Cytotoxic withaphysalins from the leaves of Acnistus arborescens

J Nat Prod. 2004 Apr;67(4):710-3. doi: 10.1021/np0340347.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Brazil
  • Drug Screening Assays, Antitumor
  • Ergosterol / analogs & derivatives
  • Ergosterol / chemistry
  • Ergosterol / isolation & purification*
  • Ergosterol / pharmacology
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Secosteroids / chemistry
  • Secosteroids / isolation & purification*
  • Secosteroids / pharmacology
  • Solanaceae / chemistry*
  • Stereoisomerism
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Secosteroids
  • withaphysalin M
  • withaphysalin N
  • withaphysalin O
  • Ergosterol