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Sex pheromone biosynthesis in the pine caterpillar moth, Dendrolimus punctatus (Lepidoptera : Lasiocampidae): pathways leading to Z5-monoene and 5,7-conjugated diene components

Zhao, Cheng-Hua LU ; Adlof, R O and Löfstedt, Christer LU (2004) In Insect Biochemistry and Molecular Biology 34(3). p.261-271
Abstract
Biosynthesis of the sex pheromone components (Z)-5-dodecenol and (Z,E)-5,7-dodecadienol in Dendrolimus punctatus was studied by topical application of deuterium-labeled fatty acids to pheromone glands and subsequent analysis of fatty acyl groups and pheromone components by gas chromatography-mass spectrometry. Our studies suggest that both (Z)-5-dodecenol and (Z,E)-5,7-dodecadienol can be biosynthetically derived from chain elongation of palmitate to stearate in the gland, and its subsequent All desaturation to produce (Z)-11-octadecenoate. After three cycles of 2-carbon chain-shortening, the pheromone glands produce (Z)-5-dodecenoate, which is then converted to (Z)-5-dodecenol by reduction. A second Delta11 desaturation of... (More)
Biosynthesis of the sex pheromone components (Z)-5-dodecenol and (Z,E)-5,7-dodecadienol in Dendrolimus punctatus was studied by topical application of deuterium-labeled fatty acids to pheromone glands and subsequent analysis of fatty acyl groups and pheromone components by gas chromatography-mass spectrometry. Our studies suggest that both (Z)-5-dodecenol and (Z,E)-5,7-dodecadienol can be biosynthetically derived from chain elongation of palmitate to stearate in the gland, and its subsequent All desaturation to produce (Z)-11-octadecenoate. After three cycles of 2-carbon chain-shortening, the pheromone glands produce (Z)-5-dodecenoate, which is then converted to (Z)-5-dodecenol by reduction. A second Delta11 desaturation of (Z)-9-hexadecenoate produces (Z, E)-9,11-hexadecadienoate, which is then chain shortened in two cycles of beta-oxidation and finally converted to (ZE)-5,7-dodecadienol by reduction. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Insect Biochemistry and Molecular Biology
volume
34
issue
3
pages
261 - 271
publisher
Elsevier
external identifiers
  • wos:000220257400007
  • pmid:14871622
  • scopus:1242299612
ISSN
1879-0240
DOI
10.1016/j.ibmb.2003.10.005
project
Evolutionary mechanisms of pheromone divergence in Lepidoptera
language
English
LU publication?
yes
id
31497fe5-4a57-4a31-884c-65eb78f5a181 (old id 135848)
date added to LUP
2007-06-27 15:29:27
date last changed
2017-01-01 06:50:28
@article{31497fe5-4a57-4a31-884c-65eb78f5a181,
  abstract     = {Biosynthesis of the sex pheromone components (Z)-5-dodecenol and (Z,E)-5,7-dodecadienol in <i>Dendrolimus punctatus</i> was studied by topical application of deuterium-labeled fatty acids to pheromone glands and subsequent analysis of fatty acyl groups and pheromone components by gas chromatography-mass spectrometry. Our studies suggest that both (Z)-5-dodecenol and (Z,E)-5,7-dodecadienol can be biosynthetically derived from chain elongation of palmitate to stearate in the gland, and its subsequent All desaturation to produce (Z)-11-octadecenoate. After three cycles of 2-carbon chain-shortening, the pheromone glands produce (Z)-5-dodecenoate, which is then converted to (Z)-5-dodecenol by reduction. A second Delta11 desaturation of (Z)-9-hexadecenoate produces (Z, E)-9,11-hexadecadienoate, which is then chain shortened in two cycles of beta-oxidation and finally converted to (ZE)-5,7-dodecadienol by reduction.},
  author       = {Zhao, Cheng-Hua and Adlof, R O and Löfstedt, Christer},
  issn         = {1879-0240},
  language     = {eng},
  number       = {3},
  pages        = {261--271},
  publisher    = {Elsevier},
  series       = {Insect Biochemistry and Molecular Biology},
  title        = {Sex pheromone biosynthesis in the pine caterpillar moth, <i>Dendrolimus punctatus</i> (Lepidoptera : Lasiocampidae): pathways leading to Z5-monoene and 5,7-conjugated diene components},
  url          = {http://dx.doi.org/10.1016/j.ibmb.2003.10.005},
  volume       = {34},
  year         = {2004},
}