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Andrena wilkella male bees discriminate between enantiomers of cephalic secretion components

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Abstract

Diastereomers of the spiroacetal, 2,8-dimethyl-1,7-dioxaspiro [5.5]undecane, represent main components of the cephalic secretion from males of the solitary bee,Andrena wilkella. The major compound proved to be of high enantiomeric purity, showing (2S,6R,8S) configuration. Only the naturally occurring enantiomer attracted patrolling males in the field; its antipode was behaviorally inactive and in a racemic mixture did not inhibit response. The (E,Z) diastereomers were also found to be almost inactive. EAG studies gave the same result as the behavioral tests. The biological function of the spiroacetal is discussed in view of the evolution of the mating behavior inA. wilkella.

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Authors and Affiliations

  1. Ecological Research Station of Uppsala University, S-386 00, Färjestaden, Sweden

    Jan Tengö, Lennart Ågren & Bruno Baur

  2. Division of Organic Chemistry 3, Chemical Centre University of Lund, P.O. Box 124, 5-227 00, Lund, Sweden

    Roland Isaksson & Tommy Liljefors

  3. Department of Agricultural Chemistry, The University of Tokyo, Bunkyo-ku, 113, Tokyo, Japan

    Kenji Mori

  4. Department of Organic Chemistry, Hamburg University, Martin-Luther-King-Platz 6, D-2000, Hamburg 13, Federal Republic of Germany

    Wilfried König & Wittko Francke

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  1. Jan Tengö
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Tengö, J., Ågren, L., Baur, B. et al. Andrena wilkella male bees discriminate between enantiomers of cephalic secretion components. J Chem Ecol 16, 429–441 (1990). https://doi.org/10.1007/BF01021775

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  • DOI: https://doi.org/10.1007/BF01021775

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