GLYCOSIDES

Introduction
A glycoside is an organic compound, usually of plant origin and is rarely of animal which on
enzymatic or acidic hydrolysis yield one or more sugar moieties (Glycone ) and a non-sugar
moiety (Aglycone / Genin).
Glycoside = Sugar group (Glycone ) + Non-sugar group (Aglycone / Genin)
Glycone and aglycone are linked by glycosidic linkage. Glycosidic linkage is formed between –OH group
of sugar and –H group of non-sugar moieties or other sugar with loss of water molecules.
Sugar in glycoside is mostly Beta-D-glucose but other sugars like galactose, mannose, rhamnose,
digitoxose can present.
Glycosides can be alpha or beta but plant contains only beta glycosides.
Therapeutic effect of glycoside is due to aglycon part only and sugar moiety facilitate absorption of
glycoside, and transportation of aglycon to site of action. So glycosides are hydrolysed to give aglycon
part for action.
Glycosides have therapeutic effect in human and animals as they are used in traditional and modern
medicines as cardiotonic, purgative, analgesic, antirheumatic, demulscent and many other uses.
Properties of glycosides
 They are crystalline or amorphous solid compound.
 Glycosides are optically active, normally levo form is more active.
 Soluble in water or alcohol but insoluble in chloroform and ether.
 Glycosides are hydrolyzed by mineral acid, water and enzymes.
GENERAL EXTRACTION METHOD OF GLYCOSIDES (STAS-OTTO METHOD)
 The drug is powdered by grinder.
 The powdered drug is extracted with alcohol by continuous hot percolation method using
Soxhlet apparatus. By this process all the enzymes present in the plant parts are deactivated.
 The extract obtained is treated with lead acetate solution to precipitate tannins and other
impurities.
 The excess of lead acetate is precipitated by passing hydrogen sulphide gas through the
solution.
 The extract is filtered and filtrate is concentrated.
 The pure glycosides can be obtained from concentrated crude extract by using fractional
crystallization, fractional solubility and chromatographic techniques.
  The characterization of isolated pure glycoside can be done by using UV, Visible, I.R, NMR
and Mass spectrometry analysis.
CLASSIFICATION
Based on atoms involved in glycosidic linkage
1. O- glycosides: In these glycosides sugar is connected to OH or phenol group.
Glycone- OH + H O-Aglycones  Glycone- O- Aglycones + H2O
Eg; Senna, Rhubarb
2. C- glycosides : these glycosides sugar is connected to carbon atom.
Glycone- OH + H C-Aglycones  Glycone- C - Aglycones + H2O
Eg; Anthraquinone glycosides such as cascaroside from cascara and aloin from aloe, flavone
glycosides
3. S- glycosides: In these glycosides Sulphur or SH group is attached to the sugar.
Glycone-OH + H S-Aglycones  Glycone- S- Aglycones + H2O
Eg; Isothiocynate glycosides like sinigrin from black mustard.
4. N- glycosides: In these glycosides N or NH (amino group) is attached to the sugar.
Glycone-OH + H N-Aglycones  Glycone- N- Aglycones + H2O
Eg; Nucleoside
Classification on the basis of chemical nature of aglycon moiety
1. Cardioactive glycosides: Digitalis, Strophanthus and white squill
2. Anthraquinone glycosides: Cascara, Aloe, Rhubarb, Cochineal and Senna
3. Saponin glycosides: Glycyrrhiza, Sarsaparilla
4. Cyanophore glycosides: Wild cherry
5. Isothiocyanate glycosides: Black Mustard
6. Lactone glycosides: Cantharide
7. Aldehyde glycosides: Vanilla
8. Miscellaneous glycosides: Gentian, Quassia, Dioscorea