Cytotoxic Activity of Some Phenanthroindolizidine N-Oxide Alkaloids from Cynanchum vincetoxicum

Two previously known phenanthroindolizidine alkaloids, (-)-10beta-antofine N-oxide (1) and (-)-10beta, 13aalpha-14beta-hydroxyantofine N-oxide (2), and a novel alkaloid, (-)-10beta,13aalpha-secoantofine N-oxide (3), were isolated from aerial parts of Cynanchum vincetoxicum. Their structures were est...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2000-11, Vol.63 (11), p.1584-1586
Main Authors: STæRK, Dan, CHRISTENSEN, Jette, LEMMICH, Else, DUUS, Jens Ø., OLSEN, Carl Erik, JAROSZEWSKI, Jerzy W.
Format: Article
Language:English
Subjects:
Alkaloids - isolation & purification
Alkaloids - pharmacology
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
Biological and medical sciences
Circular Dichroism
Drug Screening Assays, Antitumor
General pharmacology
Humans
Indolizines
Magnetic Resonance Spectroscopy
Mass Spectrometry
Medical sciences
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Phenanthrenes - isolation & purification
Phenanthrenes - pharmacology
Plant Leaves - chemistry
Plants, Medicinal - chemistry
Spectrophotometry, Ultraviolet
Tumor Cells, Cultured
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Summary:Two previously known phenanthroindolizidine alkaloids, (-)-10beta-antofine N-oxide (1) and (-)-10beta, 13aalpha-14beta-hydroxyantofine N-oxide (2), and a novel alkaloid, (-)-10beta,13aalpha-secoantofine N-oxide (3), were isolated from aerial parts of Cynanchum vincetoxicum. Their structures were established by means of NMR methods, including COSY, NOESY, HSQC, and HMBC experiments, as well as from their CD spectra. Cytotoxic activity of the alkaloids was assessed in vitro using both a drug-sensitive KB-3-1 and a multi-drug-resistant KB-V1 cancer cell line. The antofine derivatives (1 and 2) showed pronounced cytotoxicity against the drug-sensitive cell line (IC(50) values about 100 nM), whereas the secoantofine derivative (3) was considerably less active. The KB-V1 cell line showed a marginal resistance against all alkaloids, demonstrating that these compounds are poor substrates for the P-glycoprotein (P-170) efflux pump.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0003443