Glycosides
Introduction & Classification
By
Dr. Mukul Tailang
Professor
School of Studies in Pharmaceutical Sciences
Jiwaji University
Gwalior (M.P.)
GLYCOSIDES
Glycosides are the molecules in which a sugar
part is bound to some other non-sugar part.
Glycosides play numerous important roles in
living organisms.
Plants store important chemicals in the form
of inactive glycosides; if these chemicals are
needed, the glycosides are brought in contact
with water and an enzyme and the sugar part
is broken off, making the chemical available
for use.
Many such plant glycosides are used as
medications.
GLYCOSIDES
Formally, a glycoside is any molecule in
which a sugar group is bonded through its
anomeric carbon to another group via a
glycosidic bond.
The sugar group is known as the Glycone
and the non-sugar group as the Aglycone
or Genin part of the glycoside.
The glycone can consist of :
◦ Single sugar group (Monosaccharide) or
◦ Several sugar groups (Oligosaccharide).
Glycosidal Sugars:
Sugars found in glycosides may be
• Monosaccharides
– Glucose
– Rhamnose
– Fructose
• Deoxysugars (more rare)
– Cymarose
• found in the cardiac glycosides
TERMS USED TO DESCRIBE GLYCOSIDES
A Glycoside is a
• Glucoside
– Has glucose as the sugar component
• Pentoside
– Has a sugar such as arabinose
• Rhamnosides
– Contains rhamnose
• Rhanmoglucosides
– Contains both rhamnose and glucose
Glycosidic bond
• A glycosidic bond is a certain
type of a functional group that
joins alcoholic group of a
Carbohydrate molecule to an
aglycone molecule.
• A substance containing a
glycosidic bond is a Glycoside.
Glycosidic bond
Classification of Glycosides
Glycosides can be classified by :
• The nature of Glycone
• Number of sugars
• Nature of the glycoside
• Botanical source
• Therapeutic use
• The type of Glycosidic Bond
• The Glycosidal Linkage and
• Chemical nature of Aglycone.
By Glycones
• 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.
Number of sugars:
• One sugar monosides e.g. Salicin.
• Two sugar Biosides e.g. Diosmin.
• Three sugars Triosides e.g. Digoxin.
Nature of the glycoside:
• Primary glycosides: Originally present in the
plant
–e.g. Purpurea A
• Secondary glycosides: Resulted from removal of
one sugar from the primary glycosides
–e.g. Digitoxin
•Botanical source:
•Digitalis glycosides
•Senna glycosides.
•Therapeutic use:
•Analgesic glycosides.
•Purgative glycosides.
•Cardiac glycosides.
Classifications of glycosides according to
their therapeutic effects
CHF and cardiac muscles stimulators:
• Digitalis glycosides: digoxin, digitoxin,
gitoxin (Fox glove leaves)
• Ouabain: Strophanthus gratus seeds
• K-strophanthin -Strophanthus kombe seeds
• Scillaren A,B which isolated from red and
white Squill bulbs
• Convolloside: Convallaria majalis – Lily of
the Valley.
Laxative group of glycosides:
– Sennoside A,B,C,D (Senna leaves and fruits)
– Cascaroside A,B (Cascara bark)
– Frangulin and glucofrangulin (Frangula bark)
– Aloin and barbaloin (Aloe vera and A. barbadensis)
Local irritant group:
– Sinigrin (Black mustered seeds_Brassica nigra)
– Sinalbin (White mustered seeds_Brasica alba)
Analgesics and antipyretics:
– Salicin hydrolysis Salisylic acid (Willow or Salix bark)
Keeping elasticity of blood vessels like:
– Rutin, Rutoside (Bitter orange peels, Lemon peels)
Anti-inflammatory group:
– Aloin for acne &
– Glycyrrhizinin the treatment of peptic ulcer
By type of glycosidic bond
Depending on whether the
glycosidic bond lies "above" or
"below" the plane of the cyclic
sugar molecule, glycosides are
classified as:
»α-glycosides
»β-glycosides
α- & β-glycosides
H O CH3 H3CO H
H OH H OH
HO H O HO H O
H OH H OH
H H
OH OH
methyl glucoside methyl glucoside
CH2OH CH2OH
H O H H O O CH3
H H
OH H OH H
OH O CH3 OH H
H OH H OH
methyl glucoside methyl glucoside
By Linkage
Atom from the aglycone involved in the glycosidic linkage:
Aglycone- O- Sugar O-glycosides
Aglycone- C- Sugar C-glycosides
Aglycone- S- Sugar S-glycosides
Aglycone- N- Sugar N-glycosides
H - O - C6H11O5 - O - C6H11O5
-O-H +
O - Glycoside
C-H + H - O - C6H11O5 C - C6H11O5
C - Glycoside
N-H + H - O - C6 H11O5 N - C6 H11O5
N - Glycoside
- S - C6H11O5
-S-H + H - O - C6H11O5
S - Glycoside
O,C,S & N – GLYCOSIDES
OH O OH
C6H11O5. O O OH
CH2OH
10
R1
R2 CH2OH
10 '
H O
H
OH H
C6H11O5.O O OH OH H
H OH
Sennoside
(O - Glycoside) Barbaloin
(C - Glycoside)
NH2
N N
S - Glucose
N N
CH2 = CH - CH2 - C = N - O - SO3K HO
O
Sinigrin
H H
(S - Glycoside)
H H
OH OH
Adenosine
(N - Glycoside)
By aglycone
Glycosides are also classified according to the
chemical nature of the aglycone.
