Bartelt R J, Cossé A A, Zilkowski B W, Weisleder D, Momany F A
USDA Agricultural Research Service, National Center for Agricultural Utilization Research, Peoria, Illinois 61604, USA.
J Chem Ecol. 2001 Dec;27(12):2397-423. doi: 10.1023/a:1013667229345.
It was previously reported that males of the crucifer flea beetle, Phyllotreta cruciferae, feeding on host foliage are attractive to both males and females in the field. Based on this evidence for an aggregation pheromone, volatiles were collected from male and female P. cruciferae feeding on cabbage (Brassica oleracea) and analyzed. For comparison, volatiles were also collected from males and females of three other flea beetle species, Aphthona flava, A. czwalinae, and A. cyparissiae, all feeding on their host, leafy spurge foliage (Euphorbia esula). Six male-specific compounds were isolated from P. cruciferae, and the same compounds plus two additional ones were isolated from males of Aphthona flava, A. czwalinae, and A. cyparissiae. The blends of compounds were relatively consistent within species, but there were characteristic differences between species. Compound structures were studied by mass spectrometry, NMR spectroscopy, UV spectroscopy, polarimetry, chiral and achiral gas chromatography, molecular modeling, and microchemical tests. Three of the compounds were identified as (+)-ar-himachalene; (+)-trans-alpha-himachalene; (+)-y-cadinene. Two others were new enantiomers of himachalene hydrocarbons that were previously identified from the fir trees, Abies alba and Abies nordmanniana. Finally, there were two himachalene alcohols and one norsesquiterpene ketone that is a himachalene analog. Only (+)-ar-himachalene and (+)-y-cadinene are previously known natural products. Electrophysiological activity was demonstrated for five of the compounds. The chemical and electrophysiological patterns are consistent with, but do not prove, a pheromonal function.
此前有报道称，以寄主叶片为食的十字花科跳甲（Phyllotreta cruciferae）雄性成虫在田间对雄性和雌性成虫均具有吸引力。基于这种聚集信息素的证据，收集了取食甘蓝（Brassica oleracea）的十字花科跳甲雌雄成虫释放的挥发性物质并进行了分析。为作比较，还收集了另外三种以寄主叶状大戟（Euphorbia esula）叶片为食的跳甲物种，即黄守瓜（Aphthona flava）、茨氏黄守瓜（A. czwalinae）和赛氏黄守瓜（A. cyparissiae）雌雄成虫释放的挥发性物质。从十字花科跳甲中分离出了六种雄性特异性化合物，从黄守瓜、茨氏黄守瓜和赛氏黄守瓜雄性成虫中分离出了相同的这些化合物以及另外两种化合物。化合物混合物在物种内相对一致，但不同物种之间存在特征差异。通过质谱、核磁共振光谱、紫外光谱、旋光测定、手性和非手性气相色谱、分子建模以及微量化学测试对化合物结构进行了研究。其中三种化合物被鉴定为（+）-α-雪松烯；（+）-反式-α-雪松烯；（+）-γ-杜松烯。另外两种是先前从欧洲冷杉（Abies alba）和高加索冷杉（Abies nordmanniana）中鉴定出的雪松烯类碳氢化合物的新对映体。最后，还有两种雪松烯醇和一种降倍半萜酮，后者是雪松烯类似物。只有（+）-α-雪松烯和（+）-γ-杜松烯是先前已知的天然产物。已证明其中五种化合物具有电生理活性。化学和电生理模式与信息素功能相符，但不能证明其信息素功能。
