Glycosides

By
Dr. Saleem Ahmed
Learning Objectives
At the end of this lecture students will be able to
Define Glycosides.
Know about linkage between glycone and
aglycone.
Describe role of glycosides in plants.
Know biosynthesis and method of isolation.
Families

Chemical constituents

Uses
Definition
Glycosides are organic compounds, usually of
plant origin,
that are composed of a sugar portion linked to a
non-sugar moiety.
The sugar portion is called glycone, while the
non-sugar portion is called aglycone or genin.
Glycosides are compounds that yield one or more
sugars among the products of hydrolysis.
Definition (Chemically)
Chemically the glycosides are acetals in which the
hydroxyl of the sugar is condensed with a hydroxyl
group of the non sugar component and the
secondary hydroxyl is condensed within the sugar
molecule itself to form an oxide ring.
Acetal Linkage
The linkage between the sugar and
the aglycone is an acetal linkage.
Role of Glycosides in life of plant
Regulative
Protective
Sanitary
Contd….
Converting toxic materials to non or less toxic.
Transfer water insoluble substances by using
monosaccharide.
Source of energy (sugar reservoir).
Storing harmful products such as phenol.
Regulation for certain functions(growth).
Some have beautiful colors ( helpful in pollination
process).
Contd….
Some glycosides have antibacterial activity, so they
protect the plants from bacteria and diseases.

1 3
bacteria kills

Bitter almond Amygdalin hydrolysis HCN

Emulsin
enzyme
2
Biosynthesis of Glycosides
UTP + Sugar-1-P═ UDP-Sugar + PPi
 ( uridylyl transferase)
UDP- Sugar (glycosyl transferases)
+Acceptor(aglycone) ═ Acceptor-
Sugar + UDP
UTP =uridylyl triphosphate
Method of Isolation
Stas -Otto Method

Drug containing glycoside is finely powdered and

the powder is extracted by continuous hot
percolation using Soxhlet apparatus with Alcohol
as solvent. During this process various enzymes
present in plant parts are also deactivated due to
heating. The thermolabile glycosides however
should be extracted at temperature preferably
below 45°C.
Contd….
The extract is treated with lead acetate to
precipitate tannins and thus eliminate non
glycosidal impurities. The excess of lead
acetate is precipitated as lead sulphide by
passing hydrogen sulphide gas through
solution. The extract is filtered,
concentrated to get crude glycosides.
Contd….
From the crude extract, the glycosides are
obtained in pure form by making use of
processes like fractional solubility, fractional
crystallization and chromatographic
technique such as preparative TLC and CC.
How we classify Glycosides?
I- According to atoms involved in the glycosidic
linkage:
1- O-glycosides
2- C-glycosides
3- S-glycosides
4- N-glycosides
O-Glycosides
They are very common in higher plants e.g. Senna,
Rhubarb, Frangula etc.

Glycone-OH + HO-Aglycone_____ Glycone-O-

Aglycone + H2O
C- Glycosides
Some of the Anthraquinone glycosides such as
Cascarosides from Cascara and Aloin from Aloe, as
well as, some members of flavone type of
glycosides show the presence of C-Glycosides.

Glycone-OH+HC-Aglycone____Glycone-C-
Aglycone+H2O
S- Glycosides
They are formed by interaction of Sulfhydryl
group of aglycone and hydroxyl group of glycone.

Glycone-OH + HS- Aglycone______ Glycone-S-

Aglycone + H2O
N- Glycosides
Most typical example of N-Glycosides is
Nucleosides where the amino group of base reacts
with OH group of ribose and ultimately gives N-
glycosidic form.

Glycone-OH + HN-Aglycone------- Glycone-N-

Aglycone + H2O
II- According to the configuration of the
glycosidic linkage

1- -glycosides:
Here the sugar involved in glycosidal linkage has
the  configuration.
The majority of plant glycosides isolated are -
glycosides.
Contd….
2-  -glycosides :
Here the sugar involved in glycosidal linkage has
the -configuration; the sugar is usually of the L-
series e.g. L-rhamnose. There are only few
medicinal -glycosides known, especially the
rhamnosides.
Diagrammatic representation
III- According to the sugar moiety:

1- Glucosides
2- Ribosides
3- Rhamnosides
IV- According to the therapeutic
Activity:
Cardioactive Glycosides
Cathartic Glycosides
Rubefacient
Carminative
Laxative
Antitussives
V. According to aglycone moiety or
Chemical Classification

