Elucidating structure-bioactivity relationships of methyl-branched alkanes in the contact sex pheromone of the parasitic wasp Lariophagus distinguendus

Insects

Volumn 4, Issue 4, 2013, Pages 743-760

  Kühbandner, Stephan ^a   Bello, Jan E ^b   Mori, Kenji ^c   Millar, Jocelyn G ^b   Ruther, Joachim ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c TOYO GOSEI CO LTD   (Japan)

Author keywords

3 methylheptacosane; Chemoreception; Contact sex pheromone; Cuticular hydrocarbons; Lariophagus distinguendus; Parasitic wasp; Pteromalidae

Indexed keywords

EID: 84889801453     PISSN: None     EISSN: 20754450     Source Type: Journal    
DOI: 10.3390/insects4040743     Document Type: Article

References (60)

1. Howard, R.W.; Blomquist, G.J. Ecological, behavioral, and biochemical aspects of insect hydrocarbons. Annu. Rev. Entomol. 2005, 50, 371-393.
2. Buckner, J.S. Oxygenated derivatives of hydrocarbons. In Insect Hydrocarbons: Biology, Biochemistry, and Chemical Ecology; Blomquist, G.J., Bagnères, A.G., Eds.; Cambridge University Press: Cambridge, UK, 2010; pp. 187-204.
3. Kühbandner, S.; Sperling, S.; Mori, K.; Ruther, J. Deciphering the signature of cuticular lipids with contact sex pheromone function in a parasitic wasp. J. Exp. Biol. 2012, 215, 2471-2478.
4. Yew, J.Y.; Dreisewerd, K.; de Oliveira, C.C.; Etges, W.J. Male-specific transfer and fine scale spatial differences of newly identified cuticular hydrocarbons and triacylglycerides in a Drosophila species pair. PLoS One 2011, 6, e16898.
5. Mori, K. Pheromone synthesis. Part 253: Synthesis of the racemates and enantiomers of triglycerides of male Drosophila fruit flies with special emphasis on the preparation of enantiomerically pure 1-monoglycerides. Tetrahedron 2012, 68, 8441-8449.
6. Gibbs, A.G. Lipid melting and cuticular permeability: New insights into an old problem. J. Insect Physiol. 2002, 48, 391-400.
7. Howard, R.W.; Blomquist, G.J. Chemical ecology and biochemistry of insect hydrocarbons. Annu. Rev. Entomol. 1982, 27, 149-172.
8. Singer, T.L. Roles of hydrocarbons in the recognition systems of insects. Am. Zool. 1998, 38, 394-405.
9. Blomquist, G.J.; Bagnères, A.G. Introduction: History and overview of insect hydrocarbons. In Insect Hydrocarbons: Biology, Biochemistry, and Chemical Ecology; Howard, R.W., Blomquist, G.J., Eds.; Cambridge University Press: Cambridge, UK, 2010; pp. 3-18.
10. Dani, F.R.; Jones, G.R.; Destri, S.; Spencer, S.H.; Turillazzi, S. Deciphering the recognition signature within the cuticular chemical profile of paper wasps. Anim. Behav. 2001, 62, 165-171.
11. Van Wilgenburg, E.; Sulc, R.; Shea, K.J.; Tsutsui, N.D. Deciphering the chemical basis of nestmate recognition. J. Chem. Ecol. 2010, 36, 751-758.
12. Dani, F.R.; Jones, G.R.; Corsi, S.; Beard, R.; Pradella, D.; Turillazzi, S. Nestmate recognition cues in the honey bee: Differential importance of cuticular alkanes and alkenes. Chem. Senses 2005, 30, 477-489.
13. Van Wilgenburg, E.; Felden, A.; Choe, D.H.; Sulc, R.; Luo, J.; Shea, K.J.; Elgar, M.A.; Tsutsui, N.D. Learning and discrimination of cuticular hydrocarbons in a social insect. Biol. Lett. 2012, 8, 17-20.
