The chafer pheromone buibuilactone and ant pyrazines are also produced by marine bacteria.
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.
Dickschat
Jeroen S
JS
Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
Wagner-Döbler
Irene
I
Schulz
Stefan
S
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
D010675:Pheromones; D011719:Pyrazines; C117437:buibuilactone; C504321:2-ethyl-3,6-dimethylpyrazine; D015107:4-Butyrolactone