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The Chafer Pheromone Buibuilactone and Ant Pyrazines are also Produced by Marine Bacteria

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Abstract

Headspace extracts obtained from agar plate cultures of two marine bacteria from the North Sea (Germany), Loktanella strain BIO-204 and Dinoroseobacter shibae strain DFL-27, were analyzed by GC-MS. Several γ-lactones and one δ-lactone were identified, besides pyrazines and some sulfur compounds. The absolute configuration of the major lactone (R,Z)-dodec-5-en-4-olide, known as buibuilactone, a pheromone of several scarab beetles, was determined by a new catalytic enantioselective synthesis and GC on a chiral stationary phase. Unsaturated lactones in the extracts included (E)-dodec-5-en-4-olide and the regioisomer (Z)-dodec-6-en-4-olide, previously identified as a component of black-tailed deer urine. The pyrazines 2-butyl-3,6-dimethylpyrazine and 2-isopentyl-3,6-dimethylpyrazine were identified by comparison with synthesized material. The latter compound is a known ant pheromone, as is another identified pyrazine, 2-ethyl-3,6-dimethylpyrazine. The striking similarity between insect pheromones and these bacterial volatiles is discussed, suggesting the possibility of more widespread occurrence of symbiosis between microorganisms and insects than previously thought.

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Acknowledgments

J.S.D. thanks the Fonds der Chemischen Industrie and the BMBF for a stipend.

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Authors and Affiliations

  1. Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106, Braunschweig, Germany

    Jeroen S. Dickschat & Stefan Schulz

  2. Gesellschaft für Biotechnologische Forschung mbH, Mascheroder Weg 1, D-38124, Braunschweig, Germany

    Irene Wagner-Döbler

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  1. Jeroen S. Dickschat
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  2. Irene Wagner-Döbler
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  3. Stefan Schulz
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Correspondence to Stefan Schulz.

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Dickschat, J.S., Wagner-Döbler, I. & Schulz, S. The Chafer Pheromone Buibuilactone and Ant Pyrazines are also Produced by Marine Bacteria. J Chem Ecol 31, 925–947 (2005). https://doi.org/10.1007/s10886-005-3553-9

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  • DOI: https://doi.org/10.1007/s10886-005-3553-9

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