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Glycosides: Classification of Glycosides On The Basis of Aglycone Moiety

Glycosides are organic compounds that contain a sugar component (glycone) and non-sugar component (aglycone). They are classified based on their aglycone moiety (e.g. anthraquinone, steroidal) or glycosidic linkage (e.g. C-glycosides, O-glycosides). Glycosides have properties such as being soluble in water and dilute alcohols, insoluble in organic solvents, and undergoing hydrolysis by acids, water, or enzymes to release the glycone and aglycone. They are believed to participate in growth regulation processes in plants and animals.

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148 views3 pages

Glycosides: Classification of Glycosides On The Basis of Aglycone Moiety

Glycosides are organic compounds that contain a sugar component (glycone) and non-sugar component (aglycone). They are classified based on their aglycone moiety (e.g. anthraquinone, steroidal) or glycosidic linkage (e.g. C-glycosides, O-glycosides). Glycosides have properties such as being soluble in water and dilute alcohols, insoluble in organic solvents, and undergoing hydrolysis by acids, water, or enzymes to release the glycone and aglycone. They are believed to participate in growth regulation processes in plants and animals.

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Amit Jain
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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GLYCOSIDES

GENERAL PHARMACOGNOSY OF GLYCOSIDES:

Glycosides in general may be defined as the organic compounds from plant or animal origin
which on enzymatic or acid hydrolysis gives one or more sugar moiety along with a non-
sugar moiety (Aglycone moiety).

Alpha & Mehtyl glycosides

Classification of glycosides on the basis of aglycone moiety


On the basis of aglycone moiety glycosides are classified in the following categories-
a) Anthraquinone glycosides- Senna, aloe, cascara & Rhubarb

b) Sterol or cardiac glycosides- Digitoxin & Digoxin

c) Saponin glycosides- Dioscera, Liquorice, shatavari & brahmi

d) Cyanogenetic glycosides- Bitter almond & Punarnava

e) Isothiocynate glycosides- Sinigrin

f) flavonoid glycosides- Ginkgo & buck wheat

g) Coumarin alkaloid- Visnaga & Psoralea


h) Aldehyde glycosides- Vanilla pods

i) Phenol glycosides- Bearberry

j) Steroidal Glycoalkaloids- Solanum

k) Glycosidal bitters- Gentian, pycorrhiza, chirata & henna.

Classification of glycosides on the basis of glycosidic linkage:


“Glycosidal linkage A covalent linkage formed between a carbohydrate and another group
which may or may not be the carbohydrate.”

Glycosides are also classified on the basis of the glycosidic linkage present in them. On this
basis they are classified in the following categories-
a) C-glycosides-They are represented as- Glycone-OH + HC-aglycone = Glycone-C-
Aglycone + H2O. Examples of C-glycosides are Aloe, cochineal & cascara.

b) O-glycosides- They are represented as- Glycone-OH + HO-aglycone = Glycone-O-


Aglycone + H2O. Examples of C-glycosides are Senna, rhubarb & cyanogenetic
glycosides.

c) S-glycosides- They are represented as- Glycone-OH + HS-aglycone = Glycone-S-


Aglycone + H2O. Example of C-glycosides is Sinigrin (Isothiacyanate glycoside).

d) N-glycoside- They are represented as- Glycone-OH + HN-aglycone = Glycone-N-


Aglycone + H2O. Examples of C-glycosides are adenine, guanine, cytosine &
thiamine (nucleosides).

Properties:
1. May be crystalline or amorphous
2. Soluble in water & dilute alcohol Exception: Resin glycosides
3. Insoluble in organic solvents like CHCl3 or ether
4. Aglycone soluble in non-polar solvents like benzene or ether.
5. The presence or absence of various polarity contributing functional groups in the
structure of the aglycone portion would contribute to the degree of solubility in a
given solvent e.g. thioglycosides are soluble in water partly because of the ionic
sulfate residue.
6. Easily hydrolysed by mineral acid, water & enzymes.
7. Show optical activity, normally with laevo rotatory effects.
8. Glycosides do not reduce Fehling’s solution until they are hydrolysed.
9. Believed to participate in growth regulation
Biosynthesis of Glycosides
Transfer of uridylyl group from uridine triphosphate to sugar-1-phosphate, with the
help of uridylyl transferases

UTP + Sugar-1-phosphate UDP-sugar + PP


Transfer of sugar from uridine diphosphate to aglycone moiety with the help of
glycosyl transferases

UDP – Sugar + aglycone Glycoside+ UDP

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