364Expectorant 123

angelica 248anise 248anise oil 241arnica 248asafetida 267benzoin 268black poplar 147compound benzoin tincture 268cubeb 228dogbane 281eucalyptus 244goldenrod 148hyssop 249ipecac 300licorice 149lobelia 296, 312marjoram 249mullein 149pansy 149Peru Balsam 268poplar bud 266reishi 89squill 279wild cherry 129

Expert Advisory Committee on DietaryFibre 79Expression 218Extracta fluida 335Extracta sicca 336Extraction 9, 346Eye disorders

henbane 311Eyebright 375Eyewash

goldenseal 302


General Index

Fatigue 119juniper 232reishi 88sassafras 243thyme 238

Featherfern 376Febrifuge

dogbane 281guarana 171monkshood 312white willow 150

Feingold Diet 193Felter and Lloyd, J.L. 324Fennel 107, 111, 239, 242, 249, 375, 376Fenugreek 377Ferula assafoetida 267Ferula foetida 267Ferula rubricaulis 267Fever 113

bayberry 169digitalis 279ginseng overdose 126kava kava 260

Feverfew 189, 195, 196, 249Fibrinolytic activity 205Figs 376Figwort 148, 376Filipendula ulmaria 149Filling agents 350Fireweed 377Fish 188, 203Fish body oil 186, 189Fish poison 115, 124Five Elements 14Flatulence

asafetida 267cardamon 231cinnamon 234ginger 265juniper 232

Flavonoids 102Flavoring

anise 241asafetida 267rosemary 245sassafras 243thyme 238wild cherry 129

Flax 376, 377oil 182, 183seed 74, 195

Fleawort 377Flowering ash 376Flowing agents 337, 350Fluellein 375Fluid extracts 335Flukeges 8

Fluted rollers 346Flux weed 377Foeniculum vulgare 242, 249Four components of cure 31Framingham Heart Study 204Frangula 102, 323Frankincense 216, 256Frawley, D. and V. Lad 23Free radical scavenger

hawthorn berry 138Free radicals 133, 201

ginkgo 134Free-basing 299Fu Zheng therapy 83Fu-ling 117Fulder, Stephen 117, 125Fumaria 311Fumaria officinalis 311Fumitory 376, 377Fungicidal

eugenol 239Galactogenic

basil 248goat’s rue 311

Galanthus nivalis 312Galega officinalis 311Galiums 375Gallbladder

barberry 310Gallbladder stimulant

rosemary 245Gallium aparines 147Galls, oak 169Gallstones 80

belladonna 297Gamboge 256, 266Ganoderma lucidum 119, 276Garcinia hanburyi 266Garden marjoram 229Garlic 205, 376

smell/cardamon 231Gas

cloves 241fennel 242nutmeg 243

Gassing 342Gastric (blood supply)

horse chestnut 148Gastric antispasmodic

basil 248Gastric mucosa 260Gastric secretion

gentian 143Gastric ulcers

belladonna 297



Gastritisgoldenseal 302thyme 250

Gastro-enteritis/pediatriccrab apples 172

Gastrointestinal irritationmarshmallow 93

Gaultheria 245Gaultheria procumbens 246Gbx 134Gelling agent

pectin 77Gentian 143, 375, 376Gentiana lutea 143Geranium 27, 229, 376Germ oils 277Germander 375Germicide

cinnamon 234eugenol 241

Ginger 107, 111, 205, 262, 264, 375oil 226

Ginkgo 134, 328Ginkgo biloba 133, 134Ginseng 82, 115, 118, 125, 148, 376Gladwind 377Glandular hairs 215GlobalHerb 365Glucose tolerance factor 207Glycine soja 94Glycone 101Glycyrrhiza glabra 119, 149Gnosis 8Goat’s Rue 311Goiter

bayberry 169Goldenrod 148, 376Goldenseal 301Gonorrhea 122, 260

cannabis 261cubeb 228witch hazel 168

Gonosan 260Gooseberry 376Gotu Kola 116Gout 122

asparagus fern 147broom 306cannabis 261colchicum 307sassafras 243

Goutwort 377Graham, Sylvester 77Gram positive bacteria

kelp 75Grape vine 375, 376Grapes 172

Great Works 372Green peppers 134Green tea 165Grieve, M. 358Grifola umbellata 90Grinder 346Griping

Cascara sagrada 106fennel 242mandrake 258rhubarb 110

Gritty eyes 192Gromel 376Gromwell 376Ground ivy 375Groundsel 312, 376Growth depressant

oak 170Growth inhibitor

psyllium 76Guaiac 256

resin 257, 262wood 257

Guar Gum 77, 79Guarana 165, 171, 309, 310Gum Arabic 74Gum-resins 256Gums 74

bleeding/chlorophyll 85Gutta percha 257Haemostatic

cinnamon 233horsetail 148witch hazel 168

Hair lossrosemary 245thyme 238

Hair tonicbergamot 246

Hallucinatory poisonMandragora 260

HallucinogenJimson weed 298nutmeg 242

Hamamelis 165Hamamelis virginiana 167Hammer mills 345Hangover prevention

chlorella 85Hansen, Arid 189Harmony drugs 118Hart’s tongue 376Hawkweed 375, 377Hawthorn 148, 376, 377

