Cimicifugadine from Cimicifuga foetida, a new class of triterpene alklaoids with novel reactivity

Org Lett. 2007 Apr 26;9(9):1813-6. doi: 10.1021/ol070542m. Epub 2007 Mar 29.

Abstract

[structure: see text] An unprecedented triterpene alkaloid glycoside, designated cimicifugadine (1), with a pyridine ring incorporated to a cycloartane triterpenoid nucleus, was isolated from the roots of Cimicifuga foetida. Its structure was established on the basis of extensive spectroscopic measurements and chemical transformation with the absolute configuration at C-24 determined to be S by a modified Mosher method. It demonstrated a novel reactivity in mild acidic media whereby the cyclopropane ring is opened followed by the formation of two isomeric conjugated trienes.

MeSH terms

  • Acetylation
  • Acids / chemistry
  • Alkaloids / chemistry*
  • Alkaloids / classification*
  • Cimicifuga / chemistry*
  • Cimicifuga / metabolism
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Triterpenes / chemistry*

Substances

  • Acids
  • Alkaloids
  • Triterpenes
  • cimicifugadine