Anthracene Glycosides (or Anthraquinone Glycosides)

Anthracene glycosides represent a major class of glycosides. They are

abundantly found in various dicot plant families, such as: Ericaceae,
Euphorbiaceae, Leguminoseae, Lythreaceae, Polygonaceae, Rhamnaceae,
Rubiaceae and Verbenaceae to name a few. Interestingly, some monocots
belonging to the family Liliaceae also exhibits the presence of anthracene
glycosides. Besides, they are also present in certain varieties of fungi and
lichens.
A plethora of glycosides having their aglycone moieties closely related to
anthracene are present in noticeable amounts in a variety of drug
substances, for instance: aloe, cascara, frangula, sagrada and senna. These
drugs are invariably employed as cathartics.
Phenol Glycosides
A variety of phenol glycosides are widely distributed in nature. It has been
found that quite a few simple phenol glycosides have their aglycone portion
loaded with either phenolic moieties or more often with alcoholic moieties or
carboxylic acid functions. Invariably, the natural vegetative plant products,
such as: Willow bark (containing Salicin) and Bearberry leaves (containing
arbutin) have been employed therapeutically since ages, the former as
antipyretic and the latter both as urinary antiseptic and as diuretic.
A few frequently used phenol glycosides commonly found in natural plant
products are described below; such as: Arbutin; Gaultherin; Salicin;
Populin; Glucovanillin.
Steroid Glycosides
Steroid glycosides are also referred to as Cardiac glycosides in many
available books on phytochemistry. In fact, there exists enough evidence in
literatures to reveal that a host of medicinal plants comprise of cardiac or
cardiotonic glycosides, collectively known as steriod glycosides, and they
have since been employed as arrow poisons or cardiac drugs. Interestingly,
from a therapeutic perspective this particular group of compounds may be
regarded as one of the most important of all naturally occurring plant
products.
The cardiac glycosides are basically steroids with an inherent ability to
afford a very specific and poweful action mainly on the cardiac muscle when
administered through injection into man or animal. As a word of caution, a
small amount would exhibit a much needed stimulation on a diseased heart,
whereas an excessive dose may cause even death.
Generally, the steroid glycosides are invariably employed in the
therapeutic domain primarily for two vital reasons, namely: (a) to enhance
the tone, excitability and above all the contractibility of the cardiac muscle;
and (b) to increase the diuretic action, due principally to the enhanced renal
circulation (an inherent secondary action).
A few important plant products belonging to this category are discussed in
the sections that follows, namely:
Flavonoid Glycosides

Flavonoid constitute one of the largest class of naturally occuring plant

products mostly phenols either in the free state or as their respective
glycosides. As the very name suggests they are usually yellow-coloured
compounds (flavous is a latin word yellow colour). Interestingly, more than
2000 different chemical compounds have been isolated, identified and
reported from plant sources. In fact, their chemical structures are solely
based upon a C6C3C6 carbon skeleton having a pyran or chroman ring
bearing a second benzene (aromatic) ring strategically positioned at C2, C
3 or C4 as shown below:

In nature they are invariably available as: flavones, flavanones, flavonols,

isoflavones, and anthocyanidins*. In certain specific instances either the
6-membered heterocyclic ring (pyrones) is replaced by a 5 membered
heterocyclic ring (aurones) or exists in an open-chain isomeric form
(chalcones). Besides, the normally existing glycosylated derivatives found
in nature, other types of derivatives, such as methylated, acetylated,
prenylated, or sulphated ones also exist. Nevertheless, it has been
established that a large variety of flavonoids exert a wide range of activities
in nature, namely: antimicrobial agents, signaling molecules, or stress
metabolites.
Coumarin and Furanocoumarin Glycosides
Generally, couramin and its derivativces furanocoumarin are found to be
present in a plethora of naturally occuring plants. Nevertheless, the
coumarin is presnet either in the free state or its corresponding glycosides
form in nature, but it has been observed that the former being most
common.
2.5.1 Coumarin Glycosides
These are reported to be present in about 150 different species spreading
over to nearly 30 different families, of which a few important ones are,
namely: Caprifoliaceae, Leguminosae, Oleaceae, Rubiaeeae, Solaneceae, and
Umbelliferae.
This basic nucleus of coumarin is considered to be derived from o-hydroxy
cinnamic acid (or o-coumarin acid) by its dehydration to yield the fused
lactone ring as shown below:
It has been observed that invariably most naturally occurring coumarins
essentially bear an oxygen atom either as hydroxyl (OH) or alkoxyl (OCH3
or OC2H5) at C-7 position.

