Steroids seminar M.Pharmacy 1st Semester 2022 (2021-2022) Previous Year's Question Papers/Notes Download - HK Technical PGIMS

• CONTENTS:-
Introduction of Steroids
Chemistry of Sterols
Introduction of glycoside
Sapogenin
Cardiac Glycoside
References

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STEROIDS

A steroid is an organic compound with four rings arranged in a specific molecular
configuration. The steroid core structure is composed of seventeen carbon
atoms(17), bonded in four "fused" rings .

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• These are compound which are widely distributed in animals and plant.
Steroids name derived from sterol. Steroids are the characterized by the
presence of cyclopentano phenanthrene . The steroid group includes all the
sex hormones adrenals cortical hormones, bile acids , and many other
physiologically active substances of animals and plants .
• Steroids vary from one another in the nature of attached groups, the position
of the groups, and the configuration of the steroid nucleus . Small
modifications in the molecular structures of steroids can produce remarkable
differences in their biological activitiesss

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• classification:-
• Sterols :-
• the sterols, is composed of the common 3-monohydroxy steroids of the
cholestane , ergostane, and stigmastane series and their methyl sterol
biogenetic precursors. It containing alcoholic group at C-3 position and a side
chain of 8 to 10 carbon atoms at C-17 are called sterols.
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• Sterols are classified into 3 groups based on their source of origin
• They are :-
1. ZOOSTEROLS :- It is found in animals

eg :-cholesterol

2. PHYTOSTEROLS:- It is found in plants
eg :- stigma sterols

3.MYCOSTEROLS :- It is commonly found in yeast and fungi

eg :- Ergosterols

Sterols may be found either as free sterols, acylated (sterol esters), alkylated
(steryl alkyl ethers), sulfated (sterol sulfate), or linked to a glycoside moiety
(steryl glycosides) which can be itself acylated (acylated sterol glycosides)

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CHOLESTEROL:-
Cholesterol:- It occurs
both as free form or in
ester form.
Cholesterol has a
molecular formula of
C27H25OH.
This molecule is
composed of three
region.
• A hydrocarbon tail
• A ring structure region
with4 hydrocarbon rings
• A hydroxyl group

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• The hydroxyl group is polar, which makes it water soluble
• The 4 rings of cholesterol is the signature of all steroid hormones.
• The last region is the hydrocarbon tail. Both the ring region and tail
region are non-polar

• Because cholesterol contain both a water-soluble region and a fat-
soluble region, it is called amphipathic

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• Chemistry :
• Presence of double bond and hydroxyl group:-
• a. The conversion of cholesterol into cholestanol show the presence of double
bond.

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• b. The oxidation of cholestanol with chromic acid into cholestanone shows
the presence of secondary alcoholic group in cholesterol
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• c. The clemmenson’s reduction of cholestanone yields a saturated
hydrocarbon called cholestane.

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• GLYCOSIDES

• Glycosides are organic compounds , obtained from plants
• On enzymatic or acid hydrolysis yields one or more sugar moieties
(glycone ) along with nonsugar moiety ( aglycone )

•Glycoside Aglycone (genin) + Glycone (sugar)
• Aglycone Part :- Responsible for chemical and therapeutic
property .
• Glycone Part :- Responsible for chemical absorption of
glycosides and helps in transportation of aglycone portion at
the site of action

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• Chemically they are acetals or sugar ethers fromed by interaction of
hydroxyl group each of sugar and nonsugar moiety with loss of water
molecule
• Sugar is mostly β-D glucose others are galactose ,mannose, rhamnose ,
digitoxose, cymarose etc
• Linkage between glycone and aglycone is called as glycosidic linkage and on
the basis of this linkage α and β stereoisomer is assigned .
• PROPERTIES:-
• Most glycosides are colourless ,crystalline
• Glycoside are soluble in water, alcohol, but insoluble in chloroform and
ether
• Optically –Levorotatory is more active

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• Sapogenin :-
• Sapogenins are the aglycones, or non-saccharide, portions of the
family of natural products known as saponins.
• Produced from saponins by acid or enzymatic hydrolysis
• Sapogenins contain steroid or other triterpene.
• Chemically they are steroidal compounds characterized by the
presence of a spiroketal side chain .