berry 133, 137Hazelnut 375HDL/LDL ratio 204


General Index

Headacheginseng overdose 126guarana 171peppermint 230Peru Balsam 268

Headache/menstrualguarana 171

Health Protection Branch 317Heart

stimulant/ginger 264Heart attack

feverfew 196Heart depressant

peppermint 230Heart muscle stimulant

hydrastine 302Heart palpitations

anise 242Heart problems 195

chlorella 85warning/licorice 121

Heart toniccayenne 263silver birch 149

Heart’ ease 377Hebrew tradition 369Hedeoma 235Hedera helix 148Hedge-hyssop 376Hedge-mustard 375Hedge-nettle 376Hellebore 305, 377Hematite 26Hemiacetal formation 58Hemicelluloses 69Hemlock 289, 377

pitch 262Hemorrhage

bayberry 169ginseng overdose 126wood sorrel toxicity 173

Hemorrhoids 133black poplar 147Burkitt research 78citric acids 162goldenseal 302oak 170plantain 93witch hazel 168

Hemostatickelp 75knotgrass 148wormwood 238yarrow 251

Hemp 260Henbane 311, 376, 377

Hepaticbarberry 303olive oil 183

Hepatitis 137reishi / chronic 90

Herb Research Foundation 355Herbal teas 333HerbalGram 356Herpes simplex virus 113, 195, 230Hiatal hernia

Burkitt research 78High blood pressure 135

reishi 88High cholesterol

reishi 88High performance liquid chromatography319Hippocrates 77Hippocratic Oath 1Histamine 265

ginger 265quercitin 134

Histamine inhibitionhawthorn berry 138

Histamine liberator 126Histamine release

reishi 89HIV 113HLBV 113Hoelen 90, 117Holly 377Holothuria aggazia 115HomeHerb 365Homeopathic theory 191Homeopathy

yew 312Homocysteine and Pyridoxine DeficiencyTheory 201Honeysuckle 375, 376Hookworm

chenopodium 244Hops 228, 376Hordeum vulgare 93Horehound 375Hormonal response 118Hormones 215Horse Chestnut 148, 376Horsemint oil 238Horseradish 376

root 131Horsetail 148, 377Houndstongue 311, 375House-leek 376HPLC 319, 326Hsu, Hong-Yen 358Human milk 189Humulus 228



Humulus lupulus 228Hunger 220Hyaluronidase enzyme/inhibition

echinacea 85Hydragogue

dogbane 281Hydrastis 290, 300, 301Hydrastis canadensis 301Hydrochloric acid regulator

meadowsweet 149Hydrogenation 183Hydrolysis 62Hydrophilic 339

alginates 75Hygroscopic 336Hyoscyamus 290, 296Hyoscyamus niger 311Hyperactive Children’s Support Group193Hyperactivity 189, 193Hypercritical carbon dioxide 218Hyperglycemia 79Hypertension 119, 193

chlorella 85licorice overdose 121sedum 312

Hypnoticmorphine 305opium 304

Hypocholesterolemia 205Hypotensive 115

mistletoe 312nuphar 312

Hypothalamus 118Hyssop 249, 375, 376Hyssopus officinales 249Hyssopus officinalis 277IBIS 365Identification 338Ileum (animal)

stimulant/psyllium 76Ilex cassine 172Ilex paraguariensis 172Illicium religiosum 241Illicium verum 241Img-E related allergies

reishi 89Immune cell proliferation 282Immune modulation

polysaccharides 81, 117Immune stimulant

berberine 302echinacea 85goldenseal 302kelp 75sesquiterpenes 227shiitake 90

Immune system stimulantthyme 250

Immunity 194, 208Impotency

anise 242cloves 241nuphar 312

Incensebenzoic acid 268Peru Balsam 268

Indian Hemp 281Indian Opium 304Indian Podophyllum 259Indian Tobacco 295Indigestion

cardamon 231juniper 232

Infantile convulsioncannabis 261

Inflammation 117, 189barberry 310barley 93goldenrod 148goldenseal 302

Influenza 17virus 113, 230

Infusa 335Infusions 335Injury Hypothesis 201Insanity

cannabis 261digitalis 279

Insect bitessassafras 243

Insect repellenteucalyptus 244peppermint 230

Insecticide 226chlorella 85citronella 234

Insomniacannabis 261reishi 88, 89

Insulin 70Intellectual clarity

cloves 241Interactive BodyMind Information System365Interferon 84Interferon-like activity

echinacea 85Intestinal amoebae

chenopodium 244Intestinal parasites

berberine 302Intestines 202


General Index

Intoxicantcannabis 260nutmeg 242

Inula helenium 249Ion transport 69Ionic bonds 45Ions 45Ipe Roxo 113Ipecac 290, 300Ipecacuanha 165Ipomea 256, 257Iris 375, 377Irish moss 376Irritant

allyl-isothiocyanate 102black mustard 131ginger 264

Irritant (intestinal)podophyllotoxin 258

Irritant (local)wintergreen 246

Irritants (mucous membrane) 226Ischemic heart disease 206

Burkitt research 78Isomers 50Isoprene structure 224Isothiocyanate glycosides 102, 130Isotopes 39Ivy 148, 377Jackson, B. and D.W. Snowdon 323Jalap 256, 257Jamaican Ginger 264Japanese mint 230Japanese Star Anise 241Jasmine 218, 376Jaundice

