Anatomical localization and stereoisomeric composition of Tribolium castaneum aggregation pheromones
Anatomical localization and stereoisomeric composition of Tribolium castaneum aggregation pheromones
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赤拟谷盗聚集信息素的解剖定位和立体异构组成
DOI：
10.1007/s00114-011-0824-x
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发表时间：
2011
影响因子：
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通讯作者：
T. Phillips
中科院分区：
文献类型：
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作者：
Yujie Lu;R. Beeman;J. Campbell;Yoonseong Park;M. Aikins;K. Mori;K. Akasaka;S. Tamogami;T. Phillips
本文报道了红粉甲雄性产生信息素的主要来源是腹部表皮和伴生组织，并首次描述了这一重要害虫中聚集信息素4，8-二甲基癸醛(DMD)的天然混合物的立体异构体组成。气相色谱-质谱法分析表明，单次取食的卡氏毛虫雄虫平均每天释放的DMD量为878 ± 72 ng(SE)。对不同身体部位的分析表明，腹部表皮是聚集信息素的主要来源；胸部是次要来源，而头部没有检测到DMD。没有内脏或明显的雄性专一性腺体与信息素沉积有关。通过氧化成相应的酸，用(1R，2R)-和(1S，2S)-2-(anthracene-2，3-dicarboximido)cyclohexanol)衍生化成非对映异构体，并在−54°C下用反相高效液相色谱分离，实现了DMD的所有四个立体异构体的完全分离。4种合成异构体的不同混合物在风洞中进行的步行定向生物测定进一步表明，4：4：1：1的重组天然混合物的引诱效力与天然信息素相当，而大于商品诱饵中使用的1：1混合物的引诱效力。
We report that the abdominal epidermis and associated tissues are the predominant sources of male-produced pheromones in the red flour beetle, Tribolium castaneum and, for the first time, describe the stereoisomeric composition of the natural blend of isomers of the aggregation pheromone 4,8-dimethyldecanal (DMD) in this important pest species. Quantitative analyses via gas chromatography–mass spectrometry showed that the average amount of DMD released daily by single feeding males of T. castaneum was 878 ± 72 ng (SE). Analysis of different body parts identified the abdominal epidermis as the major source of aggregation pheromone; the thorax was a minor source, while no DMD was detectable in the head. No internal organs or obvious male-specific glands were associated with pheromone deposition. Complete separation of all four stereoisomers of DMD was achieved following oxidation to the corresponding acid, derivatization with (1R, 2R)- and (1S, 2S)-2-(anthracene-2,3-dicarboximido)cyclohexanol to diastereomeric esters, and their separation on reversed-phase high-performance liquid chromatography at −54°C. Analysis of the hexane eluate from Porapak-Q-collected volatiles from feeding males revealed the presence of all four isomers (4R,8R)/(4R,8S)/(4S,8R)/(4S,8S) at a ratio of approximately 4:4:1:1. A walking orientation bioassay in a wind tunnel with various blends of the four synthetic isomers further indicated that the attractive potency of the reconstituted natural blend of 4:4:1:1 was equivalent to that of the natural pheromone and greater than that of the 1:1 blend of (4R,8R)/(4R,8S) used in commercial lures.