| Title: | Chirality of macrolide pheromones of grain beetles in the generaOryzaephilusandCryptolestes and its implications for species specificity |
| Author(s): | Oehlschlager AC; King GG; Pierce HD; Pierce AM; Slessor KN; Millar JG; Borden JH; |
| Address: | "Department of Chemistry, Simon Fraser University, V5A 1S6, Burnaby, British Columbia, Canada" |
| ISSN/ISBN: | 0098-0331 (Print) 0098-0331 (Linking) |
| 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 85ratio15 mixture ofR andS isomers byC. turcicus. (Z)-5-Tetradecen-13-olide (V) is produced in the S configuration byC. pusillus (Schonherr) and as a 33ratio67 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" |
| Notes: | "PubMed-not-MEDLINEOehlschlager, A C King, G G Pierce, H D Jr Pierce, A M Slessor, K N Millar, J G Borden, J H eng 1987/06/01 J Chem Ecol. 1987 Jun; 13(6):1543-54. doi: 10.1007/BF01012296" |