bayberry 169Jew’s ear 377Jimson weed 298Journal of Natural Products (Lloydia) 360Juniper 26, 229, 232, 249, 375, 376

tar 238Juniperus communis 232, 249Kabbala 370, 373, 377Kapha 17Kaptchuk, T. 17Karaya gum 75Kauri 257Kava Kava 260KB tumor systems 279Kelp 75Ketone 57Khat 306Ki 381Kidney

damage/rhubarb leaf 110

Kidney diseaseastragalus 91juniper 232oxalic acid 163

Kidney stimulantcubeb 228

Kidney stonesbelladonna 297juniper 232oxalic acid 163wood sorrel toxicity 173

Kidneywort 376Kinetic maceration 347King of the mucous membranes 301King’s American Dispensatory 324King’s Cure-All 191Kinos 165Klebsiella

kelp 75Knapweed 377Knotgrass 148, 377Kola 165, 309Kousso 165Krameria 165L’Obel, Matthias de 295Labiatae 215, 290Lactation inhibitor

sage 250Ladies mantle 376Lady’s smock 375Lady’s thistle 376LaPacho 113, 324Lard 177Larkspur 305Laryngitis

bryony 311datura 311peppermint 230

Laurel 375, 376Lavabre, Marcel 221Lavandin 216Lavender 216, 229, 249, 375, 376

oil 245Lavendula angustifolia 245, 249Laxative

betel 294bulk/kelp 75bulk/psyllium 76citric acids 162dogbane 281fumaria 311grapes 172guar gum 77karaya gum 75senna 149



Laxative (mild)blackthorn 147goldenseal 301linseed oil 183olive oil 183

Lazarev, N.V. 118LDL/HDL ratio 192, 264Lead

chlorella 85Legume roots 284Leguminosae 290Lemon balm 375Lemon peels 233Lemon tree 375Lemon verbena 232Lemongrass 232Lentinus edodes 90Leonurus cardiaca 312Lesser centaury 375Lettuce 375Leucorrhea

bayberry 169Leukemia (acute)

podophyllotoxin 259Leukopenia

aloe 108Leukotriene inhibition 136

hawthorn berry 138Leung, Albert 358Levisticum officinale 249Lewis structure 46Li-Ching Yun 117Licorice 115, 119, 149, 375, 376Light Stage 71Lignin 77Ligustrum 83Lilies 375Lily of the Valley 281, 375Limbic system 220Lime (mineral) 112Lime tree 375, 376Limonene 116Ling-zhi 86Liniment

cayenne 263rosemary 245

Linseed oil 183, 186Linum hesitatiasimum 183Linum spp. 74Lipid peroxidation 206Lipids 64Lipoxygenase pathway 189Lippia citriodora 232Liquid collagen 206Liquid nitrogen 346Lithium 41Little Works 369, 372

Liver 202, 208barberry 310damage/oak 171damage/rhubarb leaf 110

Liver cholesterolcayenne 264

Liver damageoak toxicity 171

Liver function 192Liver metabolism 196Liver problems 136

yew 312Liver protein synthesis 136Liver stimulant

rosemary 245Liver tonic

ginger 264Liver toxicity 137

chlorella 85Liverwort 376Liviation 346Lloyd extraction 335Lloyd Library 357Lloydia 360Lobaria pulmonaria 276Lobelia 295, 312Lobelia inflata 295, 312Longevity

reishi 88Lophophora williamsii 308Lopwood 165Lovage 249, 375Low blood sugar

cannabis 261guar gum 77

Lumbagobetel 294

Lumpy breasts 193Lung cancer

smoking 294Lung congestion

cannabis 261Lungwort 376Lymphocytic leukemia

echinacea 86Lysigenous passages 215Lysosomal enzymes 194Maceration 218, 347Maciocia, G. 17Macro-molecules 64Macrocystro pyrifera 75Macromorphology 318, 323Macrophage activator

berberine 302echinacea 85

Macrophagesgoldenseal 302


General Index

Madder 376Magnesium oxide 106Maker, Dr. Russell E. 123Malaria 113

gentian 143ginger 265

Malarial feverberberine 303cinchona 300

Malarial parasites 114Male fern 165, 173, 262, 377Malus silvestris 172Malus spp. 161Mandragora officanarum 260Mandrake 258, 375, 377Manic depression 208Mannose 70Manufacturing 334Mapis 365Maple tree 376Marc 9, 336, 348Margarine 183Marigold 249, 375Marijuana 260Marjoram 249, 375Marjorana hortensis 249Marshmallow 93, 375, 376

root 232Martial arts

tannins 164Massage oils 219Masterwort 376Mastic sandarac 257Mastrick 226Mate’ 165, 172, 309Materialists 12Mathematics 377Matsumoto, K. and S. Birch 17Mayapple 258Mayo Clinic 230Meadow saffron 307Meadowsweet 149Meat 203

red 190Medicago sativa 205Medicine Man School 24Medicine pipe 26Medicine Wheel 29Medlar tree 377MEDLINE 365Meisner 289Melancholy thistle 377Melanin pigmentation

