PMID: 11925075Apr 2, 2002Paper

Cuticular hydrocarbons and novel alkenediol iacetates from wheat stem sawfly (Cephus cinctus): natural oxidation to pheromone components

Journal of Chemical Ecology
R J BarteltDavid K Weaver

Abstract

The cuticular lipids of the wheat stem sawfly Cephus cinctus (Hymenoptera: Cephidae) were investigated as part of a chemical ecology project with this species. The major cuticular lipids were n-alkenes and n-alkanes. Alkenes were the most abundant and exhibited dramatic sexual dimorphism. (Z)-9-Tricosene accounted for about half of the total hydrocarbon in males but was nearly absent from females. The dominant alkenes in females were (Z)-9-pentacosene and (Z)-9-heptacosene. The alkane profiles were similar in both sexes, with n-tricosane being the most abundant, followed by n-pentacosane and n-heptacosane. In both sexes, there were minor amounts of alkanes and alkenes with other chain lengths and n-alkadienes of 29 and 31 carbons. In males, about one tenth of the surface lipids consisted of (Z)-9-alkene-1, omega-diol diacetates with 22-, 24-, and 26-carbon chains. The same compounds were also detected from females but in much smaller amounts. The structures of these novel diacetates were proven by synthesis. By analogy to methyl oleate, a well-studied food lipid, the alkenes and diacetates were expected to undergo slow oxidation in air to release specific aldehydes and other volatile products, and these were generally detected ...Continue Reading

Citations

Aug 24, 2013·Insect Molecular Biology·J C GressK W Wanner
Jan 8, 2020·Journal of Chemical Ecology·Hao XuTed C J Turlings
Sep 28, 2015·Journal of Chemical Ecology·Ricarda Kather, Stephen J Martin
Jan 12, 2010·Journal of Chemical Ecology·Joseph K StaplesDouglas W Whitman
Dec 22, 2009·Environmental Entomology·Micaela ButelerRobert K D Peterson

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