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Semiochemicals of the Scarabaeinae VIII : identification of active constituents of the abdominal sex-attracting secretion of the male dung beetle, Kheper bonellii, using gas chromatography with flame ionization and electroantennographic detection in parallel

dc.contributor.authorBurger, B. V.en
dc.contributor.authorPetersen, W. G. B.en
dc.contributor.authorEwig, B. T.en
dc.contributor.authorNeuhaus, J.en
dc.contributor.authorTribe, G. D.en
dc.contributor.authorSpies, H. S. C.en
dc.contributor.authorBurger, W. J. G.en
dc.date.accessioned2011-05-15T15:59:35Z
dc.date.available2011-05-15T15:59:35Z
dc.date.issued2008-04
dc.identifier.citationBurger, B. V. et al. 2008. Semiochemicals of the Scarabaeinae VIII : identification of active constituents of the abdominal sex-attracting secretion of the male dung beetle, Kheper bonellii, using gas chromatography with flame ionization and electroantennographic detection in parallel. Journal of Chromatography A, 1186(1-2):245-253, doi.org/10.1016/j.chroma.2007.09.041.en
dc.identifier.issn1873-3778 (online)
dc.identifier.issn0021-9673 (print)
dc.identifier.otherdoi:10.1016/j.chroma.2007.09.041
dc.identifier.urihttp://hdl.handle.net/10019.1/11256
dc.descriptionThe original publication is available at http://www.sciencedirect.com/science/article/pii/S0021967307016159#en
dc.description.abstractUsing gas chromatography with flame ionization detection and electroantennographic detection in parallel (GC-FID/EAD), the active constituents of the sex attractant of male dung beetles of Kheper bonellii were located in the gas chromatogram of an extract of the secretion. These constituents were identified as propanoic acid, butanoic acid, indole, 3-methylindole (skatole) and methyl cis-cascarillate (methyl cis-2-2′-hexylcyclopropylacetate) by, inter alia, GC-MS, 1H and 13C NMR analysis, and synthesis. These compounds elicited EAD responses in male as well as female antennae. Racemic methyl cis-cascarillate was synthesized for comparison with the natural methyl ester. Enantioselective GC-FID/EAD using a capillary column coated with OV-1701-OH containing 10% heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextri n showed that the natural compound co-eluted with the first-eluting enantiomer of the racemic methyl cis-cascarillate, which was the only enantiomer that elicited EAD responses in the antennae of male and female K. bonellii. The absolute configuration of this enantiomer was established by a stereoselective synthesis, which gave methyl (R,R)-cascarillate [methyl (1′R,2′R)-2-2′-hexylcyclopropylacetate] in an enantiomeric excess of 69%. © 2007 Elsevier B.V. All rights reserved.en
dc.format.extent13 p.
dc.language.isoen_ZAen_ZA
dc.publisherElsevieren
dc.subjectDung beetles -- Physiologyen_ZA
dc.subjectSemiochemicalsen_ZA
dc.subjectPheromonesen_ZA
dc.subjectAnimal sex attractantsen_ZA
dc.subjectMagnetic resonance spectroscopyen_ZA
dc.subjectColeopteraen_ZA
dc.subjectScarabaeinaeen_ZA
dc.titleSemiochemicals of the Scarabaeinae VIII : identification of active constituents of the abdominal sex-attracting secretion of the male dung beetle, Kheper bonellii, using gas chromatography with flame ionization and electroantennographic detection in parallelen_ZA
dc.typeArticleen_ZA
dc.description.versionPost-printen
dc.rights.holderAuthors retain copyrighten


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