Cascara sagrada 106Melilot 376Melissa 232, 249Melissa officinalis 232, 249

Memorycloves 241juniper 232rosemary 245

Memory/short termginkgo 135

Menorrhagiacannabis 261goldenrod 148shepherd’s purse 149

Menstrual irregularityfennel 242

Menstrual painanise 242

Menstrual problemsguarana 171sassafras 243

Menstruation 220mugwort 250

Menstruum 9, 335, 346Mental fatigue

bergamot 246peppermint 230rosemary 245

Mentha arvensis 230Mentha piperita 229, 250Mentha spicata 236Mentha viridis

spearmint 236Mercury 375

chlorella 85Mercury (french) 376Mescal Button 308Mesquite gum 74Metabolic stimulant

sarsaparilla 149Metastic cancer

reishi 90Methane 46Methyl salicylate

poplar toxicity 140Methylcellulose 75Mexican Yam 123Mezereon 376Micromorphology 318, 323Micronutrient Hypothesis 201Microvilli

pectin 77Migraine headaches

anise 242feverfew 249peppermint 230pearl powder 196

Milk thistle 133, 135, 149Milk Vetch 91



Milk/breast 189, 191nicotine 294

Milk/insufficientanise 242

Mills 345Mineral acids 112Mints 375, 376Miscella 346, 348Mistletoe 312, 375, 376Mitogenic polypeptide 202Moher, Holfdan, Dr. 356Molasses 72Molecules 45Mollusc 115Monarda oil 238Monarda punctata 238Moneywort 375, 376Monk pepper 375Monkshood 305, 312Monoanthrones

rhubarb 110Monocarboxylic acids 60Monoclonal Hypothesis 201Moonwort 375Mormon tea

ephedrine 307Morus alba 276Mosses 377Mother - son relationship 14Motherwort 312, 376Mouse-eared chickweed 375Mouth

tormentil 168Mowrey, Daniel B., Ph.D. 117, 125Moxabustion

mugwort 250Mucilages 74Mucous membrane irritants 226Mucus

ketones 235Mugwort 235, 250, 376Mulberry 375Mullein 149, 376, 377Multiple sclerosis 122, 194Munich Technical College 339Muscarinic acetylcholine receptors

ginkgo 135Muscle tone

berberine 303Mushroom poisoning 136

reishi 88Mustard 130, 376

(white) 375oil 130, 245

Mydriaticalkaloids 290atropine 290homatropine 290

Myocardial infarction 196reishi 89

Myoticphysostigmine 290pilocarpine 290

Myrica cerifera 169Myrica oil 238Myristica fragrans 242Myrobalans 165Myroxylon pereirae 268Myrrh 215, 256, 266, 376Myrtle 375Nailwort 375NAPRALERT 365Narcissus 312Narcissus exsertus 312Narcotic 119

alkaloids 290broom 306cocaine 298codeine 290morphine 290opium 304, 312

Narcotic analgesiccodeine 305morphine 305

Narcotic poisoningsafrole 243

Narcotic stimulantguarana 171

National Institute of Mental Health 24Nausea

cascara sagrada 106cinnamon 234gentian 143morphine 305wintergreen 246

Navajo school 25Nepeta cataria 248Nephritic

belladonna 311Nephritis

pine 250reishi 88

Nephritis (chronic)goldenrod 148

Nephrosisdigitalis 279

Neroli 229Nerve damage

nutmeg 242Nerve tonic

juniper 232Nervine

arnica 248betel 295catnip 248


General Index

chamomile 248feverfew 249guarana 171hops 228lobelia 312peppermint 230populin 139stimulant/guarana 171tansy 250valerian 251

Nervine (mild)lavender 245

Nervousnessreishi 88

Nettle 376Neuralgia

cannabis 261digitalis 279monkshood 312peppermint 230

Neurastheniareishi 88

Neuromuscular junction blocking 115Neurotoxic

ketones 235Neutrons 38Newton, Isaac 370Niaouli 229Nickel 183Nicotiana rustica 293Nicotiana tobacum 293Nicotine 293Night sweats

belladonna 297Nightshades 377Nipples

goldenseal 302Nipples (cracked)

benzoin 268Nitrogen 43Non-insulin-dependant diabetics 80North American Indian Medicine 23Nosebleeds

ragwort 312Nucleic acids 64Nuphar 312Nuphar lutea 312Nutmeg 226, 239, 242, 375, 376Nux 375Nux vomica 165, 290, 305, 375, 376Oak 165, 169, 376Oats 375, 376Obesity

Burkitt research 78guar gum 77

Obesity reversalgrapes 172

Ocimum basilicum 248Oenothera biennis 191Oily drug extract 336Ojibwa practitioners 30Olea europaea 183Olea medicata 336Olfactory bulb 220Olibanum 257Olives 376

oil 177, 183tree 375

Omega 3 fatty acidsborage 93

Omega 6 fatty acidborage 93

Oncogenic viruses 188Onions 376, 377Opium 300, 304, 312Oral cancer

chewing tobacco 294Orange flowers 229

tree 375Orbitals 39Orchids 376Orchitis

ginger 265Oregano 375Oregon balsam 262Oregon Grape root 302Organelle membranes 207Origanum 225Orpine 375Orris root 235, 238Oxalis acetosella 173Oxalos

oxalic acid 163Oxidation-reduction reaction 54Oxide ring 101Oxygen 43Oxytocic

broom 306P.C.B. (Polychloridebiphenyl)

chlorella 85Paan 294Pachyma hoelen 276Pain

abdominal/oak 171cannabis 261

Palladium 183Pallinea cupana 171Palmarosa 229Palpitation

digitalis 279Palsy

Lily of the Valley 281Panax ginseng 119, 318



Panax quinquefolium 125Panax spp. 148Pancreatitis

chlorella 84chlorophyll 284

Pansy 149, 377Papaver somniferum 304, 312Papaveraceae 290Papaya 375Paper chromatography 325Parasiticide

