Chemistry and tumor cell growth inhibitory activity of 11,20-epoxy-3Z,5(6)E-diene briaranes from the South China Sea gorgonian Dichotella gemmacea

Mar Drugs. 2013 May 15;11(5):1565-82. doi: 10.3390/md11051565.

Abstract

Eighteen new 11,20-epoxy-3Z,5E-dien briaranes, gemmacolides AA-AR (1-18), were isolated together with three known analogs, dichotellides F (19) and I (20), and juncenolide C (21), from the South China Sea gorgonian Dichotella gemmacea. The structures of the compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was determined based on the ECD experiment. In the in vitro bioassay, compounds 1-3, 5, 6, 8-12, and 14-19 exhibited different levels of growth inhibition activity against A549 and MG63 cell lines. Preliminary structure-activity analysis suggests that 12-O-isovalerate may increase the activity whereas 13- or 14-O-isovalerate may decrease the activity. Contribution of substitutions at C-2 and C-16 remains uncertain.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • China
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Drug Screening Assays, Antitumor
  • Humans
  • Neoplasms / drug therapy*
  • Neoplasms / pathology
  • Oceans and Seas
  • Spectrum Analysis
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Diterpenes