Cytotoxic Withaphysalins from the Leaves of Acnistus arborescens

Three withaphysalins, rel-(17S,20R,22R)-5 beta,6 beta:18,20-diepoxy-4 beta-hydroxy-1,18-dioxowitha-2,24-dienolide(withaphysalin M) (1), rel-(17S,20R,22R)-5 beta,6 beta:18,20-diepoxy-4 beta-hydroxy-18-ethoxy-1-oxowitha-2,24-dienolide (withaphysalin F ethyl ether, withaphysalin O) (2), and rel-(17S,20...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2004-04, Vol.67 (4), p.710-713
Main Authors: VERAS, Maria Leopoldina, BEZERRA, Maria Zeneide B., LEMOS, Telma Leda G., DE A. UCHOA, Daniel Esdras, BRAZ-FILHO, Raimundo, CHAI, Hee-Byung, CORDELL, Geoffrey A., PESSOA, Otília Deusdênia L.
Format: Article
Language:English
Subjects:
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
Biological and medical sciences
Brazil
Drug Screening Assays, Antitumor
Ergosterol - analogs & derivatives
Ergosterol - chemistry
Ergosterol - isolation & purification
Ergosterol - pharmacology
General pharmacology
Humans
Medical sciences
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Leaves - chemistry
Plants, Medicinal - chemistry
Secosteroids - chemistry
Secosteroids - isolation & purification
Secosteroids - pharmacology
Solanaceae - chemistry
Stereoisomerism
Tumor Cells, Cultured
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Summary:Three withaphysalins, rel-(17S,20R,22R)-5 beta,6 beta:18,20-diepoxy-4 beta-hydroxy-1,18-dioxowitha-2,24-dienolide(withaphysalin M) (1), rel-(17S,20R,22R)-5 beta,6 beta:18,20-diepoxy-4 beta-hydroxy-18-ethoxy-1-oxowitha-2,24-dienolide (withaphysalin F ethyl ether, withaphysalin O) (2), and rel-(17S,20R,22R)-5 beta,6 beta:18,20-diepoxy-4 beta-hydroxy-1,18-dioxowitha-24-enolide (withaphysalin N) (3), were isolated from the leaves of Acnistus arborescens. The structures were deduced from 1D ((1)H NMR, (13)C NMR, DEPT-(13)C NMR) and 2D (COSY, HMQC, HMBC) NMR analysis and the relative stereochemical assignments based on 1D NOESY correlations and analysis of coupling constants. Compounds 1 and 2 displayed potent cytotoxic activity against a panel of human cancer cell lines.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0340347