Upload
others
View
19
Download
0
Embed Size (px)
Citation preview
APPENDIX
SAPONIN NETWORK FOR MASS SPECTROMETRY AND NUCLEAR MAGNETIC RESONANCE SPECTROMETRY
The saponin network for MS and NMR spectra is a part of the Databases of Carbohydrate Spectra which was conceived August 18-20, 1995 in Seattle, Washington for the Complex Carbohydrate Center, The University of Georgia, Athens, GA, by Prof. Peter Albersheim, and by the Department of Bio-Organic Chemistry, The Utrecht University, Utrecht, The Netherlands by Prof. Johannes F.G. Vliegenthart, and sponsored by the U.S. Department of Energy. The curator of the mass spectra and NMR spectra for saponins is:
Dr. Tadahiro Takeda Professor of Kyoritsu College of Pharmacy 1-5-30, Shiba-Kouen, Minato-ku Tokyo 105 JAPAN Tel: +81-3-5400-2696 Fax: +81-3-5400-2666
At this time Dr. Takeda has just accepted the responsibility for collecting and disseminating the spectra of saponins, and he does not have his organizational scheme set-up as yet. The mass spectra would include fast atom bombardment (FAB), electrospray ionization (ESI), tandem MS/MS with collision-induced decomposition, matrix-assisted laser-desoription (MALDI), electron impact and/or chemical ionization spectrometry, and liquid chromatography/mass spectrometry (LC/MS). To be of value to all who use the mass spectra database the details of the instrument settings and experimental conditions used to acquire each spectrum must be submitted. These guidelines will be available from Dr. Takeda or published in the letters to the editors of the leading journals in the field.
Although there has not been time enough to prepare a proposal on mass spectrometry, Dr. J. Albert van Kuik and Professor Johannes F.G. Vliegenthart have put together a proposal on a NMR spectra database gathering and dissemination for complex carbohydrates and it is presented below:
Proposal on standardized information-exchange formats for spectral databases of complex carbohydrates.
J. Albert van Kuik and Johannes F.G. Vliegenthart Department of Bio-Organic Chemistry, University of Utrecht, P.O. Box 80.075, 3508 T Butrecht, The Netherlands, Tel: +31-30-253-5184, Fax: +31-30-254-0980
Currently, no general database format exists for the storage of spectral data for these classes of bio-molecules. Some efforts have been made to collect NMR data for specific types of biomolecules, such as proteins and peptides by BioMagResBankl, or complex carbohydrates by
575
SUGABASE2. These collections typically contain chemical-shift assignments, a description of the molecule, and experimental conditions, but no original spectral data. One major obstacle associated with collecting original spectral data is the variety of formats in which spectra are stored. Even with one NMR-instrument manufacturer, different machines and different generations of software result in many incompatible formats. Collections of chemical-shift assignments bring their own compatibility problems. To unequivocally assign a chemical shift in an arbitrary bio-molecule, this molecule needs a unique identifier, and, additionally, each atom in this molecule requires a unique identifier too. These identifiers must be universal and not classor database-dependent. The lack of standards in this field leads to a specialized nomenclature for sub-classes of bio-molecules, e.g. proteins, carbohydrates, or saponins thereby excluding other classes, and making the inclusion of combined classes, e.g. glycoproteins or saponins, virtually impossible.
Fortunately some solutions for these problems are currently emerging3. To store spectral data of carbohydrate-containing bio-molecules in a format that is compatible with databases of other classes of biomolecules, we propose to extend current examples in the field, and to keep to the recommendations of IUPAC whenever possible.
Original spectral data should be stored in JCAMP-DX4,5, a computer-readable exchange format, originally designed for infrared spectral data exchange. Data are represented as printable ASCII characters. This format has specific extensions for NMR data, and is recommended by IUPAC. It is, or will soon be, supported by major NMR manufacturers Broker, Varian and Jeol. JCAMPDX can also be used to store experimental conditions, e.g. type of instrument, solvent, concentration, original standard, conversion shift, temperature, and quality of the data.
Structures are to be submitted in the Standard Molecular Data (SMD) format6, an organic structural information exchange format, which is currently under development by the IUPAC Committee of Chemical Databases (CCDB) and others in collaboration with the United States of America standards organization ASTM. This format will be supported by major organizations, e.g. Chemical Abstracts and Beilstein Institute.
For the electronic handling of data, in particular electronic submission of spectral data and storage of these data in a computer database, not a single clear-cut standard is available. For electronic handling, we propose to adopt the format used by crystallographers and by BioMagResBank. This Self-defining Text Archival and Retrieval (STAR) format utilizes tagvalue pairs, and is suitable for electronic data submission and subsequent processing by the computer. It is also the format of choice to represent lists of chemical shift assignments. For each database, a specific data dictionary is required to clearly define each data tag and associated attribute. Crystallographers have developed CIF, the Crystallographic Information File Data Dictionary. This is now the format in which structure papers are submitted to Acta Crystallographica. BioMagResBank has defined a Data Disposition Form for submission of NMR spectra for their database. This form is specific for data stemming from proteins and peptides, but could in principle be extended to handle other bio-molecules as well. At the moment it does not handle complex branched structures such as some carbohydrates, and it doesn't mention JCAMP-DX or SMD formats.
REFERENCES
I. B.R. Seavey, E.A. Farr, W.M. Westler, and J.L. Markley, A Relational Database for Sequence-Specific Protein NMR Data, J.Biomolecular NMR 1, 217-236 (1991).
2. J.A. van Kuik and J.F.G. Vliegenthart, A NMR Spectroscopic Database of Complex Carbohydrate Structures, Carbohydr. Europe 10, 31-32 (1994).
3. C.L. Wilkins, Guidelines on Nuclear Magnetic Resonance Computerized Databases, Pure & Appl. Chem. 67, 593-596 (1995).
4. J.G. Grasselli, JCAMP-DX, A Standard Format for Exchange of Infrared Spectra in Computer Readable Form, Pure & Appli Chem., 63, 1781-1792 (1991).
576
5. A.N. Davies and P. Lampen, JCAMP-DX for NMR, Appl. Spectrosc. 41, 1093 (1993).
6. F.H. Allen, J.M. Barnard, A.P.F. Cook and S.R. Hall, The Molecular Information File (MIF): Core Specifications of a New Standard Format for Chemical Data, J. Chem. Inf. Comput. Sci. 35, 412-427 (1995).
577
CONTRffiUTORS
H. Achenbach Institut fur Pharmazie und Lebensmittelchernie
der Friedrich-Alexander-Universitat Department of Pharmaceutical Chemistry D-91052 Erlangen SchuhstraBe 19 GERMANY
Khalid Aftab H.E.J. Institute of Chemistry University of Karachi Karachi 75270 PAKISTAN
Irina G. Agafonova Pacific Institute of Bioorganic
Chemistry of Far East Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA
Suresht K. Aggarval College of Pharmacy University of Kentucky Lexington, KY 40536
Viqar Uddin Ahmad H.E.J. Institute of Chemistry University of Karachi Karachi 75270 PAKISTAN
Dmitry L. Aminin Pacific Institute of Bioorganic
Chemistry of Far East Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA
Michail M. Anisimov Pacific Institute of Bioorganic
Chemistry of Far East Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA
Magda Antal Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY
A. Aquino Dipartimento di Chimica delle Sostanze
Naturali via D.Montesano 49 Napoli 801211TALY
Y oshihisa Asada School of Pharmaceutical Sciences Kitasato University 5-9-1, Shirokane, Minato-ku Tokyo 108 JAPAN
Sergey A. A vilov Pacific Institute of Bioorganic
Chemistry of Far East Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA
Manuel Balandrin NPS Pharmaceuticals, Inc. University Research Park Salt Lake City, UT 84108
Guy Balansard Laboratoire de Pharrnacognosie Faculte de Pharnacie Universite d'Aizmarseille II 27 Bd J. Moulin 13385 Marseille Cedex FRANCE
Perry Barboza University of New England Armidale, N.S.W. AUSTRALIA
NinaBerova Department of Chemistry Columbia University New York, NY 10027
Lojos Biro Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY
G. Biro Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY
579
V. Bologa National Practical Science Center of Hygiene and
Epidemiology of the Health Ministry of the Moldova Republic
N. Testemitianu Chisinau State Medical University Chisinau 2002 MOLD A VIA
Paul Bowyer The Sainsbury Laboratory Norwich Research Park Colney Norwich NR4 7UH UNITED KINGDOM
G.N. Busuk Vitebsk Medical Institute Belorussia RUSSIA
I. Calis Department of Pharmacognosy Faculty of Pharmacy Hacettepe University Ankara TR-06100 TURKEY
V.Ya. Chirva Department of Organic Chemistry Simferopol State University Taltinskaya Str. 4 Simferopol, Crimea 333036 UKRAINE
Claus Cornett Royal Danish School of Pharmacy Department of Medicinal Chemistry Universitetparken 2, DK-2100 Copenhagen DENMARK
Michael J. Daniels The Sainsbury Laboratory Norwich Research Park Colney Norwich NR4 7UH UNITED KINGDOM
