anthraquinone

Dr. Harish kakrani

CDCP

New Vallabh vidyanagar

1Dr. Harish & Purvi Kakrani

CONTENTS :

Definition of Anthraquinone Glycosides.Different Anthracene moieties .Mechanism of action .Crude drugs Commercial productsConclusion.


DEFINITION:

• Anthracene glycosides are the organic compounds from plants or animal sources which on enzymatic or acid hydrolysis gives one or more glycones (sugar moieties) along with aglycone.

• Chemically these are the ACETALS or SUGAR ETHERS formed by the interaction of –OH group each of anthraquinone moiety and sugar ,with a loss of water molecule.


Anthracene (Anthraquinone) Anthracene (Anthraquinone) GlycosidesGlycosides

1

4

9

10

8

5

Anthraquinone

Reduction

Oxidation

OxanthroneAnthrone

O

O

O

OHH

O

HH

Oxidation

Anthranol

OH

tautomerization

Reduction

44Dr. Harish & Purvi KakraniDr. Harish & Purvi Kakrani

OH OH

CH3HO

O

O

OH OH

CH2OH

O

O

OH OH

CH3

O

O

OH OH

COOH

O

O

RheinChrysophanolEmodin Aloe-emodin

55Dr. Harish & Purvi KakraniDr. Harish & Purvi Kakrani

MECHANISM OF ACTION:

• Anthracenosides are PURGATIVE because of their irritating action on large intestine.

• They stimulate the muscular structure i.e.., smooth muscles of large intestine through which peristalitic and large intestinal movements gets accelerated results in evacuation of intestinal contents.

• Simultaneously the mucus secretion is stimulated and water absorption is hindered and soft stools will be formed.

• Action starts after 8-12 hrs.• Activity is due to anthranols ,anthrones and dianthrones.


CRUDE DRUGS CONTAINING ANTHRAQUINONE GLYCOSIDES

• Senna• Senna pods• Aloes• Rhubarb• Cascara


SENNA:• enna-ki-patti, tinnevelly senna ,cassia senna.)• BIOLOGICAL SOURCE :It iINDIAN SENNA: (senna folium ,ss obtained from dried leaflets of Cassia

angustifolia Vahl belongs to family LEGUMINOSAE.

CULTIVATION AND COLLECTION OF INDIAN SENNA:Soil-RED loamy/coarse gravelly soil.1st sowing - feb-march.2nd sowing - oct-november.1st harvesting – when leafs turn to thick ,fully grown and greenish.2nd harvesting- after 4-6 weeks of 1st harvesting.3rd harvesting- after 2weeks of 2nd harvesting.Heavy irrigation and water logging are avoided.

ALEXANDRIAN SENNA

(folia sennae alexandrinae,)

Bological source :It is obtained from dried leaflets of

Cassia acutifolia Delile belong Family LEGUMINOSAE. 8Dr. Harish & Purvi Kakrani

MACROSCOPIC CHARACTERS:

• INDIAN SENNA ALEXANDRIAN SENNA• YELLOWISH-GREEN PALE-GREYISH GREEN.

• 7-8mm width and25 -60mm length 2-4cm long and 7-12mm wide.

• Lanceolate,Asymetrical leaflets. Ovate- lanceolate, margin is curved

and Asymmetrical base.


Microscopic of senna characters• Epidermis : unicelllular ,conical, thick walled warty trichomes.• stomata: paracytic or rubiaceous.• Palisade tisssue on both sides (iso bilateral leaf lets).• Calcium oxalate crystals are present.• Spongy mesophyll, patch of sclerenchyma, cluster sheath and

presence of collenchyma are the characteristics of senna.• Indian senna Alexandrian senna• Vein-islet no 19.5 - 22.5 25 - 29.5• Stomatal index 17 – 20 11.4 – 13.3

• Palisade ratio 7.5(u) 9.5(u)

5.1(L) 7(L)



ADULTERANTS:

Tinnevelly senna and alexandrian senna are adulterated with DOG SENNA (papillose cells in lower epidermis)

PALTHE SENNA (No Anthraquinone glycosides)

MECCA and ARABIANSENNA (brown-green colour ,elongated)

SENNA PODS :

(senna legumes ,sennae fructus, senna fruit.)Biological source : Dried nearly ripe fruits of Cassia acutifolia

Delile and Cassia angustifolia Vahl belongs to leguminosae.

