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Elucidation of the sex-pheromone biosynthesis producing 5,7-dodecadienes in Dendrolimus punctatus (Lepidoptera: Lasiocampidae) reveals Delta11- and Delta9-desaturases with unusual catalytic properties

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Summary, in English

Sex pheromones produced by female moths of the Lasiocampidae family include conjugated 5,7-dodecadiene components with various oxygenated terminal groups. Here we describe the molecular cloning, heterologous expression and functional characterization of desaturases associated with the biosynthesis of these unusual chemicals. By homology-based PCR screening we characterized five cDNAs from the female moth pheromone gland that were related to other moth desaturases, and investigated their role in the production of the (Z)-5-dodecenol and (Z5,E7)-dodecadienol, major pheromone constituents of the pine caterpillar moth, Dendrolimus punctatus. Functional expression of two desaturase cDNAs belonging to the Delta11-subfamily, Dpu-Delta11(1)-APSQ and Dpu-Delta11(2)-LPAE, showed that they catalysed the formation of unsaturated fatty acyls (UFAs) that can be chain-shortened by beta-oxidation and subsequently reduced to the alcohol components. A first (Z)-11-desaturation step is performed by Dpu-Delta11(2)-LPAE on stearic acid that leads to (Z)-11-octadecenoic acyl, which is subsequently chain shortened to the (Z)-5-dodecenoic acyl precursor. The Dpu-Delta11(1)-APSQ desaturase had the unusual property of producing Delta8 mono-UFA of various chain lengths, but not when transformed yeast were grown in presence of (Z)-9-hexadecenoic acyl, in which case the biosynthetic intermediate (Z9,E11)-hexadecadienoic UFA was produced. In addition to a typical Z9 activity, a third transcript, Dpu-Delta9-KPSE produced E9 mono-UFAs of various chain lengths. When provided with the (Z)-7-tetradecenoic acyl, it formed the (Z7,E9)-tetradecadienoic UFA, another biosynthetic intermediate that can be chain-shortened to (Z5,E7)-dodecadienoic acyl. Both Dpu-Delta11(1)-APSQ and Dpu-Delta9-KPSE thus exhibited desaturase activities consistent with the biosynthesis of the dienoic precursor. The combined action of three desaturases in generating a dienoic sex-pheromone component emphasizes the diversity and complexity of chemical reactions that can be catalysed by pheromone biosynthetic fatty-acyl-CoA desaturases in moths.

Publishing year

2010

Language

English

Pages

440-452

Publication/Series

Insect Biochemistry and Molecular Biology

Volume

40

Issue

6

Document type

Journal article

Publisher

Elsevier

Topic

  • Biological Sciences

Keywords

  • Conjugated diene
  • Heterologous
  • expression
  • Gene family evolution
  • Subfunctionalization
  • Duplication
  • Sex pheromone
  • Chemical communication

Status

Published

Project

  • The pheromone brewery
  • Evolutionary mechanisms of pheromone divergence in Lepidoptera

Research group

  • Pheromone Group

ISBN/ISSN/Other

  • ISSN: 1879-0240