The Chafer Pheromone Buibuilactone and Ant Pyrazines are also Produced by Marine Bacteria |
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Authors: | Jeroen?S?Dickschat Irene?Wagner-D?bler Email author" target="_blank">Stefan?SchulzEmail author |
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Affiliation: | (1) Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany;(2) Gesellschaft für Biotechnologische Forschung mbH, Mascheroder Weg 1, D-38124 Braunschweig, Germany |
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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 -lactones and one -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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Keywords: | Alphaproteobacteria buibuilactone coleoptera headspace analysis marine bacteria pyrazines lactones Roseobacter clade symbiosis |
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