Anthraquinone or Anthracene Glycosides

e.g. Cascara, Aloe, Rhubarb, chrysorbin,Danthron
and Senna
Saponin Glycosides e.g. Glycyrrhiza, Dioscorea
Sterol or Cardioactive Glycosides e.g. Digitalis,
Strophanthus , White Squill
Cyanogenic or Cyanophore Glycosides e.g. Wild
Cherry
Contd…
Isothiocyanate Glycosides e.g. Black
Mustard or white mustrad
Lactone Glycosides /coumarine.g.
Cantharide
Aldehyde Glycosides e.g. Vanilla
Alcohol Glycosides e.g Salicin
Flavanol Glycoside e.g citrus fruits
Sugars in glycosides
It may be molecule of a monosaccharide e.g.
D-glucose or L- rhamnose.
- or composed of 2 or more sugars, forming a
di-or oligosaccharide chain e.g. Purpurea
glycoside A has a tetrasaccharide attached to
digitoxigenin.
e.g. Digitoxigenin-O-(digitoxose)3-O-
glucose.
Contd…..
b-D-glucose is the most common sugar in
glycosides.
Other sugars include :
i- Other hexoses e.g. galactose
ii- Pentoses e.g. ribose, xylose and
arabinose.
iii- 6-Deoxyhexoses e.g. rhamnose and
digitalose.
Contd….
iv - 2,6-Dideoxysugars e.g. sarmentose,
digitoxose and cymarose (rare sugars).
The 6-Deoxy sugars and 2,6-Dideoxy sugar are

common in

Cardiac glycosides.

vi- A uronic acid e.g. glucuronic acid found in

glycyrrhizin .
Properties of Glycosides
In plant glycosides are both synthesized
and hydrolyzed under the influence of
more or less specific enzymes.
They are crystalline or amorphous
substances that are soluble in water or
alcohols and insoluble in organic
solvents like benzene and ether. The
aglycone part is soluble in organic
solvents like benzene or ether.
Contd….
They are hydrolyzed by water , enzymes and
mineral acids.
They are optically active.
Glycosides do not themselves reduce Fehling
solutions, the simple sugars which they produce
on hydrolysis will do so with precipitation of red
cuprous oxide.
Salicin, with one glucose unit, is soluble in ether,
while glycosides with a larger sugar portion are
more soluble in alcohol or aqueous alcoholic
solvents.
How we separate Aglycone and Glycone
parts
Separation between glycosides parts:
Glycosides + dil HCl glycone +aglycone (Hydrolysis)
Alkali G + A +H2O
(H2O+G+A) + Chloroform (H2O+G)+(chloroform+A)
We can separate them by using separatory funnel.
The best solvent to extract aglycone is Ethyl acetate because:
immiscible in water.
always presents in the upper layer.
Alcohol and acetone are water miscible compounds,so we
can't use them as organic solvents for aglycone separation.
Anthraquinone Structure
Anthrones and Anthraquinones
Anthranol
Contd…..
Reduced form of Anthraquinone are biologically more
active. In a fresh drug these aglycones are present in a
reduced form, but are hydrolysed and oxidized during
their storage. They are present along with different
sugars like glucose, rhamnose and arabinose.
The anthraquinone and related glycosides are
stimulant cathartics and exert their action by
increasing the tone of the smooth muscles in the wall
of the large intestine.
Biosynthesis of anthroquinone
Anthroquinones has been obtained from studies of
microorganisms.
Feedings of labelled acetate to penicillium
islandicum,a species that produces several
anthraquinone derivatives ,have revealed that the
distribution of radioactivity in these compounds is
consistent with formation via a head to tail
condensation of acetate units.
Emodin like anthraquinones are formed in higher
plants by a similar pathway.
The transglycosylation reaction,which creates a
glycoside,probably occurs at a late stage in the pathway
after the anthraquinone nucleus has been formed.
Borntrager’s test
Specific test for Anthraquinone Glycosides.
In this test drug is powdered and add 5-10ml dilute HCL
boil on water bath for 10 min and filter. Filtrate was
extracted with CCL/benzene and add equal amount of
ammonia solution to filtrate and shake. Formation of pink
or red color in ammonical layer due to presence of
anthraquionone moiety.
Cascara sagrada
Dried bark of Rhamnus purshianus
Rhamnaceae
How we collect bark?
Evergreen tree growing to 6-10 m in height.
It requires moist soil.

Collections are made during the summer,

beginning at the end of May and continuing
until the rainy season starts.
Why fresh bark is not used?

Freshly collected bark contains anthranols

derivatives which causing griping action and
emetic effects. The drug become acceptable by
storing for at least one year, during which
anthranol portion is oxidized to anthraquinones.
Constituents
O-Glycosides 10-20%
C-Glycosides 80-90%
Two of c –glycosides are barbaloin and
deoxybarbaloin.
Cascarosides A, B, C and D.
Cascarosides Structural
Relationship
How we mask bitter taste of the drug and what is the general use of the drug ?

