Antimycotic spirostanol saponins from Solanum hispidum leaves and their structure-activity relationships

J Nat Prod. 2004 Jun;67(6):938-41. doi: 10.1021/np0305019.

Abstract

A new spirostanol saponin, together with three known saponins, were isolated from the leaves of Solanum hispidum. The structure of the new saponin was elucidated as 6alpha-O-beta-D-quinovopyranosyl-(25S)-5alpha-spirostan-3beta-ol (1) on the basis of spectroscopic analysis (1H NMR, 13C NMR, 1H-1H COSY, HMQC, HMBC, and HRFABMS). All of the isolated compounds showed antimycotic activity. The most active compound was 6alpha-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-quinovopyranosyl]-(25S)-5alpha-spirostan-3beta-ol (2) (MIC = 25 microg/mL against both Trichophyton mentagrophytes and T. rubrum). The structure-activity relationships of the isolated compounds and those isolated from S. chrysotrichum are discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Mexico
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Saponins / chemistry
  • Saponins / isolation & purification*
  • Saponins / pharmacology
  • Solanum / chemistry*
  • Spirostans / chemistry
  • Spirostans / isolation & purification*
  • Spirostans / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Trichophyton / drug effects*

Substances

  • 6alpha-O-(beta-D-xylopyranosyl-(1-3)-beta-D-quinovopyranosyl)-(25S)-5alpha-spirostan-3beta-ol
  • 6alpha-O-beta-D-quinovopyranosyl-(25S)-5alpha-spirostan-3beta-ol
  • Antifungal Agents
  • Saponins
  • Spirostans