Absolute Configurations of Zingiberenols Isolated from Ginger (Zingiber officinale) Rhizomes

J Nat Prod. 2015 Dec 24;78(12):3071-4. doi: 10.1021/acs.jnatprod.5b00638. Epub 2015 Nov 25.

Abstract

Two stereoisomeric zingiberenols in ginger were identified as (3R,6R,7S)-1,10-bisaboladien-3-ol (2) and (3S,6R,7S)-1,10-bisaboladien-3-ol (5). Absolute configurations were assigned by utilizing 1,10-bisaboladien-3-ol stereoisomers and two gas-chromatography columns: a 25 m Hydrodex-β-6TBDM and 60 m DB-5MS. The C-6 and C-7 absolute configurations in both zingiberenols match those of zingiberene present abundantly in ginger rhizomes. Interestingly, zingiberenol 2 has recently been identified as a male-produced sex pheromone of the rice stink bug, Oebalus poecilus, thus indicating that ginger plants may be a potential source of the sex pheromone of this bug.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Gas Chromatography-Mass Spectrometry
  • Heteroptera / drug effects
  • Heteroptera / metabolism
  • Male
  • Molecular Structure
  • Monocyclic Sesquiterpenes
  • Oils, Volatile
  • Pheromones / chemistry
  • Pheromones / isolation & purification*
  • Pheromones / pharmacology
  • Rhizome / chemistry*
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification*
  • Stereoisomerism
  • Zingiber officinale / chemistry*

Substances

  • Monocyclic Sesquiterpenes
  • Oils, Volatile
  • Pheromones
  • Sesquiterpenes
  • zingiberene