title: The chafer pheromone buibuilactone and ant pyrazines are also produced by marine bacteria.
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.
authors.affiliation: Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
authors.forename: Jeroen S
authors.initials: JS
authors.lastname: Dickschat
authors.forename: Irene
authors.initials: I
authors.lastname: Wagner-Döbler
authors.forename: Stefan
authors.initials: S
authors.lastname: Schulz
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000302:isolation & purification; D000818:Animals; D001000:Ants / Q000737:chemistry*; D001419:Bacteria / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D008386:Marine Biology; D010675:Pheromones / Q000138:chemical synthesis / Q000302:isolation & purification*; D011719:Pyrazines / Q000138:chemical synthesis / Q000302:isolation & purification*; D012623:Seawater / Q000382:microbiology; D013237:Stereoisomerism
chemical_list: D010675:Pheromones; D011719:Pyrazines; C117437:buibuilactone; C504321:2-ethyl-3,6-dimethylpyrazine; D015107:4-Butyrolactone