15,21-Cyclowithanolides from Jaborosa bergii

J Nat Prod. 2003 Nov;66(11):1471-5. doi: 10.1021/np030248c.

Abstract

Six new withanolides (1-6) were isolated from the aerial parts of Jaborosa bergii plants and characterized by spectroscopic methods (1D and 2D NMR, MS). Five of the new compounds presented a novel norbornane-type structure in ring D of the steroid nucleus (1-5), resulting from a carbon-carbon bond between C-15 and C-21. The sixth withanolide isolated was the 5alpha-chloro-6beta-hydroxy analogue (6) of 2,3-dehydrojaborosalactol M (7), previously isolated from this plant. Compound 1 showed selective phytotoxicity toward monocotiledoneous and dicotiledoneous species.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Argentina
  • Dose-Response Relationship, Drug
  • Ergosterol* / analogs & derivatives
  • Ergosterol* / chemistry
  • Ergosterol* / isolation & purification
  • Ergosterol* / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Solanaceae / chemistry*
  • Stereoisomerism

Substances

  • Ergosterol