GLYCOSIDE

CHAPTER-4
 INTRODUCTION
“ Glycoside are organic compounds from plants/animal
sources which on hydrolysis give one or more sugar moieties
along with non-sugar moiety.”
 The sugar moiety is glycone part and the non-sugar moiety is aglycone part.
 The glycone part is sugar molecule because of that it has no pharmacological
action but the aglycone part is non-sugar molecule that’s why it gives the
pharmacological action.
 The glycone and aglycone part are link with each other with a linkage called
glycosidic linkage.
 CLASSIFICATION
1. CLASSIFICATION On the Basis of Glycone:
 If the glycone group of a glycoside is glucose, then the molecule is a glucoside;

 if it is fructose, then the molecule is a fructoside;

 if it is glucuronic acid, then the molecule is a glucuronide, etc.

2. CLASSIFICATION On the Basis of Glycosidic Linkage :

1. C-glycosides (When sugar moiety is linked to carbon atom)
2. O-glycosides (When sugar moiety is attached to oxygen atom)
3. N-glycosides(When Sugar molecule is combined with N of the –NH (amino group) of
aglycon)
4. S-glycosides(When sugar is linked to sulphur atom)
3. CLASSIFICATION ON THE BASIS OF AGLYCONE:

1. Anthraquinone or anthracene glycosides,

2. Sterols or cardiac glycosides,
3. Saponin glycosides,
4. Cyanogenetic or cyanophoric glycosides,
5. Isothiocynate glycosides,
6. Flavonoids Flavonol glycosides,
7. Coumarins and Furanocoumarin glycosides,
8. Aldehyde glycosides,
9. Phenol glycosides,
10.Steroidal glycolkaloids,
11.Glycosidal bitters or miscellaneous glycosides.
 OCCURENCE
 Glycoside occur in various parts of plant like fruits, seeds,
leaves, and barks example, anthocyanins.
 Most commonly occurring sugars as a product of hydrolysis of
glycosides are glucose, mannose, and galactose.
 Glycosides are:
 Colourless,
 Solid amorphous
 Non volatile
 Water soluble but insoluble in organic solvent
 Bitter teste
 Odourless
 DISTRIBUTION
 Various medicines, condiments, and dyes from plants occur as glycosides;
 Several antibiotics are glycosides (e.g., streptomycin).
 Saponins, widely distributed in plants, are glycosides, that saponin solutions have
been used as cleansing agents.
 Leaf of Digitalis used as to control some heart problems, such as irregular
heartbeats
 Seed of strophanthus contain glycoside used as cardiotonic.
 All parts of the Urginea scilla contain glycoside but it is most concentrated in the
bulb used as cardiotonic.
 Nut of thevetia neriifolia contain glycoside.
 Dried fruits of Momordica (Saponin) used as hypoglycemic.
ISOLATION Sta-Otto-Method
 The plant part containing glycoside is finely powdered.
 Then obtained the extraction by continuous hot percolation process using Soxhlet apparatus
below 45ºC with alcohol as solvent.
 During this process, various enzymes present in plant parts are also deactivated due to
heating.
 Then treat this extract with lead acetate for removing tannins & other impurities.
 The excess of lead acetate is precipitated as lead sulphide by passing hydrogen sulphide gas
through solution.
 Finally obtain the crude glycoside.
 From the crude extract, the glycosides are obtained in pure form by making use of processes
like fractional solubility, fractional crystallization and chromatographic techniques such as
preparative thin layer and column chromatography.
 After purification of glycoside we have to perform characterization study by UV, IR, NMR, Mass
Spectroscopy.
 IDENTIFICATION TEST
1. Killer-Killiani test:
 1gm glycoside powder in 10ml alcohol (70%) boiling for 2-3min the filter the solution.
 Add 5ml water & 0.5ml strong lead acetate, shake well and filtered.
 Filtrate was extracted with equal volume of chloroform. Chloroform extract was
evaporated to dryness and residue was dissolved in 3 ml of glacial acetic acid and
few drops of ferric chloride (FeCl3) solution.
 The resultant solution was transferred to a test tube containing 2 ml of conc.
Sulphuric acid (H2SO4).
 Reddish brown layer is formed, which turns bluish green after standing due to
presence of digitoxose (glycoside).
2. Borntrager test:
 Take 1gm of powder glycoside add 5-10ml of HCl and boil on water bath for 10 minutes
and filter.
 Filtrate was extracted with Benzene and add equal amount of ammonia solution and shake
well.
 Formation of pink or red color in ammonia layer due top resence of anthraquinone
glycoside.
3. Haemolysis test:
 Take the crude drug on slide add some drops of blood and mixed well.
 Then RBC's becomes ruptured due presence of saponin (alkaloid).
4. Baljet test:
 Thick section of leaf of digitalis or the part of drug containing cardiac glycoside, dipped in
sodium picrate solution.
 It forms yellow to orange color in presence of aglycones or glycosides.
5. Legal test:
 To the alcoholic extract of drug equal volume of water and 0.5 ml of strong
lead acetate solution was added, Shaked and filtered.
 Filtrate was extracted with equal volume of chloroform and the chloroform
extract was evaporated to dryness.
 The residue was dissolved in 2 ml of pyridine and 2ml of sodium
nitroprusside was added, then the solution is made alkaline by adding
NaOH.
 Formation of pink color in presence of glycosides or aglycon moiety.
 THERAPEUTIC ACTIVITY &
PHARMACEUTICAL APPLICATION
Glycoside used as  anti-inflammatory effects.
 laxative (treat constipation).  irritating,
 stimulating purgatives.  pain killer in anti-inflammatory
 Cardiotonic processes,
 sedative (anesthesia).  Rheumatism
 Anti-depressant  Flavouring Agent
 Coloring Agent  Anti-diabetic
 Nervine tonic  Anti-fungal
 Diuretic  Sweetening Agent
 Hypoglycemic  Preparation of Cosmetics
 Counter irritation  Perfumes
 antiseptic effect.  Ink
 analgesic(painkiller),
 antipyretic (fever)