Selective production of cis- and trans-verbenol from (-)-and (+)-alpha by a bark beetle.
A unique biological system whereby optical isomers are selectively transformed to geometrical isomers is demonstrated in Ips paraconfusus. Exposure of adult male and female beetles to vapor of (-)-alpha-pinene resulted in the production of (+)-cis-verbenol, a pheromone of this species, whereas (+)-alpha-pinene was oxidized to (+)-trans-verbenol. It appears, therefore, that the ability of a bark beetle to produce its aggregation pheromone can be governed by the chirality of a precursor in the host tree.
D000818:Animals; D001517:Coleoptera / Q000378:metabolism*; D005260:Female; D007413:Intestinal Mucosa / Q000378:metabolism; D008297:Male; D010084:Oxidation-Reduction; D010675:Pheromones / Q000096:biosynthesis*; D013237:Stereoisomerism; D013729:Terpenes / Q000378:metabolism*
D010675:Pheromones; D013729:Terpenes