Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Koganei, Japan.
J Chem Ecol. 2011 Nov;37(11):1222-30. doi: 10.1007/s10886-011-0032-3. Epub 2011 Nov 24.
The pear barkminer moth, Spulerina astaurota Meyrick (Gracillariidae: Gracillariinae), is a harmful pest of the Asian-pear tree. Pheromone components of the female were analyzed by gas chromatography (GC) with an electroantennographic (EAG) detector and GC coupled with mass spectrometry. The analyses of a crude pheromone extract and those of a fractionated extract on a Florisil column indicated three EAG-active components, tetradecadien-1-ol, its acetate, and an aldehyde derivative. Characteristic fragment ions in the mass spectra of the dienyl compounds and derivatives with 4-methyl-1,2,4-triazoline-3,5-dione revealed double bonds at the 9- and 11-positions. By comparing the chromatographic behaviors to those of four authentic geometrical isomers, which were synthesized by three different routes starting from 1,8-octanediol or 1,9-nonanediol, the configuration of each natural component was assigned to be 9Z,11Z; i.e., it was concluded that the S. astaurota females secreted (9Z,11Z)-9,11-tetradecadien-1-ol (Z9,Z11-14:OH) as a main pheromone component, and the acetate and aldehyde derivatives (Z9,Z11-14:OAc and Z9,Z11-14:Ald) as minor components. This identification was confirmed by a field evaluation of the synthetic pheromone. While the male moths could be attracted to a lure baited with Z9,Z11-14:OH alone, Z9,Z11-14:OAc showed a strong synergistic effect on the attraction. Among the lures tested, the mixture of alcohol and acetate in a ratio of 7:3 exhibited the strongest attraction. Addition of Z9,Z11-14:Ald in the mixture did not significantly increase the number of males attracted. Furthermore, the field test indicated that some contamination of a geometrical isomer of the alcohol did not impair the activity of the binary mixture with the 9Z,11Z configuration.
梨木潜叶蛾,Spulerina astaurota Meyrick(Gracillariidae:Gracillariinae),是亚洲梨树的有害害虫。通过气相色谱(GC)与触角电位(EAG)检测器和 GC 与质谱联用分析了雌蛾的信息素成分。粗提物和 Florisil 柱分离提取物的分析表明有三种 EAG 活性成分,十四碳二烯-1-醇、其醋酸酯和一种醛衍生物。二烯化合物和具有 4-甲基-1,2,4-三唑啉-3,5-二酮的衍生物的质谱中特征碎片离子表明双键位于 9-和 11-位。通过比较色谱行为与从 1,8-辛二醇或 1,9-壬二醇开始通过三种不同路线合成的四个立体异构体,每个天然成分的构型均被分配为 9Z,11Z;即,得出结论,S. astaurota 雌虫分泌(9Z,11Z)-9,11-十四碳二烯-1-醇(Z9,Z11-14:OH)作为主要信息素成分,醋酸酯和醛衍生物(Z9,Z11-14:OAc 和 Z9,Z11-14:Ald)作为次要成分。这一鉴定通过对合成信息素的野外评估得到了证实。虽然雄蛾可以被单独用 Z9,Z11-14:OH 引诱的诱饵吸引,但 Z9,Z11-14:OAc 对吸引具有强烈的协同作用。在所测试的诱饵中,醇和醋酸酯的混合物以 7:3 的比例表现出最强的吸引力。在混合物中添加 Z9,Z11-14:Ald 并没有显著增加被吸引的雄性数量。此外,野外试验表明,醇的某种立体异构体的污染不会损害具有 9Z,11Z 构型的二元混合物的活性。