14. Ozaki, M.; Wada-Katsumata, A.; Fujikawa, K.; Iwasaki, M.; Yokohari, F.; Satoji, Y.; Nisimura, T.; Yamaoka, R. Ant nestmate and non-nestmate discrimination by a chemo sensory sensillum. Science 2005, 309, 311-314.
15. Ozaki, M.; Wada-Katsumata, A. Perception and olfaction of cuticular compounds. In Insect Hydrocarbons: Biology, Biochemistry and Chemical Ecology; Blomquist, G.J., Bagnères, A.G., Eds.; Cambridge University Press: Cambridge, UK, 2010; pp. 207-221.
16. Espelie, K.E.; Wenzel, J.W.; Chang, G. Surface lipids of social wasp Polistes metricus Say and its nest and nest pedicel and their relation to nestmate recognition. J. Chem. Ecol. 1990, 16, 2229-2241.
17. Ginzel, M.D.; Blomquist, G.J.; Millar, J.G.; Hanks, L.M. Role of contact pheromones in mate recognition in Xylotrechus colonus. J. Chem. Ecol. 2003, 29, 533-545.
18. Sugeno, W.; Hori, M.; Matsuda, K. Identification of the contact sex pheromone of Gastrophysa atrocyanea (Coleoptera: Chrysomelidae). Appl. Entomol. Zool. 2006, 41, 269-276.
19. Lacey, E.S.; Ginzel, M.D.; Millar, J.G.; Hanks, L.M. 7-Methylheptacosane is a major component of the contact sex pheromone of the cerambycid beetle Neoclytus acuminatus acuminatus. Physiol. Entomol. 2008, 33, 209-216.
20. Silk, P.J.; Ryall, K.; Barry Lyons, D.; Sweeney, J.; Wu, J. A contact sex pheromone component of the emerald ash borer Agrilus planipennis Fairmaire (Coleoptera: Buprestidae). Naturwissenschaften 2009, 96, 601-608.
21. Châline, N.; Sandoz, J.C.; Martin, S.J.; Ratnieks, F.L.W.; Jones, G.R. Learning and discrimination of individual cuticular hydrocarbons by honeybees (Apis mellifera). Chem. Senses 2005, 30, 327-335.
22. Ginzel, M.D.; Moreira, J.A.; Ray, A.M.; Millar, J.G.; Hanks, L.M. (Z)-9-Nonacosene-Major component of the contact sex pheromone of the beetle Megacyllene caryae. J. Chem. Ecol. 2006, 32, 435-451.
23. Espelie, K.E.; Gamboa, G.J.; Grudzien, T.A.; Bura, E.A. Cuticular hydrocarbons of the paper wasp Polistes fuscatus: A search for recognition pheromones. J. Chem. Ecol. 1994, 20, 1677-1687.
24. Bos, N.; Dreier, S.; Jørgensen, C.G.; Nielsen, J.; Guerrieri, F.J.; D'Ettorre, P. Learning and perceptual similarity among cuticular hydrocarbons in ants. J. Insect Physiol. 2012, 58, 138-146.
25. Ablard, K.; Gries, R.; Khaskin, G.; Schaefer, P.W.; Gries, G. Does the stereochemistry of methylated cuticular hydrocarbons contribute to mate recognition in the egg parasitoid wasp Ooencyrtus kuvanae? J. Chem. Ecol. 2012, 38, 1306-1317.
26. Duff, C.M.; Gries, G.; Mori, K.; Shirai, Y.; Seki, M.; Takikawa, H.; Sheng, T.; Slessor, K.N.; Gries, R.; Maier, C.T.; et al. Does pheromone biology of Lambdina athasaria and L. pellucidaria contribute to their reproductive isolation? J. Chem. Ecol. 2001, 27, 431-442.
27. Hansen, L.S.; Lövei, G.L.; Székács, A. Survival and development of a stored-product pest, Sitophilus zeamais (Coleoptera: Curculionidae), and its natural enemy, the parasitoid Lariophagus distinguendus (Hymenoptera: Pteromalidae), on transgenic Bt maize. Pest Manag. Sci. 2013, 69, 602-606.
28. Steidle, J.L.M.; Schöller, M. Olfactory host location and learning in the granary weevil parasitoid Lariophagus distinguendus (Hymenoptera: Pteromalidae). J. Insect Behav. 1997, 10, 331-342.