Peru Balsam 268Parenchyma cells 215Parkinson’s disease

belladonna 297, 311jimson weed 298

Parsley 239, 375Parsnips 375, 376Particularists 12Parturient

cannabis 261cinnamon 234

Passion flower 375Pasteurization 349Pau D’Arco 113Peach 127, 376Peanut oil 177, 183Pearl powder 195, 196Pears 376Pectin 77Pectoral

anise oil 241fennel 249hyssop 249

Pellitory 375Penaceae 215Penicillium viridicatum 299Pennyroyal 234, 235, 238, 376Peony 375Pepper 375Peppermint 218, 229, 235, 236, 250, 376Pepperwort 376Percolation 344, 348Pereina, Jonathan 268Perfume and Flavor Material of NaturalOrigin 221Perfumery: The Psychology and Biologyof Fragrance 220Periodic Table 38Periploca sepium 317Peristalsis 105

Cascara sagrada 106Peristalsis depressant

opium 304Peristaltic (light)

myrrh 267Periwinkle 375-377

Peru Balsam 256, 268Peruvian bark 112, 299Pest control 341Pesticides 216

chlorella 85Petitgrain 229Peyer’s patches 82Peyote 306, 308PH 60, 346Phagocyte stimulation 92Phagocytic activity

ginger oil 265Phagocytic potential 196Pharmacognosy 2, 8Pharmakon 8Pharyngitis 113

elder 148Phellinus igniarius 276Phenol glycosides 102Phenolic

aspidinol 262chlorophyll 284

Philosopher’s gold 372Phospholipase A2 264Photosynthesis 69, 71Physostigma 305Phytopharmaceutical Technology 334,342Pilocarpus 305Pimpernel 375, 376Pimpinella anisum 241, 248Pin mills 345Pine 117, 229, 250, 376, 377

oil 226stump 9tar 234turpentine 255

Pineapple 376Pinene 224Pinocytosis 82Pinus silvestris 250Pinus sp. 256Piper cubeba 228Piper methysticum 260Piperaceae 215Pipsissewa 277Pitta 17Planetary Rulers 375PlanetHerb 365Plant stones 369Plantago 76Plantago psyllium 76Plantago sp. 74, 93Plantain 76, 93, 375-377Plasma cholesterol 206Plasmodium

gentiopicrin 143


General Index

Platelet aggregation 187, 189, 194, 196,202, 205, 206, 264

capsaicin 264cayenne 311ginger 264gingko / inhibition 134lobelia 296

Platelet deposition 189, 196Pleurisy

bryony 311coltsfoot 93

Plums 127, 376, 377Pneumonia

bryony 311pine 250reishi 88

Podophyllin 257Podophyllum 256, 258Podophyllum emodi 259Podophyllum peltatum 258Poison

rhubarb leaf 110Poison antidote kits

ipecac 301Polio virus 113Poliomyelitis

snow drop 312Polyarthritis

bryony 311Polychloridebiphenyl

chlorella 85Polygonaceae 103Polygonum 377Polygonum aviculare 148Polypodium vulgare 93Polypody 376Polysaccharides 70Pomegranate 165, 290, 296Poplars 139, 376, 377

buds 139, 262, 265Poppies 312, 375-377Populus balsamifera 265Populus candicans 139Populus nigra 147Populus spp. 265Poria cocos 90, 117Pot 260Potentilla anserina 150Potentilla erecta 168Potentilla silvestris 168Potentilla tormentilla 168Poultice

internal/psyllium 76Prana 381

Pregnancycontraindication/gentian 143raspberry 173warning/aloe 109

Premenstrual syndrome 121, 189, 191Preservative

benzoic acid 268Primose 376Principals 9Privet 375, 376ProHerb 365Prolapsus uteri

cannabis 261Properdin

echinacea 86Prophylactic

beta-carotene 282Prosopis spp. 74Prostate (blood supply)

horse chestnut 148infection 237

Prostatitis 113Proteases enzymes

inhibition/chlorella 85Protectant

compound benzoin tincture 268myrrh 267pectin 77Peru Balsam 268

Protein precipitantoak 170

Proteins 64Proteus

kelp 75Proteus vulgaris

echinacea 86Protons 38Prunus amygdalus 129, 147Prunus serotina 128Prunus sp. 74Prunus spinosa 147Prunus virginiana 128Pruritus

ginseng overdose 126Pseudomonas aeringosa 107, 342Psilocybe mexicana 308Psyllium ovata 76Psoriasis 122, 137Psoric miasms 191Psychiatric problems 194Psyllium 74, 76Pulmonary disease

thyme 238Pulmonary edema

wintergreen 246Pumpkin 375Punica granatum 296



Pupil dilationbelladonna 311

Purgativeadder fern 93aloe 147barberry 303buckthorn 147colchicum 307gamboge 266rhubarb 149

