Page 77 - Phytochemistry 2 (06-PG 605)
P. 77
N Indole
H
NH2
NH2 H2C CH
H2C CH2
COOH
N Tryptamine
H N Tryptophane
H
The clavine alkaloids of Ergot as well as the lysergic acid
moiety of all Ergot alkaloids are products of condensation of
tryptophan with an isoprenyl moiety; where the two carbon side
chain of trptophan together with the C5 prenyl moiety provided
rings C and D.
NH
N
H
Ergot alkaloids
(Tryptophan with one prenyl moiety)
On the other hand, Rauwolfia and Yohimbe alkaloids are
examples of the latter classes, where ring C is formed by
cyclization of the two carbon side chain of tryptophan, upon
condensation with the C10-geranyl portion that provides rings D
and E.
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