(+)-Angchibangkine, a New Type of Bisbenzylisoquinoline Alkaloid, and Other Dimers from Pachygone dasycarpa

Analysis of the alkaloidal fraction of the stem bark extract of Pachygone dasycarpa (Menispermaceae) resulted in the isolation of 10 known bisbenzylisoquinolines, (+)-tetrandrine, (+)-penduline, (+)-fangchinoline, (+)-atherospermoline, (+)-N-methyl-7-O-demethylpeinamine, (+)-daphnoline, (+)-isotrilo...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1997-03, Vol.60 (3), p.258-260
Main Authors: Guinaudeau, Hélène, Böhlke, Mark, Lin, Long-Ze, Angerhofer, Cindy K, Cordell, Geoffrey A, Ruangrungsi, Nijsiri
Format: Article
Language:English
Subjects:
ALCALOIDE QUINOLIQUE
ALCALOIDES DE LA QUINOLINA
Animals
ANTIMALARIALS
Antimalarials - isolation & purification
Antimalarials - pharmacology
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
ANTIPROTOZOAIRE
ANTIPROTOZOAL AGENTS
BARK
Biological and medical sciences
CHEMICAL COMPOSITION
CHEMICAL STRUCTURE
COMPOSICION QUIMICA
COMPOSITION CHIMIQUE
CORTEZA
ECORCE
ESPECTROMETRIA
ESTRUCTURA QUIMICA
General pharmacology
Humans
Isoquinolines - isolation & purification
Isoquinolines - pharmacology
KB Cells
Magnetic Resonance Spectroscopy
Medical sciences
MEDICAMENTOS CONTRA PROTOZOARIOS
PACHYGONE
PHARMACEUTICAL PRODUCTS
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Epidermis - chemistry
Plants, Medicinal - chemistry
PLASMODIUM FALCIPARUM
Plasmodium falciparum - drug effects
QUINOLINE ALKALOIDS
SPECTRAL ANALYSIS
SPECTROMETRIE
SPECTROMETRY
STEMS
STRUCTURE CHIMIQUE
TAILANDIA
TALLO
THAILAND
THAILANDE
TIGE
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Summary:Analysis of the alkaloidal fraction of the stem bark extract of Pachygone dasycarpa (Menispermaceae) resulted in the isolation of 10 known bisbenzylisoquinolines, (+)-tetrandrine, (+)-penduline, (+)-fangchinoline, (+)-atherospermoline, (+)-N-methyl-7-O-demethylpeinamine, (+)-daphnoline, (+)-isotrilobine (1), (+)-cocsuline (2), (+)-tricordatine (3), (+)-2‘-norcocsuline, and the new alkaloid (+)-12-O-methyltricordatine (4). The last bisbenzylisoquinoline alkaloid isolated, (+)-angchibangkine (5), is the first member of this alkaloid class found to possess three diphenyl ether bridges in the 7−6‘, 8−7‘, and 11−12‘ positions. Structure elucidation of these alkaloids and of (+)-O-methylangchibangkine (6) was achieved by analysis of spectral data. Compounds 4−6 show antiplasmodial activity against Plasmodium falciparum.
ISSN:0163-3864
1520-6025
DOI:10.1021/np960568e