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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 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
hydrolysis
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
OH
H OH
O
H H
H OH
H
H
O
O CH3
OH
H OH
O
H H
H OH
H
O
H
H3
CO
O
CH2OH
H
H
OH
OH
H
H
OH H
O CH3
O
CH2OH
H
H
OH
OH
H
OH H
H
O CH3
 methyl glucoside  methyl glucoside
 methyl glucoside  methyl glucoside
By Linkage
- O - C6H11O5
- O - H H - O - C6
H11
O5
+
O - Glycoside
C - H C - C6
H11
O5
H - O - C6
H11
O5
+
C - Glycoside
N - H N - C6
H11
O5
H - O - C6
H11
O5
+
N - Glycoside
- S - H - S - C6H11O5
H - O - C6H11O5
+
S - Glycoside
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
O,C,S & N – GLYCOSIDES
CH2
= CH - CH2
- C = N - O - SO3
K
S - Glucose
O
O OH
R1
R2
OH
O O
C6
H11
O5
.
C6
H11
O5
.
OH OH
CH2
OH
O
O
CH2OH
H
H
OH
OH
H
OH H
H
O
H
H
OH
H
OH
H
O
H
N
N
N
N
NH2
Sinigrin
10
10'
Barbaloin
(S - Glycoside)
Sennoside
(O - Glycoside)
(C - Glycoside)
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
O
OH
O
H H
O
H OH
O
O
OH OH
O
O
OH OH
CH3
O
H
O
O
OH OH
CH2
OH
O
O
OH
OH
O
OH OH
CH3
O
H
O
CH3
O
H
OH OH
O
OH OH
O
CH3
OH OH
OH OH
O
O
COOH
O
O
OH OH
CH3
O
H
A B C


(I) Anthraquinone (II) Anthranol
(III) Anthrone (IV) Oxyanthrone Fizacine
Emodine Aloe emodine Alizarine
Emodindianthron
Rizofanoldianthron
Rhein
Frangula emodine
Simple phenolic glycoside
O OMe
O CH2
CH2 OH
O
CH2
OH
O
OH
COOH
O
O
CH2OH
H
H
OH
OH
H
OH H
H
O
CH2OH
H
H
OH
OH
H
OH H
H
O
CH2OH
H
H
OH
OH
H
OH H
H
O
CH2OH
H
H
OH
OH
H
OH H
H
O
CH2OH
H
H
OH
OH
H
OH H
H
Methyl arbutin
Salidrozine
Salicine
Glycoside of Salysilic acid
Arbutin
Thioglycosides
CH2
= CH - CH2
- C = N - O - SO3
K
S - Glucose
O
MeO
MeO
O5
H11
C6
- S : N - H2
C CH : CH . CO
OCH2
.CH2
.N(CH3
)3
.H2
SO4
Sinigrin
+
Sinalbin
Flavonoid glycosides
O
O
O
O
O
OH
O
O
OH
O
O
O
O
O
OH
OH
O
H
OH
R
R'
O
OH
O
O
O
CH
O
O
OH
OH
Glucose - O
Rhamnose
O
OH
O
H
O
O - Glucose - Rhamnose
OH
OH
O
OH
OH
O
H
OH
OH
H
Flavone
Flavan
Flavanol
Flavanone Flavanonol
+
Anthocyanidine
Chalcone
Catechine
Aurones
Pelargonidine - R=H, R'=H
Cynadine - R=OH, R'=H
Naringin
Rutin
+
Cynadine
Steroidal glycosides or
cardiac glycosides
CH3
OH
O
H
H
H
H
H
OH
O
H
O O
H
O
O
O O
CH3
OH
O
H
H
H
H
H
OH
O O
CH3
OH
O
H
H
H
H
H
O-C-H
O O
O
CH3
OH
O
H
H
H
H
H
O O
Digitoxigenin
C
Strophanthidin
H-C-H
OH
OH
OH
HO
Gellebrigenol
Gitoxigenin
Gitaloxigenin
Digitoxigenin
Saponins
O
H
O
O
O
H
O
O
O
O
H
O
H
O
H
O
Diosgenin
Hecogenin
-amyrin -amyrin
Lupeol
Damaran
Coumarin glycosides
O O
Coumarin
Cyanogenic glycosides
O
CH2
OH
H
H
OH
H
H
OH H
O
CH2
H
H
OH
OH
H
OH H
CH(CN)
C
C
H3
O-C6
H11
O5
CN
C
H3
O
O
Amygdalin
Linamarin

