Cytotoxic withaphysalins from the leaves of Acnistus arborescens.

Maria Leopoldina Veras, Maria Zeneide B Bezerra, Telma Leda G Lemos, Daniel Esdras de A Uchoa, Raimundo Braz-Filho, Hee-Byung Chai, Geoffrey A Cordell, Otília Deusdênia L Pessoa

Curso de Pós-Graduação em Química Orgânica, Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, 12.200, Fortaleza, CE, 60021-970, Brazil.

Journal of natural products 2004 Apr

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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.

Citation

Maria Leopoldina Veras, Maria Zeneide B Bezerra, Telma Leda G Lemos, Daniel Esdras de A Uchoa, Raimundo Braz-Filho, Hee-Byung Chai, Geoffrey A Cordell, Otília Deusdênia L Pessoa. Cytotoxic withaphysalins from the leaves of Acnistus arborescens. Journal of natural products. 2004 Apr;67(4):710-3