title: (R)-desmolactone, a female-produced sex pheromone component of the cerambycid beetle Desmocerus californicus californicus (subfamily Lepturinae).
abstract: We report the identification, synthesis, and field bioassays of a female-produced sex attractant pheromone for the cerambycid beetle Desmocerus californicus californicus Horn. Headspace volatiles from females contained a sex-specific compound, (R)-desmolactone [(4R,9Z)-hexadec-9-en-4-olide], which elicited strong responses from the antennae of adult males in coupled gas chromatography-electroantennogram analyses. Short syntheses of both enantiomers were developed from commercial chiral synthons. In field bioassays, significant numbers of males were collected in traps baited with (R)-desmolactone, whereas the (S)-enantiomer attracted no males. The racemate was less attractive than the pure (R)-enantiomer, indicating some degree of antagonism by the unnatural enantiomer. This compound is the first example of a new structural class of cerambycid pheromones, and is the second pheromone identified for a species in the subfamily Lepturinae.
authors.affiliation: Department of Biology, Xavier University, Cincinnati, OH 45207, USA. raya6@xavier.edu
authors.forename: Ann M
authors.initials: AM
authors.lastname: Ray
authors.forename: Ian P
authors.initials: IP
authors.lastname: Swift
authors.forename: J Steven
authors.initials: JS
authors.lastname: McElfresh
authors.forename: Ronald L
authors.initials: RL
authors.lastname: Alten
authors.forename: Jocelyn G
authors.initials: JG
authors.lastname: Millar
mesh_terms: D000818:Animals; D001681:Biological Assay; D001517:Coleoptera / Q000187:drug effects / Q000378:metabolism*; D005260:Female; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D008297:Male; D012724:Sex Attractants / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology
chemical_list: C572792:(R)-desmolactone; D007783:Lactones; D012724:Sex Attractants