A New Lavandulol-related Monoterpene in the Sex Pheromone of the Grey Pineapple Mealybug, Dysmicoccus neobrevipes
A New Lavandulol-related Monoterpene in the Sex Pheromone of the Grey Pineapple Mealybug, Dysmicoccus neobrevipes
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DOI：
10.1007/s10886-015-0545-2
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发表时间：
2015-01
影响因子：
2.3
通讯作者：
J. Tabata;R. Ichiki
中科院分区：
文献类型：
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作者：
J. Tabata;R. Ichiki
灰菠萝粉蚧（Dysmicoccus neobrevipes）是一种严重的害虫，在热带地区袭击各种作物。最近，在日本西南部的一个岛屿上记录了它，这表明它的分布正在扩大。作为应对这种扩张的措施，迫切需要一种监控工具。本研究确定了D. neobrevipes，以开发一个有效的诱饵监测陷阱。从处女成年女性收集的挥发物进行了分馏，高效液相色谱法（HPLC）和气相色谱法，馏分进行了测试，在实验室生物测定的吸引力男性。一个单一的化合物被分离出来，这是有吸引力的男性作为粗集合，这被认为是主要的，如果不是唯一的，组成部分的女性产生的性信息素。通过气相色谱/质谱和核磁共振分析确定其结构为（E）-2-异丙基-5-甲基己-3，5-二烯基乙酸酯。该化合物通过四步合成，合成的化学品在温室生物测定中与天然产物一样具有吸引力。通过对映选择性HPLC分离，得到了合成乙酸酯的对映异构体，天然信息素为（+）-异构体。这种新化合物的碳骨架与lavandulol有关，lavandulol是一种单萜，具有不寻常的异戊二烯单元的非首尾连接，通常在粉蚧信息素中发现。
The grey pineapple mealybug,Dysmicoccus neobrevipes, is a serious pest that attacks a variety of crops in tropical regions. Recently, it was recorded on an island in southwestern Japan, suggesting that its distribution is expanding. As a measure against this expansion, a monitoring tool is urgently needed. In this study we determined the structure of the sex pheromone ofD. neobrevipesin order to develop an efficient lure for monitoring traps. Volatiles collected from virgin adult females were fractionated by high performance liquid chromatography (HPLC) and gas chromatography, and fractions were tested for attractiveness to males in a laboratory bioassay. A single compound was isolated which was as attractive to males as the crude collections, and this was proposed to be the main, if not the only, component of the female-produced sex pheromone. The structure of this was determined to be (E)-2-isopropyl-5-methylhexa-3,5-dienyl acetate by gas chromatography/mass spectrometry and nuclear magnetic resonance analyses. This compound was synthesized through four steps, and the synthetic chemical was as attractive as the natural product in a greenhouse bioassay. The enantiomers of the synthetic acetate were obtained by enantioselective HPLC fractionation of the corresponding alcohols, and the natural pheromone was shown to be the (+)-isomer. The carbon skeleton of this novel compound is related to lavandulol, a monoterpene with an unusual non-head-to-tail connection of isoprene units that is often found in mealybug pheromones.