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Phytochemistry-I ( Practical )

Dr. Sultan AlKaleh

2. Glycosides

Introduction

Definition:Compounds containing a carbohydrate (sugar) and a non-carbohydrate molecule (called the


aglycone).

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.

d. other classification schemes as specific properties:


1. Simple phenolic compounds existing as Arbutin found in Bearberry leaves.
2. Cardioactivesteroid-like, act on heart, some poisonous; Digitalis (Digitalis purpurea), Lily
of the valley (Convallaria majalis).
3. AnthraquinoneCascara sagrada, Aloe, Senna, Frangula.
4. Saponin
a. common characteristicsbitter taste, hemolytic activity, forms stable foams when
shaken in water
b. Notable actionshepato-protective, adaptogenic, 1nti-i-modulating, hormonal
modulation, anti-microbial, 1nti-inflammatory, expectorant (stimulant to mucosal
secretions), diuretic, tonic.
c. Common to plants such asSiberian ginseng, gentian, Liquorice, Korean ginseng,
American ginseng, Sage, Comfrey, Dandelion, Fenugreek (antiinflammatory,
hypotensive, hypoglycemic)
5. Cyanophosewater soluble, many in the rose family (kernels of Apricots, Cherries, Plums,
Bitter Almond etc).
6. IsothiocyanateMustard, horseradish root
7. FlavonolGinkgo, Milk thistle, Hawthorne berry
8. Alcoholsalicin from Willow (Salix), Poplar (Populus), wintergreens
9. AldehydeVanilla
10. Lactoseno useful plants containing this compound
11. OthersGentian (Gentiana lutea), saffron (crocus sativa)

Phytochemistry-I ( Practical )

Dr. Sultan AlKaleh

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).

Glycyrrhizin is the Ca2+ and K+ salts of glycyrrhizinic acid.

Dr. Sultan AlKaleh

Phytochemistry-I ( Practical )

Dr. Sultan AlKaleh

Phytochemistry-I ( Practical )

Dr. Sultan AlKaleh

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 )

Dr. Sultan AlKaleh

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.

2.1 Identification tests Cardiac glycosides: Digoxin


Duration: 10 mins

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 )

Dr. Sultan AlKaleh


OH
NO2

O2N

O
O
beta

alfa

gamma

OH-

O
NO2

- H2O

beta

+O
O
O
beta

NO2

O2 N

-O

O-

B) Keller-Killiani test (works on glycone part)


Duration: 10 mins
1- Dissolve about 0.001 g of digoxin in 1 ml of glacial acetic acid.
2- Add few drops of 1% FeCl3 /CH3COOH solution
3- Cautiously add 1 ml of sulfuric acid avoiding mixing the two liquids
4- A brown ring develops at the interface and on standing a green then blue color
passes to the upper layer.

Phytochemistry-I ( Practical )

Dr. Sultan AlKaleh

Phytochemistry report no. 7


Exp ( 7): .
Purpose of the exp:

Theory:

Result:

Conclusion and comment:

Phytochemistry-I ( Practical )

Dr. Sultan AlKaleh

2.2 Identification Tests of Anthraquinone Glycosides


Duration: 30 mins

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 )

Dr. Sultan AlKaleh

Phytochemistry report no. 8


Exp ( 8): .
Purpose of the exp:

Theory:

Result:

Conclusion and comment:

Phytochemistry-I ( Practical )

Dr. Sultan AlKaleh

2.3 Identification Tests of Saponins and flavonoides


Duration: 10 mins

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 )

Dr. Sultan AlKaleh

Phytochemistry report no. 9


Exp ( 9): .
Purpose of the exp:

Theory:

Result:

Conclusion and comment:

Phytochemistry-I ( Practical )

Dr. Sultan AlKaleh

2.4. TLC Test of Flavonoids


Duration: 30 mins

Detection the presence of rutin (rutinoside) in flavonoides containing powders:


1- Take 1 g of the powder with 10 ml methanol.
2- Shake for 5 minutes at 65C in water bath.
3- Cool and filter.
4- Apply on TLC plate using the mobile phase: Ethyl acetate
Formic acid + water (90 + 5 + 5)
5- Detect the spots under UV light.
Identification tests of Flavanoids
Flavonoid
Rutin
Vitixin
Naringin
Hespiridin

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 )

Dr. Sultan AlKaleh

Phytochemistry report no. 10


Exp (10): .
Purpose of the exp:

Theory:

Result:

Conclusion and comment:

Phytochemistry-I ( Practical )

Dr. Sultan AlKaleh

2.5. Identification test of Anthocyanidins in Red


Cabbage
Duration: 1 hour

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 )

Dr. Sultan AlKaleh

Phytochemistry report no. 11


Exp ( 11): .
Purpose of the exp:

Theory:

Result:

Conclusion and comment:

Phytochemistry-I ( Practical )

Dr. Sultan AlKaleh

2.6 Isolation of Capsaicin from Habanero peppers


Duration: 12 hours + 1 hour

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 )

Dr. Sultan AlKaleh

Phytochemistry report no. 12


Exp ( 12): .
Purpose of the exp:

Theory:

Result:

Conclusion and comment: