Abstract
We identified 4-methylquinazoline (4-MeQ) as a minor component of the male sex pheromone of the parasitoid Nasonia vitripennis. Like the major components (4R,5R)- and (4R,5S)-5-hydroxy-4-decanolide (HDL), 4-MeQ is synthesized in the abdomen of males. At doses of 6 or 1 ng, 4-MeQ synergized the response of virgin females to the HDL-diastereomers in a still-air olfactometer, but was not attractive as a single component. 4-MeQ is also responsible for the characteristic medicinal odor of N. vitripennis males.
This is a preview of subscription content, log in via an institution to check access.
References
Bailey, R. J. E., Birkett, M. A., Ingvarsdottir, A., Mordue, A. J., Mordue, W., O’Shea, B., Pickett, J. A., and Wadhams, L. J. 2006. The role of semiochemicals in host location and non-host avoidance by salmon louse (Lepeophtheirus salmonis) copepodids. Can. J. Fish. Aqu. Sci. 63:448–456.
Bergmann, J., Brynolf, A., Elman, B., and Vuorinen, E. 1986. Synthesis of quinazolines. Tetrahedron 42:3697–3706.
Cônsoli, F. L., Williams, H. J., Vinson, S. B., Matthews, R. W., and Cooperband, M. F. 2002. trans-Bergamotenes-male pheromone of the ectoparasitoid Melittobia digitata. J. Chem. Ecol 28:1675–1689.
Cruz-López, L. and Morgan, D. 1995. Chemical investigation of aggregation behavior of Triatoma bugs (Hemiptera: Reduviidae). J. Chem. Ecol 21:2069–2078.
D’yakonov, A. L. and Telezhenetskaya, M. V. 1997. Quinazoline alkaloids in nature. Chem. Nat. Prod 33:221–267.
Garbe, L. A. and Tressl, R. 2003. Metabolism of deuterated isomeric 6,7-dihydroxydodecanoic acids in Saccharomyces cerevisiae—diastereo- and enantioselective formation and characterization of 5-hydroxydecano-4-lactone (= 4,5-dihydro-5-(1-hydroxyhexyl)furan-2(3H)-one) isomers. Helv. Chim. Acta 86:2349–2363.
Ruther, J., Stahl, L. M., Steiner, S., Garbe, L. A., and Tolasch, T. 2007. A male sex pheromone in a parasitic wasp and control of the behavioral response by the female’s mating status. J. Exp. Biol 210:2163–2169.
Steiner, S., Hermann, N., and Ruther, J. 2006. Characterization of a female-produced courtship pheromone in the parasitoid Nasonia vitripennis. J. Chem. Ecol 32:1687–1702.
Van den Assem, J., Jachmann, F., and Simbolotti, P. 1980. Courtship behaviour of Nasonia vitripennis (Hym., Pteromalidae): Some qualitative, experimental evidence for the role of pheromones. Behaviour 75:301–307.
Zhang, J. X., Soini, H. A., Bruce, K. E., Wiesler, D., Woodley, S. K., Baum, M. J., and Novotny, M. V. 2005. Putative chemosignals of the ferret (Mustela furo) associated with individual and gender recognition. Chem. Senses 30:727–737.
Acknowledgements
This research was funded by the Deutsche Forschungsgemeinschaft (DFG, grant RU-717/8-1). J. R. was supported by a Heisenberg fellowship of the DFG (grant RU-717/7-1). The authors thank Waltraud Poppe (Technical University of Berlin) for technical assistance.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ruther, J., Steiner, S. & Garbe, LA. 4-Methylquinazoline is a Minor Component of the Male Sex Pheromone in Nasonia vitripennis . J Chem Ecol 34, 99–102 (2008). https://doi.org/10.1007/s10886-007-9411-1
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10886-007-9411-1