In mild doses it is used as bitter stomachic

and tonic and in larger doses as purgative
and Cathartic.
The bitter taste reduced by treating with
alkaline earth or magnesium oxide.
Dosage
Cascara sagrada bitter fluid extract 1ml
Aromatic sweet Cascara sagrada fluid extract 5ml

Uses
Cathartic
Specialty Products
Cas- Evac
Phenolphthalein- Oxothalein
Phenolphthalein, bile salts, and aloin-Amlax
Aloe-Nature’s Remedy
Petrogalar with cascara sagrada
Dioctyl sodium sulfosuccinate
Aloe barbadensis and Aloe ferox
Aloe vera
Aloe vera is obtained from mucilaginous tissue in the
centre of the Aloe vera leaf.
Two important types of Aloe:
Curacao Aloe: Aloe barbadensis
Cape Aloe: Aloe ferox
Aloe meaning shinning,bitter substances,vera meaning
true,ferox meaning true and barbadensis is Barbados
islands.
Family: Liliaceae
What is Aloes?

It is obtained by evaporation of water from the bitter

yellow juice that is drained from the leaf.
Time of collection
Aloes are typical Xerophytic plant that have fleshy
leaves and usually have spines at margins.
The leaves are cut in March and April.
Preparation of Aloe
Barbados or Curacao Aloe
It is prepared in islands of Aruba and Bonaire in
West Indies. After giving the transverse cuts near
the bases of the fleshy leaves of Aloe barbadensis,
the cut leaves are placed along the sides of V-
Shaped wooden troughs in tilted position to drain
out all the juice. The juice collected by this way is
allowed to boil in large copper pans. During
boiling, the latex evaporates and juice is further
thickened. The thick juice is then poured into
metal containers where it hardens.
Preparation of Cape Aloes
It is obtained from Aloe ferox and its hybrids in
South Africa.
The transversely cut leaves are arranged in a
circular manner in the basin shaped depression,
dug in the ground which is lined either with goat
skin or canvas, They are kept in this position for 5-
6 hours, till all the juice exude out and is collected
in goat skin.
The collected juice is transferred to large iron
kettles , where it is boiled and continuously stirred
with a wooden paddle type instruments. When
desired concentration should achieved transfer it
to wooden cases.
Constituents of Aloes
Aloe contains a number of anthraquinone
glycosides , the principal one of which is barbaloin.
O-glycosides, Chrysophanic acid (10-30% ),
Resinous material plus a volatile oil (16-63%).
Different tests for detection
Nitrous acid test
Crystals of sodium nitrite along with small quantity of Acetic
acid are added to aqueous solution of Aloes it gives
Sharp pink color with Curacao Aloe
Faint pink color with Cape Aloe
Nitric acid test
Directly applying nitric acid to drug or its aqueous solution it
gives:
Deep brownish red color with Curacao Aloe
Brownish color changing to green in Cape Aloe
Use and Dose
Application of fresh jell
Pharmaceutic aid for compound benzoin tincture
Gel preparation have been reported to be effective
against radiations, burns, skin ulcers and minimizes
the keratosis and peptic ulcers.
Antiinflammatory
15mg
Contra indications
Aloes contra-indicated its use in individual with
hemorrhoids, existing kidney diseases and
inflammatory disease of colon.
Products
Alophen
Amlax
Rhubarb
Dried Rhizome and roots of Rheum officinale L.
Polygonaceae
Constituents
Hydroxyanthracenes: primarily anthraquinone O-
Glycosides
Rhein anthrones
Tannins: Hyrolysable and Condensed tannins
Other constituents: Calcium oxalate, fatty acids, rutin,
resins, starch 16%, volatile oil (trace).
Food use
Listed by Council of Europe as a natural source of food
flavoring.
It can be added in small quantities in food stuffs.
Rhubarb stems are commonly eaten as food.
Herbal Use
As a Laxative and Cathartic. (At high
doses/Anthraquinone) and Antidiarrheal (At Low
doses/Tannins).
Dosage: Rhizome/root 0.2 -1 g
Side-effects, Toxicity
Rhubarb leaves are toxic because of the oxalic acid
content which is a nephrotoxic and corrosive and
should not be ingested. These substances
are cathartic and laxative, explaining the sporadic use
of rhubarb as a dieting aid
Contra-indications, warnings
Should be avoided by individuals suffering from
arthritis, kidney disease or urinary problems.
Products
Rhubetts
Senna
Dried leaflet of Cassia acutifolia
Tinnevelly Senna (Cassia angustifolia)
Alexandria Senna (Cassia acutifolia)
Family: Leguminosae
Constituents of Senna
Primarily Sennosides A & B (rhein dianthrones)
Sennosides C & D (rhein aloe- emodin
heterodianthrones)
Sennosides A & B yield Sennidin A and B.
Carbohydrates, Flavonoids, salicylic acid, saponin,
resin, volatile oil (trace).
Herbal Use
Cathartic properties (Leaf greater than fruit) or
as herbal tea made from the leaves..
In combination with Ispaghula.
Short term use in cases of occasional constipation.
 Senna is considered to be a bowel stimulant on
the myenteric plexus of the colon to
induce peristaltic contractions and decrease water
absorption from inside the colon, effects that would
provide relief from constipation.
Dosage
Dried pods 3-6 pods (Alexandrian) or 4-12 pods
(Tinnevelly) steeped in 150 ml of warm water for 6-12
hours.
Dried leaflets 0.5-2 g
Side effects
Colic or cramps
Prolong use can result in diarrhea with excessive loss
of potassium, albuminuria and hematuria.
Contra-indications/Warnings
Intestinal obstruction, atony, inflammatory colon
disorders.
May cause Hypokalemia.
Product
Dr. Caldwell’s Senna Laxative
Fletcher’s castoria
Black Draught
With Hydrocolloid or Surfactant
Gentalex
Senokap
Chrysarobin (Goa Powder)
Family –Leguminosae