Purgative/drasticbryony 311

Purshean (herbalist) 105Purslane 376Pyrola rotundiflia 150QBL 370Qi 13, 381Quadgyric method 337Quality 328

Control 334, 342Quantitative Methods 328Quantum physics 371Queen of the meadow 376Quercus infectoria 169Quince tree 377Quinta Essentia 380Quintessence 380Racemic 9Radiation 119, 342Radiation/ionizing 188Radishes 376Ragwort 312, 376Ranunculaceae 290Rapeseed 130Rare gas 45Rash

ginseng overdose 126Raspberries 173, 376Rattle-grass 375Rauwolfia 305Rectal cancer

Burkitt research 78Rectal mucosa

Cascara sagrada 106Red blood corpuscles 115Red clover 277Red meat 188, 190Redmond clay 106Reishi 82, 86, 117Relaxant

belladonna 297muscle/poplar 140

Relaxant (muscle)kava kava 260

Renal failurewood sorrel toxicity 173

Resin Acids 256Resin trees 119Respiratory center

stimulant/ginger 264Respiratory poison 114Respiratory problems 113Respiratory stimulant

lobelia 296, 312saffron 144

Respiratory tractadder fern 93cinnamon 234

Restharrow 376Reverse transcriptase 113Rhamnaceae 103Rhamnus catharticus 147Rhamnus frangula 323Rhamnus purshianus 105Rheum

oxalic acid 163Rheum officinale 109Rheum palmatum 109, 149Rheumatic pain

coriander 248Rheumatism 122, 194

cannabis 261cayenne 263eucalyptus 244ginger 265henbane 311nutmeg 243peppermint 230Peru Balsam 268pine 250poplar buds 265sassafras 243silver birch 149yew 312

Rheumatism/muscularbryony 311

Rheumatoid arthritis 120Rhinitis/allergic 188Rhubarb 102, 149, 165, 376

anthracene-related aglycones 103oxalic acid 163

Rhubarb (Turkey or Chinese) 109Ribes spp. 195Rice 375Ricinus communis 183Rinsing 346RNA 65Rock cocaine 299Rocky Mountain spotted fevers

berberine 303Rollers 346Rosaceae 127, 290


General Index

Rose 229, 376hips 134oil 216petals 165

Rosemary 216, 250, 375Rosemary oil 245Roses 376Rosewood 229Rosin 256Rosmarinus officinalis 163, 245, 250Roundworm

chenopodium 244Royal fern 377Rubefacient

black mustard 131cayenne 263, 311Peru Balsam 268rosemary 245

Rubiaceae 103Rubraceae 290Rubus idaeus 173Rubus spp. 161Rue 375Rumex

oxalic acid 163Rutaceae 215Rye 376, 377Sabal serrulate 92Saccharum officinarum 71Safflower oil 182, 185, 195Saffron 143, 250, 375Sage 216, 235, 250, 376Salivation

nutmeg 242Salix alba 150Salmonella 342

kelp 75Salvia officinalis 250Sambucus nigra 148Samphire 376Sandalwood 229, 260, 376Sandarac 256Sanguinaria 290, 300Sanicle 376Saponin glycosides 102, 115Sapotoxins 115Saracen’s compound 377Sarcoma 180

aloe 108Sarsaparilla 115, 122, 149, 277, 376Sassafras 122, 243Sassafras albidum 243Satan’s Apple 260Savin oil 225Savine 376Savory 375Saxifrage 375

Scabius 375Scalp infection

mandrake 259Scammony 257Scarlet fever

bayberry 169berberine 303

Scarslavender 245

Schizogenous passages 215Schizophrenia 194Sciatica

bryony 311monkshood 312pine 250

Scophularia nodosa 148Scurvy grass 376Sea cucumber 115Seafood 190Seasoning

chervil 147Sedative 117

aldehyde volatile oils 233belladonna 297chamomile 248lavender 249lupilin 228melissa 249saffron 250wild cherry 129

Sedum 312, 375Sedum acre 312Self heal 376Senecio vulgaris 312Senility

ginkgo 134Senna 102, 111, 149, 324, 376, 377

anthracene-related aglycones 103Sephera 377Serine proteases prostaglandin inhibition

hawthorn berry 138Serthurmer 289Serum cholesterol inhibition

hawthorn berry 138Service tree 377Sex 220

glands 202hormones 200

Seydler, C.A. 8Shaman 23Shellac 256Shellfish 203Shepherd’s Purse 149, 377Shigella 342Shigella dysenteriae

astragalus 91Shiitake 82, 90



Shredding 343mills 345

Shrimp 190Siberian ginseng 82, 83, 116, 119, 317Sickle cell anemia 127Sieving 343Silk vine 317Silver Birch 149Silverweed 150Silybum marianum 133, 135, 149Sinus problems

reishi 89Sinusitis

eucalyptus 244peppermint 230

Sjogren’s Syndrome 192Skin disease 122, 191

Peru Balsam 268sassafras 243

Skin problemschlorella 85nuphar 312pansy 149pearl powder 196

Skin protectant 200Sleep 228

cannabis 261Slippery Elm 74Small intestine 105, 258

pectin 77Smallage 375Smell 220Smilax regelii 149Smilax spp. 122Smooth muscle depressant