G.A. Drozd Department of Organic Chemistry Simferopol State University Taltinskaya Str. 4 Simferopol, Crimea 333036 UKRAINE
Olga A. Drozdova Pacific Institute of Bioorganic
Chemistry of Far East Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA
580
Nguyen Minh Due Science-Production Union of Ginseng and
Medicinal Plants Ho Chi Minh City University of Medicine
and Pharmacy 41 Dinh Tien Hoang Street, District 1 Ho Chi Minh City, VIETNAM
Earnest Dworshak Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY
Y. Ebizuka Faculty of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113 JAPAN
Robert Faure URA1411 University Aix-Marseille III A v. Escadrille Normandi-Niemen 13997 Marseille Cedex 13 FRANCE
Tsutomu Furuya Faculty of Science Okayarna University of Science Okayarna 700 JAPAN
Odon Gaa! Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY
Monique Gasquet Laboratoire de Parasitology Faculte de Pharnacie Universite d'Aizmarseille II 27 Bd I. Moulin 13385 Marseille Cedex FRANCE
Sergey N. Gnedoi Pacific Institute of Bioorganic
Chemistry of Far East Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA
Jack P. Goodman College of Pharmacy University of Kentucky Lexington, KY 40536
L.A. Gorbacheva Department of Organic Chemistry Sirnferopol State University Taltinskaya Str. 4 Sirnferopol, Crimea 333036 UKRAINE
V.I. Grishkovets Department of Organic Chemistry Sirnferopol State University Taltinskaya Str. 4 Sirnferopol, Crimea 333036 UKRAINE
Katalin Gruiz Technical University of Budapest Agricultural Chemical Technology H-1521, Budapest Szt. Gellert er 4 HUNGARY
T. Grushko National Practical Science Center of Hygiene and
Epidemiology of the Health Ministry of the Moldova Republic
N. Testemitianu Chisinau State Medical University Chisinau 2002 MOLD A VIA
Garner T. Haupert, Jr. Department of Chemistry Columbia University New York, NY 10027
Kurt Hostettmann Institut de Pharmacognosie et Phytochimie Universite De Lausanne BEP, CH-1015 Lausanne-Dorigny SWITZERLAND
Harald Hiibner Institut fur Pharmazie und Lebensmittelchemie
der Friedrich-Alexander-Universitat Department of Pharmaceutical Chemistry D-91052 Erlangen SchuhstraBe 19 GERMANY
Kentaro Inoue Faculty of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113 JAPAN
M. lorizzi Department of Natural Products University of Naples Naples 80131 ITALY
Aiko Ito Institute of Pharmaceutical Sciences Hirostirna Univesity School of Medicine 1-2-3- Kasumi, Minarni-ku Hirostirna 734 JAPAN
D. lurea Institute of Biological Research Blvd. Copou 20A Iassy 6600 ROMANIA
M.M.Iwu Walter Reed Institute of Research Division of Experimental Therapeutics Walter Reed Medical Center Washington, DC 20307-5100
J.E. Jackson Walter Reed Institute of Research Division of Experimental Therapeutics Walter Reed Medical Center Washington, DC 20307-5100
Marian L. Jurzysta Department of Biochemistry Institute of Soil Science & Plant Cultivation Pulawy 24-1000 POLAND
Vladimir I. Kalinin Pacific Institute of Bioorganic
Chemistry of Far East Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA
Molgorzata Kalinowska Department of Biochemistry Warsaw University 02-089 Warszawa ul. Zwirki i Wigury 93 POLAND
Geun Hyung Kang College of Pharmacy Chonnam National University Kwangju 500-757 KOREA
Ryoji Kasai Institute of Pharmaceutical Sciences Hirostirna University School of Medicine 1-2-3 Kasumi, Minarni-ku Hirostirna 734 JAPAN
Charlotte Kensil Cambridge Biotech Corporation Worcester, MA 01605
581
Dong Hyun Kim Faculty ofPhannaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113 JAPAN
Junei Kinjo Faculty ofPhannaceutical Sciences Kumamoto University Kumamoto 862 JAPAN
Dr. P. Kintia Institute of Genetics Academy of Sciences Padurii str. 20 Kishinev 277002 MOLDOVA
Takao Konoshirna Kyoto Phannaceutical University Misasagi, Yarnashina-Ku Kyoto 607 JAPAN
Maroufath Larnidi Laboratoire de Phannacognosie Faculte de Pharnacie Universite d'Aizmarseille II 27 Bd J. Moulin 13385 Marseille Cedex FRANCE
N.V. Lattserdis Institute of Genetics Academy of Sciences Padurii str. 20 Kishinev 277002 MOLDOVA
Ik-SooLee College of Pharmacy Chonnam National University Kwangju 500-757 KOREA
Else Lemmich Royal Danish School of Phannacy Department of Medicinal Chemistry Universitetparken 2, DK-2100 Copenhagen DENMARK
Xing-Cong Li Laboratory of Phytochemistry Kunming Institute of Botany Chinese Academy of Sciences Heilongtan, Kunrning 650204 CHINA
Galina N. Likhatskaya Pacific Institute of Bioorganic
Chemistry of Far East Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA
582
Lee-Chiang Lo Department of Chemistry Columbia University New York, NY 10027
Maja Ja. Lovkova Bach Institute of Biochemistry Leninsky Prospekt, 33 Russian Academy of Science Moscow 117071 RUSSIA
James H. Ludens Department of Chemistry Columbia University New York, NY 10027
S.B. Mahato Indian Institute of Chemical Biology 4, Raja S.C. Mullick Road Jadavpur, Calcutta 700-032 INDIA
M. Maillard Institut de Phannacognosie et Phytochimie Universite De Lausanne BEP, CH-1015 Lausanne-Dorigny SWITZERLAN:
A Marston Institut de Phannacognosie et Phytochimie Universite De Lausanne BEP, CH-1015 Lausanne-Dorigny SWITZERLANl
Y oshihiro Mimaki SchoolofPhannacy Tokyo College of Pharmacy & Life Sciences 1423-1, Horinouchi Hachioji, Tokyo 192-03 JAPAN
L. Minale Department of Natural Products University of Naples Naples 80131 ITALY
Faryal Vali Mohammad H.E.J. Institute of Chemistry University of Karachi Karachi 75270 PAKISTAN
Tsuneatsu Nagao Faculty ofPhannaceutical Sciences Fukuoka University, Nanakurna 8-19-1, Jonan-ku, Fukuoka 814-01 JAPAN
Katalin Nagy Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a BudapestH-1097 HUNGARY
Mohamad A. Naibi Institute of Genetics Academy of Sciences Padurii str. 20 Kishinev 277002 MOLDOVA
Koji Nakanishi Department of Chemistry Columbia University New York, NY 10027
Nguyen Thoi Nham Science-Production Union of Ginseng and
Medicinal Plants Ho Chi Minh City University of Medicine
and Pharmacy 41 Dinh Tien Hoang Street District 1 Ho Chi Minh City VIETNAM
Toshihiro Nohara Faculty of Pharmaceutical Sciences Kumamoto University Kumamoto 862 JAPAN
Mushtaq Noorwala H.E.J. Institute of Chemistry University of Karachi Karachi 75270 PAKISTAN
Lucienne Nze-Ekekang Iphametra (Cenerest) Libreville B.P. 842 GABON
Kazuhiro Ohtani Institute of Pharmaceutical Sciences Hirostima University School of Medicine 1-2-3 Kasumi, Minarni-ku Hirostirna 734 JAPAN
HikamOkabe Faculty of Pharmaceutical Sciences Fukuoka University Nanakuma 8-19-1 Jonan-ku, Fukuoka 814-01 JAPAN
C.O. Okunji Walter Reed Institute of Research Division of Experimental Therapeutics Walter Reed Medical Center Washington, DC 20307-5100
Evelyne Ollivier Laboratoire de Pharmacognosie Faculte de Pharnacie Universite d'Aizmarseille II 27 Bd J. Moulin 13385 Marseille Cedex FRANCE
Anne Osborne The Sainsbury Laboratory Norwich Research Park Colney Norwich NR4 7UH UNITED KINGDOM
Cezary Paczkowski Department of Biochemistry Warsaw University 02-089 Warszawa ul. Zwirki i Wigury 93 POLAND
E. Palagiano Department of Natural Products University of Naples Naples 80131 ITALY
Valentina A. Paseshnichenko A.N. Bach Institute of Biochemistry Leninskiy pr. 33 Moscow 117071 RUSSIA
Jun-peng Peng Institute of Radiation Medicine, Beijing 27 Tai-ping Road Beijing 100850 CHINA
S. Piacente Dipartimento di Chimica delle Sostanze Naturali via D.Montesano 49 Napoli 80121 ITALY
C. Pizza Dipartimento di Chimica delle Sostanze Naturali via D. Montesano 49 Napoli 80121 ITALY
ltzhack Polacheck Department of Clinical Microbiology and Infectious Diseases The Hebrew University Jerusalem 91120 ISAREL
S.M. Ponomareva Bach Institute of Biochemistry Leninsky Prospekt, 33 Russian Academy of Science Moscow 117071 RUSSIA
Nina G. Prokofieva Pacific Institute of Bioorganic
Chemistry of Far East Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA
583
GuoweiQin Shanghai Institute of Materia Medica Academia Sinica 319 Yue-yang Road Shanghai 200031 CHINA
A. Regoly-Merei Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY
Melchior Reiter lnstitut fur Pharmazie und Lebensmittelchemie
der Friedrich-Alexander-Universitat Department of Pharmaceutical Chemistry D-91052 Erlangen SchuhstraBe 19 GERMANY
R. Riccio Department of Natural Products University of Naples Naples 80131 ITALY
J.G. Roddick Department of Biological Science University of Exeter Exeter EX4 4QG UNITED KINGDOM
Ushiro Sankawa Faculty of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113 JAPAN
Yutaka Sashida SchoolofPharmacy Tokyo College of Pharmacy & Life Science 1423-1, Horinouchi Hachioji, Tokyo 192-03 JAPAN
Elena B. Schentsova Pacific Institute of Bioorganic
Chemistry of Far East Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA
Dirk C. van Setten National Institute of Public Health
& Environmental Protection Department of Molecular Spectroscopy P.O. Box 1 Bilthoven 3720 BA THE NETHERLANDS
584
Fehmeena Shaheen H.E.J. Institute of Chemistry University of Karachi Karachi 75270 PAKISTAN
Baoping Shao Shanghai Inst. of Materia Medica Academia Sinica 319 Yue-yang Road Shanghai 200031 CHINA
O.V. Shelepova N.Y. Tsitsin Main Botanical Garden Russian Academy of Science Moscow RUSSIA
Stepan A. Shvets Institute of Genetics Academy of Sciences Padurii str. 20 Kishinev 277002 MOLDOVA
F. DeSimone Dipartimento di Chimica delle Sostanze Naturali via D. Montesano 49 Napoli 80121 ITALY
P. Skofertsa National Practical Science Center of Hygiene and
Epidemiology of the Health Ministry of the Moldova Republic