Goa powder is light yellow when fresh but on exposure to air become dark brown or brownish purple.
Constituents
50 to 75% of neutral principle
Chrysarobin about 2% of resins
7% of bitter extractive
Small amount of chrysophanic acid
Chrysarobin is prepared by extracting goa powder
with hot benzene evaporating the solution to dryness
and powdering
It is brown to orange yellow microcrystalline powder
that is odorless and tasteless
Uses
Keratolytic agent
Psoriasis ,trichphytosis,chronic eczema
Use in ointments (0 to 0.2%)
Because of irritating properties it should not be used
on the face or scalp
Saponin Glycosides
Widely distributed in higher plants.
Form colloidal solutions in water that foam upon shaking ,they
have bitter acrid taste and drugs containing them are usually
sternutatory and otherwise irritating to the mucous
membrane
Why we called Saponin?
Poison to cold blooded animals
They destroy red blood corpuscles by hemolysis and are toxic.
What is Sapogenin?
Upon hydrolysis yield an aglycone, readily crystallizable
compound upon acetylation and are known as sapogenin
Precursor of cortisone
isolated from adrenal cortex and synthesized from certain bile acid
of cattle
Valuable in Research
Precursors for Cortisone.
e.g. Diosgenin.
 More poisonous saponin are often called sapotoxins
Glycyrrhiza and Sarsaparilla are among the drugs
containing saponins
Plants of the members of the liliaceae, Amarylidaceae
and Dioscoreaceae show the presence of sapogenins
among the monocotyledons
Two types of Structures:
• Acid saponins possess Triterpenoid Structure.
• Neutral saponins are derivatives of steroids with
spirochetal side chains.
• Spirochetal steroids

 Acetate mevalonate Squalene Cholesterol

Pentacyclic
triperpenoids
Glycyrrhiza
Glycyrrhiza
Licorice
Part use: Dried Rhizome and root of Glycyrrhiza
glabra.
Glycyrrihiza means sweet roots glabra means smooth
Two varities
Family: Leguminosae
Constituents
Glycyrrhizin ,50 times as sweet as sugar
Upon hydrolysis glycosides loses its sweet taste and its
converted to aglycone glycyrrhetic acid and 2
molecules glucouronic acid
Liquirtin, Isoliquirtin, Rhamnoliquirtin, Liquiritoside,
Stigmasterol, glucose, Mannitol, Starch 20%
Glycyrrhetic acid is a pentacyclic triterpene derivative
of the beta –amyrin type.
Uses
As a Flavoring agent.
For Masking the bitter taste of Drug.
Demulcent and expectorants properties
As a Surfactant.
Anti inflammatory in Dermatologic practice in Europe
Peptic ulcers
Addison’s disease, chronic adrenocortical insufficiency
Added to chewing gums, chocolate candy, cigarettes,
smoking mixtures
Pure Extract and Fluid Extract
How we prepare Glycyrrhiza fluid extract?
Licorice root extracting with warm water alkaline with
ammonium hydroxide, concentrating make a final
volume with water and alcohol
Dosage
Powdered root 1-4 g as a decoction 3 times daily.
Licorice Extract 0.6-2.0 g

Contra-indicated to Hypertensives
Interaction with Cardiac Glycosides, thiazide, loop
diuretics.
Yam is the common name for 600 species of flowering
plants in the genus Dioscorea
(family Dioscoreaceae)
These are perennial, herbaceous cultivated for the
consumption of their starchy tubers in Africa, Asia and
Latin America, it is native to throughout the tropical and
warm temperate regions of the world.

Dioscorea or Yam
Various species of Dioscorea known as Mexican Yams
represent rich sources of the principles used as
Cortisone precursors.
Botogenin and Diosgenin are obtained from the root
of Dioscorea spiculiflora, a cultivated species.

