16 毒蛾が分泌する新規なエポキシ系性フェロモン(口頭発表の部)

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Sex pheromones have been identified from female moths of more than 500 species. About 75% of them are composed of unsaturated C_<10>-C_<18> straight chain compounds with a functional group at the terminal position (type I). Another 15% of the pheromones consist of unbranched C_<17>-C_<23> (3Z,6Z,9Z)-trienes, (6Z,9Z)-dienes, and their monoepoxy derivatives (type II), which lack a terminal functional group. The type II pheromones have been identified from species in highly evolved families, such as Geometridae, Noctuidae, Arctiidae, and Lymantriidae. In spite of the great number of species in the above families, the structural diversity known to date for the pheromones in type II is limited. It is expected that some females produced further modified compounds, and recently we successfully identified novel pheromone components from two lymantrid species. From virgin females of the tussock moth, Orgyia postica, single EAG-active component was found in a pheromone extract. This compound named posticlure possesses a trans-epoxy ring and was identified as (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene by means of GC-MS, ^1H NMR and chiral HPLC analyses, and further chemical derivation followed by the GC-MS analysis. In a field test with the pheromone synthesized stereoselectively, the male moths were specifically attracted to the (11S,12S)-isomer but not to the antipode. Based on the information of a diepoxy pheromone produced by Leucoma salicis, we synthesized all stereoiosmers of diepoxyalkenes derived from (3Z,6Z,9Z)-trienes with a C_<18>, C_<19>, or C_<21> straight chain by a MCPBA oxidation of optically active epoxyalkadienes. While the positional isomers showed similar Rts on a capillary GC, detailed inspection of their mass spectra indicated the following diagnostic ions for determining the chemical structures; m/z 128, 167, M-87, and M-85 for (Z)-cis-3,4-cis-6,7-diepoxy-9-enes, m/z 111, M-125, and M-69 for (Z)-cis-6,7-cis-9,10-diepoxy-3-enes, and m/z M-125 and M-139 for (Z)-cis-3,4-cis-9,10-diepoxy-6-enes. Mass chromatographic analysis monitoring these fragment ions revealed the existence of new pheromonal compounds, (3R,4S,6S,7R,9Z)-3,4-6,7-diepoxyhenicos-9-ene and its (3S,4R,6S,7R)-isomer, in an extract from virgin females of another tussock moth, Perina nuda. These two diepoxy compounds effectively enhanced attractiveness of the major component, (3Z,6S,7R,9Z)-6,7-eopxyhenicosa-3,9-diene, in a field.
2001-09-01

16 毒蛾が分泌する新規なエポキシ系性フェロモン(口頭発表の部)

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