PHARM.

D Chemical Pharmacognosy- I Lecture 23 April 28th, 2011

ANTHRAQUINONE GLYCOSIDES - III

M. Ahsan Khalid, B.Pharm, Pharm. D B.Pharm,
M.Phil Scholar (RIPS/RIU) HIPSHIPS-HUKIC

CASCARA

Cascara Bark- Rhamnaceae Bark

Definition: Official cascara sagrada is the dried bark of Rhamnus purshianus. purshianus. Bark is collected from wild trees (depletion is leading to the increase of cultivation)

Cascara
 

Rhamnus pershiana (Rhamnaceae) Rhamnaceae) bark extract



collected, dried and stored for 12 months ( anthraquinone content -> less toxic) discovered 100 years ago Rocky Mtns, W.Coast, US Mtns, W.Coast, griping action harder to eliminate

modern substance
 

more violent purgative

 

Use: Use: night before to clear bowels for x-rays and barium meal

Rhamnus purhsianus - Cascara



Etymology


Rhamnos Greek, branch, shiny shrub. Purshiana after Pursh, botanist 1st described herb in 1814.

Other Common Names



Bearwood, bitterbark, buckthorn, coffeeberry, mountain cranberry, persiana, sacred bark.

Cascara Bark - History



Recently introduced to Modern Medicine. Known to early Mexican and Spanish priests. Not introduced to medicine until 1877.

Cascara Collection & Preparation



Collected from mid-April to end of midAugust, when it separates readily from the rest of the trunk. Longitudinal incisions are made 10cm apart and the bark removed. Tree is then usually felled and the branch bark separated. Bark is then dried in the shade with the cork facing upwards. This is referred to as natural cascara. Commercial supplies are comminuted to give small, even fragments called evenized, evenized, processed, or compact cascara.

Cascara Bark - Storage



During preparation and storage the bark should be protected from rain and damp (partial extraction of constituents may occur or bark may become mouldy). Should be stored for at least 1 year before use. Bark appears to increase in medicinal value up unto its 4 years old (stored bark)

Cascara Bark Why Stored for a Year?



When stored for at least a year better tolerated by patient (less griping pains due to increased peristalsis) Yet as effective as fresh bark. Reason?


Due to Hydrolysis and other changes that occur during storage. Bitter taste of Cascara can also be reduced by treating the bark with alkali (alkali earths or MgO).

Chemical constituents:
(i) 4 primary glycosides


O- and C- linkages C-

To get aglycones FeCl3 To get aloins oxidise with acid

(ii) C-glycosides - two aloins C 

barbaloin derived from aloe-emodin aloechrysaloin derived from chrysophanol derived from emodin oxanthrone, aloe-emodin, chrysophanol oxanthrone, aloe-emodin, incl. emodin, aloe-emodin, chrysophanol, herterodianthrones emodin, aloe-emodin, chrysophanol, palmidin A B C

(iii) a number of O-glycosides O

(iv) various dianthrones



(v) aloe-emodin, chrysophanol, emodin in free state aloe-emodin, chrysophanol,

Cascara Bark Constituents 1



4 main glycosides Called Cascarosides

Cascaroside A  Cascaroside B  Cascaroside C  Cascaroside D


Cascara Bark Constituents 2



2 aloins:
C Glycosides  Breakdown products of Cascarosides A-D A
 Barbaloin

(derived from aloe-emodin) aloe Chrysaloin (derived from chrysopanol anthrone)

Cascara Bark Constituents 3

O-glycosides  Derived from


Emodin  Emodin oxanthrone  Aloe emodin  chrysophanol



Cascara Bark Constituents 4



Dianthrones
Those from  Emodin  Aloe-emodin Aloe Chrysophanol
 

Hetrodianthrones
 Palmidin

A, B and C (Rhubarb)

Cascara Bark Constituents 5

Emodin  Aloe-emodin Aloe Chrysophanol


(in the free state)

Cascara Bark - Substitutes



Rhamnus alnifolia (too rare) Rhamnus crocea (bark is very different from official drug) Rhamnus californica (so closely related to Rhamnus purshianus some botanists do not consider them to be separate species). Rhamnus fallax

Cascara Bark - Uses

Purgative  Similar to Senna  Normally as a tablet  Also used on animals


Cascara Bark Additional



Physiological Action


Astringent (bark tannins), bitter tonic, chologogue, emetic, hepatic, stomachic.

Excessive use: nausea, vomiting, heamatorrhoea. Long term use: Weakens intestinal muscles. ContraContra-indications: children younger than 14, during pregnancy, lactation, IBS, Crohns, intestinal obstruction, and idiopathic abdominal pain.

Medicinal Uses Move stagnation, clear heat. The most widely used laxative worldworld-wide. Topically: Used as a wash for herpes lesions


RHUBARB

Rhubarb - Polygonaceae


Definition: Rhubarb/Chinese Rhubarb is the rhizome of Rheum palmatum. palmatum. Other species and hybrids of Rheum, except R. Rheum, rhaponticum, rhaponticum, may also be included.

Chinese Rhubarb - History

  

Chinese Rhubarb has a long history. Mentioned in a herbal of 2700BC. Formed an important article of commerce on the Chinese trade routes to Europe. Still used medicinally today.

Chinese Rhubarb Collection & Preparation

 

  

Rhizomes are grown at high altitudes (+3000m). Collected in Autumn or spring (6-10yrs old) (6Cork is removed, cut. Artificially dried. Packed in tin-lined tinwooden cases. Inferior quality herbs are packed in hessian bags

Chinese Rhubarb - Constituents

1.

Anthraquinones without a carboxyl group chrysophanol, emodin, aloealoe-emodin & physcion. Also the glycosides of these substances.

2. Anthraquinones with a carboxyl group (rhein and its glycoside: glucorhein).

Chinese Rhubarb - Constituents

3.

Anthrones and dianthrones of chrysophanol, emodin, aloealoeemodin or physcoin.

5. Hetrodianthrones derived from 2 different anthrone molecules: Palmidin A and Palmidin B. B.

4. Dianthrone glucosides of rhein (Sennosides A and B).

Chinese Rhubarb - Constituents



Free anthraquinones: anthraquinones: chrysophanol, emodin, aloe-emodin aloeand rhein. Some of the above constituents may also occur as glycosides.

Chinese Rhubarb - Uses

Bitter stomachic Diarrhoea (low doses) contains tannins Purgative (high doses) followed by an astringent effect. Suitable only for occasional for occasional use, not for chronic constipation.

Rhubarb - Additional


Etymology


Topical Uses:


Rheo Greek, to flow, in reference to the purgative properties.

Medicinal Actions


Poultice to treat boils, burns, wounds. Used to stop bleeding (tannins stypic and astringent). Used as a mouthwash for oral ulcers.

AntiAnti-helminthic, antiantibacterial, antiantiinflammatory, antiseptic, astringent (low doses), sialagoge, vulnerary

Other uses: Acid content: fresh root can be used to polish brass. Caution


Leaves should be avoided high calcium oxalate toxic