Significance because of Cortisone Production

 The steroid nucleus of
botogenin was altered by
transferring an oxygen atom
from the 12 to the 11 position
of the polycyclic mol before it Botogenin
could be utilized an
intermediate in the
production of cortisone.

Cortisone

Changes in Botogenin structure for production

of cortisone
Diosgenin obtained by hydrolysis
of Dioscin is now the major
precursor of progesterone and
cortisone which are prepared by
process that involve microbial
transformation.

Progesterone

Diosgenin, major precursor of

glucocorticosteroids
A Mexican Yam derived from D. floribunda is
considered by US Dept. of Agriculture as the best
source of steroids.
Uses
Rheumatoid arthritis
Rheumatic fever
Some of them are rich in vitamins B1,B2 and B6

Best Source of Steroids &Uses

Chemical test of saponin
glycosides
Foam test
To 1 gm of drug add 10-20ml of water ,shake for few
minutes, formation of frothing which persists for 60-
120s in presence of saponin.
 ANY QUESTIONS.
Cyanophore Glycosides
Several glycosides yielding hydrocyanic acid as
one of the products of hydrolysis are commonly
found in rosaceous plants.
They are sometimes designated as cyanogenic
glycosides.
Most widely distributed glycoside is amygdalin.
Amygdalin is found in large quantities in bitter
almonds, in kernels of apricots, cherries,
peaches, plums etc.and also by prunasin which
occurs in Prunus serotine. Both yield D-
mandelonitrile as the agylcone.
Hydrolysis of Amygdalin
Hydrolysis takes place in 3 steps:
By the action of an enzyme amygdalase
amygdalin first to liberate one mol of glucose and
one mol of mandelonitrile glucoside.
The second mol of glucose is liberated with the
formation of mandelonitrile.
The mandelonitrile then breaks down with the
formation of benzaldehyde and hydrocyanic acid.
 Bitter Almond
Scientific name: Prunus Amygdalus
Family :Rosaceae
Cultivation: Cold and dry climate but a fairly warm weather
during its ripening period. Tree is about to 5m height. Bitter
almond 1.5-2cm long, rounded at one end and pointed at the
other.
Constituents: fixed oil (40-55%),proteins (20%),mucilage
and emulsin. Colorless, crystalline, Cynogentic glycoside
amygdalin (about 3%).
A casein like protein, amandin,is also present in bitter
almond.

Uses:
Demulcent,
mild laxative,
stimulant and nerve tonic properties,
flavorings agent in the preparation of toilet articles as a
vehicle for oily injections and in manufacturing of
liquors.
Relief bronchitis.
Laetrils or vit B12 and possibility for the control of sickle
cell anemia with cynogenic glycosides
Wild cherry
Wild Cherry
Wild Cherry is the carefully dried stem bark of
Prunus serotina also known as
Prunus viriginiana
belongs to family Rosaceae.
Common names
Commonly called Black Cherry, Wild Black
Cherry, Rum Cherry, or Mountain Black
Cherry. This cherry is native to eastern North
America.
Active Constituents of wild
cherry
Cyanogenic glycoside, prunasin (D-mandelonitrile
glucoside); prunase, trimethylgallic acid, coumarins;
tannins, resin, starch and traces of volatile oil.
The bark possesses resin which yields the fluorescent
componds.e.g. scopoletin on hydrolysis.
What is the effect of Chloroplastids in the cells of bark?
The percentage of D-mandelonitrile glucoside is higher
in bark.the cell do not take part in the
photosynthesis ,the percentage of glucoside is lower.In
the later case the bark is yellowish brown.
Wild Cherry Health Benefits
 In syrup form, is employed as flavored vehicle,
especially in cough remedies and considered as a
sedative expectorant.
 Used in Bronchitis, Cold, Cough, Insomnia.
Cardioactive Glycosides
Steroid aglycones or genins are of two types:
Cardenolide ,C23 Steroids
17 Beta side chain an alpha, beta unsaturated 5-membered
lactone ring.

