Anomala osakana

Japonilure R), the sex pheromone of the female Japanese beetle. Papilla japonica and its enantiomer, (5)-(+)-(5Z )-tetradecen-4-olide, which is the pheromone of the Osaka beetle, Anomala osakana have been synthesized using a highly convergent procedure and in satisfactory overall yields. 

Anomala cuprea Scarabaeiformia Scarabaeidae Rutelinae Anomala octiescostata Scarabaeidae Rutelinae Anomala osakana Scarabaeidae Rutelinae Exomala orientalis Scarabaeidae Rutelinae Holotrichia parallela Scarabaeidae Melolonthinae... 

In particular, the importance of chirality in diverse pheromone systems has been reviewed recently (Mori, 1998). For example, olive fruit flies (Bactrocera oleae) emit racemic 2 the males detect the R enantiomer, while females detect the S (Haniotakis et al., 1986). The sex pheromone of the Osaka beetle (Anomala osakana) is 4a, while the closely related Japanese beetle (Popilia japonica) uses 4b (Table 16.1). Interestingly, 4a is a powerful behavioral antagonist in P. japonica (Tumlinson et al., 1977). The hemlock looper, Lambdina fiscellaria, responds only to (5R, 1 S)-5,I I -dimethylheptadecane. The enantiomer or the R/R or S/S diastereomers do not elicit electrophysiological or behavioral responses (Li et al., 1993). Table 16.1 gives an overview of those species where proteins from the pheromone olfactory system have been identified. 

Because synthetic ( )-87 was pheromonally inactive, Tumlinson et al. carefully studied in 1977 the relationship between the enantiomeric purity of 87 and its pheromone activity.60 They synthesized the enantiomers of 87, starting from the enantiomers of glutamic acid. The bioactive enantiomer is (/ )-(—)-87, and (5 )-(+)-87 severely inhibits the action of (R)-87. Accordingly, (R)-87 of 99% ee is only two-thirds as active as pure (R)-S7 that of 90% ee is one-third as active, that of 80% ee is one-fifth as active as pure (R)-87. Both (7v )-87 of 60% ee and ( )-87 were inactive. These results illustrate convincingly the importance of enantiomeric composition in chemical communication. Later in 1996, Leal found that the sex pheromone of the female scarab beetle (Anomala osakana) is (S )-87, while (R)-87 interrupts the attraction caused by (.S )-87,61 Thus, chirality accounts for species discrimination. 

Protein extracts from antennae and legs of the Japanese beetle, the Osaka beetle, Anomala osakana, and the other scarab beetle species (Phyllopertha diversa, Holotrichia parallela, and Exomala orientalis) were incubated either... 

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