A few important naturally occurring coumarin glycosides along with their

respective biological sources have been summarised in Table 4.3.
2.5.1.1 Coumarin Coumarin is abundantly found in a variety of natural
products which are used profusely as a flavouring agent in pharmaceutical
preparations.
Synonyms Tonka bean camphor; Cumarin; Coumarimic anhydride.
2 Furanocoumarin Glycosides
In general, the furanocoumarins are obtained by the fusion of the furan
ring to the coumarin nucleus either at C-6 and C-7 positons or at C-7 and C8 positions. A few typical examples belonging to this class of glycosides are
discussed in the sections that follows, namely: Khellolglucoside; Psoralea;
and Cantharides
Cyanogenetic Glycosides
The cyanogenetic glycosides are named so because they yield either
hydrocyanic acid upon hydrolysis or they essesntially possess a hydrocyanic
acid in the aglycone moiety. They are also designated as cyanophore
glycosides. Interestingly, about 110 families belonging to the plant
kingdom have been reported to contain the cyanogenetic glycosides;
however, Rosaceae being the most prominent one amongst them.
It is pertinent to mention here that cyanogenetic glycoside containing
drug substances, as such do not exert any specific therapeutic activity, but
they are invariably employed as viable pharmaceutical aids, such as:
flavouring agents.
A large number of cyanogenetic glycosides were isolated and identified
from various plant sources, namely: Linamarin, Linustatin, Lotaustralin and
Lucumin as shown in Table 4.5.
A few important examples of naturally occurring drug substances containing
cyanogenetic glycosides shall be discussed here, namely; Bitter almond,
Wild cherry bark and Linseed. These drugs shall be discussed in the pages
that follows:
Bitter Glycosides
In general, bitters are the edible natural products mostly consumed before
any normal meals to stimulate as well as enhance the appetite. However, the
bitter glycosides as a class do possess almost similar activities like the
bitters such as: digestive, stomachic and febrifuge. Therapeutically, the
bitters have been found to exert their stimulant effects on the gustatory (i.e.;
related to the sense of taste) nerves located in the mouth and ultimately
give rise to an improved gastric juice secretion in the stomach.
The bitter glycosides have been found not confined to the same chemical
class, but the most important ones amongst them essentially possess the
pyran cyclopentane ring.
A number of bitter glycosides isolated from natural plants have been put
into actual therapeutic practice, namely: Picrorhiza, Gentian, and Chirata,
which shall be discussed in the sections that follow.
Miscellaneous Glycosides

There are a number of glycosides which do not fall into the various
classifications discussed under Sections 2.1 to 2.10 ; therefore, they have
been grouped together under the present head i.e., Miscellaneous
Glycosides A few imortant members of this group shall be described here
briefly.
Steroidal Alkaloidal Glycosides
They are sepecifically abundant in two families,
namely: Liliaceae and Solanaceae. Just like saponins, the steroidal
alkaloidal glycosides do possess significant haemolytic activities
Antibiotic Glycosides
Streptomycin is the glaring example of an antibiotic glycosides produced
by the soil Actinomycete, Streptomyces griseus (Krainsky) Waksman et
Henrici belonging to family Actinomycetaceae. It is usually formed by the
combination of the genin Streptidine a nitrogen containing cyclohexane
derivative and Stretobiosamine a disaccharide representing two-thirds of
the streptomycin molecule, through a glycosidic linkage
Saponin Glycosides
In general a group of plant glycosides commonly referred to as saponin
glycosides, usually share in different extents, the following two specific
characteristics namely:
(a) They produce foam in aqueous solution, and
(b) They cause haemolysis of Red Blood Corpuscles (RBC).
The saponin glycosides are broadly regarded as haemotoxic in nature by
virtue of the fact that
they afford the haemolysis of erythrocytes, which render most of them as
fish poisons. Invaribaly, they possess a bitter and acrid taste, besides
causing irritation to mucous membranes. They are mostly amorphous in
nature, soluble in alcohol and water, but insoluble in non-polar organic
solvents like benzene, n-hexane etc.
Interestingly, the naturally occurring plant materials consisting of saponin
glycosides have been extensively employed in various parts of the globe for
their exclusive detergent characteristics, for instance: In South Africa the
bark of Quillaia saponaria belonging to family Rosaceae and in Europe the
root of Saponaria officinalis belonging to family Caryophyllaceae.
SapogeninsThe aglycone of the saponin glycosides are collectively
known as sapogenins. Sapotoxinsthe harmful and poisonous sapogenine/
saponins are aften referred to as sapotoxins. Based on the nature of the
aglycone residue present in the saponin glycosides, they are broadly
classified into the following two categories, namely:
(i) Tetracyclic triterpenoid saponins (or Steroidal saponins), and
(ii) Pentacyclic triterpenoid saponins.
These two categories of saponin glycosides will be discussed with suitable
examples from plant sources in the sections that follows:
2.8.1 Tetracyclic Triterpenoid Saponins (or Steroidal Saponins)
Due to the enormous pharmaceutical importance a plethora of plants have
been screened thoroughly for the detection of steroidal saponins. They are

