Biologically Active Aspidofractinine, Rhazinilam, Akuammiline, and Vincorine Alkaloids from Kopsia

Eleven new indole alkaloids, in addition to the previously reported rhazinal (1), and 14 other known alkaloids, were obtained from the Malayan Kopsia singapurensis, viz., kopsiloscines A–F (2–7), 16-epikopsinine (8), kopsilongine-N-oxide (9), 16-epiakuammiline (10), aspidophylline A (11), and vincop...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2007-11, Vol.70 (11), p.1783-1789
Main Authors: Subramaniam, G, Hiraku, Osamu, Hayashi, Masahiko, Koyano, Takashi, Komiyama, Kanki, Kam, Toh-Seok
Format: Article
Language:English
Subjects:
akuammiline
Alkaloids - chemistry
Alkaloids - classification
Alkaloids - isolation & purification
Alkaloids - pharmacology
anticarcinogenic activity
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
aspidofractinine
aspidophylline
Biological and medical sciences
chemical structure
cultured cells
cytotoxicity
Drug Resistance, Multiple - drug effects
Drug Resistance, Neoplasm - drug effects
Drug Screening Assays, Antitumor
epiakuammiline
epikopsinine
General pharmacology
Gentianales
Humans
indole alkaloids
Indolizines - chemistry
Indolizines - isolation & purification
Indolizines - pharmacology
KB Cells
Kopsia singapurensis
kopsilongine-N-oxide
kopsiloscine
Lactams - chemistry
Lactams - isolation & purification
Lactams - pharmacology
Malaysia
Medical sciences
medicinal properties
Molecular Structure
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plants, Medicinal - chemistry
rhazinal
rhazinicine
rhazinilam
spectral analysis
vincophylline
vincorine
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Summary:Eleven new indole alkaloids, in addition to the previously reported rhazinal (1), and 14 other known alkaloids, were obtained from the Malayan Kopsia singapurensis, viz., kopsiloscines A–F (2–7), 16-epikopsinine (8), kopsilongine-N-oxide (9), 16-epiakuammiline (10), aspidophylline A (11), and vincophylline (12). The structures of these alkaloids were determined using NMR and MS analyses. Rhazinal (1), rhazinilam (17), and rhazinicine (18) showed appreciable cytotoxicity toward drug-sensitive as well as vincristine-resistant KB cells, while kopsiloscines A (2), B (3), and D (5) and aspidophylline A (11) were found to reverse drug-resistance in drug-resistant KB cells.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0703747