Identification of novel C(20) and C (22) trienoic acids from arctiid and geometrid female moths that produce polyenyl Type II Sex pheromone components.

Gas chromatography-mass spectrometry (GC-MS) and GC-electroantennographic detection (EAD) analyses of the sex pheromone extract from a wasp moth, Syntomoides imaon (Lepidoptera: Arctiidae: Syntominae), showed that virgin females produced (Z,Z,Z)-3,6,9-henicosatriene and (Z,Z,Z)-1,3,6,9-henicosatetraene with a trace amount of their C(20) analogs. Identification of the chemical structures was facilitated by comparison with authentic standards and the double-bond positions were confirmed by dimethyl disulfide derivatization of monoenes produced by a diimide reduction. In a field test in the Yonaguni-jima Islands, males of the diurnal species were captured in traps baited with a 1:2 mixture of the above-described synthetic C(21) polyenes. Lipids were extracted from the abdominal integument and its associated oenocytes and peripheral fat bodies. Following derivatization, fatty acid methyl esters (FAMEs) were fractionated by HPLC equipped with an ODS column, and methyl (Z,Z,Z)-11,14,17-icosatrienoate and (Z,Z,Z)-13,16,19-docosatrienoate were identified by GC-MS. These novel C(20) and C(22) acid moieties are longer-chain analogs of linolenic acid, (Z,Z,Z)-9,12,15-octadecatrienoic acid. They are presumed to be biosynthetic precursors of the S. imaon pheromone because the C(21) trienyl component might be formed by decarboxylation of the C(22) acid. On the other hand, the C(20) acid, but not the C(22) acid, was found in FAMEs of Ascotis selenaria cretacea (Lepidoptera: Geometridae), which secretes C(19) pheromone components, (Z,Z,Z)-3,6,9-nonadecatriene and the monoepoxy derivative, indicating that different systems of the chain elongation might play an important role in developing species-specific communication systems mediated with polyunsaturated hydrocarbons and/or epoxy derivatives, components of Type II lepidopteran sex pheromones.