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J Chem Ecol

Title:		The chafer pheromone buibuilactone and ant pyrazines are also produced by marine bacteria
Author(s):		Dickschat JS; Wagner-Dobler I; Schulz S;
Address:		"Institut fur Organische Chemie, Technische Universitat Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany"
Journal Title:		J Chem Ecol
Year:		2005
Volume:		31
Issue:		4
Page Number:		925 - 947
DOI:		10.1007/s10886-005-3553-9
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
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 gamma-lactones and one delta-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"
Keywords:		4-Butyrolactone/*analogs & derivatives/isolation & purification Animals Ants/*chemistry Bacteria/*chemistry Gas Chromatography-Mass Spectrometry Marine Biology Pheromones/chemical synthesis/*isolation & purification Pyrazines/chemical synthesis/*isolation;
Notes:		"MedlineDickschat, Jeroen S Wagner-Dobler, Irene Schulz, Stefan eng Comparative Study Research Support, Non-U.S. Gov't 2005/08/30 J Chem Ecol. 2005 Apr; 31(4):925-47. doi: 10.1007/s10886-005-3553-9"