Bioactive pregnane steroids from a South China Sea gorgonian Carijoa sp

Molecules. 2013 Mar 15;18(3):3458-66. doi: 10.3390/molecules18033458.

Abstract

A new pregnane steroid, 1, and three known analogues 2-4, have been isolated from a gorgonian Carijoa sp. collected from the South China Sea. The planar structure and relative configuration of 1 were elucidated from comprehensive spectroscopic data. Its absolute configuration was determined by application of the modified Mosher method. Compounds 1, 3 and 4 exhibited cytotoxicity against the human hepatoma cell line Bel-7402, with IC50 values of 9.33, 11.02 and 18.68 µM, respectively. Additionally, compound 1 exhibited promising antibacterial activity against Pseudomona puido, with a MIC value of 31 nM, which is approximately 5-fold more potent than ciprofloxacin (MIC = 156 nM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • China
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Oceans and Seas
  • Pregnatrienes / isolation & purification*
  • Pregnatrienes / pharmacology
  • Pseudomonas putida / drug effects

Substances

  • 15beta-hydroxypregna-1,4,20-trien-3-one
  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Pregnatrienes