Elucidation of the sex-pheromone biosynthesis producing 5,7-dodecadienes in Dendrolimus punctatus (Lepidoptera: Lasiocampidae) reveals Delta11- and Delta9-desaturases with unusual catalytic properties
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/1595089
- author
- Liénard, Marjorie LU ; Lassance, Jean-Marc LU ; Wang, Hong-Lei LU ; Zhao, Cheng-Hua ; Piskur, Jure LU ; Johansson, Tomas LU and Löfstedt, Christer LU
- organization
- publishing date
- 2010
- 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
- 2024-02-22 14:49:45
@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}}, }