| Title: | Carbonyl reduction in the biosynthesis of a male sex pheromone secreted by the grape borer Xylotrechus pyrrhoderus |
| Author(s): | Iwabuchi K; Arakawa M; Kiyota R; Hoshino K; Ando T; |
| Address: | "Department of Applied Biological Science, Faculty of Agriculture, Tokyo University of Agriculture and Technology, Fuchu, Tokyo, 183-8509, Japan" |
| DOI: | 10.1007/s10886-014-0508-z |
| ISSN/ISBN: | 1573-1561 (Electronic) 0098-0331 (Linking) |
| Abstract: | "Males of the cerambycid beetle Xylotrechus pyrrhoderus release a mixture of (S)-2-hydroxy-3-octanone [(S)-1] and (2S,3S)-2,3-octanediol [(2S,3S)-2] as a sex pheromone that attracts conspecific females. The chemical structures of these pheromone components include a common motif and are assumed to be biosynthetically related. Here, we show that deuterated (S)-1, applied on the cuticle of a pronotal pheromone gland, was converted into (2S,3S)-2, that included deuterium atoms, but a reverse conversion did not take place. These results reveal a carbonyl reductase to be active in the pheromone gland, and that the ketol is a biosynthetic precursor of the diol. Males did not produce (R)-1; however, deuterated (R)-1 was converted into (2R,3R)-2, indicating an attack of the enzyme from the opposite side of the hydroxyl group at the 2-position. Furthermore, to understand the substrate specificity of the enzyme, racemates of 2-hydroxy-3-hexanone and 2-hydroxy-3-decanone were synthesized and applied to the gland. Their conversion into the corresponding diols suggests that the enzyme reduces the carbonyl group at the 3-position, regardless of the chain length" |
| Keywords: | Animals Coleoptera/*physiology Female Ketones/analysis/metabolism Male Octanols/analysis/metabolism Oxidation-Reduction Sex Attractants/analysis/*metabolism Vitis/*parasitology; |
| Notes: | "MedlineIwabuchi, Kikuo Arakawa, Maki Kiyota, Ryutaro Hoshino, Keita Ando, Tetsu eng 2014/10/11 J Chem Ecol. 2014 Oct; 40(10):1146-51. doi: 10.1007/s10886-014-0508-z. Epub 2014 Oct 10" |