N. Testemitianu Chisinau State Medical University Chisinau 2002 MOLDAVIA
S.M. Sokolova N.Y. Tsitsin Main Botanical Garden Russian Academy of Science Moscow RUSSIA
Sean Soltysik Cambridge Biotech Corporation Worcester, MA 01605
K. Spinu National Practical Science Center of Hygiene and
Epidemiology of the Health Ministry of the Moldova Republic
N. Testemitianu Chisinau State Medical University Chisinau 2002 MOLDAVIA
Jan St. Pyrek College of Pharmacy University of Kentucky Lexington, KY 40536
Otto Stieber Department of Pharmacy Swiss Deferal Institute of Technology
(ETH-Z) Zurich 8057 SWITZERLAND
Lybov I. Strigina Pacific Institute of Bioorganic
Chemistry of Far East Division of Russian Academy of Sciences Vladivostok 690022 RUSSIA
Chung Ki Sung College of Pharmacy Chonnam National University Kwangju 500-757 KOREA
J. Szepvolgyi Department of Protein and Vitamin Research Institute of Food-Hygiene and Nutrition Gyali ut 3/a Budapest H-1097 HUNGARY
J.D. Tally Walter Reed Institute of Research Division of Experimental Therapeutics Walter Reed Medical Center Washington, DC 20307-5100
Osamu Tanaka Suzugamine Women's College Inokuchi 4-chome 6-18 Nishi-ku Hiroshima 733 JAPAN
Ryuichiro Tanaka Faculty of Pharmaceutical Sciences Fukuoka University, Nanakuma 8-19-1, Jonan-ku, Fukuoka 814-01 JAPAN
Susan Thiilborg Royal Danish School of Pharmacy Department of Medicinal Chemistry Universitetparken 2, DK-2100 Copenhagen DENMARK
N. De Tommasi Dipartimento di Chimica delle Sostanze Naturali via D. Montesano 49 Napoli 80121 ITALY
Adrienne A. Tymiak Department of Chemistry Columbia University New York, NY 10027
C.V. Uglea Institute of Biological Research Blvd. Copou 20A lassy 6600 ROMANIA
Inessa S. Vasilvera A.N. Bach Institute of Biochemistry Leninskiy pr. 33 Moscow 117071 RUSSIA
V. Vorozhbit National Practical Science Center of Hygiene
and Epidemiology of the Health Ministry of the Moldova Republic
N. Testemitianu Chisinau State Medical University Chisinau 2002 MOLD A VIA
V. Vutkaryov National Practical Science Center of Hygiene and
Epidemiology of the Health Ministry of the Moldova Republic
N. Testemitianu Chisinau State Medical University Chisinau 2002 MOLDAVIA
George R. Waller Department of Biochemistry and Molecular Biology Oklahoma State University 246B Noble Research Center Stillwater, OK 74078-0454
Bethanne Warrack Department of Chemistry Columbia University New York, NY 10027
Gerrit van de Werken National Institute of Public Health
& Environmental Protection Department of Molecular Spectroscopy P.O. Box 1 Bilthoven 3720 BATHE NETHERLANDS
Deborah A. Wheeler Cambridge Biotech Corporation Worcester, MA 01605
J.L. Wofender Institut de Pharmacognosie et Phytochimie Universite De Lausanne BEP, Lausanne-Dorigny CH-1015 SWITZERLAND
Zdzislav A. Wojciechowski Department of Biochemistry Warsaw University 02-089 Warszawa ul. Zwirki i Wigury 93 POLAND
585
Roland Woldanski Department of Biochemistry Warsaw University 02-089 Warszawa ul. Zwirki i Wigury 93 POLAND
Jia-YanWu Cambridge Biotech Corporation Worcester, MA 01605
JunpingXu Pharmagenesis 3183 Porter Drive Palo Alto, CA 94304
Ren-sheng Xu Shanghai Inst. of Materia Medica Academia Sinica 319 Yue-yang Road Shanghai 200031 CHINA
and/or Pharmagenesis 3183 Porter Drive Palo Alto, CA 94304
Shoji Y ahara Faculty of Pharmaceutical Sciences Kumamoto University Kumamoto 862 JAPAN
Johji Y amahara Natural Medicinal Resources Division Research Institute for Production Development Kyoto 606 JAPAN
Kazuo Yamasaki Institute of Pharmaceutical Science Hiroshima University School of Medicine 1-2-3 Kasumi, Minami-ku Hiroshima 734 JAPAN
Chong-Ren Yang Laboratory of Phytochemistry Kunming Institute of Botany Chinese Academy of Sciences Heilongtan, Kunming 650204 CHINA
586
Pei-Ying Yang College of Pharmacy University of Kentucky Lexington, KY 40536
Xin-sheng Y ao Institute of Radiation Medicine, Beijing 27 Tai-ping Road Beijing 100850 CHINA
Sang Sun Y oon College of Pharmacy Chonnam National University Kwangju 500-757 KOREA
Masayuki Yoshikawa Kyoto Pharmaceutical University 5, Nakauchi-cho, Misasgi Yamashina-ku, Kyoto 607 JAPAN
UriZehavi The Hebrew University of Jerusalem Faculty of Agriculture Department of Biochemistry, Food Science,
and Nutrition P.O.B. 12, Rehovot 76100 ISRAEL
NingZhao Department of Chemistry Columbia University New York, NY 10027
WeiminZhao Shanghai Inst. of Materia Medica Academia Sinica 319 Yue-yang Road Shanghai 200031 CHINA
Jan Zimowski Department of Biochemistry Warsaw University Warszawa 02-089 POLAND
LATIN NAME INDEX
Abrus cantoniensis, 267, 271 Abrus precatorius, 271 Acacia auriculiformis, 173, 178 Acanthaster planci, 344 Acebia quinata, 239 Achillea millefolium, 7 Acorus calamus, 198 Aesculus hippocastanum, 5, 83, 85,207-208,
212,471 Agaricus bisporus, 31 Agathis philippinensis, 198 Agava americana, 310,313,323 Agava lecheguilla, 443 Agava sisalana, 3, 11 Agava spp., 11 Agrobacterium rhizogenes, 31 Albizzia julibrissin, 271 Alcyonum spp., 337-338 Aletris farinosa, 7 Allium albopilosum, 101 Allium ampeloprasum, 8, 511 Allium bakeri, 517 Allium cepa, 8, 310, 5ll Allium chinense, 107-108,512,517-518,
521-522 Allium macrostemon, 512-514,521-522 Allium narcissiflorum, 310, 314, 323 Allium porrum, 8 Allium sativum, 4, 8, 511-512, 520-522 Allium schoenoprasum, 8 Allium spp., 511 Allium vineale, 511 Aloe barbadensis, 4 Aloe vera, 4 Alternaria brassicicola, 287 Alternaria solani, 283, 553 Anemoclema glaucifolium, 229 Anthoplexaura dimorpha, 337-338 Arachis hypogaea, 9 Aralia elata, 83-84, 198, 207-208 Aralia racemosa, 7 Arcangelisiajlava, 198 Ardisia crenata, 494 Ardisia japonica, 403-404 Asparagus cochinchinensis, 408-409 Asparagus filicinus, 226-227
Asparagus mairei, 226-227 Asparagus officinalis, 8, 37,41-43,310,
314a,323 Asparagus plumosus, 37,41-43,45 Aspergillus fumigatus, 233-234 Aspergillus niger, 30, 31,536,565 Aspergillus spp., 120 Aspergillus wentii, 552 Aster scaber, 297, 299-301 Aster spp., 297 Aster tataricus, 297 Asterias amurensis, 342 Asterina pectinifera, 347-348 Asteropus sarasinosum, 335-336 Astragalus complanatus, 271 Astragalus falcatus, 83-84, Astragalus melanophrurius, 495 Astragalus membranaceus, 5, 225 Astragalus oleifolius, 495 Astragalus sinicus, 271 Astropecten indicus, 350 Atriplex canescens, 12 Atropa belladonna, 310,475,477,481-482 Aucuba japonica, 26 Avena longiglumis, 549 A vena sativa, 8-9
Bacillus subtilis, 328, 368 Bacteroides JY-6, 29-32, 35, Bacteroides fragilis, 27 Beshorneria yuccoides, 310 Beta vulgaris, 9, 208 Bifido-bacterium pseudo-longam, 27 Bifidobacterium breve, 27 Biomphalaria glabrata, 119-121, 152, 161,
426 Biomphalaria pfeifferi, 425-426 Blumea balsamifera, 198 Borago officinalis, 7 Borrelia burgdoiferi, 165 Botrytis cinerea, 553 Brachiaria decumbens, 443 Bufo spp., 219 Bulinusforskalii, 426 Bulinus globosus, 119, 425-426 Bupleurumfalcatum, 7, 28,30
587
Bupleurumfruticosum, 403,405
Caesalpinia sapan, 198 Caldocellum saccharolyticum, 30-31, Calendula arvensis, 403,404,407-408 Calendula officinalis, 5, 83-84, Caltha silvestris, 239 Camelliajaponica, 207-208, 213 Camellia sinensis, 9 Candida alba, 327 Candida albicans, 120, 233-234, 418, 565 Candida guilliermondii, 565 Candida krusli, 327,565 Candida lipol., 327 Candida parapsilosis, 565 Candida pelliculosa, 552 Candida pseudotropicalis, 565 Candida rugosa, 327 Candida tropicalis, 327, 418, 565 Candida utilis, 327 Capsicum annuum, 10,253,310,323, 325,
332 Capsicum frutescens, 10 Cassia tora, 30 Caulophyllum robustum, 239, 242 Caulophyllum thalictroides, 7 Centella asiatica, 6 Cephalosporium gramineum, 565 Chamaelirium luteum, 7 Charonia lampas, 347-348 Chenopodium quinoa, 9 Chlorogalum pomeridianum, 11 Chlorophytum malayense, 226, 228-229 Cicer arietinum, 9 Cimicifuga racemose, 6 Cinchona spp., 402 Cinnamomum mercadoi, 198 Citrullus vulgaris, 30, 198
· Cladosporium carrionii, 418, 420 Cladosporium cladosporioides, 420 Cladosporium cucumerinum, 120-121,420,
425 Cladosporium spp., 120 Cladosporium tenuissimum, 418,420,425 Clematis chinensis, 371, 373, 381 Clerodendrum wildii, 121 Codonopsis pilosula, 5 Codonopsis spp., 5 Codonopsis tangshen, 5 Coleus forskolii, 196 Cordia myxa, 198 Coriolus consors, 31 Coriolus versicolor, 31 Corticium rolfsii, 282 Corynebacterium sepedonicum, 283 Coscinasterias tenuispina, 344 Costus speciosus, 57, 59-62
588
Crataegus spp., 6 Crocosmia crocosmiiflora, 459-460, 464,
469 Crocosmia masoniorum, 459,464-465, 46~ Crotalaria albida, 271 Cryptococcus neoformans, 535,538,541,
543 Cucumaria echinata, 563 Cucumaria japonica, 557 Cucurbita moschata, 198 Culcita novaeguineae, 344 Cyclamen coum, 489,491-492,494 Cyclamen mirabile, 489,491,492
Dalbergia hupeana, 271 Datura stramonium, 310 Decaisnea fargesii, 229 Desmodium styracifolium, 271 Digitalis barbasco, 11 Digitalis deltoidea, 11 Digitalis lanata, 11 Digitalis macrostachya, 11 Digitalis purpurea, 1, 11,219,310,323,
325,332 Digitalis spiculiflora, 11 Digitalis tokoro, 11 Dioscorea batatus, 30 Dioscorea caucasica, 323 Dioscorea composita, 2, 11 Dioscorea deltoidea, 15-21, 83-84 Dioscorea floribunda, 2, 11, 59 Dioscorea mexicana, 2, 11 Dioscorea nipponica, 16, 18, 83-84 Dioscorea spp., 3, 10, 11, 15 Dioscorea terpinapensis, 11 Dioscorea tokoro, 30 Dioscorea villosa, 4 Diospyros kaki, 30 Diuranthera major, 226, 229 Dolichos kilimandscharicus, 120 Dolicusfalcata, 536 Dracaena arborea, 415,417,425 Dracaena mannii, 415-417 Dracaena spp., 415-426 Duasmodactyla kurilensis, 340-341
