title: Identification of the sex pheromone of the currant shoot borer Lampronia capitella.
abstract: Under an artificial light:dark cycle, females of Lampronia capitella were observed calling, with extended terminal abdominal segments, during the first 2 hr of the photoperiod. Extracts of terminal abdominal segments from females elicited large electroantennographic responses from male antennae. Gas chromatography with electroantennographic detection revealed three active peaks. Based on comparison of retention times and mass spectra of synthetic standards, these compounds were identified as (Z,Z)-9,11-tetradecadienol and the corresponding acetate and aldehyde. The electroantennographic activity of the four geometric isomers of all three compounds was investigated, and the respective (Z,Z)-isomer was found to be the most active in all cases. Aldehydes generally elicited larger antennal responses than alcohols, whereas acetates were the least active compounds. A subtractive trapping assay in the field, based on a 13:26:100 micrograms mixture of (Z,Z)-9,11-tetradecadienal, (Z,Z)-9,11-tetradecadienyl acetate, and (Z,Z)-9,11-tetradecadienol confirmed that all three compounds are pheromone components. Subtraction of (Z,Z)-9,11-tetradecadienol from the blend completely eliminated its attractiveness, whereas the other two-component blends showed reduced activity. This is the first pheromone identification from the monotrysian superfamily Incurvarioidea, confirming that the common pheromones among ditrysian moths (long-chain fatty acid derivatives comprising alcohols, acetates, and aldehydes with one or more double bonds) is not an autapomorphy of Ditrysia, but a synapomorphy of the more advanced heteroneuran lineages.
authors.affiliation: Department of Ecology, Lund University, SE-223 62 Lund, Sweden. christer.lofstedt@ekol.lu.se
authors.forename: Christer
authors.initials: C
authors.lastname: Löfstedt
authors.forename: Junwei
authors.initials: J
authors.lastname: Zhu
authors.forename: Mikhail V
authors.initials: MV
authors.lastname: Kozlov
authors.forename: Vincas
authors.initials: V
authors.lastname: Buda
authors.forename: Erling V
authors.initials: EV
authors.lastname: Jirle
authors.forename: Sven
authors.initials: S
authors.lastname: Hellqvist
authors.forename: Jan
authors.initials: J
authors.lastname: Löfqvist
authors.forename: Ernst
authors.initials: E
authors.lastname: Plass
authors.forename: Stephan
authors.initials: S
authors.lastname: Franke
authors.forename: Wittko
authors.initials: W
authors.lastname: Francke
mesh_terms: D000085:Acetates / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000447:Aldehydes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000825:Animal Structures / Q000187:drug effects / Q000502:physiology; D000818:Animals; D002849:Chromatography, Gas; D005260:Female; D007659:Ketones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008297:Male; D013058:Mass Spectrometry; D009036:Moths / Q000737:chemistry*; D012015:Reference Standards; D012724:Sex Attractants / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D012726:Sexual Behavior, Animal / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000447:Aldehydes; D007659:Ketones; D012724:Sex Attractants