Wuweizidilactones A-F: novel highly oxygenated nortriterpenoids with unusual skeletons isolated from Schisandra chinensis

Chemistry. 2007;13(17):4816-22. doi: 10.1002/chem.200700346.

Abstract

A phytochemical study of secondary metabolites produced by Schisandra chinensis has led to the isolation of six novel highly oxygenated nortriterpenoids, wuweizidilactones A-F (1-6). Compounds 3-6 possess an unprecedented 3,4-seco-18(13-->14)-abeo-artane skeleton. Interestingly, structures 3-6 have a beta-oriented methyl group at the C-14 position. This structural feature corroborates the biogenetic pathway proposed for the formation of 18-norschiartane-type compounds 1 and 2. The structures of these novel metabolites were established on the basis of their detailed spectroscopic analysis. The structure of 1 was also confirmed by single-crystal X-ray diffraction analysis. For the first time, the absolute configuration of these nortriterpenoids was determined by using a modified Mosher method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Lactones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxygen / chemistry
  • Schisandra / metabolism*
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification

Substances

  • Lactones
  • Triterpenes
  • Oxygen