ephedra 311Snails 142Snake bites 113

cinnamon 234Snow drop 312SNS stimulant

ephedra 311Soaps 256Soapwort 376Sodium Alginate 75Sodium bicarbonate 299Sohxlet extraction 335Solanaceae 290Solidago virgaurea 148Solomon’s seal 377Solvent 9

olive oil 183peanut oil 183

Solvent Extraction 218Sorrel 376

oxalic acid 163Southernwood 375

Sow-thistle 376Soy Beans 94, 117

oil 186, 276Spagyric extracts 336Spasmolytic/mild

meadowsweet 149Spearmint 218, 235, 236Speedwell 375Spermatorrhea

belladonna 297Spicknel 376Spikenard 122Spiraea ulmaria 149Spleen

barberry 310goldenseal 302

Spleen-wort 377Spleen/blood flow

berberine 302Spoerke, D. 359Spurge-laurel 376Squill 101, 279, 376, 377St. John’s wort 375St. Jude Children’s Residential Hospital259Standardization 328Staphylococcus 113

astragalus 91echinacea 86kelp 75reishi 90uva-ursi 142

Staphylococcus aureus 342Star of David 380Star thistle 376Starch 69Starvation 188Steeping 346Stellaria media 147Sterculia gum 75Sterculin urens 75Sterols 116, 119, 350Stimulant

angelica 248anise 248benzoin 268cardamon 231catnip 248chamomile 248cinnamon 233cloves 240coffee 310cubeb 228digitalis 279eucalyptus 244horseradish root 132hyssop 249


General Index

lavender 249peppermint 230rosemary 250sage 250sassafras 243spearmint 237tansy 250valerian 251vanilla 140yarrow 251

Stimulant (Circulation)cayenne 311

Stimulant (diffuse)ginger 264

Stimulant (general)thyme 238

Stimulant (local)arnica 248cayenne 206cinnamon 234myrrh 267

Stimulant (mild)bergamot 246caraway 237

Stimulant cathartics 104Stimulant tonic

castor bean oil 183Stoddart, D.M. 220Stomach disease

reishi 88Stomach problems

elder 148Stomach tonic

basil 248caraway 237hops 228

Stomachicaloe 147burdock 248chamomile 248cinnamon 233fennel 249fumaria 311gentian 143juniper 232lavender 249melissa 249peppermint 250wood sorrel 173

Stonecrop 375Stramonium 296, 298Strawberries 375, 376Streptococcus

astragalus 91kelp 75reishi 90

Streptococcus haemolyticus

Stroke 196Strontium

kelp 75Strontium absorption

sodium alginate 75Strophanthus 101Strychnine poisoning 260Stupor

saffron 144Styptic

oak 170Styrax 256, 257, 268Styrax benzoin 268Sublimation 336Substance P 264

cayenne 311Sudorific

borage 93burdock 248sarsaparilla 149

Sugars 69relative sweetness 73beet 71cane 71, 376

Sulfur-containing compounds 63Sun (protection)

horse chestnut 148Sun Yan, Dr. 83Sundew 375Sunflower 375Supercritical Gas extraction 348Surgery (post)

citric acids 162Suspension 75Suspension agent

pection 77sodium alginate 75

Sweat lodge 26Sweating

profuse/goldenseal 302Sweet orange peels 233Sweetgrass 26Syphilis 113, 122

sassafras 243Systemic lupus-like disease 194Systolic contraction 278T-cells

chlorella 84kelp 75

T-lymphocytes 86function 189, 194helper cells 282

T-suppressor cells 194Tabebuia avellanedae 113, 324Tablets 337, 350Tachycardia

hawthorn 148



Taeniafugebetel 294poemgranate 296

Tahebo 113Tamarind 377Tamarisk tree 377Tanacetum parthenium 249Tanacetum vulgare 250Tannins 163Tansy 235, 238, 250, 376Tapeworms 294

male fern 262Tarragon 250Taxus baccata 312Tea 172, 309, 310, 333Tea tree 229Teasel 376Tender breasts 193Terpene oxidation 256Testosterone 118Tetanus 260Tetraclinis articulata 256Tetrahedral structure 50Thakkur, C.G. 23The Alchemist’s Handbook 375The Art of Aromatherapy 221The Handbook of Aromatherapy 221The Pattern of Health 372The Secret Life of Plants 216, 372Thea sinensis 172Therapeutic Index 278Thin-layer chromatography 325Thiols 64Thirst 220Thorough wax 377Throats

oak 170tormentil 168

Thrombi formationsreishi 89

Thrombosis 189Thromboxane B2 formation 264Thuja 235Thujol alcohol 237Thyme 216, 238, 250, 376Thyme oil 238Thymo-protection 282Thymus 194, 208Thymus vulgaris 250Tierra, Michael 359Tincture of Benzoin 268Tinctures 333, 335Tinea capitis 259Tinnevelly senna 111Tinnitus

ginkgo 135Tisserand, Robert 221

Tobacco 240, 289, 293, 376Tolu Balsam 256, 268Tomatoes 376Tompkin, Peter 216Tonic 123

angelica 248anise 248barberry 303bayberry 169bergamot 246catnip 248chamomile 248digestive/gentian 143dogbane 281elecampane 249goldenseal 301hops 228lavender 249rosemary 250tansy 250valerian 251white willow 150wormwood 238

