Journal of Chemical Ecology

, Volume 28, Issue 12, pp 2541–2555 | Cite as

Identification of New Homoterpene Esters from Dufour's Gland of the Ponerine Ant Gnamptogenys striatula

  • Claudia M. Schulz
  • Lutz Lehmann
  • Rumsaïs Blatrix
  • Pierre Jaisson
  • Abraham Hefetz
  • Wittko Francke
Article

Abstract

Extracts of Dufour's gland of the ponerine ant, Gnamptogenys striatula, were analyzed by using the combination of gas chromatography and mass spectrometry. Series of esters of the new homoterpenoids (2E,6)-3,4,7-trimethyl-2,6-octadiene-1-ol (4-methylgeraniol) and (2E,6)-3,4,7-trimethyl-2, 6-nonadiene-1-ol (bishomogeraniol) with unbranched medium-chain fatty acids were identified. Transformation of the chiral natural products into 1,4-di(trifluoroacetoxy)-3-methylpentane and comparison of its gas chromatographic retention time on a modified cyclodextrin phase with that of synthetic optically active reference samples proved the stereogenic center to keep (S)-configuration. (2E,4S,6)-3,4,7-Trimethyl-2,6-octadien-1-yl decanoate and the corresponding dodecanoate are the main volatiles in the extracts.

Gnamptogenys Dufour's gland homoterpene 4-methylgeraniol terpenoid esters 

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Copyright information

© Plenum Publishing Corporation 2002

Authors and Affiliations

  • Claudia M. Schulz
    • 1
  • Lutz Lehmann
    • 1
  • Rumsaïs Blatrix
    • 2
  • Pierre Jaisson
    • 2
  • Abraham Hefetz
    • 3
  • Wittko Francke
    • 1
  1. 1.Institut für Organische ChemieUniversität HamburgHamburgGermany
  2. 2.Laboratoire d'Ethologie Experimentale et Comparé (FRE CNRS 2473)Université Paris NordVilletaneuseFrance
  3. 3.Department of Zoology, George S. Wise Faculty of Life SciencesTel Aviv UniversityRamat Aviv, Tel AvivIsrael

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