Ipsdienol-specific receptor cells in bark beetles: structure-activity relationships of various analogues and of deuterium-labelled ipsdienol |
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| Authors: | H Mustaparta B Å Tømmerås P Baeckström J M Bakke G Ohloff |
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| Institution: | (1) Department of Zoology, University of Trondheim, N-7055 Dragvoll;(2) Department of Organic Chemistry, Royal Institute of Technology, Stockholm, Sweden;(3) Laboratory of Organic Chemistry, Norwegian Institute of Technology, University of Trondheim, N-7055 Dragvoll, Norway;(4) Firmenich Company, Geneva, Switzerland |
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| Abstract: | Summary The specificity of receptor cells specialized for the bark beetle pheromone component, ipsdienol, was studied electrophysiologically (extracellular recordings) in species ofIps. Single cells were tested with both ipsdienol enantiomers, their racemate, and racemates of structurally similar compounds. The two cell types, keyed to (+)- and to (–)-ipsdienol, respectively, showed much weaker responses to the analogues, demonstrating the high specialization of the cells. The relationships between the dose-response curves of the two types were similar, favoring the concept of particular membrane receptor types (acceptors) in both cell types.The stimulatory efficacy of the various analogues suggested three key features of ipsdienol: (i) the free hydroxyl group at C-4, (ii) the C-2-C-3 double bond, and (iii) the diene system attached to C-5 which may be in acis-conformation.Substituting the C-4 hydrogen by deuterium did not affect the stimulatory effect of ipsdienol. |
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