African elephant sesquiterpenes. II. Identification and synthesis of new derivatives of 2,3-dihydrofarnesol

J Nat Prod. 2002 Sep;65(9):1319-22. doi: 10.1021/np010647c.

Abstract

A search for potential semiochemicals revealed nerolidol (6), albicanol (7), and the new 2,3-dihydrofarnesol derivatives 8-10 in the temporal gland secretions of African elephants. A novel synthesis from (E,E)-farnesol (1) provided compounds 8-10 for GC-MS comparison to the natural products. This study confirms the farnesol family as frequently occurring secondary metabolites in African elephant temporal gland secretions.

Publication types

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

MeSH terms

  • Africa
  • Animals
  • Apocrine Glands / metabolism*
  • Elephants / metabolism*
  • Farnesol / analogs & derivatives*
  • Farnesol / chemical synthesis*
  • Gas Chromatography-Mass Spectrometry
  • Male
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification*
  • Spectroscopy, Fourier Transform Infrared
  • Stereoisomerism

Substances

  • 2,3-dihydrofarnesol
  • Naphthalenes
  • Sesquiterpenes
  • Farnesol
  • albicanol
  • nerolidol