Echinaster sepositus, 342 Echinaster spp., 344-346, 353 Ejretia microphylla, 198 Eleutherococcus senticosus, 5 Entada phaseoloides, 198 Enterobacter cloacae, 31 Epidermophyton floccosum, 541 Equisetum arvense, 5 Eriobotrya japonica, 201 Escherichia coli, 328, 507
Eubacterium spp., 26, 28 Eupatorium perfoliatum, 1, 557 Eupentactafraudatrix, 340-341, 561 Exophialajeanselmei, 418
Fonsecaes pedrosoi, 418,420 Fritillaria camtschatcensis, 103 Fritillaria persica, 103 Fritillaria spp., 102 Funkia norata, 323 Funkia ovata, 310, 315, 316 Fusarium caeruleum, 283 Fusarium graminearum, 331 Fusarium oxysporum, 282-283, 536, 553, 565 Fusarium sambucinum; 283 Fusarium solani, 281, 283
Gaeumannomyces graminis, 548, 551, 565 Galega o.fficinalis, 7, 502 Gardenia ternifolia, 383 Geotrichum candidum, 418,565 Ginkgo biloba, 198 Glechoma hederacea, 198 Gleditsia japonica, 91, 93 Gloeoesporium frutctigenum, 282-283 Glycine max, 9, 208,502 Glycyrrhiza glabra, 3, 5, 12, 83-84 Glycyrrhiza spp., 27 Glycyrrhiza uralensis, 83, 84, 225, 371 Guaiacum o.fficinale, 9 Guettarda angelica, 390 Guettarda platypoda, 390, 402, 407-408 Guettarda spp., 402 Gymnema sylvestre, 7, 208 Gymnocladus chinensis, 92-93 Gynostemma pentaphyllum, 131, 405-406 Gypsophila paniculata, 12 Gypsophila spp., 12
Halityle regularis, 344 Hedera helix, 5 Heinsia crinata, 374 Helianthus annuus, 9 Heliothis zea, 284 Helix pomatia, 16 Heloniopsisjaponica, 272 Hemsleya macrosperma, 131 Henricia downeyae, 344, 352-353 Henricia laeviuscola, 344, 353 Hovenia dulcis, 208 Hydrangea arborescens, 7 Hydrocotyle asiatica, 6 Hyposoter exiguae, 284
/lex paraguariensis, 7
Klebsiella pneumoniae, 27 Kochia scoparia, 208
l.agerstroemia speciosa, 196, 198, 200-201 l.agotis stolonifera, 486 Larrea tridentata, 7 l.asiorhinus latifrons, 449, 451 Lebistes reticulatus, 529 Leishmania chagasi, 421 Leishmania donovani, 423 Leishmania panamensis, 423 Lens culinaris, 9 Leontice eversmanni, 435 Leptadenia hastata, 410-412 Leptinotarsa decemlineata, 283 Lilia henri, 310 Lilium pardarinum, 102 Lilium regale, 310,317-318 Liriope japonica, 225 Liriope platyphylla, 30 Lithospermum erythrorhizon, 41 Luidia clathrata, 342 Lupinus polyphyllus, 271 Lycopersicon esculentum, 10, 72,310,323,
326,332,505 Lymnaea natalensis, 426 Lyophyllum fusosum, 31
Manihot esculenta, 10 Marthasterias glacialis, 344 Medhuca butyracea, 237 Medicago arabica, 566,569-571 Medicago blancheana, 566,569-570 Medicago carstiensis, 566, 569-570 Medicago ciliaris, 566, 569-570 Medicago disciformis,.566, 569-571 Medicago doliata, 566,569-571 Medicago granadensis, 566, 569-570 Medicago heyniana, 566,569-571 Medicago hybrida, 566, 569-570 Medicago intenexta, 566,569-570 Medicago laciniata, 566, 569-571 Medicago lupulina, 536, 566, 569-570 Medicago minima, 566,569-570 Medicago murex, 566, 569-571 Medicago muruioleptis, 566, ·569-570 Medicago noeana, 566,569-571 Medicago polyceratia, 569-571 Medicago polymorpha, 566,569-570 Medicago praecox, 566,569-570 Medicago radiata, 566, 569-570 Medicago rotata, 566, 569-570 Medicago rugosa, 566, 569-570 Medicago sativa, 6, 9, 536, 565-567, 569-
571
589
Medicago sauvagei, 566, 569-571 Medicago scutellata, 566, 569-570 Medicago soleirolii, 566, 569-570 Medicago spp., 567-571, 573 Medicago tomata, 566, 569-570 Medicago truncatula, 566, 569-570 Medicago turbinata, 566, 569-570 Melilotus alba, 10 Melilotus officina/is, 10,310 Micoides citreum, 328 Microsporum audouinii, 418 Microsporum canis, 541 Microsporum grpseum, 418 Millettia spp., 10 Mitchella repens, 7 Momordica charantia, 198 Morinda Iucida, 383 Morus alba, 198 Muriceafruticosa, 336-337 Mussaendapubescens, 371-373,381 Myristica fragrans, 9
Nauclea diderrichii, 383, 385-386, 389-390, 392-393
Nauclea latifolia, 383 Nauclea orienta/is, 198 Nicandra spp., 264 Nicotiana plumbaginifolia, 285 Nicotiana rustic a, 310 Nicotiana tabacum, 310 Nigerian dracaena, 416 Nolina recurvata, 105-106 Nomuraea rileyi, 284
Ophipogon maglanthus, 226-227 Oplopanax elatus, 84 Oreaster reticulatus, 351 Oreosolen wattii, 237 Omithogalum saundersiae, 103-104, 108 Orthosiphon stamineus, 83-84
Pachastrella spp., 335 Paeonia lactiflora, 24 Paeonia suffruticosa, 24 Panax ginseng, 5, 84, 94-95, 97, 129, 132,
198,202,225,371 Panax japonica, 94-95,202,208 Panax notoginseng, 5, 94-99, 129, 132, 138,
202, 225-226 Panax pseudo-ginseng, 202 Panax quinquefolius, 3, 5, 129, 132, 202 Panax spp., 129, 131-132, 136, 138, 144,
202 Panax vietnamensis, 131-132, 138, 147,202 Panax zingiberensis, 202 Pandanus sp., 198
590
Panicum coloratum, 443 Panicum dichotomiflorum, 443 Panicum schinzii, 443 Pardachirus marmoratus, 338 Pardachirus pavoninus, 338 Pardachirus spp., 335 Passiflora incamata, 6 Patiria miniata, 344 Paullinia cupana, 6 Pavetta crassipes, 383 Peliosanthes sinica, 226-227, 229 Penicillium spp., 120 Pentacta australis, 340, 341 Peptostreptococcus intermedius, 27 Petunia hybrida, 251, 261, 310,480 Pfaffia paniculata, 5 Phaseolus aconitifolius, 9 Phaseolus acutifolius, 9 Phaseolus angularis, 9 Phaseolus aureus, 9 Phaseolus coccineus, 9 Phaseolus lunatus, 9 Phaseolus mungo, 9 Phaseolus vulgaris, 9 Phialophora verrucosa, 418 Phoma exigua, 283 Phoma medicaginis, 288 Physalis spp., 264 Phytolacca americana, 7, 487 Phytolacca dodecandra, 118-119, 125-126,
151-156, 160-161 Phytolacca spp., 152-153 Phytophthora cinnamomi, 536, 565 Phytophthora infestans, 21, 282-283, 324 Phytophthora spp., 281, 548 Pisum sativum, 9 Plasmodiumfalciparum, 385, 388, 394-397,
417,420 Pleurotus ostreatus, 31 Polemonium coeruleum, 83, 84 Polygala senega, 6, 207-208, 214 Polygonatum biflorum, 7 Polygonatum kingianum, 225-227 Polygonatum latofolium, 310, 327 Polygonatum multiflorum, 7 Polygonatum officinale, 7 Polygonatum pratti, 226-227 Primula elatior, 6 Primula officina/is, 6 Primulaceae auriculata, 487 Primulaceae elatior, 487 Primulaceae longipes, 487 Primulaceae megaseifolia, 487 Primulaceae veris, 487 Protoreaster nodosus, 344 Prunus armeniaca, 30
Prunus persica, 30 Prunus salicina, 30 Pseudoplexaura wagenaari, 337-338 Psolusfabricii, 340-341,557 Pueraria lobatta, 9, 266, 268, 271 Pueraria thunbergiana, 9 Pulsatilla campanella, 229 Pythium aphanidermatum, 536, 565 Pythium spp., 280, 548
Quercus alba, 5 Quillaja saponaria, 9, 12, 165, 167, 170,
185-191
ftamichloridium subulatum, 418, 425 Rapanea melanophloeos, 120-121 Rheum officinale, 25 Rheum palmatum, 25 Rheum spp., 25 Rhinanthus spp., 27 Rhizoctonia solani, 283, 536, 565 Rhizopus mucco, 536 Rhodotorula glutinis, 565 Rhodotorula spp., 418 Robinia pseudo-acacia, 271 Rosa canina, 6 Rubus fruticosus, 9 Ruscus aculeatus, 4, 1 04
Saccharomyces cerevisiae, 327 Saccharomycopsisfibuligera, 527, 552 Sapindus mukurossi, 12, 208, 211 Sap indus rarak, 12 Sapindus saponaria, 12 Saponaria officinalis , 12 Saprolegnia asterophora, 368 Sarcina lutea, 328 Schistosoma haematobium, 118 Schistosomajaponicum, 118 Schistosoma mansoni, 118 Schistosoma spp., 285 Scilla peruviana, 104, 107, 108 Sclerotium rolfsii, 536, 565 Scrophularia ilwensis, 486 Scrophularia spp., 486 Septaria lycopersici, 553 Sesamum indicum, 9 Setaria cervi, 177 Sinularia crispa, 337, 338 Smilacina racemosa, 7 Smilax aristolochiaefolia, 4, 8 Smilax febrifuga, 8 Smilax officinalis, 8 Smilax regelii, 8 Solanum abittiloides, 264, 266 Solanum achrolcucum, 264
Solanum aculeatissimum, 264 Solanum aethiopicum, 264 Solanum anguivi, 264 Solanum arundo, 286 Solanum bijlorum, 264 Solanum chacoense, 264, 283 Solanum cynathem, 264 Solanum demissum, 264 Solanum dubium, 286 Solanum dulcamara, 7, 263,264, 285 Solanum ferox, 263 Solanum gila, 264 Solanum incanum, 282 Solanum indicum, 264 Solanum integrifolum, 264 Solanum japonense, 264 Solanum jurpeva, 264 Solanum khasianum, 264 Solanum laciniatum, 47 Solanum lycocarpum, 264 Solanum lycopersicum, 10 Solanum lyratum, 263,264 Solanum macrocarpon, 264 Solanum mammosum, 264 Solanum melongena, 10,37-39,41-43,47,
264,310,319-321,327 Solanum nigrum, 263-264 Solanum paniculatum, 264 Solanum sanitwongsei, 264 Solanum sisymbrifolium, 263 Solanum sodomaeum, 285 Solanum spp., 47,285-286,445 Solanum stramonifolium, 264 Solanum surattense, 264 Solanum torvum, 264 Solanum toxicarium, 264 Solanum tuberosum, 10, 47, 71,264,310 Solanum vanhuerchii, 264 Solanum verbascifolium, 264 Solanum viarum, 264 Solanum xanthocarpum, 264 Solidago canadensis, 5 Solidago serotina, 5 Solidago virgaurea, 5 Sophora flavescens, 271, 503 Sophora japonica, 501-503 Sophora subprostrata, 271 Sorghum bicolor, 30 Spinacea oleracea, 9 Staphylococcus aureus, 328 Stellaria media, 5 Streptomyces scabies, 283 Strophanthus gratus, 219 Swartzia madagascariensis, 119, 123, 124 Symphytum officinale, 7, 429-431, 436, 439-
440
591
Tamus communis, 408-409 Taraxacum officinale, 5 Taxus cuspidata, 198 Tenebrio molitor, 529 Tetrapleura tetraptera, 119, 122, 124-125 Thalictrum spp., 273 Thea sinensis, 9, 208 Tinospora cordifolia, 198 Tinospora rumphii, 198 Torulopsis candida, 565 Torulopsis glabrata, 538, 565 Tremaster novaecaledonia, 350 Tribulus cistoides, 357, 358, 362-363, 367 Tribulus terrestris, 83-84, 310, 323, 329,
357 Trichoderma koningii, 530, 532 Trichoderma pseudokoningii, 530, 532 Trichoderma reesei, 530, 532, 552 Trichoderma viride, 527-530, 532-534, 536-
567,569,571 Trichophyton mentagrophytes, 233-234,
418,535,538,541 Trichophyton rub rum, 418 Trichophyton soudanense, 418, 425 Trichophyton tonsurans, 418 Trichosporon cutaneum, 418 Trichosurus vulpecula, 449 Trifolium pratense, 6 Trifolium repens, 63 Trigonellafoenum-graecum, 4, 8, 310,444 Trillium erectum, 7
592
