title: Terminal fatty-acyl-CoA desaturase involved in sex pheromone biosynthesis in the winter moth (Operophtera brumata).
abstract: The winter moth (Operophtera brumata L., Lepidoptera: Geometridae) utilizes a single hydrocarbon, 1,Z3,Z6,Z9-nonadecatetraene, as its sex pheromone. We tested the hypothesis that a fatty acid precursor, Z11,Z14,Z17,19-nonadecanoic acid, is biosynthesized from α-linolenic acid, through chain elongation by one 2-carbon unit, and subsequent methyl-terminus desaturation. Our results show that labeled α-linolenic acid is indeed incorporated into the pheromone component in vivo. A fatty-acyl-CoA desaturase gene that we found to be expressed in the abdominal epidermal tissue, the presumed site of biosynthesis for type II pheromones, was characterized and expressed heterologously in a yeast system. The transgenic yeast expressing this insect derived gene could convert Z11,Z14,Z17-eicosatrienoic acid into Z11,Z14,Z17,19-eicosatetraenoic acid. These results provide evidence that a terminal desaturation step is involved in the winter moth pheromone biosynthesis, prior to the decarboxylation.
authors.affiliation: Functional Zoology, Department of Biology, Lund University, Sölvegatan 37, SE-22362 Lund, Sweden. bao-jian.ding@biol.lu.se
authors.forename: Bao-Jian
authors.initials: BJ
authors.lastname: Ding
authors.forename: Marjorie A
authors.initials: MA
authors.lastname: Liénard
authors.forename: Hong-Lei
authors.initials: HL
authors.lastname: Wang
authors.forename: Cheng-Hua
authors.initials: CH
authors.lastname: Zhao
authors.forename: Christer
authors.initials: C
authors.lastname: Löfstedt
mesh_terms: D015126:8,11,14-Eicosatrienoic Acid / Q000378:metabolism; D000595:Amino Acid Sequence; D000818:Animals; D016718:Arachidonic Acid / Q000378:metabolism; D001483:Base Sequence; D003001:Cloning, Molecular; D018076:DNA, Complementary; D044943:Fatty Acid Desaturases / Q000235:genetics* / Q000378:metabolism; D005227:Fatty Acids / Q000378:metabolism; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D019476:Insect Proteins / Q000378:metabolism*; D008969:Molecular Sequence Data; D009036:Moths / Q000201:enzymology / Q000235:genetics*; D010802:Phylogeny; D020133:Reverse Transcriptase Polymerase Chain Reaction; D012441:Saccharomyces cerevisiae; D017385:Sequence Homology; D012724:Sex Attractants / Q000096:biosynthesis* / Q000737:chemistry; D013548:Sweden; D017962:alpha-Linolenic Acid / Q000378:metabolism
chemical_list: D018076:DNA, Complementary; D005227:Fatty Acids; D019476:Insect Proteins; D012724:Sex Attractants; D017962:alpha-Linolenic Acid; C034152:11,14,17-eicosatrienoic acid; D016718:Arachidonic Acid; D044943:Fatty Acid Desaturases; D015126:8,11,14-Eicosatrienoic Acid; C517969:nonadecanoic acid