36 ワモンゴキブリの性フェロモンミミクverbenyl acetateに関する研究 : 活性に重要な化学的因子

抄録

Our discovery of the monoterpenoid sex pheromone mimic, (+)-trans-verbenyl acetate (1'), of the American cockroach (Periplaneta americana L.) stimulated us into elucidating chemical factors important for sex pheromonal activity of this compound. For the purpose, 1' and related analogs (about 100 compounds) having the 6,6-dimethylbicyclo[3.1.1]heptane skeleton were synthesized. In the behavioral assay with the males of the cockroach, the roaches showed the typical sexual display to several compounds (5', 16', 22', 38, 39 and 41'). On the basis of the assay results, the moiety, -O-C=O-R (R=CH_3 or C_2H_5) with α-orientation was revealed to be an important factor when the moiety is at the C-2 of the skeleton. Another key factor may be the methyl group at the C-4. From the stereo-structures of the active compounds and their structurally resemble analogs, a possible shape of the sex pheromone receptor could be seen, although it is incomplete. The EAG responses were recorded using the synthesized compounds. The active compounds were discriminated from inactive ones showing larger M/F ratios in the EAG analysis. This implies that the active compounds are concerned with the sex pheromone receptors.