Structure-response relationships in noctuid sex pheromone reception. An introductory report

Abstract

Electroantennogram (EAG) data reflecting response spectra of male pheromone receptors have been analyzed for 16 species of Noctuidae (Lepidoptera). The test compounds included 100 pheromone analogues, altered in chain length, in position and configuration of double bond(s), and in the functional end groups. On comparison of amounts of substance required to elicit an equivalent EAG response, a single compound was determined to be most effective on a given species: these structures, either known or proposed as the natural sex pheromones of the species, were cis-7-dodecen-1-y1 acetate, cis-7-tetradecen-1-y1 acetate, cis-9-tetradecen-1-yu acetate, trans-9-tetradecen-1-y1 acetate, cis-11-hexadecen-1-y1 acetate, cis-9, trans-12-tetradecadien-1-y1 acetate, cis-9-tetradecen-1-y1 formate, and cis-9-tetradecen-1-ol, respectively. Elongation (shortening) of the chain by 1 or 2 methylene groups, the movement of a double bond 1 carbon from the optimum, a change to the opposite geometrical isomer, or the introduction of a second double bond invariably reduced EAG responses to 1.8 to 56 times below that observed with the most stimulating compound, in all 16 species. Further alterations in chain length or in double bond position caused even greater reduction in activity, as did certain in end group (Tables I and II). A set of distinct rules could be derived from these structure-response relationships; one of these rules concerns the optimum position of the double bond(s) in relation to chain length, and another one the ratios in activity values produced by end group variations, irrespective of chain length. The same rules described here for 16 noctuid species held also for the structure-response relationships observed within various additional groups of Lepidoptera. From EAG values determined in this study, an attempt has been made to calculate physicochemical propteries of underlying acceptor structures.