title: Stylopsal: the first identified female-produced sex pheromone of strepsiptera.
abstract: 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.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, vvi., Flemingovo nám. 2, 16610, Prague 6, Czech Republic.
authors.forename: Josef
authors.initials: J
authors.lastname: Cvačka
authors.forename: Pavel
authors.initials: P
authors.lastname: Jiroš
authors.forename: Blanka
authors.initials: B
authors.lastname: Kalinová
authors.forename: Jakub
authors.initials: J
authors.lastname: Straka
authors.forename: Kateřina
authors.initials: K
authors.lastname: Cerná
authors.forename: Petr
authors.initials: P
authors.lastname: Šebesta
authors.forename: Aleš
authors.initials: A
authors.lastname: Tomčala
authors.forename: Soňa
authors.initials: S
authors.lastname: Vašíčková
authors.forename: Ullrich
authors.initials: U
authors.lastname: Jahn
authors.forename: Jan
authors.initials: J
authors.lastname: Šobotník
mesh_terms: D000447:Aldehydes / Q000032:analysis* / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D005216:Fat Body / Q000737:chemistry; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D007313:Insecta / Q000737:chemistry / Q000502:physiology*; D008297:Male; D012724:Sex Attractants / Q000737:chemistry*; D012726:Sexual Behavior, Animal / Q000187:drug effects / Q000502:physiology; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
chemical_list: C581542:3,5,9-trimethyldodecanal; D000447:Aldehydes; D012724:Sex Attractants