Oculatol, oculatolide, and A-nor sterols from the sponge Haliclona oculata

J Nat Prod. 2006 Sep;69(9):1330-4. doi: 10.1021/np0600494.

Abstract

Chemical investigation of the marine sponge Haliclona oculata resulted in the isolation of eight new compounds including oculatol (1) and oculatolide (2) and six unusual A-nor steroids, 2-ethoxycarbonyl-2beta-hydroxy-A-nor-ergosta-5,24(28)-dien-4-one (3), 2-ethoxycarbonyl-24-ethyl-2beta-hydroxy-A-nor-cholesta-5-en-4-one (4), 2-ethoxycarbonyl-2beta,7beta-dihydroxy-A-nor-ergosta-5,24(28)-dien-4-one (5), 2-ethoxycarbonyl-2beta,7beta-dihydroxy-A-nor-cholesta-5-en-4-one (6), 2-ethoxycarbonyl-2beta,7beta-dihydroxy-24-methyl-A-nor-cholesta-5,22(E)-dien-4-one (7), and 2-ethoxycarbonyl-2beta,7beta-dihydroxy-A-nor-cholesta-5,22(E)-dien-4-one (8), along with 16 known steroids and indole derivatives. Their structures were unambiguously determined on the basis of extensive spectroscopic analyses.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / isolation & purification
  • Antineoplastic Agents* / pharmacology
  • Drug Screening Assays, Antitumor
  • Haliclona / chemistry*
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Sterols* / chemistry
  • Sterols* / isolation & purification
  • Sterols* / pharmacology
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Sterols
  • oculatol
  • oculatolide