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Journal of Chemical Ecology

, Volume 40, Issue 4, pp 387–395 | Cite as

Identification, Synthesis, and Behavioral Activity of 5,11-Dimethylpentacosane, A Novel Sex Pheromone Component of the Greater Wax Moth, Galleria Mellonella (L.)

  • Glenn P. SvenssonEmail author
  • Eylem Akman Gündüz
  • Natalia Sjöberg
  • Erik Hedenström
  • Jean-Marc Lassance
  • Hong-Lei Wang
  • Christer Löfstedt
  • Olle Anderbrant
Article

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.

Keywords

Galleria mellonella Male pheromone 5,11-dimethylpentacosane Electrophysiology Behavior Synthesis Honeybee pest Lepidoptera 

Notes

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.

Supplementary material

10886_2014_410_MOESM1_ESM.doc (1.7 mb)
ESM 1 (DOC 1777 kb)

References

  1. Abdalla FC, Jones GR, Morgan ED, Cruz-Landim C (2003) Comparative study of the cuticular hydrocarbon composition of Melipona bicolor Lepeletier, 1836 (Hymenoptera, Meliponini) workers and queens. Genet Mol Res 2:191–199PubMedGoogle Scholar
  2. Bagnères AG, Morgan ED (1990) A simple method for analysis of insect cuticular hydrocarbons. J Chem Ecol 16:3263–3276PubMedCrossRefGoogle Scholar
  3. Birch MC, Poppy GM, Baker TC (1990) Scents and eversible scent structures of male moths. Annu Rev Entomol 35:25–58CrossRefGoogle Scholar
  4. Dahm KH, Meyer D, Finn WE, Reinhold V, Röller H (1971) The olfactory and auditory mediated sex attraction in Achroia grisella (Fabr.). Naturwissenschaften 58:265–266PubMedCrossRefGoogle Scholar
  5. Flint HM, Merkle JR (1983) Mating behaviour, sex pheromone responses and radiation sterilization of the greater wax moth (Lepidoptera: Pyralidae). J Econ Entomol 76:467–472Google Scholar
  6. Kalinová B, Kindl J, Jiroš P, Žáček P, Vašíčková S, Buděšínský M, Valterová I (2009) Composition and electrophysiological activity of constituents identified in male wing gland secretion of the bumblebee parasite Aphomia sociella. J Nat Prod 72:8–13PubMedCrossRefGoogle Scholar
  7. Kindl J, Kalinová B, Červenka M, Jílek M, Valterová I (2011) Male moth songs tempt females to accept mating: the role of acoustic and pheromonal communication in the reproductive behaviour of Aphomia sociella. PLoS One 6(10):e26476PubMedCentralPubMedCrossRefGoogle Scholar
  8. Lassance JM, Löfstedt C (2009) Concerted evolution of male and female display traits in the European corn borer, Ostrinia nubilalis. BMC Biol 7:10PubMedCentralPubMedCrossRefGoogle Scholar
  9. Leyrer RL, Monroe RE (1973) Isolation and identification of the scent of the moth, Galleria melonella, and a reevaluation of its sex pheromone. J Insect Physiol 19:2267–2271CrossRefGoogle Scholar
  10. Lockey KH (1988) Lipids of the insect cuticle: origin, composition and function. Comp Biochem Physiol 89B:595–645Google Scholar
  11. Nielsen RA, Brister CD (1977) The Greater wax moth: adult behavior. Ann Entomol Soc Am 70:101–103Google Scholar
  12. Nielsen RA, Brister CD (1979) Greater wax moth: behaviour of larvae. Ann Entomol Soc Am 72:811–815Google Scholar
  13. Payne TL, Finn WE (1977) Pheromone receptor system in the females of the greater wax moth Galleria mellonella. J Insect Physiol 23:879–881CrossRefGoogle Scholar
  14. Phelan LP (1997) Evolution of mate-signaling in moths: Phylogenetic considerations and predictions from the asymmetric tracking hypothesis. In: Choe JC, Crespi BJ (eds) The evolution of mating systems in insects and arachnids. Cambridge University Press, Cambridge, pp 240–256CrossRefGoogle Scholar
  15. Romel KE, Scott-Dupree CD, Carter MH (1992) Qualitative and quantitative analyses of volatiles and pheromone gland extracts collected from Galleria mellonella (L.) (Leptidoptera: Pyralidae). J Chem Ecol 18:1255–1268PubMedCrossRefGoogle Scholar
  16. Schmidt SP, Monroe RE (1976) Biosynthesis of the waxmoth sex attractants. Insect Biochem 6:377–380CrossRefGoogle Scholar
  17. Spangler HG (1986) Functional and temporal analysis of sound production in Galleria mellonella (Lepidoptera: Pyralidae). J Comp Physiol A 159:751–756CrossRefGoogle Scholar
  18. Spangler HG (1987) Acoustically mediated pheromone release in Galleria mellonella (Lepidoptera: Pyralidae). J Insect Physiol 7:465–468CrossRefGoogle Scholar
  19. Steinmetz I, Schmolz E, Ruther J (2003) Cuticular lipids as trail pheromone in a social wasp. Proc R Soc Lond B 270:385–391CrossRefGoogle Scholar
  20. Svensson GP, Löfstedt C, Skals N (2004) The odour makes the difference: male moths attracted by sex pheromones ignore the threat from predatory bats. Oikos 104:91–97CrossRefGoogle Scholar
  21. Tachinami T, Nishimura T, Ushimaru R, Noyori R, Naka H (2013) Hydration of terminal alkynes catalyzed by water-soluble cobalt porphyrin complexes. J Am Chem Soc 135:50–53PubMedCrossRefGoogle Scholar
  22. Witzgall P (1997) Modulation of pheromone-mediated flight in male moths. In: Cardé RT, Minks A (eds) Insect pheromone research: New directions. Chapman and Hall, New York, pp 248–264Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Glenn P. Svensson
    • 1
    Email author
  • Eylem Akman Gündüz
    • 2
  • Natalia Sjöberg
    • 3
  • Erik Hedenström
    • 3
  • Jean-Marc Lassance
    • 1
    • 4
  • Hong-Lei Wang
    • 1
  • Christer Löfstedt
    • 1
  • Olle Anderbrant
    • 1
  1. 1.Department of BiologyLund UniversityLundSweden
  2. 2.Department of BiologyOndokuz Mayıs UniversitySamsunTurkey
  3. 3.Eco-Chemistry, Department of Chemical EngineeringMid Sweden UniversitySundsvallSweden
  4. 4.Department of Organismic and Evolutionary BiologyHarvard UniversityCambridgeUSA

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