not only confined to monocot plants but also extended to dicot plants, such
as:
Monocot Plants : FamilyAmaryllidaceae, Dioscoreaceae and Liliaceae
Dicot Plant : FamilyApocynaceae, Leguminosae and Solanceae
1 Dioscorea
Synonyms Rheumatism root; Yam.
Biological Source It essentially comprises of the dried tubers of Dioscorea
delitoidea Wall., Dioscorea tokora Makino, and Dioscorea composita and
other species of Dioscorea belonging to the family Dioscoreaceae.
Description
Colour : Slightly brown
Odour : Odourless
Taste : Bitter and acrid
Size : Varies dependig on the actual age of the rhizomes (tubers)
Chemical Constituents The major active constituent of dioscorea is
diosgenin usually present in the range of 4-6%. Diosgenin is the aglycone of
saponoin dioscin
Besides, the rhizomes contain starch to the extent of 75% but it has no
edible utility because of its bitter taste. They also contain phenolic
compounds and an enzyme sapogenase.
Uses
1. Dioscorea is mostly employed in the treatment of rheumatic arthritis.
2. Dioscorea has a tremendous potential as a commercial product because
of its high content of diosgenin, which in turn is invariably employed as a
starting material for the synthesis of a host of important therapeutic drugs,
for instance: sex-hormones, oral contraceptives and several corticosteroids.
Pentacyclic Triterpenoid Saponins
This particular class of saponin essentially contains the sapogenin
component with pentacyclic triterpenoid nueleus, that is eventually linked
with either sugars or uronic acids. It is pertinent to mention here that the
sapogenin may be further classified into three major categories namely: Amyrin, -Amyrin and Lupeol.
Ginseng
Synonyms Panax; Energofit; Pannag; Ninjin.
Biological Source Ginseng is the dried root of different naturally occurring
species of Panax, namely: Panax ginseng C.A. Mey or Aralia quinquefolia
Deene & Planch (Korean Ginseng);
Panax japonica (Japanese Ginseng); Panax notoginseng (Indian Ginseng)
belonging to family Araliaceae.
Description
Colour : Yellowish- brown, white or red
Odour : None
Shape : Tuberous and corpulent
Appearance : Translucent and bears the stem scars.
Chemicals Constitutents Ginseng chiefly comprises of a complex mixture
of triterpenoid

saponins which may be either a steroidal triterpene or a pentacyclic

related to oleonic acid. However, these glyscosides have been classified into
three major heads, namely:
(a) Ginsenosides,
(b) Panaxosides, and
(c) Chikusetsu Saponins.
Uses
1. In the Chinese system of medicine ginseng is the most favourite remedy
for a variety of ailments e.g., as a general tonic, stimulant, carminative and
diuretic activities.
2. It also possesses adaptogenic (antistress) properties and is found to exert
positive action on the metabolism, the endocrine system and the central
nervous system.
3. In the orient ginseng is used abundantly in the treatment of anaemia,
diabetes, insomnia, gastritis, neurasthenia and specifically to cure sexual
impotence.
4. It is found to enhance the natural resistance (i.e., non-specific resistance)
and increases the ability to overcome both exhaustion or illness to a great
extent.
5. It prolongs the life of elderly persons and cures giddiness.
2.8.2.2 Liquorice
Synonyms Glycyrrhiza; Liquorice root; Glycyrrhizae radix.
Biological Sources Liquorice is the dried, peeled or unpeeled, roots,
rhizome or stolon of Glycyrrhiza glabra Linn., invariably known in commerce
as Spanish liquorice, or of Glycyrrhiza glabra Linne. var Glandulifera
Waldstein et Kitaibel, mostly known in commerce as Russian liquorice, or of
other varieties of Glycyrrhiza glabra Linne., which produce a sweet and
yellow wood, belonging to family Leguminosae.
Description
Colour : Unpeeled Liquorice-Externally, yellowish brown or dark brown; and
internally, yellowish colour
Odour : Faint and characteristic
Taste : Sweet
Size : Length = 20 to 50 cm; Diameter = 2 cm
Shape : Unpeeled drugStraight and nearly cylindrical
Peeled drugMostly angular
Fracture : Fibrous in bark; and splintery in the wood.
Chemical Constituents Glycyrrhiza (liquorice) comprises of a saponin
like glycoside known as glycyrrhizin (or glycyrrhizic acid)
Chemical Tests
1. When sulphuric acid (80%) is added to a thick section of the drug or
powder, it instantly produced a deep yellow colour.
Substituents/Adulterants Glycyrrhiza uralansis, also known as
Manchurian Liquorice, which is pale chocholate brown in appearance
having wavy medullary rays and exfoliated cork is mostly used as an
adulterant for G. glabra. This particulr species is from sugar, but contains