Trillium spp., 7 Triplostegia grandiflora, 229 Tubocapsicum spp., 264 Tupistra wattii, 226-227
Uncaria guianensis, 390, 402 Uncaria tomentose, 6, 390,402,407-408
Verbascum thapsus, 7 Verticillium albo-atrum, 283, 324, 326, 553 Vibrio vulnificus, 31 Vicia faba, 9 Vigna aconitifolia, 9 Vigna angularis, 9, 208, 502-503 Vigna radiata, 9 Vigna sinensis, 9 Vigna umbellata, 9 Viola tricolor, 84 Vitex negundo, 198 Vombatus ursinus, 449-450, 453
Wistaria brachybotrys, 87-90, 271 Withania somnifera, 7
Yucca brevifolia, 4, 11 Yuccafilamentosa, 310, 322, 325 Yucca gloriosa, 83-84 Yucca mohavensis, 11 Yucca schidigera, 4, 11
Zizyphus jujuba, 9
SUBJECT INDEX
Abrisapogenols, 265-268 Abrisaponin I, 268-269 Abrisaponins, from Abri Herba, 269 Abutiloside A, 266 Acaciasides, 174-176, 178-182 Acacic acid lactones, 17 4-17 5, 177, 179-
180 Acacigenin A, 175-177, 181-182 Acetylcholinesterase, 281 Acetyllycopsamine acetylintermedine
(diasteroisomers), 430 Acovenosigenin, 220 Acrosome reaction, 342 Acute gastroenteritis, 371 Aculeoside A, 104-105 Acyl group in crocosmiosides, 469
enhanced inhibiting activity, 469 26-0-Acylated furostanol saponins, 102 Adjuvant activity of QS-21, 171 Adriamycin, 108,233 Adzukisaponins, 502-503 Aescin (see escin), 527, 533 Afromosin, 89-91 Agave, 4, 11 Agavosides
conversion, 310-313 hypocholesterolemic activity, 312-
313,325 fungicidal activity, 325
Aglycone distribution from Medicago spp., 570
AJ[)S, 120,535,416 AI+3 82-83 Alcoholism, treatment with saponin drugs,
207-215, 266-267 Alfalfa, 535
herbs, 472 juice, 528 meal, 528 plant resistant to molds, 527 roots, 472 saponins with antimycotic activity, 535 seed, 472
Alkannin, 430 Allelopathic activity, 324
Alliumosides, 310, 314, 323 Aloeresin, 26 Aloesin, 26 American ginseng, 129 Ames test, 154 cAMP phosphodiesterase inhibition, 101,
107-108 2H-cAMP incorporation, 241 3H-cAMP uptake, 245 Amphotericin B, 233-234, 544 Anaemia, 429 Anagalligenin, 488-489 Analgesic, 240, 373, 429, 495 Analysis of plant extracts for saponins by
LC (HPLC) and mass spectrometry, 121-127
Anemoclemosides, 230-231 Anthraquinone, 25 Anthrone glycosides, 25 Anthroquinone and anthrone glycosides,
25-26 Antiacetylcholinesterase activity, 277 Antiallergic, 27 Antiarthritic, 4-6, 208 Antibacterial activity, 324, 328, 423 Antibiotics, 535 Antibody response, 168 Anticancer agents ,1, 12, 99, 109,263,
289,410 Antidiabetic response, 101, 198, 208 Antifertility, 475,494 Antifilarial activity of saponins, 173, 177-
178 Antifungal activity of steroid saponins,
233, 286-288, 324-326 Antifungal compounds, 12, 120, 233-234,
368,416,475,511,535,557,565 extracts of fruit pulp, 425
Antiinflammatory, 1, 4-6,27-28, 173,212-213,240,373,381,402,404,429-430, 487,495
Antiedematous, 212 Antileishmanial activity, 415, 420, 423 Antimalarial activity, 392,415,417 Antimicrobial, 111, 251, 415, 420, 423,
475
593
Antimycotic, 535, 544 Antioxidative properties, 251, 324, 329,
475 Antiperspirant, 268, 495 Antiphlogistic, 25, 371, 381 Antiprotozoal, 416 Antipyretic, 268, 371,381,404 Antirheumatic, 4-5 Antiseptic, 429 Antispasmodic, 268 Antithrombotic agents, 511 Antitumor activity, 98, 101, 111, 119,251,
263,285,311,373,402,411,430 of cholestane glycosides from
Omithogalum saundersiae, 108-109 of clinically used anticancer agents,
109 promoting activities of triterpenoid
glycosides, 87-99 of Solanum species, 263-264, 285 of steroid saponins from Moldovian
plants, 311-312 of tomatoside modified by oxidation,
114-116 water extract of gladiolus corms, 459
inhibitors, 101 Antitussive inhibitors, 101 Antiulcer, 27 Antiulcer properties, 27, 429 Antiviral activity, 28, 37, 111,402, 505-
509 agents, 115 chemotherapy, Ill effect, 324 Human Immunodeficiency Virus
(HIV), 407 in vitro, 407, 505 in vivo, 505 of interferons, 506 of steroidal glycosides, 324 of tomatoside, 506, 508 of tomatoside modified by oxidation,
111-112, 114-116 varicella-zoster virus, 407
Antiyeast activity, 327 API mass spectrometer, 127 Ardisicrenosides, utero-contracting, 494 Arvenin, 486 Aspafiliosides, 234 Asparagosides, 310, 323, 325 Asterogenic acid, 297 Astersaponins, 297, 300, 342, 344 Asthma, 429 Astragalosides, 495 Astrasieversianin, 495 Astringent, 5 Atroposides, 310,476-477,479,482 Aucubin and degradation products, 26-27
594
Avenacin, fungal activity, 548-550 A venacinase
determinant of pathogenicity, 552 ~-glucosyl hydrolases, 552 gene isolation, 550, 552
Ayurvedic medicine, 357 Azoles, 535
Bacteroides QY-6 ~-glucosidase activity for various saikosaponins, 32 gene, cloning, 32-33 localization of, 33 transformants of, 33-35
Bacteriostatic activity (bacterioside), 415, 521
Banaba, as source of glucose transporter, 200-201, 204-205 antidiabetic, 200 tea leaves, 204
Barbaloin, 26 Barley seed, 453 Bayogenin, 152, 156 Baytan, 331 Benzoylation and naphthylation of sugar
moieties, 221-222 Bergenin, 26 Beshomosides, 210 Bilayer lipid membrane, 241 Bioautography for fungicidal saponins,
120 Biochemical characteristics for rats
after horse-chestnut saponins administered, 473
Biosynthesis of steroid glycosides by Dioscorea cells, 18-21
Birinetorenol, 82 Bisdesmodic forms stored as
inactive form, 547 Blood coagulation, 524, 525 Blood ethanol concentration, 208, 210 Blood hemolysis, 529 Bovine hypothalamus, 220, 221 Brasiliensoside, 345 Broad-spectrum antibiotics, 535, 538 Bronchitis, 429 Buddlejasaponins, 230, 235 Bufalin, 219 Bums,429 Butyrosides, 230, 235, 237 45Ca2+ uptake, 241, 245
Caffeic acid, 430 Calorimetry, 240 Camelliasaponins, 207, 213-214 Camptothecin, 1 08 Cancer, skin, 2859 Cancer chemopreventive agents, 87, 99 Candidiosis, 535 Capillary-protective properties, 212
Capsicosides, 253,310,323,325 effect on sex ratio in cucumber plants,
330 effect on yield of apple trees, 330
13-Carbolines, 383 Carbon tetrachloride, 267 Cardenolides, 104, 219-220 Cardiac glycosides, 108 Cardioactivity
dependance on carbonyl group at C-12, 368 on sugar moiety, 368
Cardiotonic glycosides, 6, 223,426 Cardiovascular diseases, 6, 471 Cardiovascular drug
adenosine, 524 blood coagulation, 524 platelet aggregation, 524 fibrinolysis, 524 steroidal saponins, 524
Casein, 453 Caulodiac glycosides, 219-223 Caulosides, 230, 235, 239, 242 Cardoside C
cytotoxicity, 240, 243-244 effect on 45Ca2+ uptake, 241, 245-247 effect on cell membrane, 241-242,
244-248 effect on cell proliferation, 242, 247 effect on [3H]-CAMP uptake, 241,
246 . effect on microviscosity of liposomal
membranes, 241,244-245 formation of pH-dependent channels,
239-248 hemolytic effect, 240, 242-243
+ . K release by cells, 241-243 structure, 239
Carotene, 10 Cayenne peppers, 10 Cell cultures
Dioscorea spp., 15 Cell proliferation determination, 242, 247 Cellobiose, 549, 552 Cell membranes effects of cauloside C,
240 Central nervous system depressant activity,
173 CER cell cultures, 407 Ceveratrum alkaloids, 103 CF-FAB LC-MS, 124 Chaconine,47,265,278,280,286-289 Channels formed by cauloside C, 247-248 Chemical carcinogenesis mechanism, 87,
99 Chemical defense agents, 282,338,342 Chemotaxonomic significance of steroid
saponins, 129,229,237
Chemotherapy, 425,538 Chestnut saponins, 530 Chikusetsusaponins, 203-204, 209-210 Chinenosides, 517-520, 522, 525 Chinese traditional medicine, 23, 28, 81,
91-92,202,207-208,225,371 Chlorambucil, 285 Chlorogenic acid, 430 Chlorogenin, 522 Chloromalosides, 228-229, 233, 234 Cholegenic and novel bile acids
Australian opossum, 449 Wombats, 449
Cholegenic acid methyl ester, 452 Cholegenin 444, 453 Cholestane bidesmosides, 105-106 Cholestane and lanostane glycosides,
rearranged, 103-104 Cholestane-type glycosides, 363 Cholesterol, 10-11, 19, 49, 53-54, 71, 78
biosynthetic intermediate, 19 level of serum, 456
Chronic alcoholics cyanamide,207 disulfiram, 207
Chronic wounds, 429 C/D-cis-polyoxypregnane esters and
glycosides, 410 cytotoxic, 410 tumoricidal, 410
Cisplatin, 108 Cistocardin, 258,361-362,367-368
cardioactive, 360 Clofibrate, 207 Cloning of avenacinase gene 13-
glucosidase, 551 from bacteriosides JY -6, 32 hydrolysis mechanism of saikosapon-
in-c, 30 Clotrimazole, 233, 234 Co+3, 81,83 Cold, common, 429 Comfrey, 429 Commercial utilization of saponins, 1-14 Compartmentalized in plant cell
convert plant glycosyl hydrolases, 548 monodesmodic forms, 548
Complex with membrane sterols, 547 Concavalin, 60 Consolicin, 430 Consolidin, 430 Constipation, 25 Contraceptives, 2-3, 5, 15, 324 Contusion, 404 Conversion of protodioscin
to dioscin, 59 to coprostanol, 444
Coronilla plant resistant to molds, 527
595
Corosolic acid, 200-201 Corticosteroids, 15, 426 Cortisone, 426 Q-+3, 83-84 Critical micellar concentration (CMC), 170 Crocosmioside, 459-460, 468 Crude starfish extracts Cryptococcosis, 538 eu+2, 83-84 Cucumariosides, 340-341, 557, 559-561
desulfated derivative, 557 Cucumber, effect ofpetuniosides on, 257-
259 Cucurbitacin glycosides, 487 Curaderm,285,289 Custom-made saponins within plants, 289 Cuvier's tubules, 340 Cyclacoumin, 490, 492 Cyclamin, 490, 492 Cyclaminorin, 490, 492 Cyclamiretin, 404,491 Cycloartane-type saponins, 273 Cycloartane-type triterpenoid glycosides,
495 Cyclocanthoside, 495 Cytochalasin B, 196 Cymarose, 410 Cytoplasmic leakage, 426 Cytoprotective effect
carbon tetrachloride-induced hepatic injury, 208
Cytosensor®, 415,423 Cytostatic activity, 37, 109, 233
cholestane glycosides with acyl groups, 108
Cytotoxic T lymphocyte response, 165 Cytotoxicities, 234, 243, 265
of acylated saponins, 468 of dioscin, protodioscin, and a-
