Terminal fatty-acyl-CoA desaturase involved in sex pheromone biosynthesis in the winter moth (Operophtera brumata)

Insect Biochem Mol Biol. 2011 Sep;41(9):715-22. doi: 10.1016/j.ibmb.2011.05.003. Epub 2011 May 30.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 8,11,14-Eicosatrienoic Acid / metabolism
  • Amino Acid Sequence
  • Animals
  • Arachidonic Acid / metabolism
  • Base Sequence
  • Cloning, Molecular
  • DNA, Complementary
  • Fatty Acid Desaturases / genetics*
  • Fatty Acid Desaturases / metabolism
  • Fatty Acids / metabolism
  • Female
  • Gas Chromatography-Mass Spectrometry
  • Insect Proteins / metabolism*
  • Molecular Sequence Data
  • Moths / enzymology
  • Moths / genetics*
  • Phylogeny
  • Reverse Transcriptase Polymerase Chain Reaction
  • Saccharomyces cerevisiae
  • Sequence Homology
  • Sex Attractants / biosynthesis*
  • Sex Attractants / chemistry
  • Sweden
  • alpha-Linolenic Acid / metabolism

Substances

  • DNA, Complementary
  • Fatty Acids
  • Insect Proteins
  • Sex Attractants
  • alpha-Linolenic Acid
  • 11,14,17-eicosatrienoic acid
  • Arachidonic Acid
  • Fatty Acid Desaturases
  • 8,11,14-Eicosatrienoic Acid
  • nonadecanoic acid

Associated data

  • GENBANK/HQ917684
  • GENBANK/HQ917685
  • GENBANK/HQ917686