29. Ruther, J.; Homann, M.; Steidle, J.L.M. Female-derived sex pheromone mediates courtship behaviour in the parasitoid Lariophagus distinguendus. Entomol. Exp. Appl. 2000, 96, 265-274.
30. Benelli, G.; Bonsignori, G.; Stefanini, C.; Dario, P.; Canale, A. Male wing fanning performance during successful and unsuccessful mating in the parasitic wasp Lariophagus distinguendus Förster (Hymenoptera: Pteromalidae). J. Insect Behav. 2013, 26, 228-237.
31. Steiner, S.; Steidle, J.L.M.; Ruther, J. Female sex pheromone in immature insect males-A case of pre-emergence chemical mimicry? Behav. Ecol. Sociobiol. 2005, 58, 111-120.
32. Steiner, S.; Mumm, R.; Ruther, J. Courtship pheromones in parasitic wasps: Comparison of bioactive and inactive hydrocarbon profiles by multivariate statistical methods. J. Chem. Ecol. 2007, 33, 825-838.
33. Van Zweden, J.S.; D'Ettore, P. Nestmate recognition in social insects and the role of cuticular hydrocarbons. In Insect Hydrocarbons: Biology, Biochemistry and Chemical Ecology; Blomquist, G.J., Bagnères, A.G., Eds.; Cambridge University Press: Cambridge, UK, 2010; pp. 222-243.
34. Wang, S.; Zhang, A. An improved copper-catalyzed cross-coupling reaction of alkyl triflates with primary alkyl Gringnard reagents. Org. Prep. Proced. Int. 2008, 40, 293-301.
35. Cahiez, G.; Chaboche, C.; Jézéquel, M. Cu-catalyzed alkylation of Grignard reagents: A new efficient procedure. Tetrahedron 2000, 56, 2733-2737.
36. Aizpurua, J.M.; Cossio, F.P.; Palomo, C. Reagents and synthetic methods. 61. Reaction of hindered trialkylsilyl esters and trialkylsilyl ethers with triphenylphosphine dibromide: Preparation of carboxylic acid bromides and alkyl bromides under mild neutral conditions. J. Org. Chem. 1986, 51, 4941-4943.
37. Buck, M.; Chong, J.M. Alkylation of 1-alkynes in THF. Tetrahedron Lett. 2001, 42, 5825-5827.
38. Zou, Y.; Millar, J.G. Stereoselective synthesis of the obscure mealybug pheromone by hydrogenation of a tetrasubstituted alkene precursor. Tetrahedron Lett. 2011, 52, 4224-4226.
39. Sonnet, P.E.; Heath, R.R. Stereospecific synthesis of (Z, Z)-11,13-hexadecadienal, a female sex pheromone of the navel orangeworm, Amyelois transitella (Lepidoptera: Pyralidae). J. Chem. Ecol. 1980, 6, 221-228.
40. Barth, S.; Effenberger, F. Lipase-catalyzed resolution of racemic 2-alkyl substituted 1-alkanols. Tetrahedron Asymmetry 1993, 4, 823-833.
41. Benoit, D.; Coulbeck, E.; Eames, J.; Motevalli, M. On the structure and chiroptical properties of (S)-4-isopropyl-oxazolidin-2-one. Tetrahedron Asymmetry 2008, 19, 1068-1077.
42. Kanomata, N.; Maruyama, S.; Tomono, K.; Anada, S. A simple method removing 2-oxazolidinone and 2-hydroxyethylamine auxiliaries in methoxide-carbonate systems for synthesis of planar-chiral nicotinate. Tetrahedron Lett. 2003, 44, 3599-3603.
43. Evans, D.A.; Ennis, M.D.; Mathre, D.J. Asymmetric alkylation reactions of chiral imide enolates. A practical approach to the enantioselective synthesis of. alpha.-substituted carboxylic acid derivatives. J. Am. Chem. Soc. 1982, 104, 1737-1739.
44. Williams, D.R.; Patnaik, S.; Plummer, S.V. Leucascandrolide A: A second generation formal synthesis. Org. Lett. 2003, 5, 5035-5038.