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GLYCOSIDES-Introduction & Classification.pdf

  • 1. Glycosides Introduction & Classification By Dr. Mukul Tailang Professor School of Studies in Pharmaceutical Sciences Jiwaji University Gwalior (M.P.)
  • 2. 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.
  • 3. 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).
  • 4. Glycosidal Sugars: Sugars found in glycosides may be • Monosaccharides –Glucose –Rhamnose –Fructose • Deoxysugars (more rare) –Cymarose • found in the cardiac glycosides
  • 5. 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
  • 6. 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.
  • 8. 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.
  • 9. 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.
  • 10. 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
  • 11. •Botanical source: •Digitalis glycosides •Senna glycosides. •Therapeutic use: •Analgesic glycosides. •Purgative glycosides. •Cardiac glycosides.
  • 12. 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.
  • 13. 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 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 hydrolysis
  • 14. 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
  • 15. α- & β-glycosides OH H OH O H H H OH H H O O CH3 OH H OH O H H H OH H O H H3 CO O CH2OH H H OH OH H H OH H O CH3 O CH2OH H H OH OH H OH H H O CH3  methyl glucoside  methyl glucoside  methyl glucoside  methyl glucoside
  • 16. By Linkage - O - C6H11O5 - O - H H - O - C6 H11 O5 + O - Glycoside C - H C - C6 H11 O5 H - O - C6 H11 O5 + C - Glycoside N - H N - C6 H11 O5 H - O - C6 H11 O5 + N - Glycoside - S - H - S - C6H11O5 H - O - C6H11O5 + S - Glycoside 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
  • 17. O,C,S & N – GLYCOSIDES CH2 = CH - CH2 - C = N - O - SO3 K S - Glucose O O OH R1 R2 OH O O C6 H11 O5 . C6 H11 O5 . OH OH CH2 OH O O CH2OH H H OH OH H OH H H O H H OH H OH H O H N N N N NH2 Sinigrin 10 10' Barbaloin (S - Glycoside) Sennoside (O - Glycoside) (C - Glycoside) Adenosine (N - Glycoside)
  • 18. 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
  • 19. Anthraquinone glycosides O O OH O H H O H OH O O OH OH O O OH OH CH3 O H O O OH OH CH2 OH O O OH OH O OH OH CH3 O H O CH3 O H OH OH O OH OH O CH3 OH OH OH OH O O COOH O O OH OH CH3 O H A B C   (I) Anthraquinone (II) Anthranol (III) Anthrone (IV) Oxyanthrone Fizacine Emodine Aloe emodine Alizarine Emodindianthron Rizofanoldianthron Rhein Frangula emodine
  • 20. Simple phenolic glycoside O OMe O CH2 CH2 OH O CH2 OH O OH COOH O O CH2OH H H OH OH H OH H H O CH2OH H H OH OH H OH H H O CH2OH H H OH OH H OH H H O CH2OH H H OH OH H OH H H O CH2OH H H OH OH H OH H H Methyl arbutin Salidrozine Salicine Glycoside of Salysilic acid Arbutin
  • 21. Thioglycosides CH2 = CH - CH2 - C = N - O - SO3 K S - Glucose O MeO MeO O5 H11 C6 - S : N - H2 C CH : CH . CO OCH2 .CH2 .N(CH3 )3 .H2 SO4 Sinigrin + Sinalbin
  • 22. Flavonoid glycosides O O O O O OH O O OH O O O O O OH OH O H OH R R' O OH O O O CH O O OH OH Glucose - O Rhamnose O OH O H O O - Glucose - Rhamnose OH OH O OH OH O H OH OH H Flavone Flavan Flavanol Flavanone Flavanonol + Anthocyanidine Chalcone Catechine Aurones Pelargonidine - R=H, R'=H Cynadine - R=OH, R'=H Naringin Rutin + Cynadine
  • 23. Steroidal glycosides or cardiac glycosides CH3 OH O H H H H H OH O H O O H O O O O CH3 OH O H H H H H OH O O CH3 OH O H H H H H O-C-H O O O CH3 OH O H H H H H O O Digitoxigenin C Strophanthidin H-C-H OH OH OH HO Gellebrigenol Gitoxigenin Gitaloxigenin Digitoxigenin
  • 26. Cyanogenic glycosides O CH2 OH H H OH H H OH H O CH2 H H OH OH H OH H CH(CN) C C H3 O-C6 H11 O5 CN C H3 O O Amygdalin Linamarin