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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.)

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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 ofG. 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.

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Acknowledgments

We thank Hany Dweck for sending moth larvae, Dr Palle Breistein for part of the syntheses of pentacosanes, and Dr Joakim Bång for purification of moth extracts and some initial GC/MS analyses. Jon Loman provided wax cakes for the last instar larvae. This study was supported by a joint research grant under the Middle East and North Africa – Swedish Research Links Program to EAG and OA, and from grants by The Swedish Research Council (VR) and Birgit and Sven Håkan Ohlsson foundation to CL. NS and EH are grateful for the financial support from the European Union European Regional Development Fund and the County Administrative Board of Västernorrland.

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Author notes

  1. Jean-Marc Lassance

    Present address: Department of Organismic and Evolutionary Biology, Harvard University, Cambridge, MA, 02138, USA

Authors and Affiliations

  1. Department of Biology, Lund University, 223 62, Lund, Sweden

    Glenn P. Svensson, Jean-Marc Lassance, Hong-Lei Wang, Christer Löfstedt & Olle Anderbrant

  2. Department of Biology, Ondokuz Mayıs University, 55139, Kurupelit, Samsun, Turkey

    Eylem Akman Gündüz

  3. Eco-Chemistry, Department of Chemical Engineering, Mid Sweden University, 85170, Sundsvall, Sweden

    Natalia Sjöberg & Erik Hedenström

Authors
  1. Glenn P. Svensson
  2. Eylem Akman Gündüz
  3. Natalia Sjöberg
  4. Erik Hedenström
  5. Jean-Marc Lassance
  6. Hong-Lei Wang
  7. Christer Löfstedt
  8. Olle Anderbrant

Corresponding author

Correspondence toGlenn P. Svensson.

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Svensson, G.P., Gündüz, E.A., Sjöberg, N.et al. Identification, Synthesis, and Behavioral Activity of 5,11-Dimethylpentacosane, A Novel Sex Pheromone Component of the Greater Wax Moth,Galleria Mellonella (L.).J Chem Ecol40, 387–395 (2014). https://doi.org/10.1007/s10886-014-0410-8

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