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2. Glycosides
Introduction
Classification Of Glycosides
b. Classification according to the sugar unit such as:
- Glucose = glucoside,
- Rhamnose = rhamnoside, etc. (a term hence formed by dropping ose and
adding oside.
c. Forms:11 groups having such actions as cathartics, pseudo-hormone regulators, analgesics,
counter-irritants, antioxidants, diuretics, etc.
Phytochemistry-I ( Practical )
SAPONIN GLYCOSIDES
Saponin glycosides are divided into 2 types based on the chemical structure of their aglycones (sapogenins).
Saponins on hydrolysis yield an aglycone known as "sapogenin".
They also-called NEUTRAL saponins are derivatives of steroids. The ACID saponins possess triterpenoid
structures.
Phytochemistry-I ( Practical )
Glycyrrhiza is the dried rhizome and roots of Glycyrrhiza glabra. Glycyrrhiza contains:
1. A saponin glycoside called Glycyrrhizin (glycyrrhizinic acid).
Phytochemistry-I ( Practical )
Phytochemistry-I ( Practical )
2. 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.
3. Glycyrrhetinic acid is a pentacyclic triterpenoid derivative of the beta-amyrin type.
Medical uses of glycyrrhetinic acid:
1. It has expectorant and antitussive properties. Expectorants are used to decrease the viscosity 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.
2. It is used considerably as a flavoring agent and is frequently employed to mask the taste of bitter drugs such
as aloe, quinine etc.
3. Glycyrrhetinic acid inhibits the enzymes (15-hydroxyprostaglandin dehydrogenase & delta 13prostaglandin) that metabolise the prostaglandins, PGE2 and PGF2alpha to their respective 15 keto-13,14dihydro metabolites 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.
4. PGF2alpha stimulates activity of the uterus during pregnancy and can cause abortion, therefore, licorice
should not be taken during pregnancy.
5. The structure of glycyrrhetinic acid is similar to that of cortisone. Both molecules are flat and similar at
position 3 and 11. This might be the basis for licorice's anti-inflammatory action.
6. Glycyrrhizin inhibits liver cell injury caused by many chemicals and is used in the treatment of chronic
hepatitis and cirrhosis in Japan.
7. It also inhibits the growth of several DNA and RNA viruses, inactivating herpes simplex virus particles
irreversibly.
Note:
Phytochemistry-I ( Practical )
3-Beta-D-(monoglucuronyl) 18-beta-glycyrrhetinic acid, a metabolite of glycyrrhetinic acid inhibits 11-betahydroxysteroid dehydrogenase which converts ACTIVE cortisol to INACTIVE cortisone in the kidneys. The
increased amounts of cortisol binds to the unprotected, unspecific mineralocorticoid receptors and induce
sodium and fluid retention, hypokalaemia, hypertension and inhibition of the RENIN-ANGIOTENSINALDOSTERONE 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.
Structure:
Procedure:
A) Works on aglycone part
1- Put about 0.001 g Digoxin in 0.5 ml ethanol 60%.
2-Add 5 drops dinitrobenzoic acid solution.
3- Add 5 drops of 2 N NaOH solutions.
(Observe violet color)
Phytochemistry-I ( Practical )
O2N
O
O
beta
alfa
gamma
OH-
O
NO2
- H2O
beta
+O
O
O
beta
NO2
O2 N
-O
O-
Phytochemistry-I ( Practical )
Theory:
Result:
Phytochemistry-I ( Practical )
Structure:
Bortraeger test:
Procedure:
1- Boil 0.5 g of powdered Senna leaves with 3 ml 10 N H2SO4 + 5 ml H2O2.
2- Filter and take the filtrate, dilute with 3 ml water.
3- Extract with 5 ml toluene.
4- Transfer the toluene to a clean test tube.
5- Add 1 ml of dilute NH3 to the toluene phase and observe the color
changes.
6- Red color will develop in the ammonia layer (an indication for
anthraquinone)
We also do the same test with tablets contain anthraquinone glycosides.
CH2OH
OH
OH
OH
OH
OH
OH
COOH
H2SO4
COOH
- CO2
- 2 B-D-GLUCOSE
ANTHRONE
CH2OH
OH
OH
OH
[O]
OH
OH
O-
OH
NH4+
RED COLOR
OH
NH3
ANTHRAQUINONE
Phytochemistry-I ( Practical )
Theory:
Result:
Phytochemistry-I ( Practical )
Structure:
Tests of saponins:
A) - Frothing test:
1- Place 1 ml of liquirice extract in a test tube.
2- Add 5 ml water.
3- Shake strongly and notice the formed forth.
B) - Precipitation by reagents:
1- Take 1 ml of liquirice extract.
2- Add 1 ml lead acetate solution.
3- Shake and notice the precipitated formed.
Phytochemistry-I ( Practical )
Theory:
Result:
Phytochemistry-I ( Practical )
Aq.NaOH
Yellow to orange
Yellow
Yellow to orange
as it is cold, red to
purple as it is hot
..
H2SO4 conc.
MgHCl
Yellow to orange Red
Yellow to orange Yellow to red
orange
Red,violet,blue
Phytochemistry-I ( Practical )
Theory:
Result:
Phytochemistry-I ( Practical )
Procedure
1. Take half of a head of red cabbage, and chopped it up.
2. Cover the cabbage with 800 ml of boiling water, and then cool the juice to room
temperature, then sieved it, and add 5 ml of ethanol, the Liquid should be a dark reddish-purple
color.
3. After that, prepare 7 test tubes with different PH (1.5, 3, 5, 7, 9, 11, 14) respectively
4. Mix 12 ml of cabbage juice to each test tube, and observe the
changes in the color.
Phytochemistry-I ( Practical )
Theory:
Result:
Phytochemistry-I ( Practical )
Structure:
Procedure:
1. Mix 15 parts of habanero peppers with 500 ml 200 proof (100%)
Ethanol in blender
2. Then let the mixture set for about 12 hours at room temperature.
3. Pour the mixture through paper towels, and transfer the liquid in a
Glass container.
4. After that, heat the liquid very slowly using an electric heating device
continue until 90% of the liquid has evaporated, then remove it from
the heat and let it cool.
5. Through cooling, observe the brick-red oil floating on the surface of
the ethanol, once the red oil appears, pour the red oil and the
remaining ethanol into along thin class cylinder
6. Draw off the oil by using an eye dropper and place it in a clean
Container.
(The red oil is fairly pure capsaicin, perhaps 40% capsaicin and 60%
Capsaicinoids)
Phytochemistry-I ( Practical )
Theory:
Result: