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

C. R. Unelius, K. C. Park, M. McNeill, Wee Suk Ling, B. Bohman, D. M. Suckling

Research output: Contribution to journalArticle

4 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)135-143
Number of pages9
JournalNaturwissenschaften
Volume100
Issue number2
DOIs
Publication statusPublished - Feb 2013

Fingerprint

Weevils
Medicago sativa
Olfactory Receptor Neurons
alfalfa
Curculionidae
stereoisomers
Stereoisomerism
olfactory receptors
Sensilla
neurons
sensilla
antennae
antenna
gender
Sitona
Pseudozyma antarctica
aggregation pheromone
diastereomers
aggregation pheromones
electroantennography

Keywords

  • (4S,5S)-5-hydroxy-4-methyl-3-heptanone
  • 4-Methyl-3,5- heptanedione
  • Lucerne weevil
  • Medicago
  • Pheromone
  • Sitona discoideus

ASJC Scopus subject areas

  • Ecology, Evolution, Behavior and Systematics
  • Medicine(all)

Cite this

Identification and electrophysiological studies of (4S,5S)-5-hydroxy-4- methyl-3-heptanone and 4-methyl-3,5-heptanedione in male lucerne weevils. / Unelius, C. R.; Park, K. C.; McNeill, M.; Suk Ling, Wee; Bohman, B.; Suckling, D. M.

In: Naturwissenschaften, Vol. 100, No. 2, 02.2013, p. 135-143.

Research output: Contribution to journalArticle

Unelius, C. R. ; Park, K. C. ; McNeill, M. ; Suk Ling, Wee ; Bohman, B. ; Suckling, D. M. / Identification and electrophysiological studies of (4S,5S)-5-hydroxy-4- methyl-3-heptanone and 4-methyl-3,5-heptanedione in male lucerne weevils. In: Naturwissenschaften. 2013 ; Vol. 100, No. 2. pp. 135-143.
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abstract = "An investigation to identify a sex or aggregation pheromone of Sitona discoideus Gyllenh{\aa}l (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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