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

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作者：

AC Oehlschlager，GGS King，HD Pierce，AM Pierce，JH Borden

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摘要：

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 the S configuration by Cryptolestes ferrugineus (Stephens) and in the R configuration by Oryzaephilus mercator (Fauvel). ( Z,Z )-3,6-Dodecadien-11-olide (II) is produced in the R configuration by both O. mercator and O. surinamensis (L.). ( Z,Z )-5,8-Tetradecadien-13-olide (IV) is produced in the R configuration by O. surinamensis and as a 85:15 mixture of R and S isomers by C. turcicus. ( Z )-5-Tetradecen-13-olide (V) is produced in the S configuration by C. pusillus (Schnherr) and as a 33:67 mixture of the R and S isomers by C. turcicus (Grouvelle). The results indicate that in these cucujids, species specificity in pheromone response is maintained at least in part by pheromone chirality.

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关键词：

Chiral semiochemicals pheromones enantiomeric composition enantiomeric synergism Cryptolestes ferrugineux Cryptolestes pusillus Cryptolestes turcicus Oryzaephilus mercator Oryzaephilus surinamensis Coleoptera