Collection and preparation: Pods are collected and dried . By sifting separate pods manually segregated into different

qualities Inferior quality used for preparation of galenicals.


Macroscopic characters:Pale green-brown colour,4-5cm long

2-2.5cm width.

Pods are flat ,thin and oblong shape.


ALOES: (ALOE,MUSSABBAR,KUMARI.)

• Biological source: Dried juice of leaves of Aloe barbadensis Miller (curacao aloes), Aloe perryi Baker (socotrine aloes), Aloe ferox Miller, Aloe africana Miller and Aloe spicata Baker (cape aloes) belonging to family Liliaceae.

• Cultivation and collection:Cultivated by root suckers.No water logging.Juice is collected by a cut at leaf base.

• Preparation of Aloes:Curacao aloes: Place the leaves in kerosene tins and kept in tilted position to

drain out all the juice and boil on large copper pans and pour in metal containers.

Cape Aloes :They are placed in ground in basin shaped depression which is lined by goat skin /canvas for 5-6 hrs.

Socotrine and Zanzibar Aloes: juice is collected in goat skin and solidify.14Dr. Harish & Purvi Kakrani

MACROSCOPIC CHARACTERS:

• CURACAO CAPE SOCOTRINE ZANZIBAR

• SRONG ODOUR NAUSEOUS NAuSEOUS -• BROWNISH-BLACK BROWNISH-GREEN BROWNISH-YELLLOW LIVER BROWN OPAQUE MASS MASSES OPAQUE PASTY MASS

BITTER TASTE BITTER TASTE BITTER TASTE -• UNEVEN FRACTURED GLASSY FRACTURED CONCHOIDAL EVEN

FRACTURED

MICROSCOPIC CHARACTERS• In leaf cuticle, epidermis, palisade, tissue, parenchymatous mesophyll.

(mucilagenous )• . Mesophyll encloses vascular bundles which are covered with peri-cyclic layer. • Aloeitic cells contains Aloe gel.• Calcium oxalate crystals in parenchyma.• Aloepowder: In lactophenol reagent.

CURACAO CAPE SACOTRINE ZANZIBAR • Small needles transparent,brown large prism groups/ IRREGULAR or slender prisms angular/irregular dispersed LUMPS

fragments• Crystalline amorphous ---- - --- --



Substituents & Adulterants• Socotrine, zanzibar, Natal aloes ,Mocha aloes with BLACK CATECHU.• Natal: Dry extract of aloe candelabra for cape aloes.• Mocha: Brownish black glossy fragments interior varieties.• Curacao aloes with BLACK CATECHU ,IRON,STONES.

• :


RHUBARB: (Radix rheum , Revandchini , Rheum )

• Biological source :Dried rhizomes of Rheum emodi Wallich, Rheum palmatum Linn ,Rheum webbianum Royle of family polygonaceae.

• Collection and preparation: Drug obtained from wild plants which are draught resistant .

Propagated by seeds ,rhizomes.

Harvested in spring season and the rhizomes are collected and cleaned & de-corticated ,dried and packed in wooden boxes.


Macroscopy:

• In market we will find round or flat shape rhizomes.• Barrel /cylindrical/ conical shape rhizomes which are 8-10 cm

long,4cm thick.• Flat shape rhizomes are 7-10cm long,3-6cm thick.• Sharp odour and bitter taste.• Drug with pink colour fracture are of high quality in nature.

Microscopy:• In abnormal vascular bundles medullary rays are star shaped.• Star spots are in reddish orange.• Rosette calcium oxlate crystals starch grains are also seen.• In rheum officianalis star spots are irregular and in R.palmatum

as a continous ring.• Rhaspartic rhubarb contains rhaponticin and lacks rhein,

emodin or aloe emodin.• It has estrogenic activity and shows blue flouroscence UV –

LIGHT.


:


CASCARA:(Cascara segrada ,Sacred bark,Chittem bark,Cortex Rhamnipurshianae)

Biological source: Dried bark of Rhamnus purshiana De candolle of family Rhamnaceae.

Collection: it is collected in between april-august when it is readily separates from wood.By longitudinal incission of 5-10cm.

