Absolute configuration of cembrane diterpenoids from Bursera multijuga

Nat Prod Commun. 2014 Sep;9(9):1249-52.

Abstract

The stems of Bursera multijuga afforded (-)-(1S,3E,7R,8R,11E)-7,8-epoxycembra-3,11-dien-1-ol (1) and its acetate 2, together with cembrene A (3), nephthenol (4), and cembrenol (5). The structures of 1 and 2 were elucidated by 1D and 2D NMR, HRESIMS, and X-ray diffraction. The conformational preference of flexible 1 was studied by molecular modeling at the DFT B3LYP/DGDZVP level of theory. Good agreement between calculated and experimental vibrational circular dichroism curves established the absolute configuration of 1. This is the first time that cembrane derivatives have been isolated from the genus Bursera.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bursera / chemistry*
  • Diterpenes / chemistry*
  • Molecular Structure
  • Plant Exudates / chemistry*
  • X-Ray Diffraction

Substances

  • Diterpenes
  • Plant Exudates