glycyrrhizin. Sometimes, the Russian Liquorice is also used as an

adulterant, because the drug is purplish in appreance, has long roots but
having no stolons.
Uses
1. Glycyrrhiza has demulscent and expectorant properties
2. It is used as a masking agent for bitter drugs in pharmaceutical
formulations, such as: quinine, aloe, ammonium chloride etc.
3. Ammoniated glycyrrhiza is employed as a flavouring agent in
beverages, pharmaceuticals and confectionary.
4. The inherent surfectant activity due to the presence of saponins helps to
facilitate the absorption of poorly absorbed drugs, for instance:
anthraquinone glycosides.
5. It is invariably added to beer to form stable and enhanced foaminess.
6. It imparts a distinct and characteristic bitter tastte to a number of
beverages, such as: stout, root beer and porter.
Bacopa
Synonyms Herpestis; Brahmi.
Biological Sources It comprises of the fresh stems and the fresh leaves of
Bacopa monnieri Linn., Pennell or Bacopa monnniera Wettst., or Herpestis
monniera Linn., H.B. & L., belonging to family Serophulariaceae.
Description
Colour : Green
Odour : None
Taste : Bitter
Size : Length = 1.2-1.8 cm; Breadth = 2.5-10 mm
Shape : Leaves sessile, broad, entire, ovate-oblong or spathulate with black
spots.
Chemical Constituents The leaves contain saponin glycosides known as
bacoside A and bacoside B which on acid hydrolysis give rise to
triterpenoid aglycone termed as bacogenin A and bacogenin B
respectively. It also contains asiatic acid and brahmic acid as depicted
below:
6 Cyanogenetic Glycosides
The cyanogenetic glycosides are named so because they yield either
hydrocyanic acid upon hydrolysis or they essesntially possess a hydrocyanic
acid in the aglycone moiety. They are also designated as cyanophore
glycosides. Interestingly, about 110 families belonging to the plant
kingdom have been reported to contain the cyanogenetic glycosides;
however, Rosaceae being the most prominent one amongst them.
It is pertinent to mention here that cyanogenetic glycoside containing
drug substances, as such do not exert any specific therapeutic activity, but
they are invariably employed as viable pharmaceutical aids, such as:
flavouring agents.
Bitter Almond
Synonym Amygdala amara.

Biological Source Bitter almond comprises of the dried ripe kernels of

Prunus amygdalus Batsch. Var amara (DC) Focke; Prunus communis Arcang.,
P. amygdalus Bail; and Amygdalus communis Linn., belonging to family
Rosaceae.
Geographical Source Bitter almond trees are mostly native of Persia and
Asia Minor. They are also cultivated in the cooler parts of Panjab and
Kashmir, Italy, Sicily, Portugal, Spain, Southern France and Morocco.
Description
Colour : Brown
Odour : No specific odour
Taste : Bitter
Chemical Tests The general tests of the cyanogenetic glycosides by
means of microchemical reactions in naturally occurring crude drugs are
based on their hydrolysis to yield hydrocyanic acid. In fact, there are four
speciifc and characteristic reactions to detect the presence of liberated HCN,
namely:
1. Ferriferrocyanide Test: Macerate 1 g of the powdered drug with 5 ml of
alcoholic KOH (5% w/v) for five minutes. Transfer it to an aqueous solution
containing FeSO4 (2.5 %w/v) and FeCl3 (1% w/v), and maintain at 60-70C for
10 minutes. Now, transfer the contents to HCl (20%) when the appearance of
a distinct prussian blue colour confirms the presence of HCN.
2. Precipitation of Hg from HgNO3: The reduction of aqueous mercurous
nitrate solution (3% w/v) to metallic Hg by HCN being observed by an instant
formation of black metallic Hg in the cells.
3. Grignard Reaction Test: First of all, dip a strip of white filter paper into a
solution of picric acid (1 % w/v in water) drain and then dip into a solution of
sodium carbonate (10% w/v in water) and drain. Now, place the crushed and
moistened drug material in a small Erlenmeyer flask, and subsequently
suspend the strip of the prepared sodium picrate paper above the material
and stopper the flask with an air tight cork. Maintain the flask in a warm
place for 1 hour when the liberated HCN would turn the sodium picrate paper
from its original yellow colour to brick red colour due to the formation of
sodium isopurpurate (Grignards Reaction).
4. Cuprocyanate Test: First of all, saturate pieces of filter paper in a freshly
prepared solution of guaic resin dissolved in absolute ethanol and allow them
to dry completely in air. Now, carefully moisten a piece of the above paper
with a very dilute solution of CuSO4 and place it into contact with a freshly
exposed surface of the drug. In case, HCN is generated, it will give rise to a
distinct stain on the paper.
Uses
1. Bitter almonds are employed as sedative due to HCN content.
2. The fixed oil of bitter almond finds its use as demulscent in skin-lotion.
3. It is also employed in the preparation of amygdalin and bitter almond
water.
Black Mustard

