Norlanostane triterpenoidal saponins from the marine sponge melophlussarassinorum

J Nat Prod. 2005 Aug;68(8):1231-7. doi: 10.1021/np050152d.

Abstract

Along with five known 30-norlanostane-type saponins, sarasinosides A(1) (5A), A3 (6A), I1 (7), I2 (8), and H2 (9), four new triterpenoidal saponin congeners, sarasinosides J (1), K (2), L (3), and M (4), were isolated from the Indonesian sponge Melophlus sarassinorum. Sarasinosides J (1) and K (2) are the 24,25-hydrogenated congeners of the previously described sarasinosides A1 and H2, respectively. The carbon skeleton of sarasinoside M (4) possesses a rearranged 8alpha,9alpha-epoxy-8,9-seconorlanosta-8(14),9(11),24-triene system, which is novel and unprecedented in nature. The structures of the new compounds were confirmed by spectral analyses, chemical derivatization, and GC analyses. Compounds 1 and 5A exhibited antimicrobial activity toward Bacillus subtilis and Saccharomyces cerevisiae.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Chromatography, Gas
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Lanosterol / analogs & derivatives*
  • Lanosterol / chemistry
  • Lanosterol / isolation & purification*
  • Lanosterol / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*
  • Saccharomyces cerevisiae / drug effects
  • Stereoisomerism
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Glycosides
  • Triterpenes
  • sarasinoside A1
  • Lanosterol