Bioactive briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea

Bioorg Med Chem Lett. 2012 Jul 1;22(13):4368-72. doi: 10.1016/j.bmcl.2012.05.001. Epub 2012 May 9.

Abstract

Six new briarane diterpenoids, gemmacolides T-Y (1-6), were isolated together with three known analogs, juncenolide J (7), praelolide (8), and junceellolide C (9), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was suggested based on biosynthetic considerations. In an in vitro bioassay, compounds 3 and 6 showed potent growth inhibition towards tumor cell lines of A549 and MG63, being stronger than the positive control of adriamycin. These compounds also exhibited weak antimicrobial activity against the bacterium Escherichia coli and the fungi Microbotryum violaceum and Septoria tritici.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / isolation & purification
  • Anti-Infective Agents / pharmacology
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • China
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology
  • Escherichia coli / drug effects
  • Fungi / drug effects
  • Heterocyclic Compounds, 4 or More Rings / chemistry*
  • Heterocyclic Compounds, 4 or More Rings / isolation & purification
  • Heterocyclic Compounds, 4 or More Rings / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Oceans and Seas

Substances

  • Anti-Infective Agents
  • Diterpenes
  • Heterocyclic Compounds, 4 or More Rings
  • gemmacolide V
  • gemmacolide X