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

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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.

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Authors and Affiliations

  1. Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-20146, Hamburg, Germany

    Claudia M. Schulz, Lutz Lehmann & Wittko Francke

  2. Laboratoire d'Ethologie Experimentale et Comparé (FRE CNRS 2473), Université Paris Nord, 93430, Villetaneuse, France

    Rumsaïs Blatrix & Pierre Jaisson

  3. Department of Zoology, George S. Wise Faculty of Life Sciences, Tel Aviv University, Ramat Aviv, Tel Aviv, 69978, Israel

    Abraham Hefetz

Authors
  1. Claudia M. Schulz
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  2. Lutz Lehmann
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  3. Rumsaïs Blatrix
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  4. Pierre Jaisson
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  5. Abraham Hefetz
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  6. Wittko Francke
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Correspondence to Wittko Francke.

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Schulz, C.M., Lehmann, L., Blatrix, R. et al. Identification of New Homoterpene Esters from Dufour's Gland of the Ponerine Ant Gnamptogenys striatula . J Chem Ecol 28, 2541–2555 (2002). https://doi.org/10.1023/A:1021492204400

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  • DOI: https://doi.org/10.1023/A:1021492204400

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