麦蛾科谷蠹属和窃蠹属信息素的手性及其对种特异性的影响。

Chirality of macrolide pheromones of grain beetles in the generaOryzaephilusandCryptolestes and its implications for species specificity.

机构信息

Department of Chemistry, Simon Fraser University, V5A 1S6, Burnaby, British Columbia, Canada.

出版信息

J Chem Ecol. 1987 Jun;13(6):1543-54. doi: 10.1007/BF01012296.

Abstract

The chiralities of macrolide lactone aggregation pheromones of five species of economically important grain beetles have been determined by capillary gas chromatographic separation of the diastereomeric (S)-O-acetyllactate derivatives of the hydroxy methyl esters derived from boron trifluoride-catalyzed cleavage of the macrolides in methanol. Chirally pure (Z)-3-dodecen-11-olide (I) is produced in theS configuration byCryptolestes ferrugineus (Stephens) and in theR configuration byOryzaephilus mercator (Fauvel). (Z,Z)-3,6-Dodecadien-11-olide (II) is produced in theR configuration by bothO. mercator andO. surinamensis (L.). (Z,Z)-5,8-Tetradecadien-13-olide (IV) is produced in theR configuration byO. surinamensis and as a 85∶15 mixture ofR andS isomers byC. turcicus. (Z)-5-Tetradecen-13-olide (V) is produced in the S configuration byC. pusillus (Schönherr) and as a 33∶67 mixture of theR andS isomers byC. turcicus (Grouvelle). The results indicate that in these cucujids, species specificity in pheromone response is maintained at least in part by pheromone chirality.

摘要

通过对甲醇中硼氟化物催化大环内酯裂解生成的羟甲基酯的（S）-O-乙酰乳酸酯衍生物进行毛细管气相色谱分离，确定了 5 种重要经济谷蠹的大环内酯聚集信息素的手性。（S）构型的纯（Z）-3-十二碳烯-11-内酯（I）由 Cryptolestes ferrugineus（斯蒂芬斯）产生，（R）构型的纯（Z）-3-十二碳烯-11-内酯（I）由 Oryzaephilus mercator（费韦尔）产生。（Z，Z）-3,6-十二碳二烯-11-内酯（II）由 O. mercator 和 O. surinamensis（L.）均以（R）构型产生。（Z，Z）-5,8-十四碳二烯-13-内酯（IV）由 O. surinamensis 以（R）构型产生，而由 C. turcicus 产生的（R）和（S）异构体的 85∶15 混合物。（Z）-5-十四碳烯-13-内酯（V）由 C. pusillus（舍恩赫尔）以（S）构型产生，而由 C. turcicus（Grouvelle）产生的（R）和（S）异构体的 33∶67 混合物。结果表明，在这些丽金龟中，信息素反应的种特异性至少部分通过信息素手性来维持。