Assignment

Topic: Biological Applications Of

Glycosides

Submitted to: Dr. Matloob Ahmad

OH

OH O
OH

OH
HO OH
O O
O
OH O
H3C
HO
HO
OH
 Submitted by: Ummara Rabbani
Date: 11.12.16

Glycosides:

Glycosides are (usually) non-reducing compounds, on hydrolysis by reagents or

enzymes yield one or more reducing sugars among the products of hydrolysis.
 non-sugar glycosidic
sugar
linkage
(genin) (glycone)

Classification:

1- According to the type of glycosidic linkage: α- glycoside (α-sugar) and β-

glycosides (β-sugar).

2- According to the chemical group of the aglycone involved into the acetal
union:
a. O-glycoside (OH group)
b. S-glycoside (SH group).
c. N-glycoside (NH group).
d. C-glycoside (C group).

3- According to the nature of the simple sugar component of the glycoside:

a. Glucosides (the glycone is glucose).
b. Galacosides (the glycone is galacose).
c. Mannosides (the glycone is mannose).
 d. Arabinosides (the glycone is arabinose).

4- According to the number of the monosaccharides in the sugar moiety:

a. Monoside (one monosaccharide) e.g., salicin.
b. Biosides (two monosaccharide) e.g., gentobioside.
c. Triosides (three monosaccharide) e.g., strophanthotriose.

5- According to the physiological or pharmacological activity ‘therapeutic

classification)
a. Laxative glsycosides.
b. Cardiotonic glycosides.

6- According to the chemical nature of the aglycone:

a. Alcoholic and phenolic glycosides (aglycones are alcohols or
phenols)
b. Aldehydic G (aglycones are aldehydes).
c. Cyanogenic G (aglycones are nitriles or derivatives of hydrocyanic
acid).
d. Anthracene or anthraquinone G (aglycones are anthracene der.).
e. Steroidal G (aglycones are steroidal in nature, derived from
cyclopentanoperhydrophenanthrene) .
f. Coumarin G (aglycones are derivative of benzo α-pyrone).
g. Chromone glycosides (aglycones are derivatives of benzo-δ-pyrone)
h. Flavonoidal G (aglycones are 2-phenyl chromone structure).
i. Sulphur containing or thioglycosides (aglycones are contain
sulphur).
j. Alkaloidal glycosides (aglycone is alkaloidal in nature) e.g.,
glucoalkaloids of solanum species.
1.Silymarin:

The leaves and fruits of Silybummarianum family Compositae contain silymarin

(silybin).

OH O
B O
A
OH
OH O
OH O OCH3

Silybin OH
Uses:

1- Silymarin is a very effective lipotropic and hepato protective therapy.

2- It is a free radical scavenger.

3- Supportive treatment of acute and chronic alcoholic poisoning and toxin induce
hepatitis.

4- It is used for treatment of liver cirrhosis caused by plant toxins (mushroom,

amanita),silymarin is applied as intravenous injection.

5- Silymarin is available in the market in the form of tablets, effervescent granules.

Trade name legalon, silyhexal, silirex…etc.

2.Flavoxate:

Flavoxate is an anticholinergic with antimuscarinic effects. Its muscle relaxant

properties may be due to a direct action on the smooth muscle rather than by
antagonizing muscarinic receptors.
Uses:
To remove pain (anti-spasmodic) and anti-inflammatory of the genitor urinary
tract.

Flavoxate tablets are available under several names: Urispas, Uronid, Spasurit,
Genurin).

3.Diosmin:

Occurance:buchu leaves, Barosmacrenulata F. Rutaceae.

Uses: diuretic and diaphoretic action of the leaves is owed in part to diosmin,
and in part to diosphenol, the main constituent of the volatile oil of the leaf.

OH
Rha-Gl O O
B OCH3
A

OH
O

Diosmin

Uses:

Diosmin is used for treating various disorders of blood vessels

including hemorrhoids, varicose veins, poor circulation in the legs (venous stasis),
and bleeding (hemorrhage) in the eye or gums. It is also used to treat swelling of
the arms (lymphedema) following breast cancer surgery, and to protect
against liver toxicity. It is often taken in combination with hesperidin, another
plant chemical.

diuretic and diaphoretic action of the leaves is owed in part to diosmin, and in part
to diosphenol, the main constituent of the volatile oil of the leaf.

