PHARMACOGNOSY

3RD CLASS, 2ND SEMESTER

Lab.7

INDOLE ALKALOIDS
INTRODUCTION
 Indole alkaloids are a class of alkaloids containing a structural
moiety of indole.
 Indole is an aromatic heterocyclic organic compound. It has a
bicyclic structure
INTRODUCTION
HARMALA ALKALOIDS:-

Peganum harmala of the family Nitrariaceae

It is a woody, perennial, succulent shrub, native to arid regions.
The leaves are bright green, finely divided and about 1cm long. Both
the roots and seeds contain significant quantities of beta-carbolines
(indole) alkaloids. Which are absent from the rest of the plant.
 Botanical name: Peganum harmala
 Family name: Nitrariaceae
 Part used: seed
 Local name:‫ا لحرمل‬
 The round seed capsules measure about 1–1.5 cm in diameter,
have three chambers and carry more than 50 seeds.
-:TRADITIONAL / MEDICINAL USES
 This plant has a long history of traditional uses including as dye
((turkey red)) is a color that was widely used to dye cotton in the
18th and 19th century and as incense from ancient times.

 Peganum harmala seeds were known to possess hypothermic and

essentially hallucinogenic properties since it is MAO (monoamine
oxidase) inhibitor agent.
 Many studies were conducted to antibacterial, antifungal and
antiviral effects of Peganum harmala seeds.
 In Moroccan it is used as traditional medicine.
 Seed powder is used sometimes for skin and subcutaneous tumors.
THE ACTIVE ALKALOIDS OF HARMAL SEEDS

A. Harmane
B. Harmine
C. Harmaline
D. Harmalol
E. Tetrahydroharmine
F. Vasicine & Vasicinone (quinazoline derivatives)
ISOLATION OF THE HARMALA ALKALOIDS
Aim: - To isolation the harmala alkaloids
Equipments and reagents:-
1) Large beaker 9) 2%HCL
2) Reflux instrument 10) Ammonium hydroxide solution
3) Water bath 11) Chloroform
4) Large evaporating dish 12) Methanol
5) Separatory funnel
6) Litmus paper
7) Petroleum ether
8) 90 % ethanol
Procedure:-
1) Take 50 gm. of harmala seeds.
2) Macerate with 500ml of petroleum ether over night.
3) Filter off the maceration solvent of the seeds.
4) And then reflux with 500ml of 90 %ethanol for one hour.
5) Evaporate the resultant filtrate on the steam bath to syrup liquid.
6) Add to the concentrated filtrate 5 ml of 2%HCL.
7) Remove all the remaining alcohol by evaporating in large evaporating dish on
the steam bath.
8) The acidic extract is then cooled, filtered and placed in a separatory funnel where
it is made alkaline by adding ammonium hydroxide solution (according to litmus
paper).
9) The alkaline solution is then extracted three times with 100 ml of chloroform.
10) The chloroform solution is then concentrated to give the product crude alkaloid
(fraction A).
11) Add 10 ml methanol to fraction A, then filter, the result is two fractions,
fraction B (filtrate), fraction C (precipitate).
Results:-
Fraction A contains the crude alkaloids.
Fraction B contains (vasicine and deoxyvasicine alkaloids)
Fraction C contains (harmine and harmaline).
Discussion:-
1) Maceration process is for defatting process.
2) Use of reflux condenser since the plant is not affected by heat.
3) Use of methanol is to separate some of harmala alkaloids, since some are soluble
in methanol and others are not.
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