Title : The chafer pheromone buibuilactone and ant pyrazines are also produced by marine bacteria - Dickschat_2005_J.Chem.Ecol_31_925 |
Author(s) : Dickschat JS , Wagner-Dobler I , Schulz S |
Ref : J Chem Ecol , 31 :925 , 2005 |
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. |
PubMedSearch : Dickschat_2005_J.Chem.Ecol_31_925 |
PubMedID: 16124260 |
Substrate | Buibuilactone |
Dickschat JS, Wagner-Dobler I, Schulz S (2005)
The chafer pheromone buibuilactone and ant pyrazines are also produced by marine bacteria
J Chem Ecol
31 :925
Dickschat JS, Wagner-Dobler I, Schulz S (2005)
J Chem Ecol
31 :925