Schizanthines N, O, and P, Tropane Alkaloids from the Aerial Parts of Schizanthus tricolor

Three tropane alkaloids, named schizanthines N, O, and P (1−3), have been isolated from the crude alkaloid extract of the endemic Chilean plant Schizanthus tricolor. On the basis of extensive NMR studies and MS fragmentation analysis, their structures were determined to be 3α-(E)-4-hydroxysenecioylo...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2011-01, Vol.74 (1), p.50-53
Main Authors: Humam, Munir, Kehrli, Thomas, Jeannerat, Damien, Muñoz, Orlando, Hostettmann, Kurt, Christen, Philippe
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - isolation & purification
Biological and medical sciences
Chile
General pharmacology
Medical sciences
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Solanaceae - chemistry
Stereoisomerism
Tropanes - chemistry
Tropanes - isolation & purification
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Summary:Three tropane alkaloids, named schizanthines N, O, and P (1−3), have been isolated from the crude alkaloid extract of the endemic Chilean plant Schizanthus tricolor. On the basis of extensive NMR studies and MS fragmentation analysis, their structures were determined to be 3α-(E)-4-hydroxysenecioyloxy-6β-angeloyloxytropane (1), 3α-(E)-4-hydroxysenecioyloxy-6β-senecioyloxytropane (2), and 3α-mesaconyloxy-6β-senecioyloxytropane (3). Compounds 1 and 2 are the first isomeric alkaloids in the tropane series possessing a hydroxysenecioyl substituent as an esterifying moiety.
ISSN:0163-3864
1520-6025
DOI:10.1021/np1005423