Bufadienolide, C24 Steroids

Doubly unsaturated 6-membered lactone ring.
The more prevalent in nature is cardenolide.
In which situation we use CG?
Congestive Heart Failure
Mechanism of action
Cardiac glycosides affect the sodium-potassium ATPase
pump in cardiac muscle cells to alter their function. Normally, these
sodium-potassium pumps move potassium ions in and sodium ions
out. Cardiac glycosides, however, inhibit this pump by stabilizing it
in the E2-P transition state, so that sodium cannot be extruded:
intracellular sodium concentration therefore increases. With regards
to potassium ion movement, because both cardiac glycosides and
potassium compete for binding to the ATPase pump, changes in
extracellular potassium concentration can potentially lead to altered
drug efficacy. Nevertheless, by carefully controlling the dosage, such
adverse effects can be avoided. Continuing on with the mechanism,
raised intracellular sodium levels inhibit the function of a second
membrane ion exchanger, NCX, which is responsible for pumping
calcium ions out of the cell and sodium ions in at a ratio of 3Na+/Ca2+
.
Thus, calcium ions are also not extruded and will begin to
build up inside the cell as well.
The disrupted calcium homeostasis and increased
cytoplasmic calcium concentrations cause increased
calcium uptake into the sarcoplasmic reticulum (SR) via the
SERCA2 transporter. Raised calcium stores in the SR allow
for greater calcium release on stimulation, so the myocyte
can achieve faster and more powerful contraction by cross-
bridge cycling. The refractory period of the AV node is
increased, so cardiac glycosides also function to decrease
heart rate. For example, the ingestion of digoxin leads to
increased cardiac output and decreased heart rate without
significant changes in heart rate or blood pressure; this
quality allows it to be widely used medicinally in the
treatment of cardiac arrhythmias.
Digitalis
Foxgloves.
Digitalis purpurea
Scrophulariaceae
Constituents
Digitoxin
Gitoxin
Gitaloxin
Digoxin
 Bioassays for Digitalis
Digitalis and its preparations must be assayed
biologically to insure their potency; however, because
the crystalline glycosides are definite chemical entities,
they are assayed chemically. A number of test animals
have been used in the past: guinea pigs, frogs and cats.
The animal now employed in the assay procedure is
the pigeon.
Uses of Digitalis
CHF
Supra ventricular Tachycardia
Atrial flutter
Atrial fibrillation
Dose of Digitalis leaves
Initial Dose 1.5 g
Maintenance Dose 100mg
Dose must be reduced by 25 to 50% for the elderly,
lean body mass and for patients with metabolic or
electrolyte disorders.
Digitoxin
Source: Leaves of Digitalis purpurea.
Highly potent drug and should be handled with
exceptional care.
Digitoxin occurs as a white or pale buff, odorless,
microcrystalline powder.
Bitter substance that is practically insoluble in
water and slightly soluble in alcohol.
Use and Dose of Digitoxin
Cardiotonic that increases the tone of cardiac
muscle and thus causes the heart to empty more
effectively.
Initial rapid dose is 800 µg followed by 200 µg at 6-8
hours intervals for 2-3 doses.
Slow dose is 100-200 µg 1-3 times daily.
Digoxin
Source: Leaves of Digitalis lanata.
Highly potent drug should be deal with
exceptional care.
Digoxin occurs as colorless or white crystals or as
a white crystalline powder.
Rapid dose is 500-750 µg orally followed by 250-
500 µg every 6-8 hours.
250-500 µg IV.
Low Therapeutic index
Because of low therapeutic index of the drug, it is
recommended that, in the absence of good comparative
bioavailability data, a patient should not be changed
from one brand to another after a reasonable
therapeutic effect has been achieved with one
preparation.
Squill bulb and whole herb
Squill
Dried, fleshy inner scales of the bulb of the
White variety of Urginea maritima known in
commerce as White squill and Urginea indica
known in commerce as Indian squill.
Red Squill consists of the bulb or bulb scales of
the red variety of Urginea maritima.
Family: Liliaceae
Time of Collection and Preparation

Late in August.
After removal of membranous outer squill and the
central portion, the fleshy leaves are cut into
transverse pieces and dried.
Constituents
Scillaren A is the principal constituent.
On hydrolysis it yields the aglycone scillarenin,
rhamnose and glucose.
Other constituent include glucoscillaren A and
proscillaridin A.
Use and Dose
An expectorant but also possess emetic, cardio
tonic ,slowing and strengthening the pulse. Most
useful in chronic bronchitis, catarrhal infections
and diuretic properties. Dose is 100 mg.
Red Squill use as a rat poison i.e. Rodenticide.
Strophanthus
Strophanthus is the dried, ripe seeds of
Strophanthus Kombe.
Family: Apocynaceae
Constituents
K- Strophanthoside also known as Strophoside is a
principal glycoside present in it.choline, trigonelline,
fixed oil(30%),resin and mucilage.
What is the product of hydrolysis of Strophoside?
Medicinal use of Strophanthus
Where as Digitalis is the drug of choice in the United
States, Strophanthus and its glycosides are frequently
preferred in Europe.
Strophanthus belongs to the Cardiotonic series of
drugs and has an action similar to that of digitalis.
Chemical test for cardiac
glycosides
Legal test
To the alcoholic extract of drug equal volume of water
and 0.5ml of strong lead acetate solution was
added,shaked and filterate.Filterate was extracted with
equal volume of chloroform and the chloroform
extract was evaporated to dryness. The residue was
dissolved in 2ml of pyridine and sodium nitroprusside
2ml was added followed by addition of NaOH solution
to make alkaline. Formation of pink color in presence
of glycosides or aglcone.
 Isothiocyanate glycosides

