BIOCHEMISTRY

LESSON 19:
GLYCOSIDES

In the last two lessons on carbohydrates I have explained you Sapomin Glycosides
the properties of monosaccharides and polysaccharides. The Saponin glycosides are divided into 2 types based on the
disaccharides are formed by linking of two momosaccharides chemical structure of their aglycones (sapogenins). Saponins
molecules. In this lesson we will discuss about he molecules on hydrolysis yield an aglycone known as “sapogenin”.
formed by joining carbohydrate moiety and a non carbohydrate
moiety. These molecules have been named as Glycosides. So in
this lesson I will explain you classification of glycosides and
also the properties of some of the glycosides.
Introduction
Glycosides are compounds containing a carbohydrate and a The so-called NEUTRAL saponins are derivatives of STE-
noncarbohydrate residue in the same molecule. ROIDS with spiroketal side chains. The ACID saponins
The carbohydrate residue is attached by an acetal linkage at possess triterpenoid structures.
carbon atom 1 to a noncarbohydrate residue or ACL YCONE.
The nonsugar component is known as the AGLYCONE. The
sugar component is called the GLYCONE
If the carbohydrate portion is glucose, the resulting compound
is a GLUCOSIDE
An example is the methyl glucoside formed when a solution of
glucose in boiling methyl alcohol is treated with 0.5% HC1 as a
catalyst.

The main pathway leading to both types of sapogenins is

similar and involves the head-to-tail coupling of acetate units.
However, a branch occurs, after the formation of the
The aglycone may be methyl alcohol, glycerol, a sterol, a phenol, triterpenoid hydrocarbon, squalene, that leads to steroids in
etc. An acetal has two ether functions at a single carbon atom. one direction and to cyclic triterpenoids in the other.

CLASSIFICATION OF GLYCOSIDES
When the chemical nature of the aglycone group is used as the
basis of systematization, the classification is as follows:

© Copy Right: Rai University

88 2.503
Glycyrrhiza is the dried rhizome and roots of Glycyrrhiza
glabra. Glycyrrhiza contains: I. A saponin glycoside called
Glycyrrhizin (glycyrrhizinic acid).
Glycyrrhi/in is the Ca2+ and K+ salts of glycyrrhizinic acid
Glycyrrhizinic acid is 50 times sweeter than sugar (sucrose).
Upon hydrolysis, the glycoside loses its sweet taste and is
converted to the aglycone glycyrrhetinic acid plus two molecules
of glucuronic acid.
Glycyrrhetinic acid is a pentacyclic triterpenoid derivative of the
beta-amyrin type. It has expectorant and antitussive properties
© Copy Right: Rai University
2.503
(Chandler, 1985). Expectorants are used to decrease the viscosity
BIOCHEMISTRY
of tenacious mucus, or to increase the secretion of mucus in dry
irritant unproductive cough, thereby, lubricating the air passages
and making coughing more productive, ft is used considerably
as a flavoring agent and is frequently employed to mask the
taste of bitter drugs such as aloe, quinine etc.
Glycyrrhetinic acid inhibits the enzymes (15-
h.ydroxyprostaglandin dehydrogenase & delta
13-prostaglandin) that metabolise the prostaglandins, PGE9
and PGF2a] , to their respective 15 keto-13,14-dihydro metabo-
lites which are INACTIVE. This causes an increased level of
prostaglandins in the digestive system. Prostaglandins inhibit
gastric secretion but stimulate pancreatic secretion and mucous
secretion in the intestines and markedly increase intestinal
motility. They also cause cell proliferation in the stomach. The
effect on gastric acid secretion, promotion of mucous secretion
and cell proliferation shows why licorice has potential in treating
peptic ulcer.
PGF2alpha stimulates activity of the uterus during pregnancy
and can cause abortion, therefore, licorice should not be taken
during pregnancy.
The structure of glycyrrhetinic acid is similar to that of corti-
sone. Both molecules are Hat and similar at position 3 and 11.
This might be the basis for licorice’s anti-inflammatory action.
3-Beta-D-(monoglucuronyl)18-beta-glycyrrhetinic acid, a
metabolite of glycyrrhetinic acid inhibits 11 -beta-
hydroxysteroid dehydrogenase which converts ACTIVE cortisol
to INACTIVE cortisone in the kidneys. The increased amounts
of cortisol binds to the unprotected, unspecific mineralocorti-
coid receptors and induce sodium and fluid retention,
hypokalaemia, hypertension and inhibition of the RENIN-
ANGIOTENSIN-ALDOSTERONE system. Licorice should
not be given to patients with a known history of high blood
pressure. A prolonged usage of licorice can also cause the
formation of cataracts.
Glycyrrhizin inhibits liver cell injury caused by many chemicals
and is used in the treatment of chronic hepatitis and cirrhosis in
Japan. It also inhibits the growth of several DNA and RNA
viruses, inactivating herpes simplex virus particles irreversibly.
Reference
1. http:www.friedli.com/herbs/phytochem/glycosides.html
Problems
Q.1. Describe the classification of Glycosides
Q.2. Explain the applications of glycosides in medicines
Q.3. Describe various type of bonding of agly molecules with
sugar.
89