4.Ouabain

O O

OH
OH 17
12
OH 11 13
16
CH2 9 14
2 1 15
10 8 OH
3
Rhamnose 7
O 5
4 6
OH

Uses:
 Ouabain also known as g-strophanthin,is a plant derived toxic substance
that was traditionally used as an arrow poison in eastern Africa for both
hunting and warfare. Ouabain is a cardiac glycoside and in lower doses, can
be used medically to treat hypotension and some arrhythmias.

5.Sennoside:

Gl O
O OH

7 8 9 1 2

6 10 4 3
COOH
5 H
H
COOH

Gl O OH
O
Sennosides A &B

Uses:

Sennosides are used to treat constipation. They may also be used to clean out
the intestines before a bowel examination/surgery. Sennosides are known as
stimulant laxatives. They work by keeping water in the intestines, which
causes movement of the intestines.
6.Barbaloin

Aloin, also known as barbaloin,[1] is a bitter, yellow-brown colored

compound

O
OH OH

7 8 9 1 2

6 10 4 3
5 CH2 OH
H C6 H11 O5

Barbaloin

Uses:

It is used as a stimulant-laxative, treating constipation by

inducing bowel movements.

7.Salicin:

Salicin is classified as:

1- Alcoholic glycoside, as it contains free primary alcoholic group.

2- A phenolic glycoside, as its aglycone is phenolic in nature.

 CH2 OH

Gl O

Salicin

Uses:

1- Salicin is obtained from different species of Salix, the principle commercial

source is Salix fragilis.
2- Salicinis used for many years as a remedy in the treatment of fever and
rheumatism.
3- It is now used as an analgesic-antipyretic in case of periodic fever. It is
better tolerated in the stomach than sodium salicylate, asprin and other
antipyretics and anti-inflammatory agents, which have largely displaced in
medical practice.

8.Arbutin:

Arbutinis a phenolic glycoside that occurs in bearberry leaves

Arectostaphyllosuvaursi.
 OH OCH3

O-Gl O-Gl

Arbutin Methylarbutin

Uses:

It is used as diuretic and also has bactericidal action. This activity is due to the
hydroquinone given by hydrolysis.

Uvaursi leaf contains also methylarbutin (the methyl ether of arbutin), that also
contributes to the diuretic and urinary antiseptic action of the leave.

9. Amygdalin

1- Amygdalin is the most widely distributed cyanophore glycoside.

2- It occurs in several Prunus species, and is obtained from bitter almonds
(Prunusamygdalus Var. amara Family Rosaceae).
 CN

C
O

O
6 1
6 1 CH2
CH2 OH H
O
H 5
O
5 2
3
3 2
4
4

Amygdalin

Uses:

Amygdalin is a poisonous cyanogenic glycoside found in many plants, but

most notably in the seeds (kernels) of apricot, bitter almonds, apple, peach,
and plum.

Since the early 1950s, both amygdalin and a modified form

named laetrile have been promoted as alternative cancer treatments, often
using the misnomer Vitamin B17.[1] But studies have found them to be
clinically ineffective in the treatment of cancer, as well as potentially toxic
or lethal when taken by mouth, due to cyanide poisoning. Neither amygdalin
nor laetrile is a vitamin.
10.Digitalis:
O O

OH 12 CH3
17
11 13
1 16
R 9 14
2 15
10 8 OH
3
7
Sugar O 5
4 6

Cardenolides

Digitalis glycosides R=CH3

Uses:
Digitalis lanata is the major source of digoxin in the US. Foxglove is used
for congestive heart failure (CHF) and relieving associated fluid retention
(edema); irregular heartbeat, including atrial fibrillation and “flutter;”
asthma; epilepsy; tuberculosis; constipation; headache; and spasm.

11:Rutin:

Rutin, also called rutoside, quercetin-3-O-rutinoside and sophorin, is

the glycoside between the flavonol quercetin and the disaccharide rutinose .
It is a citrus flavonoid found in a wide variety of plants including citrus fruit.
 OH

OH O
OH

OH
HO OH
O O
O
OH O
H3C
HO
HO
OH

Uses:

Some people believe that rutin can strengthen blood vessels, so they use it
for varicose veins, internal bleeding, hemorrhoids, and to prevent strokes
due to broken veins or arteries (hemorrhagic strokes). Rutin is also used to
prevent a side effect of cancer treatment called mucositis.