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• A spiro compound is a bicyclic organic compound with rings connected
through just one atom. The rings can be different in nature or identical.
• The connecting atom is also called the spiroatom, most often a quaternary
carbon
• They are derived from C27 – cholestane

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• STEROIDAL SAPONINS

The steroidal saponins are less widely distributed in nature than the pentacyclic
triterpenoid type.
• Steroidal saponins are of great pharmaceutical importance because of their
relationship to compounds such as the sex hormones, cortisone, diuretic
steroids, vitamin D and the cardiac glycosides.
• Examples: Diosgenin (Dioscorea sylvatica),

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• PENTACYCLIC TRITERPENOID SAPONINS

• Pentacyclic triterpenoid saponins
• • Triterpenoid saponins my be classified into three groups represented by
Alpha -amyrin, Beta-amyrin and lupeol.
• Examples: Glycyrrhetinic acid (Glycyrrhiza sp.)

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• CARDIAC GLYCOSIDE

• Cardiac glycosides:- Group of steroidal glycosides act as cardiotonic
agent. They increase tone, excitability and contractility of cardiac
muscles.
General properties of Cardiac Glycosides :
• Amorphous powder
• Bitter taste
• Solubility in H2O
• Insolubility in Organic solvents
• Very toxic compounds
• Odourless

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Depending upon the type of lactone ring attached to the steroidal aglycone
nucleus, cardiac glycosides are of two types:-
1.Cardenolides
2.Bufadienolides
1.Cardenolide :-Those cardiac glycoside having an α,β-unsaturated
Five membered lactone ring which is attached to 17 β Position of steroidal
nucleus are referred as Cardenolides .
Digitalis and strophanthus species are naturally occurring plant sources of
cardenolides .

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• 2.BUFADIENOLIDES:-
It is having unsaturated six membered lactone ring at the 17 β Position .
Bufadienolides are commonly called “toad posion” because these are also
present in the skin of various toad species .eg “toad venom” contain
bufotoxin bufadienolide . Squil glycosides are medicinally important
bufadienolide type of glycoside .

Bufadienolide
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• Cardiac glycoside contain rare sugar that is deoxy sugar as glycone
moiety ,for example digitoxose ,cymarose and thevetose along with
common sugar glucose .

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• For maximum cardiac activity :-

• (1) Lactone ring is attached to - 17 β Position
Sugar part is attached to - 3 β Position
• (2) A/B , C/D ring should have Cis configuration and B/C trans
configuration
• Sugar part helps in its absorption and distribution in body
• (3)When number of hydroxyl group is increased on the molecule ,the more
rapid is the action in the body

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• USES OF CARDIAC GLYCOSIDE :-
Cardiac glycoside are a class of organic compounds that increases the
output force of heart and decrease the rate of contractions by acting on the
cellular Na+ / k+ -ATPase pump.

Blood Vessels :- Digitalis has mild direct vasoconstrictor action

It has no Prominent effect on blood pressure but , for CHF
Patients ,It increases action of systolic B.P

CNS :- It shows little effect on CNS normally ,but if consumes higher dose of
cardiac glycoside ,then it activates CTZ (chemoreceptor trigger zone ).
Kidney :-Diuresis occurs for CHF Patients but does not occur for normal
patients though

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• CHEMICAL EVALUATION OF CARDIAC GLYCOSIDE

• To confirm the presence of cardiac glycosides in a particular sample ,test
should be designed to check the presence of the following groups
(a) Steroidal nucleus
(b) Deoxy-sugar
(c) α,β-unsaturated five or six membered lactone ring
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Group to be detecteds Name of the test reagent

employed

Composition of the test Coloured produced

SteroidalNucleus (1) Libermann-Burchard

Test

(2)Carr-Price reaction

(3)Salkowski’s test

Acetic anhydride-
Sulphuric acid

Antimoney tricholoride in
acetic-anhydride

chloroform + conc.
sulphuric acid

Blue or Green colour

Deep blue coloured

Red coloured

Lactone Ring (1) Baljet test

(2)Legal’sreagent

(3) Reymond’sreagent

(4) Kedde’s reagent

2,4,6 Tri-nitrophenol
(picric Acid )

Sodium nitroprusside in
alkali

Meta dinitrobenzene in
alkali

3,5- dinitrobenzoicacid in
alkali

Orange colour

Violet colour

Blue Colour

Purple Colour

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Group to be detected Name of the test or
reagent employed

Composition of the
reagent or test

Colour Produced

Deoxy- Sugar (1) Keller –Killiani test

(2) Xanthydrol reagent

(3) Schiff’s test

Glacial acetic acid + ferric
Chloride ,Conc Sulphuric
acid

2-Xanthydrol in glacial
acetic acid + 1%
hydrochloric acid

Fuchsin Solution
decolorized with Sulphur
dioxide

Reddish brown colour

Red Colour

Blue Colour

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• References:-

• A textbook of pharmaceutical chemistry of natural products by V.Algarsamy
• Chemistry of natural products by Jaswant Kaur
• Medicinal plants products by Paul M.Dewick
• A textbook of Pharmacognosy by C.K Kokate