chaconine, 265 of embryos, 240 of modified tomatosides, 114 of sea urchin eggs, 240 of solamargines and solasodine, 265 of spirostane glycosides, 409 of steroid saponins, 233-234
D-Cymarose, 410
Dammar resin with triterpenes from trees and resinous exudates, 144
Dammarane saponins, 95, 129-133, 136, 138-139,141,143-144,147,235,237,
406 biogenesis, 130, 144-147
Daturosides, 210 Deacetylmetaplexigenin, 410 Decaisosides, 230 Decne,410 Deglucocyclamin dodecaacetate, 491 Deglucocyclamin, 490, 494
596
Dehydrosoyasaponin, 89,269 Delphinidin acid, 430 Deltonin, 233, 234 Deltoside, 16-21 Deltostim, 21 Demissine, 281 Demissidine, 78 2-Deoxy-D-glucose (2-DG), 197-199 201-
205 ' 5-Deoxyisonodoside, 349-350 DEPT,389 pH-Dependency on
cauloside C, 239 Dermatiaceous fungi, 420 Dermatophytes, 538
infections of hair, nail, and skin 425 535 ' '
Desacylcamelliasaponin, 213 Desacylcrocosmioside, 461,465, 468 Desacylescin, 212 Desacylmasonoside, 465,468 Desacylsaponin from QS-21, 167-168
characterization, 167-168 lack of antibody stimulation, 168-170
Desacylsenegasaponin, 214 Desacylsenegin, 214 Designer saponins, 10, 12 Detergents, effects on enzymes, 51-52,54
in the textile industry, 11 D~toxication mushroom poisons, 371, 381 Dtabetes, 495 Diaphoretic, 371, 381 Diarrhea, 371 Diazomethane degradation, 189 449 Diderroside, 383 ' Dietary origin, 453 Digitonins, 323, 325 Digitoxigenin, digoxigenin, 215-220 2~,23-Dihydroxyacacic acid, 93 Dimethylbenz[ a ]anthracene, 90 Dimorphosides, 337 Dioscin, 57, 233, 408 Dioscine, 57-58, 65, 265, 323 2,6-trans-2,6-Dimethyl-8-hydroxyoctane-
2,6-dienoic acid, 174-175 Dioscorea, 2-4, 10-11,30, 82
cell cultures, 15-21 Diosgenin, 2-3, 11, 15-18, 20, 37-39,47-
54,57,66,82,310,409,443,475,479-480 progesterone, 2
Diosgenin glycosidic peracetate, 481 Disruption of membrane systems
a-chaconine and a-solanine, 280 Diuranthoside, 228, 229, 233-235 Diuretic, 5, 6, 91, 240, 371, 373, 381, 495 Diversity of Southwest China for saponins
225 ' Drug development
thoracic pain, 525
stenocardia, 525 heart asthma, 525
Drug permeation enhancement, 170 N-Docosanoyltyramine, 258, 369
Eagle's culture medium, 507 Echimidine, 430 Echinocystic acids, 93, 119, 297-298 Ecostim®, 332 Eczema, 429 Edema, 371 Effect on isolated guinea-pig atria, 435 Effect on isolated guinea-pig ileum and rat
uterus, 435 Eggplants, 10 Ehrlich ascites tumor (EAT), 196-197,
199,201,204-205,244 Ehrlich reagent, 476 Elatosides, 207-210 Elemental composition of plants
synthesizing saponins, 83 Emetic, 497 Emulsification agents, 11 Endod, 151, 157, 160-161 Endod plant, 118, 426
berries, 161 endod S, 153 molluscicidal saponins, 151 pericarp, 153 seeds, 153
Enzymes activity as a-rhamnosidases and ~-
glucosidases of bacteria, 31 commercial, 31 , 66 crude hesperidinase, 463-464 glycosylation oftomatidine, 71-79 of higher plants, 30 of hydrolysis, 34, 450 of mushrooms, 31, 35 naringinase, 461, 464
Eosin, 242 3-Epidigitoxigenin, 220 Epiosarsapogenin, 444 Epi-smilagenin, 444
~-D-g1ucuronide, 443 Epstein-Barr virus, 87-89, 93-96 Ergosterol, 532-534
fatty acid composition, 533 without saponin, 530 with saponin, 530
Eruboside, 521 Erylosides, 336 Erythrocyte K +
loss of, 559 dependence on the sulfate group in the
carbohydrate chain, 559 presence of the 3- 0-methyl group in a
terminal monosaccharide required, 559
Escape reaction, 340 Escins, 207, 212-213, 527, 533 Esculentoside, 487 Ethanol absorption, inhibition, 210-215
by methanol extracts of natural medicines, 208
by saponins, 207-215 Eukaryotic organisms, 279 Exciton-coupled circular dichroism, 221 Exogenously added sterols and fatty acids
fungal membrane composition, 532 Expectorant, 5, 6, 91, 92, 487
mollusks, 340 sea anemones, 340 sea urchins, 340 starfishes, 340
Extract of Panax notoginseng, 97-99
FAB~S, 189,388,404,459,465,467 FAB MS~S, 189 Fascioliasis, 426 Fast atom bombardment (FAB), 123 Fatty acid composition
saponin-sensitive, 531 nonsensitive trichoderma strains, 532
Fatty acid domain of QS-21, 166-171 fu+3, 81,83-84 Feeding furostanol saponins
dogs, fecal excretion, 444 epi-srnilagenin, 444 epi-sarsapogenin, 444 srnilagenin, 444 diosgenin, 444 gitogenin, 444
Feeding-deterrent properties, 342 Fermentation, 3 Fever, 383 Fibrinolysis, 524, 525 Fire extinguisher, 11 Fish poisons, 431 Fish test, 529 Flavor agent, 4, 5 Flavor-modifying substances, 1 Fluconazole, 233-234 Foaming agent
baked goods, 185 beverages, 185 confectionery, 185 dairy desserts, 185
Foetidissimoside, 299-301 Food and beverage plants containing
saponins, 8-10 Formononetin, 81 Forskolin, 196-198, 204 Fouling, 336, 342 Fragmentation product of
elucidated sugar sequences, 127 Froth forming, 101 Fruit extract of S. japonica, 501 Fructose, 107
597
Fungicidal activity, 21, 37, 111, 117, 120, 251,281,415,475,487,527,529-530, 565 plant pathogens, 535 human dermatophytes, 535 medically important yeasts, 535
Funkiosides, 210,233,234,315,316 Furostanol glycosides
26-0-acylated, 102 biological activity, 21 biosythesis, 20 conversion to spirostanol glycosides,
312 from various plants, 314,316,321 26-0-~-glucosidases (E-26G)
assay, 59 occurrence, 60-61 properties, 60-61, 66-68 purification, 61-63 specificity, 64-66
substrate specificity, 64, 65 N-terminal amino acid sequence, 63-64 tetraglycosides, 409
Garlic, 520 Gastrointestinal absorption
inhibition, 10 Gastrointestinal indigestion, 25 GenBank, 552 Gene disruption, 551 Geniposide and relatives, 27 Ginseng, 225
extract, effect on 2-DG uptake, 202 saponins, 205 varieties, 202
Ginseng extract, 207 Ginseng root, 472 Ginsenosides, 95-97, 130-133, 135, 146,
202-205,232-233,235,237 Gi taloxigenin, 219-220 Gitogenin, 252-254,255-256, 310,323,
325,44 Gleditsia saponins, 92-94 Glucose transport systems, 195-205
inhibitors, 196 location, 195
~-Glucosidases, 23 converter furostanol glycosides to
spirostanol glycosides, 57 Glucosylrheinanthrone, rheinanthrone,
rhein, 25-26 ~-D-Glucuronides
hepatic formation, 444 GLUT family, 195 Glycoalkaloids, steroid, 10, 47, 54, 277-
289 consequencesforhumans,284-285
mechanism, 279-281 symptoms, 280
create 'pores' in membranes, 280
598
inhibitors of acetylcholinesterase, 281 role in chemical defense, 282-283 structures, 278 synergistic interactions, 286-289 toxicity, 279-282, 284
Glycosidases, 348, 402 Glycosidases converting natural glycosides
to bioactive compounds, 23-35 Glycyrrhiza, 82 Glycyrrhetic acid, 82, 89-90, 94, 96-97 Glycyrrhizin, 407
glycyrrhetyl monoglucuronide, g1ycyrrhetic acid, 27-28
Gomophioside, 349-350 Gracillin, 57-59, 66, 330,409 Granulatoside, 349-350 Green peppers, 10 Growth-enhancing ability of plants
petuniosides, 257-259, 261 Growth inhibitor of rice, 272 Growth inhibition of a diatom, 336 Guinea pigs
curing skin lesions in, 535 Gum tragacanth
foodstuff, 495 pharmaceutical emulsifier, 495
Gymnocladus saponins, 92-94 Gypanoside, 131 Gypsogenin, 191 Gypsogenic acid, 191
Halityloside, 349-350 Haikomari's method, 460 Heart ailments
Chinese medicine, 107 Heart asthma, 517 Hecogenin,39,42,313,323,330 Hederagenin, 120, 152, 156, 210, 237, 432,
528,565,568,571 glycosides, 211, 240 hemolytic and fungistatic glycosides,
571,573 Heinsiagenin, 374 HeLA cells, 407 Helojaposide, 272 Hematological examinations for horse
chestnut saponins, 472 Hematopoesis, 114 Hemolysis and rate of K +, 561 Hemolytic activity, 101, 115, 160-162,
170-171,240,340,382,538,557,559, 565-573
Hemorrhoids 429 Hemostatic drug, 94 Hemsloside-Ma3, 131 Hepatic hydroxylation, 457 Hepatitis, 94 Hepatoprotective action, 28 Herbal medicinal products, 3-7, 485 Hexadecanoic acid, 531
HL-60 cells inhibiting activity of acylated saponins, 468
Holostane, 339 Holothurin, 339 Home and garden fungicidal applications,
12 22-Homo-23-norcholestane skeleton, 22-
homo-23-norlanostane skeleton, 104 Homologous recombination, 552 Hormones, 2 Homoorientin, 26 Horse-chestnut saponins, 472, 530 HPLC,
coupled with mass spectral analysis, 117
for analysis of saponins, 121-122, 225-226
for cell cultures, 18 profiles of derivatives of ouabain,
OLC, and HIP, 222-223 Human basophils, 25 Human blood platelet aggregation, 513-
517 Human inflammatory fungal infections,
538 Human interferons, 505 Human platelet aggregation, 513 Human promyelocytic leukemia HL-60
cells, 108 Human spermatozoa, 235, 236 Human vaccines, 186 Hydrolysis with NaHC03
masonoside A, 468 Hydroxycholegenic acid, 447 Hydroxycholegenin, 447 2a-Hydroxy-heinsiagenin, 374 (S)-3-Hydroxy-3-methylglutaryl (HMG)
group, 101-102 Hydroxy protobassic acid, 237 5'-(Hydroxysulfonyloxy)jasmonic acid,
358,362,369 2~-Hydroxyoleanolic acid, 152, 156 Hypercholesterolemia, 1, 313, 320, 472 Hyperplasia of liver
in mice, 98 Hyperplastic nodules, 99 Hypertension, 220 Hypocholesterolemic activity, 4-6, 10, 37,
323 Hypotensive effects, 431, 440, 495
leontoside-A, 435a symphytoxide-A, 435a
Hypothalamic inhibitory factor, 220
Ichthyotoxicity, 340 Ilwensisaponin, 486 Immune stimulating, 1 Immunization studies, 167 Immunoadjuvant properties, 185 Immunocytochemical studies, 68
Immunodeficency syndrome (AIDS), 416 Immunological adjuvant, 165 Immunological assays, 167 Immunomodulatory action, 21, 28
sea cucumber glycosides, 340 Immunopromotive, 382 Immunosuppressive drugs in transplant
patients, 535 mycoses, 538
In vitro antimalarial test, 388 In vitro culture of C. speciosus, 59-68 Indicoside, 349-350 Indolepyridines, 383 Induced hypercholesterolemia, 472 Inducing immune interferon ,487 Infectious hepatitis, 267 Infertility, 489 Inflammatory agent, 404 Inhibition
butyrosides, 237 mimengoside A, 237 of cAMP phosphodiesterase, 101 motility of human spermatozoa, 237 replication of some DNA and RNA
