(S)-13-hydroxygeranylgeraniol-derived furanoditerpenes from Bifurcaria bifurcata

Phytochemistry. 1995 May;39(1):145-9. doi: 10.1016/0031-9422(94)00849-o.

Abstract

Two new diterpenes were isolated from a sample of the brown alga Bifurcaria bifurcata collected from Brittany on the Atlantic coast and their structures established by spectroscopic methods. The new diterpenes are derived from (S)-13-hydroxygeranylgeraniol by terminal cyclization and oxidation leading to a furan-3-yl ring or a beta,gamma-epoxy-gamma-lactone. One of them showed a cytotoxic effect to fertilized sea urchin eggs. The chemical shifts of the methyl groups and quaternary carbons in (S)-13-hydroxygeranylgeraniol have been revised to take account of the results obtained in a 2D NMR long-range C-H correlation experiment and the absolute configuration at C-13 determined for the first time. The geographical variation in the diterpenoid composition of B. bifurcata was also studied.

MeSH terms

  • Animals
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Ovum / drug effects
  • Phaeophyceae / chemistry*
  • Sea Urchins / embryology

Substances

  • Diterpenes