Glycosides

By:

Leena Awad

Adila Ibrahim
Yousra Mudathir

Introduction
Glycosides are non-reducing substances which on hydrolysis (by acid, base, or enzyme) yield glycone and aglycone. They are soluble in water and dilute alcohol but insoluble in organic solvents (eg. Chloroform) Their aglycones are soluble in non-polar organic solvents Their glycones are soluble in polar solvents

 They are mainly used as medications (eg. Laxatives, analgesics, and cardiotonics) In animals and humans their poisons are bound to the sugar portion which helps in their elimination from the body

Example: salicin which is used as an analgesic

Classification
Glycosides can be classified in different ways. Example: 1. On the basis of the sugar (eg. Glucoside, rhamnoside, etc.) 2. On the basis of the therapeutic activity. Example: Cardiac glycosides-Digitalis Laxative glycosides-Aloe, Senna, Cascara

Most common method of classification:

According to the chemical nature of the aglycone: 1. Anthraquinone glycosides 2. Alcoholic glycosides 3. Saponin glycosides 4. Cyanophore glycosides 5. Thiocyanate glycosides 6. Phenolic glycosides 7. Steroidal glycosides 8. Lactone or coumarin glycosides 9. Flavone glycosides 10. Aldehyde glycosides 11. Miscellaneous glycosides

Extraction
Glycosides are extracted from a crude drug
with a polar solvent, usually alcohol or water mixed with different proportions of methanol or ethanol Acidic conditions should be avoided to prevent the cleavage of the glycosidic linkage

It is also important to inactivate the hydrolytic enzymes that are present in the plant cell to prevent cleavage of the glycosides. This is done in several ways: 1. Place plant material in boiling alcohol or water for 10-20 minutes 2. Boiling with acetone 3. Placing it in a low temperature 4. Precipitating the enzymes with ammonium sulfate 5. Freeze-drying

Method extraction & isolation of glycosides STEPS :

1-destruction of the hydrolysing enzymes 2-Defatting with petroleum ether 3-extraction of the glycosides by alcohol , water and diluted alcohol 4-concentration of the alcoholic extract, subsequent addition of water and filtering (to get rid of water insoluble impurities ) 5- further purification of the aquoeus solution by the extraction with an immisible organic solvent (to get rid of nonpolar impurities) 6-preciptation of water-soluble impurities as tannins by the addition of lead acetate (salts of heavy metals) 7-preciptation of excess lead acetate and obtain the glycosides in pure form by crystillization

Purification
Glycosides that are relatively free of impurities are obtained by concentration of the alcoholic extract under vacuum. It is subject to fractional crystallization from organic solvents. Isolation is usually completed by various chromatographic techniques ex. Cardiac glycosides using TLC The molecular structure of the extract is determined using spectroscopic methods (eg.IR, NMR, and spectrophotometer)

Thank u