viruses in vitro, 407 settlement of larvae barnacles and
bryozoans, 342 triplosides B, 237
Inotropic cardioactivity effect, 357, 367-368
Inotropic drugs, 107 Insecticidal agent, 373, 381, 383 Interferon-inducing activity, 408 Interferons, 505, 508
antiviral activity, 506 Intestinal flora, 444 Ion permeability of mycelia
Trichoderma strains, 531 Iridoid glycosides, 26-27 Ischemic heart diseases
Hungarian population, 471 Isocholegenin, 38-45, 444, 453 Isocyclamin, 490, 492-493 Isoeruboside, 521-522
blood ocagulation inhibitory effect, 525 firinolysis-promoting effect, 525
Isonodoside, 349-350 Isonuatigenin, 39, 42, 445
Jaundice, 25 Jones' oxidation reagent, 449, 455-456 Julibrosides, 271-272,274
Kampferol acid, 430 Kaikasaponins, 266, 269 Kalopanax saponin, 230 Kampferol-3-sulfate, 200-201 KB cells
inhibitory activity of acylated saponins, 468
599
Ketoconazole, 418, 425 Kidney diseases, 429 Kingianosides, 233 Killing kinetics
leakage of potassium, 544 leakage of magnesium, 544 phosphate ions, 544
Koryoginsenosides, 233 Kudzusaponins, 269,270 Kurilosides, 340-341 Kuroyurinidine, 103
Lachrymal glands, 382 Laryngopharyngitis, 371 Lasiocapine, 430 Laxative, 25 Laxogenin, 517,521 Laxoside, 522
blood coagulation, 525 Lectins, 264 Leishmania species/strains, 421 Leishmaniasis, 416 Leontoside, 230,235,429,431,435
hederagenin 429 Leptine, 281, 286 Leucocytosis, 114 Leukemia, 495 Licorice, 225 Life cycle of Schistosoma, 118 Liliaceous plants, species containing
steroid saponins 226, 227 medical uses, 226-227
Lilioglycosides, 310, 317-318 Linoleic acid, 430, 531 Liposome, 240, 280 Liquid chromatography-mass spectrometry
(LC-MS), 121-122 comparison of methods, 124-125
Lithium aluminum hydride reduction, 452 Lithospermic acid, 430 Livers
triglycerides, 472 cholesterol, 472
Livestock feed and forage plants and crops, 10
Longevity, ginseng aids, 202 Low-saponin alfalfa
breeding of cultivars, 529 Lowering effect in plasma, 185 Lycopsamine/intermedine
(diastereoisomers), 430 Lysis, 547
Macrophase-phagocyte liposomal system, 543
liposomal G2, 543 Macrophyllogenin, 498 Macrophyllosaponin, 496, 498 Macrostemonoside, 513-516,522,525 Maize, 453
600
Majonoside-R2, 130-131, 133, 138, 143 Malaria, 416
people attacked annually, 383 Malignant neoplasms
cholesterol reduction, 475 Malignant tumor cells, 109 Malvidin acid, 430 Mammalian erythrocytes, 286 Mangiferin, 26 Marsupials, bile, 445 Marthasterosides, 343-344 Maslinic acid, 200-201 Masonoside, 466 Mass spectrometry (MS), 124, 157, 387
chemical ionization (NH3), 363 mono- or bidesmosidic structure, 363
Mass spectral (MS) interfaces, 122-123 comparisons of methods, 123-124
Mass spectrometry for structural studies, 157, 298, 302-303
Mechanism of action antisera recognised, 553 anti-avenacinase, 553 tomatinase, 553
Medicagenic acid, 120, 528, 535-536, 565, 568
hemolytic and fungistatic, 573 Medicago spp. for commercial
development, 573 Medicinal plants
medical uses, 230 as sources of triterpenoid saponins,
229-230 Melanoma, 285 Melilotosides, 310 Melongosides, 38,310,319,330 Membranes, 241-248,280-281 Membrane-lytic properties, 277 Menstrual disorders, 494 Metabolites of nuatigenin, 454 Methotrexate, 108 Methyl a-linolenate, 207 Methyl polygalactate, 468 Methylallyl trisulfide, 512 Methylation of atroposides, 482 Metropolis Monte Carlo method, 105 Miconazole, 418, 425 Microencapsulation, 11 Microviscosity, 241, 244 Mimengosides, 230, 235, 237 Mirabilin, 490,494 Mirabilin lactone, 490, 494 Mirabilin methyl ester, 490 Mitomycin, 108 Mn+2, 83-84 Moldstim®-type and Pavstim®-type
saponins, 112-113, 331-332 Molecular dynamics
computations, 105-106 Molluscicidal activity, 117, 160-161,285,
415,426,487
extracts of fruit pulp, 425 Molluscicidal potency test, 425 Molluscicidal saponins, 118-119, 125,
151-154, 160-162 Monodesmodic formation, 548 Mosaic virus, 326 Mosesins, 338 Mold cell chemical composition, 531 MS-III, 211 MS/MS, 127 Muricins, 337 Murine cryptococcosis, 535
among AIDS patients, 541 Mussaendosides, 375-376, 382 Myristic acid, 531
N aringinase, 221 Natural detergents, 431 Naucledal, 383 Necic acid 430 Necine, 430 Nematocide activity, 21, 282 Neochlorogenin, 522 Neogitogenin, 368-369 Neoglycolipid synthesis, 274 Neohecogenin, 229, 358, 368-369 (25S)-Neospirost-4-en-3-one, 366 Neotigogenin, 229, 310,358,367-369 Nephritis, 495 Neurological-type toxicity, 291 Nicaphipalin, 266 Nicaphysalins, 266 Nicotianosides, 312 4-Nitroquinoline N-oxide, 98 N-Nitrosodiethylamine, 98 NMR, use in structure studies, 157, 233,
302,304 of aglycone moieties, 134 COLOC, 410-411 COSY, 158,388,404,410-411,432, 452,461,463,480,497
COSY and TOCSY, 137, 150, 158, 233,254,305,374,463,468
HETCOR, 404,410-411 HOHAHA, 404, 411 HMBC, 374, 388,433,498,516 HMQC, 374, 388 ID lH, ID proton-decoupled Be, 158 J-resolved lH, NOESY lH, 158, 235 NOE, 302-303,305 NOEs and lH-BC long-range
correlations, 141, 159, 233, 363, 365,376,402,405
NOESY, 159, 233, 374 13C-NMR, 362-363, 374, 389, 401,
404 l3C-NMR chemical shift
BC-NMR spectra, 174, 180, 182, 189, 201,252-253,410-411,431-432, 434,438,452,461,463-465,467-468,475
2D-NMR, 388, 402, 410 lH NMR, 189, 351,360, 362-363,
365,404,410-411,431,434,438, 459, 464-465, 467
lH-lH DQF COSY, 138,305,374 Refocused INEPT Be, 160 ROED lH, 303-304 ROESY lH, 254, 374, 404-405,480 of sugar moieties, 135, 138
NMR coupling constants, 137, 139, 142-143,253-254,256,298,303,305-306
Nodososides cytotoxicity from starfish, 342-343
Nonoxynol-9, 234 Norlanostane, 335 Notoginsenosides, 130, 138, 233 Nuatigenin, 37, 39,445 Nystatin, 233, 234, 544
Oat pathogenic, 548 Oat seeds and sprouts, 453 Octillol-type saponins, 130, 133, 136, 138,
143, 146-147 Oleanane saponins, 229-230, 235-236, 271 Oleandrose, 410 Oleanen-28-oic acid, 208-210, 271 Oleanolic acid, 82, 119-120, 131, 133,
152-153,156,202,208-209,297-298, 430,565,568
desmosides, 208, 236 Oleanolic glycosides, 403
inhibitory effect against VSV, 407 Oleic acid, 531 Ononin, 89 Oomycete fungi, 548 Ophydianosides, 342 Opportunistic pathogens of humans, 425 Oral contraceptives, 2, 426 Oreasterosides, 351 Ouabagenin, 219-220, 223 Ouabain "OLC", "HIF", 220-222 Ouabain-like compound, 220 Ouabain pentanaphthoate, 222 OVA, antibodies to, 167-170 Ovarian cancer, 285 Ovulation process, 2, 21, 251 Oxoquinovic acid, 385, 392-393
Pachastrellosides, 336 inhibition cell division of fertilized starfish eggs, 335
Paeoniflorin, paeoninmetabolins, 24 Palmitic acid, 461 20(S)-Panaxadiol, 140, 147
601
Panax:ynol, 96 Panax:ytriol, 95-96, 147 Papaverine, 107 Papillary muscle
guinea pigs, 367 Papillomas, 91, 93-94, 97 Pardanosides,
see 26-0-Acylated furostanol saponins
Partial hydrolysis of atroposides, 482 Patiriosides, 343-344 Pavstim®, 332 Pavonins, 338 Pectiniosides, 345, 347-348 Peliosanthosides, 228 Penaustrosides, 340-341 Pentanaphthoate, 222 Peripheral vascular disorders, 212 Periplogenin, 220 Permethylation of desacylcrocosmioside,
462 Persicanidine A, 103 Pesticides, 289, 309 Petuniosides, 251-261, 266, 310,480
determination of structure, 252-257 hydrolysis, 260 methylation, 260 purification and properties, 259-260 sugar components, 252-257
Pharmacological activity of dammarane triterpenoids, 129
Phaseoside, 219, 269 Phenobarbital, 98 Phospholipids, effect on glycosy lation, 51,
54 Photoeruboside, 521 Photographic chemicals and emulsions, 11 Photoisoeruboside, 521-522
fibrinolysis, 525 Photosensitization
hepatic dysfunction, 443 kleingrass, 443 lambs, 443
Phytoalexins, 547 Phytoanticipin, 547 Phytolaccasaponin, 487 Phytopathogenic fungi, 324 Phytosterols, 74 Pinitol, 358, 362-363 Pisasteroside, 349-350 Piscicidal activity, 160 Plant glycosyl hydrolases
bidesmodic and monodesmodic forms, 548
Plant pathogens, 536-543, 547-553 Plasmid, 33-35 Platelet aggregation, 101, 524
assay, 522 Polyclonal antibody, 68 Polygalacic acid 3-0-vicianoside, 463
602
Polygonatosides, 310, 329 Polyhydroxypregnane derivatives, 412 Polisaponin, 323 Potato Y -virus, 326 Potato glycoalkaloids, 281, 284 Potatoes, 10 Pratioside, 233, 234 Pregnane17 (20)-ene-type glycoside, 369 Pregnane-type glycosides, 363 Presenegenin, 214, 215 Primacrosaponin, 487, 488 Primulasaponin, 487, 488 Priverogenin, 489 Priverosaponin, 487, 488 Priverosaponin B-monoacetate, 487 Proacaciasides, 174-175
isolation, 178-179 permethylation and hydrolysis, 179,
181 properties, 178-180
Progenins from petuniosides, 252, 256, 260
Promastigotes, 421 Prophylactic effects, 407
chronic viral hepatitis, 407 Prosaikogenin, 9, 29, 35 Prosapogenin, 191,361,461,463 Prosapogenin of butyroside, 235 Prosapogenin of diocin, 233-235 Prosapogenol,347 Protein concentrates, alfalfa, 528 Protobassic acid saponins, 121, 237 Protobioside, 16-20 Protodescigenin, 82 Protodigitonin, 325 Protodioscin, 16-18-21, 57, 64-65, 265 Protoeruboside, 521 Protogracillin, 57, 64-66 Protoisoeruboside, 522 Protopanax:adiol, 57, 82, 130, 144, 202,
205 Protopanax:atriols, 130-131, 133, 136, 139-
140,144-145,147,202,205 20(S)-Protopanax:atriol oxides, 136, 140-
144 Protopolygonatoside, 329, 330 Protoprimulagenin and relatives, 120-121,
488-489 Protozoan infections
immunodeficiency syndrome (AIDS), 416
immunosuppressed patients, 416 morbidity, 416 mortality, 416
Psolusosides, 340, 341, 559 desulfated derivative, 557
Pulsatilosides, 230, 235, 237 Purpureagitoside, 210, 325, 329
QS-ill structure, 186-187
QS-21, an acylated triterpene glycoside deacylation and fatty acid domain,
166-170 stimulation of cytotoxic and
lypmphocyte response, 165, 171 structure, 166-168
