Purine Alkaloids
Purine Alkaloids
Purine 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
N N H Xant ine
1
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.
2- Sublimable.
3- Amphoteric.
Uses:
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
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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
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.
CH3
N H H H
Solasonine
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2- Veratrum alkaloids
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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Sources:
1- Natural. 2- Semisynthesis from Baccatin III.
Ac O NH O H OH O
H Ac O
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Mechanism
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10