Two new bicyclic cembranolides from a new Sarcophyton species and determination of the absolute configuration of sarcoglaucol-16-one

Org Biomol Chem. 2004 Apr 21;2(8):1133-8. doi: 10.1039/b314332e. Epub 2004 Mar 17.

Abstract

During the chemical investigation of a new species of soft coral belonging to the genus Sarcophyton, two novel cembranoid compounds with a 12Z double bond (1 and 2) were obtained. Determination of the double bond configurations was done using NMR spectroscopic data and the results of molecular modeling studies. Compound 3, one of several known compounds (3-5), was found to be cytotoxic toward an MCF7 tumor cell line.Additionally, we report the absolute stereochemistry of the cembrane sarcoglaucol-16-one (6), which was determined using the modified Mosher[prime or minute]s method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Bridged Bicyclo Compounds / chemistry*
  • Cell Line, Tumor
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Bridged Bicyclo Compounds
  • Diterpenes
  • sarcoglaucol-16-one
  • cembrane