Withanolide artifacts formed in methanol

J Nat Prod. 2013 Nov 22;76(11):2040-6. doi: 10.1021/np400296s. Epub 2013 Oct 23.

Abstract

Methanol solutions of the main withanolides (6-8) naturally present in Physalis longifolia yielded five artificial withanolides (1-5), including three new compounds (1-3). Withanolides 1 and 2 were identified as intramolecular Michael addition derivatives, while withanolides 3-5 were the result of intermolecular Michael addition. A comprehensive literature investigation was conducted to identify potential withanolide Michael addition artifacts isolated from Solanaceous species to date.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ergosterol / analogs & derivatives
  • Methanol / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Physalis / chemistry*
  • Withanolides / chemistry*
  • Withanolides / isolation & purification

Substances

  • 3-rhamnopyranosyl(1-4)-glucopyranosyl-12-diacetoxy-20-hydroxywitha-5,24-dienolide
  • Withanolides
  • withanolide-5
  • Methanol
  • Ergosterol