Purification, Stereoisomeric Analysis and Quantification of Sex Pheromone Precursors in Female Whole Body Extracts from Pine Sawfly Species
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A GC-MS method to analyze the stereoisomeric composition of chiral secondary alcohols found in whole body extracts of pine sawfly females was developed. The tested alcohols were derivatized with optically pure (S)-2-acetoxypropionyl chloride prior to GC-MS analysis. Baseline separation was obtained for all sixteen stereoisomers of 3,7,9-trimethyltridecan-2-ol and for the four 3-methylpentadecan-2-ol stereoisomers. For 3,7-dimethyltridecan-2-ol, 3,7-dimethyltetradecan-2-ol and 3,7-dimethylpentadecan-2-ol baseline separation was obtained for 6 of the possible 8 stereoisomers. When a mixture of 16 stereoisomers of 3,7,11-trimethyltridecan-2-ol was tested, baseline separation of 7 peaks out of 16 possible was obtained. The investigated alcohols are pheromone precursors for some pine sawfly species that are severe defoliators of pine. Females from several Diprion, Neodiprion, Macrodiprion, Microdiprion, and Gilpinia species emit esters of such secondary alcohols as sex pheromones that attract males for mating. To quantify the small amounts of the precursor alcohol and its stereoisomeric composition found in whole body extracts from female pine sawflies, a purification method was optimized. An extract of 20 females of D. pini contained about 8 ng of (2S,3R,7R)-3,7-dimethyltridecan-2-ol per female, and three extracts of 18, 20, and 90 females of N. sertifer contained between 5 and 13 ng of (2S,3S,7S)-3,7-dimethylpentadecan-2-ol per female.
Key WordsSex pheromone Pine sawflies Diprion pini Neodiprion sertifer Gilpinia frutetorum Gilpinia pallida Gilpinia socia Macrodiprion nemoralis Microdiprion pallipes 3,7-dimethyltridecan-2-ol 3,7,9-trimethyltridecan-2-ol 3,7,11-trimethyltridecan-2-ol 3,7-dimethyltetradecan-2-ol 3,7-dimethylpentadecan-2-ol 3-methylpentadecan-2-ol Stereoisomers Analysis GC-MS
We are grateful for the financial support from EU (Objective 2 the region of South Forest Counties) and Länsstyrelsen i Västernorrlands län.
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