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Glycosides

Glycosides
Condensation products of sugars with various kinds of organic hydroxy compounds. Widely distributed especially in roots, barks and fruits and to a less extent in leaves. White crystalline substances with bitter taste, soluble in water and most organic solvents except ether.

Non-reducing substances which on hydrolysis brought about by reagents or enzymes yield one or more sugars and the non-sugar(aglycone).

Glycoside are classified: Nature of sugar Chemical Structure Pharmacological Use

Classification of Glycoside
Cyanogenetic glycosides or cyanophoric glycosides Isothiocyanate Cardiac glycosides Saponin group Phenol group Anthraquinone group Alcohol group Aldehyde group Lactone group Neutral or Miscellaneous principles

Cyanogenetic glycoside or cyanophoric glycosides characterized by yielding hydrocyanic acids on hydrolysis with appropriate enzyme e.g
1.
amygdalin from bitter almonds HCl glucose + benzaldehyde +HCN

amygdalin amygdalase or emulsin prunasin

prunase

benzaldehyde +

glucose + HCN

Mannihoxitin from Mannihot utilessimus (cassava) Phaseolunatin Phaseolus lunatus Prunasin Prunus serotina

2. Isothiocyanate Producing glycoside or mustard oil glycosides They are sulfur- containing substances chiefly found in Cruciferae. On hydrolysis they yield mustard oils which are organic compounds containing isothiocyanate (-N=C=S) grouping and have a characteristic

e.g
Sinigrin in KHSO4 black mustard seed myrinosae isothiocyanate glucose +allylisothiocyanate +

Enzymes myrosin accompanies isothiocyanate-producing glycosides in plants. Presence of this glycoside increases the resistance of plants to microorganisms.

3. Cardiac glycosides Steroidal glycosides They are used therapeutically to strengthen a weakened chart and allow it to function more efficiently. The aglycones have steroidal structure and are chemically related to bile acids.

Some of the sugar units of cardiac glycosides are glucose, rhamnose, deoxy sugar and some rare sugars like digitalose (a methyl ether of deoxyglucose), digitoxose (a dioxyhexose),cymarose(a methyl ether of digitoxose)

Genins have a steroidal structure and two types maybe distinguished:


Cardenolides (e.g digitoxinogen) - contain five membered lactone ring attachedd to ring D of the steroid nucleus Buffanolides or bufadienolides (e.g) scillarenin - which possess a six-membered lactone ring

4. Saponin group Plant materials containing saponins have long been used for their detergent properties. Characterized by their foaming when shaken with aqueous solution. Have a HMW and their isolation in a state of purity is difficult.

They can be purified by making use of the fact that they form molecular compound with steroids like cholesterol. Most saponin give a red or violet coloration with concentrate Sulfuric Acid.

Two kinds of Saponin Steroidal Triterpenoid types

Sapogenin they have hemolytic properties e.g Sarsaparilla rich in saponin but is widely used as flavoring of pharmaceuticals and beverages.

5. Phenol group The aglycone groups of many naturally occuring phenolic in character. e.g
Arbutin
hydrolysis

quinone + glucose

6. Anthraquinone group The glycones of anthracene derivatives a) Anthraquinone b) Anthranols and anthrones c) Oxanthrones d) Dianthrones e) Aloin type

a.) Anthraquinone Present in cathartic or purgative drugs maybe dihydroxyphenols such as chrysophanol or trihydroxyphenols such as emodin.

b.) Anthranols and anthrones Reduced anthraquinone derivatives are tautomeric and one may be converted to the other in solution. They are main constituent of Chrysarobin.

c.) Oxanthrones Intermediate between anthraquinones and anthranols. d.) Dianthrones Divided from two molecules which may be identical or different Sennoside derived from two molecules of rheinanthrone and two molecules of glucose.

e.) Aloin or C-glycoside C- glycosides are barbaloin (in Cascara and Aloe) and chrysaloin (in Cascara). Aglycone of barbaloin is aloeemodin anthrone. Aglycone of chrysaloin is chrysaphanol.

7. Flavonoid group Derivatives of flavonoid, isoflavone, flavonol and flavonone. They are widely distributed in nature in the free state or as glycosides but are common in higher plants particularly in red, blue and yellow of flowers and fruit.

e.g
1.
2.

Rutin Hesperidin

hydrolysis
hydrolysis

quercetin (a flavonol)

hesperitin (flavonone )+ rhamnose+glucose

Flavonoids dissolve in alkalies giving yellow solutions in addition of acid become colorless. They maybe separated and identified by chromatography, with color reactions and use of ultra violet light by paper electrophoresis, colorimetry and spectrometry.

9. Alcohol group e.g


1.

Salicin Coniferin Populin

hydrolysis

Salicyl acid + glucose Coniferyl alcohol + glucose Populin alcohol + glucose

2.

hydrolysis

3.

hydrolysis

10. Lactone group Coumarin a derivative of ben- pyrone 11. Neutral or Miscellaneous Principle Applied to some glycosides, bitter principles, carotenoids and other types of constituents that are not chemically related.

Many glycosides have a bitter taste principles, some of them are described as bitter principles long before their chemical structure was elucidated. e.g

Crocus
hydrolysis

gentibiose + crocetin (carotenoid)

Test for Glycosides

Anthroquinone test
Drug is powdered and extracted with ether and ammonia or caustic soda. The aqueous layer shows pink color

Keller-killani test
This is for cardiac glycosides. chloroform extract of drug and 0.4 glacial acetic acid are mixed with ferrous chloride and 0.5 mi of concentrated sulphuric acid. The acetic acid layer shows blue color.