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Naturwissenschaften

Title:		"Identification and electrophysiological studies of (4S,5S)-5-hydroxy-4-methyl-3-heptanone and 4-methyl-3,5-heptanedione in male lucerne weevils"
Author(s):		Unelius CR; Park KC; McNeill M; Wee SL; Bohman B; Suckling DM;
Address:		"The New Zealand Institute for Plant & Food Research Limited, PB 4704, Christchurch, 8140, New Zealand. rikard.unelius@lnu.se"
Journal Title:		Naturwissenschaften
Year:		2013
Volume:		20121213
Issue:		2
Page Number:		135 - 143
DOI:		10.1007/s00114-012-1003-4
ISSN/ISBN:		1432-1904 (Electronic) 0028-1042 (Linking)
Abstract:		"An investigation to identify a sex or aggregation pheromone of Sitona discoideus Gyllenhal (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"
Keywords:		"Animals Arthropod Antennae/drug effects Behavior, Animal/drug effects Chromatography, Gas Electrophysiological Phenomena/*drug effects Female Ketones/isolation & purification/pharmacology Male Olfactory Receptor Neurons/drug effects/metabolism Sex Attract;"
Notes:		"MedlineUnelius, C R Park, K-C McNeill, M Wee, S L Bohman, B Suckling, D M eng Research Support, Non-U.S. Gov't Germany 2012/12/15 Naturwissenschaften. 2013 Feb; 100(2):135-43. doi: 10.1007/s00114-012-1003-4. Epub 2012 Dec 13"