Abstract
Studies on structure–activity relationships were carried out to characterize the response specificity of the benzoic acid cell of the female of the moth Bombyx mori by means of single sensillum electrophysiological recordings. We demonstrated that this cell type responds best to a natural key substance (benzoic acid) and has similar response profiles for less effective compounds, including various halogen substitutes of benzoic acid, benzaldehyde and other derivates of the key compound. Using different halogen substitutes (F, Cl, Br, I), we showed that the cellular response decreases with increasing atomic size of the substitute and that halogen substitutes were most effective in the meta-position. Thus, m-fluor benzoic acid was even more effective than benzoic acid. These results indicate that a critical feature of the stimulus molecule is the inductive effect generated by the halogen substitutes. Increasing the atomic size of the halogen substitute impairs the recognition of the molecule by the receptor cell, possibly due to steric effects. Decreasing the electron density in the aromatic ring improves the receptor response. The benzoic acid receptor cell can be considered as specialist despite not being involved in pheromone detection as it responds maximally to a key substance and has similar response profiles for less effective compounds.
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Acknowledgements
We are very grateful to B. Pophof for invaluable help and support, to J. Kovensky for useful discussions on organic chemistry topics, to Didier Bourissou and Christelle Freund (Laboratory of Basic and Applied Heterochemistry, University Paul Sabatier of Toulouse) for much help with organic chemistry databases and to M. Gauthier, M. Giurfa and two anonymous referees for comments and corrections on earlier versions of the manuscript. Thanks are due to D. Conesa for language corrections. G. de Brito Sanchez acknowledges the support of C. Lazzari and J. Núñez and the doctoral fellowships of the Max-Planck Gesellschaft and the DAAD (German Academic Exchange Service).
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Sanchez, M.G.d.B., Kaissling, KE. The antennal benzoic acid receptor cell of the female silk moth Bombyx mori L.: structure–activity relationship studies with halogen substitutes. J Comp Physiol A 191, 189–196 (2005). https://doi.org/10.1007/s00359-004-0588-2
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DOI: https://doi.org/10.1007/s00359-004-0588-2