Synonym Brown Mustard.

Biological Sources These are dried ripe seeds of Brassica nigra Linn., Koch
or Brassica juncea Linn, Czern & Coss, belonging to family Cruciferae.
Description
Colour : Black, dark brown or reddish brown
Odour : Whole seed-none; Crushed seed-pungent characteristic odour.
Taste : Bitter
Size : Approx. 0.9-1.0 mm in diameter
Shape : Mostly spherical in shape
Special Features Seeds are normally covered with a brittle testa and the
kernel is oily and greenish yellow in colour. The approx. weight of 100 seeds
ranges between 150 to 170 mg.
Chemical Constituents The black mustard seed contains a thioglycoside
i.e., a -glucopyranoside termed as sinigrin.
Coumarin and Furanocoumarin Glycosides
Generally, couramin and its derivativces furanocoumarin are found to be
present in a plethora of naturally occuring plants. Nevertheless, the
coumarin is presnet either in the free state or its corresponding glycosides
form in nature, but it has been observed that the former being most
common.
2.5.1 Coumarin Glycosides
These are reported to be present in about 150 different species spreading
over to nearly 30 different families, of which a few important ones are,
namely: Caprifoliaceae, Leguminosae, Oleaceae, Rubiaeeae, Solaneceae, and
Umbelliferae.
This basic nucleus of coumarin is considered to be derived from o-hydroxy
cinnamic acid (or o-coumarin acid) by its dehydration to yield the fused
lactone ring as shown below:
It has been observed that invariably most naturally occurring coumarins
essentially bear an oxygen atom either as hydroxyl (OH) or alkoxyl (OCH3
or OC2H5) at C-7 position.
A few important naturally occurring coumarin glycosides along with their
respective biological sources have been summarised in Table 4.3.
2.5.1.1 Coumarin Coumarin is abundantly found in a variety of natural
products which are used profusely as a flavouring agent in pharmaceutical
preparations.
Synonyms Tonka bean camphor; Cumarin; Coumarimic anhydride.
Chemical Structures Coumarin has the following structure:

Uses It is mostly employed as a pharmaceutical aid.

2.5.2 Furanocoumarin Glycosides

In general, the furanocoumarins are obtained by the fusion of the furan
ring to the coumarin nucleus either at C-6 and C-7 positons or at C-7 and C8 positions. A few typical examples belonging to this class of glycosides are
discussed in the sections that follows, namely: Khellolglucoside; Psoralea;
and Cantharides.
2 Psoralen
Synonyms Lata-kasturi (Bengali); Bahuchi (Sanskrit).
Biological Sources They are the dried ripe fruits of Psoralea corylifolia
Linn., belonging to the family Leguminosae. Psoralen is also found naturally
in more than two dozen plant sources, namely: Bergernot, Limes, Cloves:
family Rutaceae; Figs.: family Moraceae.
Description
Colour : Dark chocholate to black
Odour : Pungent and characteristic after crushing the fruits
Taste : Unpleasant, bitter and acrid
Size : 3 to 5 2 to 3 mm
Shape : Pods are ovoid, oblong beam shaped
Chemical Constituents The fruits of P. corylifolia invariably contain
fluorocoumarin compounds known as psoralen and isopsoralen
Besides the fruit contains a variety of other chemical constituents, for
instance: fixed oil (10%); resin (8.9%); essential oil (0.05%) and small
amounts of raffinose and a pigment.
Chemical Tests (For Psoralen)
1. To a small amount of drug add a minimum quantity of alcohol for complete
dissolution. Add to this 3 volumes of propylene glycol, 5 volumes of acetic
acid and 43 volumes of water and shake well. The appearance of a blue
fluorescence under UV-light indicates its presence.
2. The drug is dissolved in minimum amount of alcohol and on addition of a
little sodium hydroxide solution exhibits a yellow fluorescence in UV-light.
Uses
1. The seeds are recommended in leprosy, leucoderma and other skin
manifestations. They are also used for snake bite and scorpion sting.
2. The oleroesin extracts of seeds are employed to cure leucoderma patches.
3. The seeds also find their use as stomachic, anthelmintic, diuretic and
diaphoretic.
4. It is used orally as a laxative.
Flavonoid Glycosides
Flavonoid constitute one of the largest class of naturally occuring plant
products mostly phenols either in the free state or as their respective
glycosides. As the very name suggests they are usually yellow-coloured
compounds (flavous is a latin word yellow colour). Interestingly, more than
2000 different chemical compounds have been isolated, identified and
reported from plant sources. In fact, their chemical structures are solely
based upon a C6C3C6 carbon skeleton having a pyran or chroman ring