• Cruciferous plants contain glycosides, the

aglycone are isothiocyanate
• these may be aliphatic or aromatic
derivatives
• Sinigrin from black mustard and sinalbin
from white mustard
• When hydrolysed by the enzyme myrosin
they yield the mustard oils.
Isothiocyanate
e.g.Sinigrin
Glycosides
Black Mustard sinapis nigra or
brown mustard
Botanical Name:
Brassica nigra
Family:Cruciferae
Black Mustard
The plant produces striking yellow flowers in
season, around May through July and these bear
black pods sometime from June to October. Each
of these pods contains the tiny brown to black
seeds called the mustard seeds.
CONSTITUENTS
Sinigrin, Mucilage, fixed oil, volatile oil.
30-35% fixed Oil.
Sinigrin is Potassium myronate which is
accompanied by an enzyme Myrosin.
Hydrolysis of Sinigrin
Upon addition of water to the crushed or
powdered seeds, the myrosin effects the hydrolysis
of sinigrin.
Sinigrin+Myrosin____ Allyl isothiocyanate
(Mustard oil)+Pot. Acid sulfate+ Glucose
The allyl isothiocyanate produced volatile
commonly called volatile mustard oil.
As a flavoring agent.
As a condiment.
In Pickles.
Essential component of various traditional dishes.
Seeds and Herb (Over the ground) are used.
Local irritant
emetic
Rubefacient
Vesicant

Uses of Mustard
Cantharis vesicatoria,
DeGeer"—(U. S. P)
Class: Insecta.
Family. Meloidae
COMMON NAME AND
SYNONYM: Spanish flies
Cantharis is greek means
beetle and vesicatoria mean
bladder and refers to
blistering qualities.
Found in Oleaceae and
caprifloliaceae plants
Cantharide
Grow in southern and central
europe
How we collect Cantharides?

Mature insects are brilliant green with a metallic

luster.
Time of collection? June and July
How they obtain? In the early morning ,when the
insects are still sluggish from the cold night air the
shrub are shaken or beaten with holes, and the insects
are collected on cloths spread on the ground.
How they killed? by plunging them into dilute vinegar
by exposure to the fumes of hot vinegar, ammonia or
sulfur dioxide or by means of chloroform, ether or
similar drugs
Drying and Storage Conditions? dried at 40°C and
stored in a tight container few drops of chloroform or
carbon tetra chloride should be added.
Cantharidin 0.6-1% a lactone
glycoside
12% Fat
Irritant, Vesicant and Rubefacient
As an aphrodisiac.
What is toxicity?Internal
administration is dangerous.
Effective in the removal of warts

Constituents, Actions, Uses and Toxicity

Lactone glycosides
Coumarin and tonka bean coumarin containing seeds
of Dipteryx odorata (Aublet) Willdenow
D.oppositifolia (Aublet) Willdenow
Family Leguminosae
Uses
Flavouring agents
Anticoagulant
Antispasmodic activity

Coumarin
α-hydroxyl cinnamic acid
Prismatic crystals and has characteristic fragrant,
odour,bitter aromatic, burning taste
It is soluble in alcohol
Brshydrxycoumarin or Dicumarol coumarin
Melilotus officinalis
Family Leguminosae
Used as anticoagulant
Dose- 200-300mg once a day by prothrombin time
Flavanol Glycosides
Yellow pigments
Constituents
Rutin,quercetin and citrus bioflavonoids including
hesperidin,hesperitin,diosmin and naringen
Rutin and hesperdin called Vitamin P or permeability
factors
Uses
Capillary bleeding
Cold
Dietary supplements
Aldehyde Glycoside

Vanillin
Vanilla
Scientific Name(s): Vanilla planifolia Andrews
Family: Orchidaceae
Vanilla planifolia also known in commerce as
Mexican or Bourbon Vanilla.
Vanilla tahitensis known in commerce as Tahiti
Vanilla.
Vanilla is from the Spanish vania,sheathlike pod and
illa,meaning small;planifolia is from the latin
planus,meaning flat and folium,meaning leaf,tahitensis
refers to Tahiti,its adopted home.

Vanilla or Vanilla bean

Plant is a native to the woods of Eastern Mexico but is
cultivated in Tropical Countries where the
temperature does not fall below 18°C and where the
humidity is high.
 The plant is usually propagated by cutting and after
2-3 years reaches flowering stage.
 The plant continue to bear fruit for 30 or 40 years.
The flowers approximately 30 on each plant are hand
pollinated thus producing larger and between fruits.