Tonic (bladder)blackthorn 147

Tonic (stomach)blackthorn 147

Tonic water 300Tonsillitis

elder 148Tooth decay

vanilla 140Toothaches

cloves 240peppermint 230

Tormentil 168, 375Tormentilla 376Totem 28Totem pole 371Toxin/cold-blooded animals

houndstongue 311Tracheitis

bryony 311Tranquilizers 192Trans 52Tree of Life 377Tremella spp. 90Trichocereus sp. 308Trichophyton 113Tricyclic antidepressants 135Tridosha 17Tswett, Michael 324Tuberculosis 113

horsetail 148plantain 93saffron 144


General Index

Tumor systems 276berberine sulfate 302

Tumorssquill 280

Tumors (indolent)digitalis 279

Turkish galls 165Turkish Opium 304Turmeric 251, 375Turnsole 375Turpentine 116, 226, 255, 262Turpentine oil 228Tussilago farfara 93Tutsan woad 377Twayblade 377TylenolR 337

codeine 305Tyler, Varro, Dr. 356Typhoid fever

berberine 303U.S. Cancer Foundation 184U.S. Heart Foundation 184Ulcers 113, 120

alginates 75bayberry 169chlorella 85hemostatic/kelp 75indolent/goldenseal 302licorice 149reishi 90

Ulcers/indolentgoldenseal 302

Ulmus fulva 74Ultrasound extraction 348Umbelliferae 215Umstimnungs therapie 83United States Dispensatory 360Unsaturated compounds 46Uranium

chlorella 85Urginea maritima 279Uric acid crystals 237Urinary antiseptic

buchu 237juniper 249

Urinary insufficienciessilver birch 149

Urinary irritationmarshmallow 93

Urinary passage inflammation 195Urinary problems

yew 312Urinary stimulation

cubeb 228Urinary tract infection

black poplar 147

Urination (painful)cannabis 261

Uterine contractionephedra 307

Uterine hemorrhagecinnamon 234hydrastine 302shepherd’s purse 149

Uterine inflammationgoldenseal 302

Uterine stimulantcelery 248

Uva ursi 141, 371Vaginal douche

oak 170Vaginal inflammation

goldenseal 302Vaginal problems

nuphar 312Vaginal trichomonads 264Valerian 251, 375Valeriana officinalis 251Vanilla 140Vanilla planifolia 140Vanilla tahitensis 140Varicose veins

Burkitt research 78witch hazel 168

Varnishes 256Vascular cholesterol 205Vascular disease 133Vascular insufficiency

ginkgo 135Vascular obstruction 194Vasoconstriction

nicotine 294Vasodilation 189

black mustard 131ginkgo 134mistletoe /peripheral 312

Vasomotor centerstimulant/ginger 264

Vasospasm 189Vata 17Vegetable Husbandry program 339Vegetable sterol 350Vegetable-source capsules 337Vegetarian diet 188Venereal disease 122Venereal warts

mandrake 259Veratrum 305Verbascum thapsiform 149Vermifuge

betel 294male fern 173mugwort 250



pomegranate 296wormwood 238

Vertigoginseng overdose 126Lily of the Valley 281saffron 144

Vertigo headachesginkgo 135

Vervain 376Vesicula stomatitis virus 113Villi

pectin 77Vinca 305Vine viper’s bugloss 375Viola tricolor 149Violet 235Viral infections

echinacea 85Viruses

lipid coat/chlorella 84Viscum album 312Vision Quest 24Vital energy 381Vitalist tradition 12Vitamin B antagonist

goldenseal 302Vitamin F 184Vitis vinifera 172Vittae 215Volatile oils 215, 336Volatilization 346Vomiting

cascara sagrada 106gentian 143morphine 305rhubarb leaf 110saffron 144wintergreen 246

Vomiting (pregnancy)cinnamon 234

Vulneraryarnica 248cleaver 147horsetail 148knotgrass 148Peru Balsam 268vanilla 140wintergreen 150

Wagner, Dr. 83and Proksch 85

Walker carcinosarcomaechinacea 86

Wallflower 375Walnut 375

oil 186Water chestnut 375Water Distillation 217

Watercress 375Wei Qi 16Weight loss diets 206Westlake, Aubrey, M.D. 372Wheat 376White mustard 130White pine bark 262White Willow 150Whooping cough 280

belladonna 297coltsfoot 93fennel 242ivy 148saffron 144

Wild Cherry 128, 165Wildcrafting 318Willows 139, 165, 375

herb 377Wintergreen 102, 139, 150, 246, 377

oil 245Witch hazel 165, 167Wood sorrel 173

oxalic acid 163Worcestershire sauce 267World Health Organization 356World Patent Index 365Worms

fennel 242male fern 262

Wormwood 27, 235, 237, 376Wound healing 113

echinacea 85marigold 249plantain 93

WPI (World Patent Index) 365Yam 115, 123Yang 14Yarrow 27, 251, 376Yew 312, 377Yin 14Yin-yang qualities 221Yucca 115, 122Yun zhi 90Zedoary 375Zhuling 90Zingiber officinale 205, 264

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Textbook Of - Wild Rose College