Page 60 - phytochemistry general program

The most important solanaceous plants that contain tropane alkaloids are
species of the genera, Atropa, Datura, Hyoscyamus, Duboisia, Scopolia and

Anisodus.

There are considerable variations in alkaloidal contents among different
plants of the same genus e.g. Datura species, D. stramonium, D. tatula, D.
sanguinea accumulate more hyoscyamine than scopolamine. On the other hand,
D. metel, D. ferox, D. innoxia, D. arborea accumulate more scopolamine than

hyoscyamine.

Alcoholic bases in solanaceous tropane alkaloids

Tropine: (3-α-hydroxytropane), base of atropine and hyoscyamine. .1
Scopine: (6, 7-oxytropine), base of hyoscine. .1
Pseudotropine (3-β-hydroxytropane). .1

Note : Ecgonine (pseudotropine-2- carboxylic acid) is the base for coca
alkaloids.

71 2 8 R-N
R-N
8 N-R 3 H 2 N-R 3 OR1
1 3H H
OR1 OR1 3 OR1
65 4 5 H
4

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Tropine Pseudotropine
R = CH3, R1 = H
R = CH3, R1 = H

7 R-N 1 H COOR 2 R-N COOR 2
2 1 2
H OR1
O N-R 3 3H H
OR1 N-R 3 3 OR1
OR1 O 7 H
H H
6 6
H
Scopine
Ecgonie
R = CH3, R1 = H R = CH3, R1 = H

Volatile bases

Beside the above mentioned bases, Solanaceous plants contain
volatile bases e.g. choline, pyrrol, pyrollidine, pyrroline, N-methyl pyrolline, N-

methyl pyrrolidine and trimethylamine.

Esterifying acids in tropane alkaloids
1- Tropic acid: (α -phenyl- β-hydroxy-propionic acid).
The optically active l-form occurs in hyoscyamine and hyoscine. .1

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