bearing a second benzene (aromatic) ring strategically positioned at C2, C

3 or C4 as shown below:

In nature they are invariably available as: flavones, flavanones, flavonols,

isoflavones, and anthocyanidins*. In certain specific instances either the
6-membered heterocyclic ring (pyrones) is replaced by a 5 membered
heterocyclic ring (aurones) or exists in an open-chain isomeric form
(chalcones). Besides, the normally existing glycosylated derivatives found
in nature, other types of derivatives, such as methylated, acetylated,
prenylated, or sulphated ones also exist. Nevertheless, it has been
established that a large variety of flavonoids exert a wide range of activities
in nature, namely: antimicrobial agents, signaling molecules, or stress
metabolites. The structures of a few typical flavonoids are represented here
as follows:
--------------------------------------------* Anthocyanidins are the colored aglycones found as a large number of
pigments from flowerd and fruits (Gr. Antho flower + Gr. Kyanos, blue).
Investigations of these pigments were initiated by Willstatter in 1914 and
later on extended by Karner R Robinson, GM Robinson and others.
4 Strophanthus
Synonyms Semino stropanthi.
Biological Source These are the dried and ripe seeds of Strophanthus
hispidus De*, or of Strophanthus kombe Oliver, belonging to the family
Apocynaceae, deprived of the awns.
Description
Colour : Greyish green to light yellowish brown
Odour : Slight unpleasant
Taste : Bitter
Size : Length 1- 2 cm; Breadth = 3-5 mm; Thickness = 2 mm
Shape : Lanceolate to linear-lanceolate, acute at the apex, rounded or blunt
at the base
Weight : For 100 seeds 3-4 g
Specific : On treating with 80% H2SO4 the endosperm exhibits a deep
feature Emerald green colour.
Chemical Constituents The seeds of strophanthus usually contain three
vital glycosides, namely:

K-strophanthoside, K-strophanthride b and cymarin. Interestingly, all

these glycosides undergo hydrolysis to yield strophanthidin.
Chemical Tests
1. Generally, the strophanthus glycosides exhibit an emerald green
colouration on the addition of sulphuric acid.
2. Dissolve about 0.1g of strophanthin in 5 ml of water and add to it a few
drops of ferric chloride solution followed by a 1-2 ml of concentrated
sulphuric acid; the appearance of an initial red precipitate that finally turns
green within a period of 1-2 hours.
3. To 50 mg of strophanthin add 5 ml of water, shake and add 2 ml of 2%
tannic acid solution, the appearance of a distinct precipitate affirms its
presence.
4. It shows positive Baljet Test, Legal Test and Keller Killiani Test (see
Section 2.3.1).
Uses
1. It is used intravenously for treating emergency cardiac conditions.
However, orally strophanthin is not so active.
2. These glycosides have been found to exert less cumulative effect unlike
the digitalis glycosides.
3. Overall their therapeutic actions are very much similar to those of
Digitalis.
Squill
A survey of literature reveals that the Squill bulbs was thoroughly and
repeatedly investigated since 1879. However, Stoll in 1933 was first able to
separate and isolate two glycosides in their purest form, namely: Scillaren A
and Scillaren B. These two naturally occurring glyosides are usually present
in the crude drug in the ratio 2:1 (i.e., 2 parts of Scillaren A and 1 part of
Scillaren B). Generally, the squill is available in three varieties, namely:
(a) European Squill
(b) Indian Squill, and
(c) Red Squill.
2.3.3.1 European Squill
Synonyms Sea, onion, Bulbus Scillae; Meerzweibel, White Squill, Squill bulb;
Scila.
Biological Source European squill is the fleshy inner bulb scales of the
white variety of Urginea maritima (L.) Baker (Scilla maritima L.) belonging to
family Liliaceae.
Description
Colour : White; Whitish yellow;
Taste : Bitter and gummy;
Size : Length = 3.5-5 cm; Width = 5-8 mm; Thickness = 2-5 mm;
Shape : Available as strips with tapering both ends.
Chemical Constituents Squill has the following glycosides, namely:
Glucoscillaren A = Scillarenin + Rhamnose + Glucose + Glucose;
Scillaren A = Scillarenin + Rhamnose + Glucose;
Proscillaridin A = Scillarenin + Rhamnose.