Habitat
The fruits are collected, 6-10 months after pollination
and are cured by dipping in warm water and repeated
sweating between woolen blankets in the sun during
the day and packing in wool covered boxes at night.
This requires about 2 months during which the pods
lose from 70 to 80% of their original weight and take
on the characteristic color and odor. The pods are then
graded, tied into bundles of about 50 to 75 and sealed
in tin containers for shipment.

Curing Process
Green Vanilla contains two glycosides Glucovanillin and
Glucovanillic alcohol.
Glucovanillin is hydrolyzed by an enzyme during the
curing process into Glucose and Vanillin and later is
hydrolyzed into glucose and vanillic alcohol which in turn
oxidized to Vanillic aldehyde.

Main Chemical Constituents

 Vanilla is 4-hydroxyl-3-methoxybenzaldehyde or
methylprotocatechuic aldehyde.
 It may be obtained from vanilla or prepared
synthetically from other sources;
 coniferrin a glycoside present in the cambium
sap of pine trees.
 eugenol,a phenol present in clove oil
lignin,a product of the pulp industry.
 most of the vanillin in commerce is made from
lignin
Vanillin consists of fine, white to slightly yellow,
needle ike crystals that have an odor and taste
resembling vanilla. It is slightly soluble in water and
glycerin and freely soluble in alcohol, chloroform and
ether.

Vanillin
As a flavoring agent
Antimicrobial
Antioxidant
An antisickling effect has been demonstrated for vanillin
in vitro in animal experiments.
Anticancer
Vanillin may exert antimutagenic and anticarcinogenic
activity by inhibiting a DNA repair process leading to the
production of mutagenic cells. Antioxidant action may also
contribute to this effect.

Vanilla Uses
Oil properties
Vanilla oil has a rich, sweet, vanilla-like odor.
Vanilla oil is used as a flavoring agent in
pharmaceutical products, in food and in tobacco and
is also an ingredient in some oriental type perfumes.

Vanilla essential oil

 None well documented.
Although allergenic properties have been associated
with vanilla, Workers preparing vanilla have reported
headache, dermatitis, and insomnia, which together have
been characterized as a syndrome known as vanillism.
In a survey of ingredients in prescription and
nonprescription health care products, vanilla was the
second most common flavoring superseded only by cherry,
suggesting that people with a known hypersensitivity to
vanilla extract should be vigilant to the widespread use of
this flavoring in pharmaceuticals.

Adverse Reactions and Interactions

Alcohol glycosides
Salicin
Salicin is a glycoside obtained from several species od Salix
and populous.
 Most willow and poplar barks yield salicin but the
principal sources are salix purpura and S.fragilis.
 The glycoside,populin (benzoyl-salicin),is also
associated with salicin in the barks of the Salicaceae.
 Salicin is hydrolyzed into D-glucose and saligenin
(salicyl alcohol) by emulsin.
 Salicin has antirheumatic properties.(1g dose).
 Its action closely resembles that of salicylic acid, and its
probably oxidized to salicylic acid in the human system.
Miscellaneous Glycosides (Gentian)
Gentian or Gentian root is the dried rhizome and
roots of Gentiana lutea.
Family: Gentianaceae.
'Yellow Gentian', 'Bitter Root', Great Yellow Gentian.

Gentian
Gentian native to the mountains of central and
southern Europe and to Asia Minor.
Amarogentin, gentiopicrin (2%), are the bitter
glycosides from gentian root.

Constituents
Gentian is useful as a blood-builder and has been
popular to use during convalescence. Gentian
strengthens the entire system even when given in
moderate doses. One way it does this is by stimulating
general circulation.
It has been found that Gentian root increases the
activities of many glands and organs.

Medicinal Use of Gentian

In modern medicine gentian is used as bitter tonic in
anorexia and dyspepsia.
It is still widely used in Europe as an ingredient in
alcoholic beverages valued for their stomachic
properties.

Medicinal Actions and Current Use

Quassia is the stem wood of Picrasma excelsa (also
known as Quassia excelsa)
Family: Simaroubaceae
Other common names: Bitter Wood, Picrasma,
Jamaica Quassia, Bitter Ash, Bitter Bark

Quassia
Quassia is a tall, graceful tree that is native to tropical
America.
The tree may grow to a height of one hundred feet and
requires moderate to high humidity.

Quassia Tree
 Quassia contains the amaroid (terpenoid) compound
Quassin, an intensely bitter lactone, also neoquassin,
18 hydroxyquassin and scopoletin.

Constituents of Quassia
Quassia is used as bitter tonic, as an insecticide and as
an enema for the expulsion of thread worms.
Quassia is a very valuable commercial crop that is an
ingredient in soft drinks, candies, baked goods,
marmalades and alcoholic drinks.

Medicinal Actions and Uses