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,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.
Veras
Maria Leopoldina
ML
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.
Bezerra
Maria Zeneide B
MZ
Lemos
Telma Leda G
TL
Uchoa
Daniel Esdras de A
DE
Braz-Filho
Raimundo
R
Chai
Hee-Byung
HB
Cordell
Geoffrey A
GA
Pessoa
Otília Deusdênia L
OD
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001938:Brazil; D004354:Drug Screening Assays, Antitumor; D004875:Ergosterol / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012632:Secosteroids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019657:Solanaceae / Q000737:chemistry*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D012632:Secosteroids; C486267:withaphysalin M; C486265:withaphysalin N; C486266:withaphysalin O; D004875:Ergosterol