Classification of Glycosides

A.A. On the basis of sugar moiety such as glucoside , rhamnoside, etc.

CH2 OH O C6H11O5

CH2OH H H OH OH H O H H O OH O

Salicin (saligenin + glucose)

OH Arbutin (hydroquinone + glucose)

A.B. On the basis of therapeutic activity such as

- Cardiac glycosides, e.g. Digitalis, Strophenthuss, etc. - Laxative glycosides, e.g. Aloe, Senna, Cascara sagrada, etc.

C. On the basis of linkage of sugar molecule with the aglycon a) O- Glycosides: here the sugar is combined with the alcoholic or phenolic hydroxyl group of the aglycone.

R = Glucose in daucosterol

RO
OCH3 RO O OH

R = Rhamnose - glucose

OH

b) N- Glycosides: In these glycosides the amino group (-NH2 / -NH-) is condensed with the sugar, e.g. nucleosides, coenzyme, etc.
NH2 N

NH2 N N O
O

N N

N N CH2OH OH H H H

CH2 H H O O CH3 H CH N OH P O

O H H OH OH N

HO PH OOH H

O HO PH OCH2 H3C HO C C H

Adenosine (Adenine + ribose)

CH OH

SH

Coenzyme A

c) S- Glycosides: These glycosides contain a sugar moiety attached to the sulfur of the aglycone, e.g. isothiocyanate glycosides.
C 3H 5 C N S O C6H11O5
HO CH2 C S C6H11O5 N O SO2-O-K

SO3K
Sinalbin

Sinigrin

d) C- Glycosides: Condensation of a sugar directly to a carbon atom of the aglycone gives c-glycosides, e.g. aloin, chrysaloin, etc.
C6H11O5

OH

OH
HO O CH3

CH2R H C6H11O5
R = OH, Barbaloin H, Chrysaloin
CH3 O

Aloesin

D) On the basis of the chemical nature of aglycone, the glycosides can be classified into following groups:
O

1. Cardioactive
CH3 CH3 OH HO H

Digitalis Strophenthus

+ digitoxose Digitoxigenin (cardenolide, C23 steroid)

O O

CH3 CH3 OH RO H

Squill

R = H, Scillarenin A (bufadienolide, C24 steroid) R = rham glu, Scillaren A 5

2. Anthraquinone

OH

OH

Cascara sagrada Aloe Senna Rhubarb

CH2R

H C6H11O5 R = OH, Barbaloin H , Chrysaloin

3. Saponin
CH3

O CH3

Glycyrrhiza Dioscorea

HO

HO
+ rhamnose, + glucose

Spiroketal steroid nucleus (neutral) diosgenin

amyrin (aglycone, pentacyclic triterpenoid, acidic)

4. Cyanophore

H C CN O C6H11O5

Mandelonitrile glucoside

Wild cherry Bitter almond

H CH OH

H C C6H12O6 + CN Mandelonitrile OH

+ HCN Benzadehyde

5. Isothiocyanates
C 3H 5 C N S O C6H11O 5 SO3K

Black mustard White mustard

Sinigrin myrosin H2O S C CH2 C CH2 + KHSO 4 + C6H12O6 H glucose Allyl isothiocyanate N

6. Flavanol / flavanoid
OH HO O OH O OH O C12H21O9

Citrus fruit

Rutin

7. Alcohol
CH2OH O C6H 11O 5 + H2 O Salicin Saligenin CH 2OH OH + glucose

Salix Populus

8. Aldehyde

CHO

Vanilla

OCH3 OR R = H, vanillin R = glu, glucovanillin

9. Lactone

Cantharide Tonka beans

HO O
Coumarin

10. Phenol

OC6H11O5

OH

Uva ursi
+ glu

+ H2O

OH Arbutin

OH Hydroquinine

11. Tannin
HO

OH OH

Nutgall Hamamelis leaf

COO C 6H11O5 Glucogallin (glucoside of gallic acid)

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An acetal is a molecule with two single bonded oxygen attached to the same carbon atom. Hemiacetals and hemiketals are compounds derived from aldehyde and ketones respectively. These compounds are formed by formal addition of an alcohol to the carbonyl group.

H H+ R C O + ROH R'

H C OR

OH Hemiacetal H H+ R' C OR + ROH R' C OR acetal OR OH Hemiacetal (an alcohol) H

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H COOH H NH2

H H

H COOH NHOH

H CH NOH

L-Phenylalamime

N-Hydroxy-L-phenylalanine

Phenylacetaldoxime

H C N

OH C N
glucosyl transferase + UDP glucose

Mandelonitrile

a-Hydroxymandelonitrile

H HO O H O C H N

H OH OH H H OH

Prunasin

The biosynthetic pathway for the cyanogenic glycoside, prunasin.

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