Stylopsal: The First Identified Female-produced Sex Pheromone of Strepsiptera
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A female-produced sex pheromone of Stylops muelleri was identified as an unusually branched saturated aldehyde (9R)-3,5-syn-3,5,9-trimethyldodecanal. We named it stylopsal. Its structure was established by using mass spectrometry, infrared spectroscopy, and organic synthesis of candidate compounds. The synthetic standard of (9R)-3,5-syn-3,5,9-trimethyldodecanal gave identical chromatographic and mass spectrometric data as the natural pheromone and also was active in electroantennographic and behavioral assays. The female fat body lipids contained the corresponding fatty acid, indicating a possible link between lipid metabolism and the pheromone biosynthesis.
KeywordsStrepsiptera Stylops Sex pheromone Aldehyde Trimethyldodecanal Fat body
This research was funded by the Czech Science Foundation (Project No. P506/10/1466) and the Academy of Sciences of the Czech Republic (Project RVO: 61388963). The authors wish to thank all colleagues and students involved in digging parasitized bees, to Martin Weisser for helping us with statistical analyses, to Pavel Krásenský for pictures, and Mr. Sean Mark Miller for proofreading the manuscript and making corrections.
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