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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
Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.ORCID iD: 0000-0001-7158-6393
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2013 (English)In: Die Naturwissenschaften, ISSN 0028-1042, E-ISSN 1432-1904, Vol. 100, no 2, 135-143 p.Article in journal (Refereed) Published
Abstract [en]

An investigation to identify a sex or aggregation pheromone of Sitona discoideus GyllenhAyenl (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.

Place, publisher, year, edition, pages
2013. Vol. 100, no 2, 135-143 p.
Keyword [en]
Sitona discoideus, Lucerne weevil, Medicago, Pheromone, 4-Methyl-3, 5-heptanedione, (4S, 5S)-5hydroxy-4-methyl-3-heptanone
National Category
Biochemistry and Molecular Biology
Research subject
Natural Science, Ecological chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-24746DOI: 10.1007/s00114-012-1003-4ISI: 000314275500003OAI: oai:DiVA.org:lnu-24746DiVA: diva2:610603
Available from: 2013-03-12 Created: 2013-03-12 Last updated: 2017-01-11Bibliographically approved

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Unelius, C. RikardBohman, Björn
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