Laboratoire des Médiateurs Chimiques, Institut National de la Recherche Agronomique, Route de St Cyr, F78026, Versailles, France.
J Chem Ecol. 1994 Dec;20(12):3133-47. doi: 10.1007/BF02033716.
Thetrans- andcis-(Z)-α-bisabolene epoxides (trans- andcis-(Z)-αBE) are the main components of the male sex pheromone inNezara viridula. The role of thecis isomer and the importance of thecis/trans proportion for the activity and the specificity of the pheromone are not clearly elucidated and were studied here. Interindividual variation of thecis/trans proportion produced by males was studied by individual hexanic extracts in two strains originating from the south of France (SF) and French West Indies (FWI). Thetrans isomer composed 42-82% of bisabolene epoxides in SF males and 74-94% of bisabolene epoxides in FWI males. Means (± SD) significantly differ between SF (62.8%±8.4) and FWI (82.4%±5.9) males in spite of this interindividual variation. Different isomers of bisabolene epoxide were synthesized and their EAG activity on female antennae was compared. Racemictrans- andcis-(Z)-αBE elicited low EAGs, not different from the nonnaturaltrans andcis (E)-αBE that were inactive on behavior. Behavioral tests revealed that racemictrans- andcis-(Z)-αBE attracted 45% (P<0.05) and 25% (P<0.05) of females, respectively. The same levels of attraction were obtained with (-) enantiomers oftrans- andcis-(Z)-αBE, which attracted 40% (P<0.05) and 20% (P>0.05) of the females, respectively. Binary blends containing 75/25, 50/50, and 25/75 proportions ofcis/trans isomers were more attractive thantrans-(Z)-αBE alone and response of females to the 25%cis/75%trans blend was significantly more important than the response totrans-isomer alone (P<0.05). The importance of thecis/trans proportion in relation with the specificity of the male pheromone is discussed.
(Z)-α-反式-和(Z)-α-顺式-大根香叶烯环氧化物(trans- 和 cis-(Z)-αBE)是南美芫菁雄性信息素的主要成分。cis-异构体的作用以及顺式/反式比例对信息素活性和特异性的重要性尚不清楚，本研究对此进行了探讨。通过对来自法国南部（SF）和法属西印度群岛（FWI）的两个品系的雄性个体的正己烷提取物进行个体研究，研究了雄性个体产生的顺式/反式比例的个体间差异。SF 雄性个体的大根香叶烯环氧化物中反式异构体组成 42-82%，FWI 雄性个体的大根香叶烯环氧化物中反式异构体组成 74-94%。尽管存在这种个体间差异，但 SF（62.8%±8.4）和 FWI（82.4%±5.9）雄性个体的平均值（± SD）有显著差异。合成了大根香叶烯环氧化物的不同异构体，并比较了它们对雌性触角的 EAG 活性。外消旋 trans- 和 cis-(Z)-αBE 引起的 EAG 活性较低，与无活性的非天然 trans- 和 cis-(E)-αBE 没有区别。行为测试表明，外消旋 trans- 和 cis-(Z)-αBE 分别吸引了 45%（P<0.05）和 25%（P<0.05）的雌性个体。trans- 和 cis-(Z)-αBE 的（-）对映异构体也获得了相同水平的吸引力，分别吸引了 40%（P<0.05）和 20%（P>0.05）的雌性个体。含有 75/25、50/50 和 25/75 比例顺式/反式异构体的二元混合物比单独的 trans-(Z)-αBE 更具吸引力，而且女性对 25%顺式/75%反式混合物的反应比单独对反式异构体的反应更重要（P<0.05）。讨论了顺式/反式比例与雄性信息素特异性之间的关系。
