P-57 ヒトリガ科昆虫が分泌する新規性フェロモン成分の同定と合成研究(ポスター発表の部)

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Sex pheromones have been identified from about 600 lepidopteran species, but information of chemicals secreted by species in the Arctiidae, one of the evolved families including various species. Particularly for the species in the Lithosiinae, a subfamily of the including, pheromones have never been reported. In order to understand structural diversity of the pheromones, we caught adults of several Lithosiinae species, using a black-light trap in the Iriomote Islands, located in a subtropical zone. Among the collected insects, females of Lyclene dharma dharma produced a 2:1:1 mixture of novel pheromone components (I-III), which strongly stimulated male antennae on a GC-EAD analysis. Using GC-MS analysis and chemical derivatizations, such as removal of a carbonyl function by the Wolff-Kishner reaction, the following structures were estimated: 6-methyl-2-octadecanone (I), 14-methyl-2-octadecanone (II), and 6,14-dimethyl-2-octadecanone (III). These methyl-branched ketones have not been identified as a natural product, indicating that they constitute a new chemical group of lepidopteran female sex pheromones. While the stereochemistry of the chiral centers could not be determined because it was difficult to collect a sufficient amount of a pheromone extract, their plain structures were confirmed by synthesis of racemic I-III starting from diols. The mass spectrum of each synthetic ketone coincided well with that of the natural component, and the 2:1:1 mixture of the racemates successfully attracted many males in a field in the Iriomote Islands. Furthermore, we are now examining to improve the synthetic yield and established another route via Wacker oxidation terminal alkenes, where all of the three components were constructed with common synthetic units.
天然有機化合物討論会の論文
2008-09-01

P-57 ヒトリガ科昆虫が分泌する新規性フェロモン成分の同定と合成研究(ポスター発表の部)

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