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

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)2541-2555
Number of pages15
JournalJournal of Chemical Ecology
Volume28
Issue number12
DOIs
StatePublished - 1 Dec 2002

Keywords

  • 4-methylgeraniol
  • Dufour's gland
  • Gnamptogenys
  • Homoterpene
  • Terpenoid esters

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