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Identification and electrophysiological studies of (4S,5S)-5-hydroxy-4-methyl-3-heptanone and 4-methyl-3,5-heptanedione in male lucerne weevils

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Abstract

An investigation to identify a sex or aggregation pheromone of Sitona discoideus Gyllenhål (Coleoptera: Curculionidae) is presented. Antenna flicking and attraction behaviors evoked by conspecifics of both sexes were recorded in arena bioassays, where attraction of females to males was observed. Air entrainment of both males and females was conducted in separate chambers. Gas chromatographic–mass spectrometric analysis of headspace volatiles revealed that two male-specific compounds, 4-methyl-3,5-heptanedione (major) and (4S,5S)-5-hydroxy-4-methyl-3-heptanone (minor), were emitted during the autumnal post-aestivatory flight period. The stereoisomers of the minor component were separated by enantioselective gas chromatography and their absolute configurations assigned by NMR (diastereomers) and the known preference of enantioselective transesterification reactions catalyzed by Candida antarctica lipase B. Electroantennogram and single sensillum recording studies indicate that 4-methyl-3,5-heptanedione as well as all individual stereoisomers of 5-hydroxy-4-methyl-3-heptanone are detected by the antennae of male and female S. discoideus. Further, single sensillum recordings suggest that both sexes of S. discoideus have specialized olfactory receptor neurons (ORNs) for detecting 4-methyl-3,5-heptanedione and different populations of stereoselective ORNs for detecting the stereoisomers of 5-hydroxy-4-methyl-3-heptanone. Some of these stereoselective ORNs appear to be sex-specific in S. discoideus.

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Acknowledgments

We thank B. J. Bunn for synthesis of 4-methyl-3,5-heptanedione and J. Daly and A. R. Gibb for their assistance in the initial studies. This research was funded by the Ministry of Building Innovation and Employment through the Bio-Protection Research Centre (LINX0304, contract 25949). The Linnaeus University, Kalmar, Sweden, is gratefully acknowledged for financial support of BB and CRU.

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Authors and Affiliations

  1. The New Zealand Institute for Plant & Food Research Limited, PB 4704, Christchurch, 8140, New Zealand

    C. R. Unelius, K.-C. Park, S. L. Wee & D. M. Suckling

  2. AgResearch Limited, Lincoln Research Centre, PB 4749, Christchurch, 8140, New Zealand

    M. McNeill

  3. School of Natural Sciences, Linnaeus University, 391 82, Kalmar, Sweden

    C. R. Unelius & B. Bohman

  4. School of Environmental and Natural Resource Sciences, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, Bangi, Malaysia

    S. L. Wee

  5. Research School of Chemistry and Research School of Biology, The Australian National University, Canberra, ACT 0200, Australia

    B. Bohman

Authors
  1. C. R. Unelius
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  2. K.-C. Park
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  3. M. McNeill
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  4. S. L. Wee
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  5. B. Bohman
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  6. D. M. Suckling
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Correspondence to C. R. Unelius.

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Communicated by: Sven Thatje

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Unelius, C.R., Park, KC., McNeill, M. et al. Identification and electrophysiological studies of (4S,5S)-5-hydroxy-4-methyl-3-heptanone and 4-methyl-3,5-heptanedione in male lucerne weevils. Naturwissenschaften 100, 135–143 (2013). https://doi.org/10.1007/s00114-012-1003-4

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  • DOI: https://doi.org/10.1007/s00114-012-1003-4

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