Anthraquinone Glycosides

Lecture No: 3

Ms. Aamna Iqbal

M. Phil (Pharmacognosy)
Hajvery University (HU
Outline
Introduction to Anthraquinone Glycoside

Crude Drugs Included in Anthraquinone

Glycoside
 Biological source , Geographical Distribution

Chemical Composition and Medicinal Uses

Learning Outcomes for this Lecture:
By end of this lecture you will be able to :
I. Define and describe the Anthraquinone Glycoside
II. Describe the biological source, geographical
distribution, chemical composition and chemical
structure of the main active constituents present in
Cascara, Aloe, Rhubarb, Cochineal and Senna.
III. Understand the Therapeutic and Pharmaceutical uses
of Cascara, Aloe, Rhubarb, Cochineal and Senna.
 Anthraquinone glycosides.
The glycosides which on hydrolysis yield
anthraquinone among the products of
hydrolysis, are called anthraquinone
glycosides.

Anthraquinone glycosides are mostly used as

cathartic.
 Anthraquinone Glycosides

1. Cascara
2. Aloe
3. Rhubarb
4. Cochineal
5. Senna
Anthraquinone anthracene

is the aglycon,
derivative of
anthracene

Anthraquinone
s are acidic due
to phenolic
groups
 Cascara
Cascara is the dried bark of Rhamnus purshiana
(Fam. Rhamnaceae)
It should be aged for at least 1 year prior to use in
medicinal preparations
• Reduced forms of the emodin-type glycosides are
present in the fresh bark
•During the minimum 1-year storage period, these
glycosides are converted to monomeric oxidized
glycosides, which exhibit a milder cathartic activity
The plant is a tree that attains a height of 10 meters
 Chemical Constituents
• The cascara sagrada bark is found to contain two
major types of anthracene compounds, namely:
• Normal O-Glycosides These are based on
emodin like structures and constitute about 10 to
20% of the total glycosides, and Aloin-like C
Glycosides. These comprise of about 80 to 90% of
the total glycosides.
• The two C-glycosides are known as barbaloin
and deoxybarbaloin (or chrysaloin) .
 Chemical Constituents....
• The main active constituents are four
glycosides usually designed as Cascarosides A,
B, C and D. it has been established that the
cascarosides A and B are solely based on
optical isomers of barbaloin ; whereas
cascarosides C and D on optical isomers of
deoxybarbaloin.
Chemical Structures
Chemical Structures.....
 Medicinal Uses

• Correction of habitual constipation; it not only

acts as laxative but restores natural tone of the
colon
• Cathartic
 Aloe
Aloe or aloes is the dried latex of the leaves of Aloe
barbadensis (A. vera), or of A. ferox and hybrids of
this species with A. Africana and A. spicata
Family: Liliaceae
Drug obtained from A. barbadensis (A. vera) is
known in commerce as Curacao aloe
Drug obtained from A. ferox and hybrids of this
species with A. Africana and A. spicata is known in
commerce as Cape aloe
 Collection and Preparation
 Leaves are cut in March and April
 Cut ends are placed downward on a V-shaped
trough
 This trough is inclined, to direct the latex to a
vessel
 The collected latex is evaporated in a copper
kettle
 After getting proper consistency, poured into metal
containers and allowed to harden
 Chemical Composition
• Barbaloin (major constituent) [Aglycon part is aloe-
emodin anthrone]
• Aloinoside (O-glycoside of barbaloin with an
additional sugar)
• Aloe-emodin
• Chrysophanic acid
• Curacao aloe is superior to Cape aloe because it
contains two-and-one-half (2.1/2) times much
aloeemodin
Chemical Composition.....
• Inactive ingredients: Resinous material,
volatile oil
• Aloin: Aloin is a mixture of active principles
obtained from aloe.It varies in chemical
composition and in physical and chemical
properties according to the variety of aloe
from which it is derived.
 Medicinal Uses
1. Cathartic
2. Pharmaceutic aid for compound benzoin tincture.
3. Recommended to treat third degree x-ray burns
and atomic radiation burns .
4. At present, available in the form of ointment,
containing fresh gel. This ointment is
recommended for the treatment of sun burns, deep
thermal burns and radiation burns .
5. It relieves pain and itching and tends to minimize
ulceration
 Rhubarb
Rhubarb, rheum or Chinese rhubarb consists of the
dried rhizome and roots that are deprived of periderm
tissues of Rheum officinale, of R. palmatum, of other
species (except R. rhaponticum), or of hybrids of
Rheum (Fam. Polygonaceae) and are grown in China
Indian rhubarb or Himalayan rhubarb consists of
the dried rhizome and roots of R. emodi, of R.
webbianum, or of some related Rheum species (Fam.
Polygonaceae) that are native to India, Pakistan or
Nepal
Rhizome
 Chemical Composition
• ‘Chrysophanol’ and its glycoside ‘chrysophanein’
• ‘Aloe-emodin’ and its glycoside ‘glucoaloe-
emodin’
• ‘Rhein’ and its glycoside ‘glucorhein’
• Emodin
Homodianthrones;
Sennoside A and B: Dianthrone of ‘rhein’
Chemical Composition...
Heterodianthrones;
• Palmidin A: Dianthrone of ‘aloe-emodin
anthrone’ and ‘emodin anthrone’
• Palmidin B: Dianthrone of ‘aloe-emodin
anthrone’ and ‘chrysophanol anthrone’
• Palmidin C: Dianthrone of ‘emodin anthrone’
and ‘chrysophanol anthrone’
Chemical Structure and Use
 Cochineal
• Cochineal consists of the dried female insects
Dactylopius coccus (Coccus cacti) containing
eggs and larvae (Oder: Hemiptera)
Geographical Distribution:
• Cochineal insects are indigenous to Central
America
 Chemical Composition
• Carminic acid (10%) [C-glycoside,
anthraquinone derivative]
• Fat (10%)
• Wax (2%)
Chemical Structure
 Uses

• Coloring agent for liquids and solids

• It is also used as Indicator .
 Senna
• Senna or senna leaf consists of the dried leaflet
of Cassia acutifolia, or of C. angustifolia (Fam.
Leguminosae)
• Drug obtained from C. acutifolia is known in
commerce as Alexandria senna
• Drug obtained from C. angustifolia is known in
commerce as Tinnevelly senna
• Senna was introduced into European medicine in
the ninth or tenth century by the Arabians
Chemical Composition
Chemical Structure
 Medicinal Use
It is used as a cathartic
 SUMMARY
 Anthraquinone is the aglycon, derivative of
anthracene.
The glycosides which on hydrolysis yield
anthraquinone among the products of hydrolysis,
are called anthraquinone glycosides.

Anthroquinone glycosides are mostly used as

cathartic
SUMMARY......

 Cascara, Aloe, Rhubarb, Cochineal and

Senna contain anthraquinone glycosides
 Text Books
Following books were considered during lecture
to ehance your knowledge
Read Chapter of Glycosides from these Books
Sr. No.l Books Name Author Name
1 Trease and Evans Evans, W.C.
Pharmacognosy
2 Text book of Mohammed Ali
Pharmacognosy
3 Pharmacognosy Varro E. Tyler
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