title: Identification, synthesis, and behavioral activity of 5,11-dimethylpentacosane, a novel sex pheromone component of the greater wax moth, Galleria mellonella (L.).
abstract: The greater wax moth, Galleria mellonella (L.), is a serious and widespread pest of the honeybee, Apis mellifera L. In contrast to most moths, for which long-range mate finding is mediated by female-produced sex pheromones, G. mellonella males attract conspecific females over long distances by emitting large amounts of a characteristic scent in combination with bursts of ultrasonic calls. The male scent for this species was previously identified as a blend of nonanal and undecanal. When these compounds were bioassayed, characteristic short-range sexual behavior, including wing fanning, was triggered in conspecific females, but the aldehyde blend failed to elicit attraction over longer distances. We identified, via analysis and synthesis, a third male-specific compound, 5,11-dimethylpentacosane. We show that it acts as a behavioral synergist to the aldehydes. In wind tunnel experiments, very few female moths responded to the aldehyde blend or to 5,11-dimethylpentacosane tested separately, but consistently showed orientation and source contact when a combination of all three compounds was applied. The level of attraction to the three-component mixture was still lower than that to male extract, indicating that the composition of compounds in the synthetic blend is suboptimal, or that additional pheromone components of G. mellonella are yet to be identified. The identification of 5,11-dimethylpentacosane is an important step for the development of an efficient long-range attractant that will be integrated with other environmentally safe strategies to reduce damage to beehives caused by wax moths.
authors.affiliation: Department of Biology, Lund University, 223 62, Lund, Sweden, glenn.svensson@biol.lu.se.
authors.forename: Glenn P
authors.initials: GP
authors.lastname: Svensson
authors.forename: Eylem Akman
authors.initials: EA
authors.lastname: Gündüz
authors.forename: Natalia
authors.initials: N
authors.lastname: Sjöberg
authors.forename: Erik
authors.initials: E
authors.lastname: Hedenström
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Lassance
authors.forename: Hong-Lei
authors.initials: HL
authors.lastname: Wang
authors.forename: Christer
authors.initials: C
authors.lastname: Löfstedt
authors.forename: Olle
authors.initials: O
authors.lastname: Anderbrant
mesh_terms: D000818:Animals; D004357:Drug Synergism; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D007300:Insect Control; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D009036:Moths; D010675:Pheromones / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D012724:Sex Attractants / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D012726:Sexual Behavior, Animal / Q000187:drug effects*; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D010675:Pheromones; D012724:Sex Attractants; C010411:insect attractants