| Title: | "Elucidation of the sex-pheromone biosynthesis producing 5,7-dodecadienes in Dendrolimus punctatus (Lepidoptera: Lasiocampidae) reveals Delta 11- and Delta 9-desaturases with unusual catalytic properties" |
| Author(s): | Lienard MA; Lassance JM; Wang HL; Zhao CH; Piskur J; Johansson T; Lofstedt C; |
| Address: | "Chemical Ecology and Ecotoxicology, Department of Biology, Lund University, Lund, Sweden. marjorie.lienard@ekol.lu.se" |
| DOI: | 10.1016/j.ibmb.2010.04.003 |
| ISSN/ISBN: | 1879-0240 (Electronic) 0965-1748 (Linking) |
| 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 Delta 11-subfamily, Dpu-Delta 11(1)-APSQ and Dpu-Delta 11(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-Delta 11(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-Delta 11(1)-APSQ desaturase had the unusual property of producing Delta 8 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-Delta 9-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-Delta 11(1)-APSQ and Dpu-Delta 9-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" |
| Keywords: | "Amino Acid Sequence Animals Base Sequence Catalysis DNA, Complementary/chemistry Fatty Acid Desaturases/*chemistry/isolation & purification/physiology Female Gas Chromatography-Mass Spectrometry Insect Proteins/*chemistry/isolation & purification/physiolo;" |
| Notes: | "MedlineLienard, Marjorie A Lassance, Jean-Marc Wang, Hong-Lei Zhao, Cheng-Hua Piskur, Jure Johansson, Tomas Lofstedt, Christer eng Research Support, Non-U.S. Gov't England 2010/04/21 Insect Biochem Mol Biol. 2010 Jun; 40(6):440-52. doi: 10.1016/j.ibmb.2010.04.003. Epub 2010 Apr 18" |
