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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

Liénard, Marjorie LU orcid ; Lassance, Jean-Marc LU ; Wang, Hong-Lei LU ; Zhao, Cheng-Hua ; Piskur, Jure LU ; Johansson, Tomas LU and Löfstedt, Christer LU (2010) In Insect Biochemistry and Molecular Biology 40(6). p.440-452
Abstract
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... (More)
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. (Less)
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author
; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Conjugated diene, Heterologous, expression, Gene family evolution, Subfunctionalization, Duplication, Sex pheromone, Chemical communication
in
Insect Biochemistry and Molecular Biology
volume
40
issue
6
pages
440 - 452
publisher
Elsevier
external identifiers
  • wos:000279368700002
  • scopus:77953129084
  • pmid:20403437
ISSN
1879-0240
DOI
10.1016/j.ibmb.2010.04.003
project
The pheromone brewery
Evolutionary mechanisms of pheromone divergence in Lepidoptera
language
English
LU publication?
yes
id
8febe779-bace-449c-bbb2-029fce31fe86 (old id 1595089)
date added to LUP
2016-04-01 10:57:40
date last changed
2025-10-14 09:06:05
@article{8febe779-bace-449c-bbb2-029fce31fe86,
  abstract     = {{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.}},
  author       = {{Liénard, Marjorie and Lassance, Jean-Marc and Wang, Hong-Lei and Zhao, Cheng-Hua and Piskur, Jure and Johansson, Tomas and Löfstedt, Christer}},
  issn         = {{1879-0240}},
  keywords     = {{Conjugated diene; Heterologous; expression; Gene family evolution; Subfunctionalization; Duplication; Sex pheromone; Chemical communication}},
  language     = {{eng}},
  number       = {{6}},
  pages        = {{440--452}},
  publisher    = {{Elsevier}},
  series       = {{Insect Biochemistry and Molecular Biology}},
  title        = {{Elucidation of the sex-pheromone biosynthesis producing 5,7-dodecadienes in <i>Dendrolimus punctatus</i> (Lepidoptera: Lasiocampidae) reveals Delta11- and Delta9-desaturases with unusual catalytic properties}},
  url          = {{http://dx.doi.org/10.1016/j.ibmb.2010.04.003}},
  doi          = {{10.1016/j.ibmb.2010.04.003}},
  volume       = {{40}},
  year         = {{2010}},
}