For purposes of biochemistry and pharmacology, this
is the most useful classification.
»Anthraquinone glycosides
»Simple phenolic glycoside
»Thioglycosides
»Flavonoid glycosides
»Steroidal glycosides or cardiac glycosides.
»Saponins
»Coumarin glycosides
»Cyanogenic glycosides
Anthraquinone glycosides O OH
A B C
O
(I) Anthraquinone (II) Anthranol
O O OH O OH
H H H OH O
(III) Anthrone (IV) Oxyanthrone Fizacine
OH O OH OH O OH O OH
OH
HO CH3 CH2OH
O O O
Emodine Aloe e modine Alizarine
OH O OH
OH O OH OH O OH
COOH
O
HO CH3
CH3 Rhe in
HO CH3
OH O OH
OH O OH OH O OH
Rizofanoldianthron
Emodindianthron
HO CH3
O
Frangula e modine
Simple phenolic glycoside
CH2OH CH2OH
O
H O H O O OMe
H H
OH H OH H
OH H OH H
H OH H OH
Arbutin M ethyl arbutin
CH2OH
CH2OH CH2OH
H O O O
O CH2CH2 OH
H H
OH H H
OH H
OH H
OH H
H OH H OH
Salicine Salidrozine
COOH
CH2OH
H O O
H
OH H OH
OH H
H OH
Glycoside of Salysilic acid
Thioglycosides
S - Glucose
CH2 = CH - CH2 - C = N - O - SO3K
Sinigrin
MeO
O5H11C6 - S : N - H2C O CH : CH . CO
+
MeO OCH2.CH2.N(CH3)3.H2SO4
Sinalbin
Flavonoid glycosides
O O O
OH
O O O
Flavone Flavanol
OH
O O O
HO
OH
OH O - Glucose - Rhamnose
O O OH O
Flavanone Flavanonol
Rutin
OH
+ R
O HO O +
OH HO O
OH
OH H
Flavan OH R'
OH
Cynadine OH Anthocyanidine
Pelargonidine - R=H, R'=H
Cynadine - R=OH, R'=H
O
O
Chalcone OH
Rhamnose
Catechine
Glucose - O O
OH
O
CH
O OH O
Aurones Naringin
Steroidal glycosides or
cardiac glycosides
O O O O
H H
OH
CH3 H CH3 H
H OH H OH
HO HO O O
H H
Digitoxigenin Gitoxigenin
H
O-C-H
O H CH3 H O
C
H OH
O O HO
OH H
HO Gitaloxigenin
Strophanthidin
O O
OH
H H-C-H
CH3 H O
OH
H OH
HO HO
H OH
Digitoxigenin Gellebrigenol
Saponins
O
O
O
O
O
HO
HO
Diosge nin
He coge nin
HO
HO
-amyrin -amyrin
HO
Lupe ol
Damaran
Coumarin glycosides
O O
Coumarin
Cyanogenic glycosides
CH2 OH
H O
O
H
OH H CH2
OH
H O O CH(CN)
H H H
OH H
OH
H OH
Amygdalin
H 3C CN
C
H 3C O-C6H11O5
Linamarin
