Journal of Chemical Ecology

, Volume 40, Issue 10, pp 1146–1151 | Cite as

Carbonyl Reduction in the Biosynthesis of a Male Sex Pheromone Secreted by the Grape Borer Xylotrechus pyrrhoderus

  • Kikuo Iwabuchi
  • Maki Arakawa
  • Ryutaro Kiyota
  • Keita Hoshino
  • Tetsu Ando


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.


Male sex pheromone Coleoptera Cerambycidae Long-horn beetle Pheromone biosynthesis Carbonyl reductase Deuterated precursor Stereospecific reduction of 2-hydroxy-3-octanone into 2,3-octanediol 


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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Kikuo Iwabuchi
    • 1
  • Maki Arakawa
    • 2
  • Ryutaro Kiyota
    • 2
  • Keita Hoshino
    • 1
  • Tetsu Ando
    • 2
  1. 1.Department of Applied Biological Science, Faculty of AgricultureTokyo University of Agriculture and TechnologyFuchuJapan
  2. 2.Graduate School of Bio-Applications and Systems EngineeringTokyo University of Agriculture and TechnologyKoganeiJapan

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