Cytotoxic biscembranes from the soft coral Sarcophyton glaucum

J Nat Prod. 2009 May 22;72(5):946-9. doi: 10.1021/np8003485.

Abstract

Seven new tetracyclic biscembranes (1-7) have been isolated from the soft coral Sarcophyton glaucum. Four (1-4) may be formed biogenetically by a Diels-Alder reaction of Delta(4(5)) and Delta(8(9)) geometrical isomers of methyl sarcoate and Delta(21(34), 35(36)) dienes, including two with a tetrahydrofuran ring between C-27 and C-30 (3, 4), and three biscembranes (5-7) are probably derived from methyl sarcoate isomers with Delta(1(14), 4(5), 8(9)) and a cembrane diene. Their structures were established on the basis of spectroscopic methods. Six of them (1-5, 7) exhibited weak cytotoxic activity against proliferation of human promyelocytic leukemia cells (HL-60).

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology*
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Diterpenes