Purine (Xanthine) Alkaloids

The purines are consisting of a six-membered pyrimidine ring fused to a sixfivefive-membered imidazole ring. ring. The pharmaceutically important bases of this group are all methylated derivatives of 2,6 dioxy-purine (Xanthine). This group includes mainly dioxy(Xanthine). Caffeine, theobromine and theophylline alkaloids. These alkaloids are weak bases, they give no precipitate with Mayer's reagent.
6 1 N 2 N 4 3 Puri
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7 N

H HN 8 O

O H N

N 9

Dr. Harish Kakrani & Purvi Kakrani

N N H Xant ine
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Caffeine, Theobromine and Theophylline

O R1 N R3 N R1=R2=R3=CH3 R1=H, R2=R3=CH3 R1=R2=CH3, R3=H Caffeine Theobromine Theophylline

N R2

Caffeine


Occurrence:
Tea leaves (2- 5%), Coffee seeds (1-2 %), Cola leaves (2- 3%), Gurana seeds (2.5- 5 %) and Cacao seeds, (0.2- 0.5 %). seeds, (0

 

Properties:
1- Water soluble. 2- Sublimable.

Uses:

Dr. Harish Caffeine has a CNS stimulant effect,Kakrani & Purvi it is used mainly to relieve headache. 7/15/2011 Kakrani 2

Theobromine
Occurrence:  Properties:
 

Cacao seeds.

1- Sparingly soluble in water.

2- Sublimable.

3- Amphoteric.

Uses:

Theobromine is used mainly as a diuretic.

Theophylline
Occurrence: Traces in Tea leaves, mostly synthetic.  Properties: 1- Sparingly soluble in water.


Uses:
Theophylline and derivatives are smooth muscle relaxant especially in the upper respiratory tract. They used as bronchodilator. Theophylline also act as duiretic.
Dr. Harish Kakrani & Purvi Kakrani

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 Color


tests:

Murexide test: (caffeine, theobromine and theophylline). theophylline). Crystals of caffeine + drops of concentrated HCl and traces of KClO3 evaporated on water bath red color is produced wich turns to violet on exposure to ammonia vapor. vapor. Tannic acid test: (caffeine and theophylline): theophylline): A concentrated solution of the alkaloid + tannic acid white precipitate is obtained that dissolves in excess of the reagent. reagent. Ferrous sulfate test: (theobromine): (theobromine): To a solution of the alkaloid + drops of concentrated HCl + few drops of Br2- water + a drop of FeSO4 + few drops of ammonia
Dr. Harish Kakrani & Purvi Kakrani

Blue color. color.

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Steroidal Alkaloids


These contain the perhydrocyclopentano-phenanthrene skeleton perhydrocyclopentanocharacteristic of sterols. They usually occur in glycosidal combination with sugars and thus called glucoalkaloids e.g. Solanum and Veratrum alkaloids.

H H HO
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1- Solanum alkaloids



Occurrence: They occurs in Solanum spp.

Consitituents: Solanine, Solasonine.

Properties: They are glucoalklaloids with a sugar parts.  Uses:



1- The aglycone of both alkaloids are used as a starting material for the synthesis of steroidal drugs. 2- Solasonine is used as agricultural insecticide.

H H H H Glc GalO Rha H

Solanine

H N H O H H Glc Gal O Rha

Dr. Harish Kakrani & Purvi Kakrani

CH3

N H H H

Solasonine

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2- Veratrum alkaloids


They are of two types:

1- Typical or atypical steroidal alkamines containing one or two non estrified hydroxyl groups e.g. Rubijervine and Veratramine. Veratramine. 2- Highly oxygenated alkamines estrified with organic acids e.g. Protoveratrines A& B.  Uses:
The second group posses hypotensive effect.
O N N HO O
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HO Rubijervi e
Dr. Harish Kakrani & Purvi Kakrani

Ver tr

i e

Diterpene Alkaloids
Taxol
Occurrence: Barks of Taxus brevifolia known as Pacific Yew.  Yield: 0.015 %. The bark obtained from about 4000 trees yields about one Yield:


kg of Taxol. The amount isolated from three trees is required from treatment Taxol. of only one cancer patient. patient.

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Dr. Harish Kakrani & Purvi Kakrani

 

Sources:
1- Natural. 2- Semisynthesis from Baccatin III.

Uses: Breast, varian, lung and other solid tumors.

Ac O NH O H OH O

H Ac O

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Dr. Harish Kakrani & Purvi Kakrani

 Mechanism

of Action: Antimitotic agent.

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Dr. Harish Kakrani & Purvi Kakrani

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