MACROSCOPY:Externally purplish brown an internally reddish brown.Nauseous odour, bitter taste .1-4mm thick in size.Broken pieces small and flat occurs as quills/channels.Internally longitudinal striations.


R.Emodi , R.webianum R.officinale , R.palmatum


MICROSCOPY:• Contains cortex , sclerides , primary & secondary phloem

• Cork has several layers of cells with yellowish brown substance.

• Cortex with collenchyma.

• Parenchyma is cellulosoic.

• Calcium oxalate crystals are present.

• Phloem fibres, sieve tubes are present.• Substituents and adulterants: Barks of R. californica ,

R.fallax and frangula bark are substituted for cascara.

• Former bark has more uniform coat of lichens and wide medullary rays than original species.

:


DRUG DRUG

CHEMICALCONSTITUENTSCHEMICALCONSTITUENTS CHEMICAL TESTCHEMICAL TEST USESUSES

SENNASENNA SENNOSIDES ASENNOSIDES A

SENNOSIDES BSENNOSIDES B

SENNOSIDES C SENNOSIDES C

SENNOSIDES DSENNOSIDES D

BORNTRAGERS TESTBORNTRAGERS TEST PURGATIVE,PURGATIVE,

COUNTERACTGCOUNTERACTGRIPPING EFFECTRIPPING EFFECT

SENNA PODSSENNA PODS 2.5-4.5% SENNOSIDE A&B , 2.5-4.5% SENNOSIDE A&B , SENIDIN,SENIDIN,

8,8’Di-GLUCOSIDE8,8’Di-GLUCOSIDE

BORNTRAGERS TESTBORNTRAGERS TEST PURGATIVE,PURGATIVE,

ALOESALOES BARBALOIN ,BARBALOIN ,

ISOBARBALOIN ,ISOBARBALOIN ,

ALOESONE ,ALOESONE ,

ALOETIC ACIDALOETIC ACID

BROMINE WATER TEST,BROMINE WATER TEST,

BORAX TEST(SCHOENTENS TEST),BORAX TEST(SCHOENTENS TEST),

MODIFIED BORNTRAGERS TEST.MODIFIED BORNTRAGERS TEST.

PURGATIVE,PURGATIVE,

COMPONENT IN COMPONENT IN COMPOUND COMPOUND BENZOIN BENZOIN TINCTURE,TINCTURE,

ANTI-ANTI-INFLAMMATORY,INFLAMMATORY,

IN PAINS & IN PAINS & ITCHING,ITCHING,

ULCERS.ULCERS.

RHUBARBRHUBARB PALMIDIN-A,B,CPALMIDIN-A,B,C BORNTRAGERS TEST BORNTRAGERS TEST

& &

SAMPLE +ALKALI-------REDSAMPLE +ALKALI-------RED

BITTER BITTER STOMACHIC ,STOMACHIC ,

IN DIARRHOEA IN DIARRHOEA AND PURGATIVEAND PURGATIVE

CASCARACASCARA CASCAROSIDE A,B,CCASCAROSIDE A,B,C MODIFIED BORNTRAGERS TEST MODIFIED BORNTRAGERS TEST

&&

SAMPLE+5%KOH------REDSAMPLE+5%KOH------RED

BITTER TONIC,BITTER TONIC,

STOMACHICH,STOMACHICH,

EMETIC,EMETIC,

PURGAIVEPURGAIVE2424Dr. Harish & Purvi KakraniDr. Harish & Purvi Kakrani

O O

HCOOH

OH

O OH

COOH

O

H

2

3

5

6

7 9

10 4

8 1

Gl

Gl

Sennosides A&B

Sennosides C&D

O O

HCOOH

OH

O OH

CH2OH

O

H

2

3

5

6

7 9

10 4

8 1

Gl

Gl

OH OH

CH2OH

O

H Gl

O OH

CH2OH

O

H Gl

Gl

Barbaloin Cascaroside A& B

OH OH

CH3

O

H Gl

O OH

CH3

O

H Gl

Gl

Chrysaloin Cascaroside C & D

CHEMICAL CONSTITUENTS


REFERANCES:

• PHARMACOGNOSY BY C.K.KOKATE,A.P.PUROHIT,S.B.GOKHALE.

• PHARMACOGNOSY BY W.C. EVANS


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anthraquinone