Bioactive polyhydroxylated sterols from the marine sponge Haliclona crassiloba

Steroids. 2013 Dec 20;78(14):1353-8. doi: 10.1016/j.steroids.2013.10.004. Epub 2013 Oct 23.

Abstract

Four new polyhydroxylated sterols, named halicrasterols A-D (1-4), together with six known analogs (5-10) were isolated from the marine sponge Haliclona crassiloba. Compounds 1 and 2 represented rare examples of steroids featuring 17(20)E-double bonds. The structures of 1-10 were elucidated by spectroscopic analysis and comparison with reported data. This is the first report of a steroid profile for this species. The antimicrobial activities of 1-10 were evaluated against a panel of bacterial and fungal strains in vitro, and compounds 4 and 9 showed moderate activity against some of the Gram-positive strains with MICs ranging from 4 to 32 μg/mL.

Keywords: Antibacterial activity; Haliclona crassiloba; Polyhydroxylated sterols; Structure elucidation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / isolation & purification
  • Anti-Infective Agents / pharmacology
  • Bacillus / drug effects
  • Bacillus / growth & development
  • Bacillus subtilis / drug effects
  • Bacillus subtilis / growth & development
  • Candida / drug effects
  • Candida / growth & development
  • Enterococcus faecalis / drug effects
  • Enterococcus faecalis / growth & development
  • Haliclona / chemistry*
  • Haliclona / metabolism
  • Hydroxylation
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Staphylococcus aureus / drug effects
  • Staphylococcus aureus / growth & development
  • Sterols / chemistry*
  • Sterols / isolation & purification
  • Sterols / pharmacology

Substances

  • Anti-Infective Agents
  • Sterols