Novel cytotoxic polyoxygenated steroids from an Okinawan sponge Dysidea sp

Biosci Biotechnol Biochem. 2012;76(5):999-1002. doi: 10.1271/bbb.120017. Epub 2012 May 7.


A library of extracts established from hundreds of marine organisms was screened by a cytotoxicity test. The active organic extract of an Okinawan marine sponge of the genus Dysidea was subjected to bioassay-guided fractionation to give three new polyoxygenated steroids dysideasterols F-H (1-3), together with two known related compounds (4 and 5). Their structures were confirmed by NMR and mass spectroscopic analyses. A characteristic structural feature of 2, 4 and 5 is an allylic epoxide, whereas this epoxide undergoes ring-opening by a neighbouring hydroxyl group to give a tetrahydrofuran ring in 1 and 3. All compounds 1-5 exhibited a similar cytotoxic effect with IC50 values of 0.15-0.3 µM against human epidermoid carcinoma A431 cells, demonstrating that the allylic epoxide moiety was not responsible for this cytotoxic effect.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Aquatic Organisms / chemistry*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Dysidea / chemistry*
  • Humans
  • Inhibitory Concentration 50
  • Japan
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Sterols / chemistry
  • Sterols / isolation & purification*
  • Sterols / pharmacology


  • Antineoplastic Agents
  • Sterols
  • dysideasterol F
  • dysideasterol G
  • dysideasterol H