Uses
1. It is a potent cardiotonic without having any cumulative effect (unlike
Digitalis).
2. It is mostly employed in small doses as an effective expectorant specially
in chronic bronchitis.
3. It causes emesis in relatively higher doses.
4. The squill glycosides usually produce copious diuresis.
5. By virtue of the fact that the squill glycosides possess high therapeutic
index and rapid elimination they invariably maintain compensation in such
patients where a prolonged treatment is required.
2.3.3.2 Indian Squill
Synonyms Scilla; Sea onion; Jangli Pyaj; Urginae.
Biological Source Indian squill comprises of the dried slices of the bulbs
of Urginbea indica Kunth; belonging to the family Liliaceae
Description
Colour : Yellowish to White
Odour : Slight and characteristic
Taste : Acrid, bitter and mucilaginous
Size : Length = 30-60 cm; Breadth = 3-8 mm
Shape : Usually 4 to 8 slices are placed one on the top of other and gives it
a curved shape.
Chemical Constituents Indian Squill essentially comprises of cardiac
glycosides (0.3%), alcohol soluble extractives (20-40%), mucilages (40%)
and calcium oxalate.
The two major cardiac glycosides present in the drug are Scillaren A and
Scillaren B (see Section 2.3.3.1).
Substituents/Adulterants The bulbs of different species of Ledebouria
(Scilla, Linn) are sold in the Indian bazars, under vernacular names which are
equivalent to small squill.
Ledebouria hyacinthoides, is used as a substitute for squill. It has a scaly
bulb, about the size and shape of a small pear, composed of very amooth
and fleshyscales, which are so imbricated that they might be mistaken for
entire coats if not carefully examined.
Uses
1. It is largely employed as a cardiotonic , stimulant and also an expectorant.
2. It is used as a very effective expectorant both in asthma and chronic
bronchitis.
3. It possesses anticancer activity against human epidermoid carcinoma of
the masopharynx in tissue culture.
4. It is in no way a perfect replacement for Digitalis since it possesses not
only irritant effect but also is very poorly absorbed systemically.
Anthracene Glycosides (or Anthraquinone Glycosides)
Anthracene glycosides represent a major class of glycosides. They are
abundantly found in various dicot plant families, such as: Ericaceae,
Euphorbiaceae, Leguminoseae, Lythreaceae, Polygonaceae, Rhamnaceae,
Rubiaceae and Verbenaceae to name a few. Interestingly, some monocots