Quercetin, 25 Quillaic acid, 191 Quillaja saponins, 185-192
molecular structure, 186-192 aglycones of, 191 by cleavage and analysis of
products, 188-192 reported, 186-188
Quil A and QS-21 fractions, 185-186 Quinovic acid, 385, 393 Quinovic acid, 3-0-a-lr
rhamnopyranoside, 392 Quinovic acid, 3-0-glycosides, 383, 385 Quinovic acid glycosides, 383
inhibitory effect against VSV, 407 Quinquenosides, 130 Quinquina, 383 Quis, 345
Rabbits, 445 Radiorespirometry, 415 Raji cells, 88-90, 93, 95-96 RAM drug test procedure, 416, 420-421 Recombinant analysis, 552-553 Recurvosides, 106-107 Reductive cleavage of permethylated
acaciaside C, 181 Red ginseng, 94 K+ release, 241 Renal sodium excretion, 220 Resistance of alfalfa cotyledons to molds,
529 Resistance to saponin action, 548 Respiratory tract infections, 494 Restriction map, 34 Reverse genetics approach, 550 a-Rhamnosidase, 31 Rhein, 26 Rheinanthrone, 26 Rheumatic arthritis, 404, 431 Rheumatic diseases, 431 Rhinovirus type, 407 Robinioside E, 269 Rockogenin, rockosides, 323, 325 Robinioside, 269 Rosmarinic acid, 430 Rumen content, 444 Rutin, 24-25
Saikosaponins, 28-32, 35, 237 Salivary glands, 382 Sanchi ginseng, 129 Sapindosides, 211
Saponins as fungicides, 120 as molluscicides, 118-119, 125, 151-
154, 160-162 of P. dodecandra, 125-127
Saponin-containing herbs, 7 Saponin-detoxifying enzymes, 548
pathogens of oat and tomato, 553 Saponin Network
Mass Spectrometry, 575 Nuclear Magnetic Resonance
Spectrometry, 575 Saponinases, 548 Sarasinosides, 211,335-336 Sarcosine, 410-411 Sarsasapogenin, 37, 39,41-42,310,323,
443 Sativoside, 521 Scaberoside, 298 Scaberoside methyl esters
determination of structure, 298 NMR data, 298 mass spectra, 298
isolation, 299 structures, 300-301, 306
Schistosomes in the bladder or intestines, 118
Schistosome, schistosomiasis, 118-119, 151, 153-155, 161,285
Sclerotium rolfsii from snails, 118, 119, 161 insoluble complexes with sterols, 536 high cholesterol, 536 lower cholesterol, 536
Screening of plant extracts for GT uptake, 198-199
Sea cucumbers, 335, 339, 557 Secoiridoids, 383 Sedative effect, 6, 495 Senegae radix, 214-215
effect on ethanol absorption, 214 Senegasaponins, 207, 214-215 Senegines, 214-215 Sennoside A and degradation products, 25-
26 Sepositosides, 343 Sex hormones, 15,426 Sex ratio shifts in cucumbers, 330 Shampoo liquids, 11 Shark antifeedant, 339 Shark-repellent secretions and
peptidic pardaxins, 338 steroid glycosides, mosesins, 338
pavonins, 338 Shark's olfactory sense, 339 Sheep erythrocytes, 196-197, 202, 204
effect of ginseng, 202 Shikonin, 430 Shionane, 297 Shoot tip cultures, 57
603
Sister Chromatid Exchange, I 54 Sitosterol, 75, 78, 430 ~-Sitosteryl, 3-0- ~-D-glucopyranoside,
I30 Skin cancer, 285 Smilagenin, 39, 4I-42, 433,52 I Soap substitute, II8 ~-Solamargine, 285 Solamarines, solamargine, 285-286, 289 Solanaceous plants,
antitumor activity, 263-264 chemical constituents, 263-264
Solanidane, 47-52, 278 Solanidine, 47-52, 7I, 78-79,286 Solanine, 47-52, 28I, 286 Solanine/chaconine, 28I Solasonine/solamargine, 28I Solaplumbin, 285 Solasodine, 47-52, 7I, 78,265,285-286 Solamins,278,280,286,289 Sophoraflavosides, 269 Sophorose, 549 ~-Sophorosyl moiety, 136 Southern blot analysis, 552-553 Soyasapogenol B substituted, 502 Soyasapogenols, 565, 568 Soyasaponins, 268-270, 502-503 Spawning inhibitors, 340 Spermicidal activity, 2I, 330
of steroid saponins, 234-235, 239 of triterpenoid saponins, 235-236
Spinasaponins, 209-210 Spiroconazole, 4I5, 4I7-4I8, 425-427 Spirostane glycosides, 409 Spirostanol biosynthesis, 44 Spirostanol saponins
biosynthesis 37-45 formation from furostanol glycosides,
57, IOI, 312 from various plants, 313-315, 317,
319-320,322 polyhydroxylated, 106, 107 with an HMG group, 10I-102
Starfishes, 335, 339 Steamed ginseng, 94 Stearic acid, 531 Steroid glycosides in bacterial tests, 328 Steroid glycosides as bioregulators, 331 Steroid hormones, I,2 Steroid sapogenins,
precursors of drugs and hormones, 2 structure and biosynthesis, 43-45
Steroidal glycosides
604
antifungal activity, 233-234 cytotoxicity, 233-234 isolation from plants, 3II of Allium chinensis, 107 -I 08 of lilaceous plants, medical uses,
isolated ones, and structures thereof, 226-228, 3I8
spermicidal activity, 239, 330 spirostanes and furostanes, 228 stimulating action on plants, 251
Steroidal saponins in food and beverage plants, 8
Steroidal saponins, botanical sources, II Sterol binding by glycoalkaloids, 28I Sterol metabolism by demethylases, 28I Stenocardia, 517 Stichlorosides, 339 Stichopodidae, 340 Stigmasterol, 430 Stimulant beverage, 6 Stipuleanoside R, 209-210 Stomach ache, 202, 213, 273 Streptomycin, 425 Strophanthidin, 2I9-220 Structure-activity relationship
antitumor activity, 4I3 dendrochirotid a order, 557-563 ethanol absorption, 210-2I5 glycosides of medicagenic acid, 407,
535 protopanaxatriol, 205 quinoic acid derivatives, 403 spermicidal activity, 234-237
Subprosides, 269 Sulfated digitogenin, 330 Sulfated neotigogenin trioside, 330 Sunflower oil, 533 Surface activity, 170-17I Surfactant, I2 Suspension stabilizer in pharmacuetical
additive, I85 Suspension cultures of Dioscorea
deltoidea cells, 15-2I Symphitine, 430 Symphytocynoglossin, 420 Symphytoxide, 429-43I, 436-439 Synergistic interactions
chaconine/solamargine, 286 detoxification mechanisms of
pathogens or predators, 287 solanine/chaconine, 296 solasonine/solamargine, 286 significance to man, 287-289
Synthetic medicagenic acid glycosides treatment of fungal infections, 543
Synthetic molluscicides, 151
Tannin, 20I Tarasaponin, 209 Taxol, I08 Taxonomic relationship, I38, 229, 277 Tenuifolin, 214-215 N-Tetracosanoyltyramine, 358 I2- 0-Tetradecanoylphorbol-13-acetate,
87-88, 90-91, 93-97 3a,5a-Tetrahydrodesoxycordifoline, 392,
393
Tenuispinosides, 343, 344 Termination early pregnancy, 371, 381 Thalictoside, 273 Therapeutic effects on viral hepatitis, 407 Thermal burn, 25 Thermotropic behavior of liposomes, 244,
246 Thoracic pain, 525 Thornasterol, 344 Thornasterosides, 343, 344 Thrombosis
cure effect from saponins from Allium plants, 522
Tigogenins, 39,41-42,47,252,255-256, 325,475,479,517,521
Tigogenin glucogalactopyranoside, 479 Tigogenin glycosidic peracetate, 481 Tigogenin monoside, 479 Tigogenin trioside, 479 Tomatidine, 47-48
glycosylation, 71-79 a-Tomatine, 71-72,281,283,285,323,
325,549,550,553 molecular complex with 3f3-hydroxy
steroids, 279 role in plant self-defense, 71 tomato pathogens detoxification, 552
Tomatinases hydrolysus sugar molecules, 553
Tomato, 10, 548 Tomato bronzetop, 326 Tomatoside saponins, 112-116, 310, 323,
325,330 antiviral activity, 505-508 modified biological effects, 114-116
Tonic,4,5,6,202,208 Toxicity
antiprotozoal drugs, 416 complex with membrane sterols, 547 glycoalkaloids, 279, 284 humans, 279, 284 potatoes, 284 sapogenols, 456 starfishes, 340
Traditional medicine, 401, 415 Brazilian, 402 Peruvian, 402 percent of the population using, 383 developing countries, 383
Transglycosylation, 274-275 Tremasterols, 350 Tribulosides, 310 Tribulosin, 358, 360-363, 367-369 Tribulus toxicity
bladder, 357 kidney, 357 leaf extract, 367 malaria, 357 sheep toxicity, 357
Trichoderma strains growth inhibition, 569 ion permeability, 531, 532 nonsensitive, 530, 534 resistant to saponins, 534 sensitive, 530, 534
Trichophyton mentagrophytes long life, 535 C.neoformans,535 liposomes, 535
Trichophyton soudanense, 425 Trigonellosides, 310 Trilline, 323 Triplosides, 230-232, 235, 237 Triterpene saponins
in food and beverage plants, 9, 12 of Scilla pervians, 107-108 spermicidal activity, 235 structures, 229-232
Triterpenoid acids of dietary origin, 453
Triton X-100, 51-52,74,76 Tuberculosis, 429 Tuberosides, 310, 320-321 Tubocaposide B, 266 Tumor necrosis factor, 487 Two-stage carcinogenesis test, 90, 94, 97
UDP-galactose, UDP-glucose, 71-78 UDP-galactose: tomatidine
galactosy ltransferases activity, 74, 79 assay, 73 molecular weight, 73 purification, 72-73, 76-77 specificity, 78
UDP-glucose: diosgenin/solasodine glucosyltransferases, 47-54
assay for, 49 occurrence, 48 molecular weight 49 phospholipids, 53 purification, 52
UDP-glucose: diosgenin/tigogenin glucosyltransferases, 37-45
assay for, 38-39 occurrence, 39 properties, 42-43, 47-51, 54 purification, 38-42 specificity, 41-42
UDP-glucuronic acid, 77-78 Ulcers, 431 Ursane, 205 Uterine cancer, 495 Utero-contracting saponins
ardisicrenosides, 494 Uzarigenin, 220
Varicella-zoster virus, 263
605
Vegetarians European and Asiatic countries, 472
Vesicular stomatitis virus, 407 Veterinary vaccines
anti parasite vaccines for malaria, babesiosis, and trypanosomiasis, 185
foot-and-mouth disease, 185 Vietnamese ginseng, 129
discovery and distribution, 129-130 saponins
extraction, 130 structure, 133-136 varieties, 130-132
Vina-ginsenosides, 131-133, 136, 138, 139, 142, 144, 147
Vinblastine, 285 Vincristine, 108 Virucidal effects, 251 Virus-infected cells, 410 Vulpecholic acid, 449
Walker tumor, 115 Warts,285 Western blot analysis, 68 Wheat
606
pathogens, 548 White ginseng, 94 Wistariasaponins, 89, 269 Wistin, 89 Wrinkles, 429 Wound-healing activities, 4, 430-431,495
Xiebai, drugs use, 512
Yamogenin, 37, 39,41-42,45,310,433 Yeast, 538 Yield of saponin from Dracaena spp for
commerce, 426 Yucca,4, 11 Yuccosides, 310, 322
Zanhic acid, 565, 568 Zimbabwean-Danish project
agronomic investigations, 154 biological activities, 160 chemical and analytical investigations,
155 structure elucidation, 157
Zingibroside R 1, 204 Zn+2, 83-84