45. Corey, E.J.; Fuchs, P.L. A synthetic method for formyl→ethynyl conversion (RCHO→RCξCH or RC=CR'). Tetrahedron Lett. 1972, 13, 3769-3772.
46. Armstrong-Chong, R.J.; Matthews, K.; Chong, J.M. Sequential alkynylation of ω-bromoalkyl triflates: Facile access to unsymmetrical non-conjugated diynes including precursors to diene pheromones. Tetrahedron 2004, 60, 10239-10244.
47. Bello, J.E.; Millar, J.G. Efficient asymmetric synthesis of long chain methyl-branched hydrocarbons, components of the contact sex pheromone of females of the cerambycid beetle, Neoclytus acuminatus acuminatus. Tetrahedron Asymmetry 2013, 24, 822-826.
48. Marukawa, K.; Takikawa, H.; Mori, K. Synthesis of the enantiomers of some methyl-branched cuticular hydrocarbons of the ant Diacamma sp. Biosci. Biotechnol. Biochem. 2001, 65, 305-314.
49. R Core Team R. A Language and Environment for Statistical Computing; R Foundation for Statistical Computing: Vienna, Austria, 2012.
50. Ruther, J.; Steiner, S. Costs of female odour in males of the parasitic wasp Lariophagus distinguendus (Hymenoptera: Pteromalidae). Naturwissenschaften 2008, 95, 547-552.
51. Carlson, D.A.; Langley, P.A.; Huyton, P. Sex pheromone of the tsetse fly: Isolation, identification, and synthesis of contact aphrodisiacs. Science 1978, 201, 750-753.
52. Carlson, D.A.; Offor, I.I.; El Messoussi, S.; Matsuyama, K.; Mori, K.; Jallon, J.M. Sex pheromone of Glossina tachinoides: Isolation, identification, and synthesis. J. Chem. Ecol. 1998, 24, 1563-1575.
53. Rutledge, C.E.; Millar, J.G.; Romero, C.M.; Hanks, L.M. Identification of an important component of the contact sex pheromone of Callidiellum rufipenne (Coleoptera: Cerambycidae). Environ. Entomol. 2009, 38, 1267-1275.
54. Spikes, A.E.; Paschen, M.A.; Millar, J.G.; Moreira, J.A.; Hamel, P.B.; Schiff, N.M.; Ginzel, M.D. First contact pheromone identified for a longhorned beetle (Coleoptera: Cerambycidae) in the subfamily Prioninae. J. Chem. Ecol. 2010, 36, 943-954.
55. Guerrieri, F.J.; Nehring, V.; Jorgensen, C.G.; Nielsen, J.; Galizia, C.G.; d'Ettorre, P. Ants recognize foes and not friends. Proc. R. Soc. B 2009, 276, 2461-2468.
56. Steiner, S.; Hermann, N.; Ruther, J. Characterization of a female-produced courtship pheromone in the parasitoid Nasonia vitripennis. J. Chem. Ecol. 2006, 32, 1687-1702.
57. Ruther, J.; Döring, M.; Steiner, S. Cuticular hydrocarbons as contact sex pheromone in the parasitoid Dibrachys cavus. Entomol. Exp. Appl. 2011, 140, 59-68.
58. Hefetz, A.; Wicker-Thomas, C.; Bagnères, A.G. Future directions in hydrocarbon research. In Insect Hydrocarbons: Biology, Biochemistry and Chemical Ecology; Blomquist, G.J., Bagnères, A.G., Eds.; Cambridge University Press: Cambridge, UK, 2010; pp. 477-485.
59. Millar, J.G. Chemical synthesis of insect cuticular hydrocarbons. In Insect Hydrocarbons: Biology, Biochemistry and Chemical Ecology; Blomquist, G.J., Bagnères, A.G., Eds.; Cambridge University Press: Cambridge, UK, 2010; pp. 163-186.
60. Ruther, J. Novel insights into pheromone-mediated communication in parasitic hymenopterans. In Chemical Ecology of Insect Parasitoids; Wajnberg, E., Colazza, S., Eds.; Wiley-Blackwell: Chichester, UK, 2013; pp. 112-144.