belonging to the family Liliaceae also exhibits the presence of anthracene

glycosides. Besides, they are also present in certain varieties of fungi and
lichens.
A plethora of glycosides having their aglycone moieties closely related to
anthracene are present in noticeable amounts in a variety of drug
substances, for instance: aloe, cascara, frangula, sagrada and senna. These
drugs are invariably employed as cathartics.
2.1.1 Aloes
Synonym: Aloe
Biological Source: Aloe is the dried latex of leaves of various species of
Aloes, namely:
Aloe barbadensis Miller (or Curacao Aloe);
Aloe ferox Miller (or Cape Aloe);
Aloe perryi Baker (or Socotrine Aloe);
Aloe africana Miller and Aloe spicata Baker (or Cape Aloe).
All these species belong to the family Liliaceae.
Chemical Tests The overall chemical tests for aloes may be divided into
two separate heads, namely: (a) General Tests, and (b) Special Tests
(a) General Tests: For this prepare a 0.1% (w/v) aqueous solution of aloes
by gentle heating, add to it 0.5g of Kiesulgur and filter through. Whatman
Filter Paper No. 42 and preserve the filtrate for the following tests:
1. Borax Test (or Schoentetens Reaction): To 5 ml of the above test
solution add 0.2 g of pure borax and heat gently till it gets dissolved. Transfer
a few drops of the resulting solution into a test tube filled with distilled water,
the appearance of a green coloured fluoroscence due to the formation of
aloe emodin anthranol shows its presence.
2. Bromine Test: When equal volumes of the test solution and bromine
solution are mixed together, it yields a pale-yellow precipitate due to the
production of tetrabromaloin.
3. Modified Borntragers Test: It is known that aloin (or barbaloin)
belongs to the class of Cglycoside which does not undergo hydrolysis either
by heating with dilute acid or alkali, but it may be decomposed with ferric
chloride due to oxidative hydrolysis. Hence, the Modified Borntragers
test employing FeCl3 and HCl is used as stated below:
First of all heat together 0.1 g of powdered aloe with about 2 ml of FeCl3
solution(5% w/v) and 2 ml of dilute HCl (6N) in a test tube over a pre-heated
water bath for 5 minutes. Cool the contents and extract the liberated
anthraquinone with carbon tetrachloride. Now carefully separate the lower
layer of CCl4 and add to it ammonia solution. The appearance of a rose-pink
to cherry red colour confirms its presence.
Rhubarb
Synonyms: Rheum; Radix rhei; Rhubarb rhizome.
Biological Source: Rhubarb is the rhizome and roots of Rheum officinale
Bail., R. palmatum L., Rheum emodi Wall ; R. webbianum Royle, belonging to
the family Polygonaceae. The rhizome and roots are mostly collected from 6-

7 year old plants just prior to the following season. They are commercially
available either with intact cortex or partially decorticated.
Chemical Constituents Rhubarb essentially contains mainly the
anthraquinone glycosides and the astringent components. The former range
between 2 to 4.5% and are broadly classified into four categories as stated
below:
(a) Anthraquinones with COOH moietye.g., Rhein; Glucorhein
(b)Rhubarb in addition to the above constituents, consists of rheinolic
acid, pectin, starch, fat and calcium oxalate. The calcium oxalate
content ranges between 3-40% in various species of rhubarb which
reflects directly on the corresponding ash values (i.e., total inorganic
contents).
(c) Chemical Tests
(d)1. The Rhubarb powder on being treated with ammonia gives rise to a
pink colouration.
(e) 2. Rhubarb gives a blood-red colouration with 5% potassium hydroxide.
(f) 3. It gives a positive indication with modified Borntragers test (see
under Aloes).
(g)Uses
(h)1. It is used mainly in the form of an ointment in the treatment and
cure of chronic eczema, psoriasis and trichophytosisas a potent
keratolytic agent.
(i) 2. It is employed as a bitter stomachic in the treatment of diarrhoea.
(j) 3. It is also used as a purgative.
(k)
2.1.3 Cascara Sagrada
(l) Interestingly, the very name cascara sagrada is Spanish for the
sacred bark; Rhamnus is the ancient classical name for buckthorn, and
Purshianus was attributed as a mark of honour and respect to the great
German botanist Friedrich Pursch.
(m)
Synonyms Sacred bark; Chitten bark; Chittin bark; Purshiana
bark; Persian bark; Bearberry bark; Bearwood; Cascara bark; Cortex
Rhamni purshianae.
(n)Biological Source Cascara sagrada is the dried bark of Rhamanus
purshiana DC., belonging to
(o) family Rhamnaceae, from which a naturally occurring cathartic is
extracted. It is usually collected at least one year prior to its use.
(p)Description
(q)Colour : Outside-purplish brown; Inside reddish brown.
(r) Odour : A typically nauseatic odour.
(s) Taste : Persistently bitter.
(t) Size : Occurs in varying sizes of thickness between 1 to 4 mm.
(u)Shape : Mostly occurs in quills or channels. Also available in small, flat
and broken segments.
(v) Chemical Constituents The cascara sagrada bark is found to
contain two major types of anthracene compounds, namely:

(w)
(a) Normal O-Glycosides These are based on emodin like
structures and constitute about 10 to 20% of the total glycosides, and
(x) (b) Aloin-like C-Glycosides These comprise of about 80 to 90% of the
total glycosides.
(y) The two C-glycosides are known as barbaloin and deoxybarbaloin
(or chrysaloin) as given below:
(z) Chemical Test It gives a positive indication with Modified
Borntragers test because of the presence of C-glycosides.
(aa)
Substituents/Adulterants The barks of Rhamanus californica
and R. fallax are generally used as a substitute for cascara sagrada
bark. Sometimes the frangula bark is also used as a substitute for this
drug. However, the former types of barks (Rhamnus species) exhibit a
more uniform coat of lichens along with broader medullary rays when
compared to the original drug species.