Antifungal steroidal glycosides from the patagonian starfish anasteriasminuta: structure-activity correlations

J Nat Prod. 2002 Feb;65(2):153-7. doi: 10.1021/np010332x.

Abstract

Two new sulfated steroidal hexaglycosides, anasterosides A (2) and B (3), along with the known versicoside A (1) have been isolated from the Patagonian starfish Anasterias minuta. Their structures have been elucidated by spectroscopic analysis (NMR and FABMS) and chemical transformations. Compounds 1 and 2 and the synthetic pentaglycoside 1b derived from versicoside A showed antifungal activity against the plant pathogenic fungus Cladosporium cucumerinum. Desulfation of hexaglycoside 1 rendered a totally inactive saponin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Argentina
  • Cholestenones / chemistry
  • Cholestenones / isolation & purification*
  • Cholestenones / pharmacology
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Cladosporium / drug effects*
  • Dose-Response Relationship, Drug
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pregnenes / chemistry
  • Pregnenes / isolation & purification*
  • Pregnenes / pharmacology
  • Starfish / chemistry*
  • Structure-Activity Relationship

Substances

  • Antifungal Agents
  • Cholestenones
  • Glycosides
  • Pregnenes
  • anasteroside A
  • anasteroside B
  • versicoside A