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Identification, synthesis, and behavioral activity of 5,11-Dimethylpentacosane, A novel sex pheromone component of the greater wax moth, Galleria mellonella (L.)

Svensson, Glenn LU ; Gunduz, Eylem Akman; Sjöberg, Natalia; Hedenström, Erik; Lassance, Jean-Marc LU ; Wang, Hong-Lei LU ; Löfstedt, Christer LU and Anderbrant, Olle LU (2014) In Journal of Chemical Ecology 40(4). p.387-395
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Behavior, Synthesis, Honeybee pest, Lepidoptera, Electrophysiology, 11-dimethylpentacosane, 5, Galleria mellonella, Male pheromone
in
Journal of Chemical Ecology
volume
40
issue
4
pages
387 - 395
publisher
Springer
external identifiers
  • pmid:24692052
  • wos:000335656800018
  • scopus:84899912959
ISSN
1573-1561
DOI
10.1007/s10886-014-0410-8
project
Pheromones and kairomones of stored product pests
language
English
LU publication?
yes
id
ed64b13f-5985-4cfb-b215-d8f9b90a6fde (old id 4482239)
date added to LUP
2014-06-19 13:29:03
date last changed
2017-07-02 04:14:18
@article{ed64b13f-5985-4cfb-b215-d8f9b90a6fde,
  abstract     = {The greater wax moth, <i>Galleria mellonella</i> (L.), is a serious and widespread pest of the honeybee, <i>Apis mellifera</i> L. In contrast to most moths, for which long-range mate finding is mediated by female-produced sex pheromones, <i>G. mellonella</i> 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 <i>G. mellonella</i> 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.},
  author       = {Svensson, Glenn and Gunduz, Eylem Akman and Sjöberg, Natalia and Hedenström, Erik and Lassance, Jean-Marc and Wang, Hong-Lei and Löfstedt, Christer and Anderbrant, Olle},
  issn         = {1573-1561},
  keyword      = {Behavior,Synthesis,Honeybee pest,Lepidoptera,Electrophysiology,11-dimethylpentacosane,5,Galleria mellonella,Male pheromone},
  language     = {eng},
  number       = {4},
  pages        = {387--395},
  publisher    = {Springer},
  series       = {Journal of Chemical Ecology},
  title        = {Identification, synthesis, and behavioral activity of 5,11-Dimethylpentacosane, A novel sex pheromone component of the greater wax moth, <i>Galleria mellonella</i> (L.)},
  url          = {http://dx.doi.org/10.1007/s10886-014-0410-8},
  volume       = {40},
  year         = {2014},
}