Abstract
Stemona alkaloids represent a unique class of natural products exclusively isolated from
the monocotyledonous family Stemonaceae comprising three genera mainly distributed
in southeast Asia. Structurally the alkaloids are characterised by a pyrrolo[1,2-a]azepine nucleus usually linked with two carbon chains mostly forming terminal lactone
rings. Based on biosynthetic considerations and their various distribution the present
review describes 82 Stemona alkaloids grouped into three skeletal types. Due to different carbon chains attached
to C-9 of the pyrroloazepine nucleus they were classified into stichoneurine-, protostemonine-
and croomine-type alkaloids. The genera Croomia and Stichoneuron only accumulate croomine or stichoneurine derivatives, respectively, whereas the
genus Stemona produces all three types of alkaloids. However, species-specific accumulation trends
towards certain structural types represent valuable chemosystematic criteria. Bioassays
with larvae of Spodoptera littoralis exhibited very high insect toxicity for the roots of Stemona species containing certain protostemonine derivatives, especially didehydrostemofoline,
whereas those with dominating stichoneurine or croomine derivatives showed low toxicity
but sometimes remarkable repellence due to an accumulation of tuberostemonine. Tuberostemonine
also showed effects on the motility of helminth worms and reduced the excitatory transmission
at the crayfish neuromuscular junction. Significant antitussive activity was shown
for the stereoisomeric neotuberostemonine in guinea-pig after cough induction by citric
acid aerosol stimulation. Studies on structure-activity relationship with seven related
compounds revealed that the saturated tricyclic pyrrolobenzazepine nucleus of tuberostemonines
is the prerequisite for antitussive activity.
Key words
Stemona alkaloids - pyrrolo[1,2-a]azepine alkaloids - structural diversity - bioactivity -
Stemona
-
Croomia
-
Stichoneuron
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Prof. Dr. Harald Greger
Comparative and Ecological Phytochemistry Section
Institute of Botany
University of Vienna
Rennweg 14
1030 Wien
Austria
Telefon: +43-1-4277-54070
Fax: +43-1-4277-9541
eMail: harald.greger@univie.ac.at
