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Discovery of tetrasubstituted pyrazines as semiochemicals in a sexually deceptive orchid

dc.contributor.authorBohman, Bjorn
dc.contributor.authorJeffares, Lynne
dc.contributor.authorFlematti, Gavin
dc.contributor.authorByrne, Lindsay T.
dc.contributor.authorSkelton, Brian
dc.contributor.authorPhillips, Ryan
dc.contributor.authorDixon, Kingsley
dc.contributor.authorPeakall, Rodney
dc.contributor.authorBarrow, Russell
dc.date.accessioned2015-12-10T23:24:22Z
dc.date.issued2012
dc.date.updated2016-02-24T08:46:15Z
dc.description.abstractSexually deceptive orchids employ mimicry of insect sex pheromones to exploit a diverse group of pollinators. The chemical structures of five semiochemicals (1-3, 7, 8) produced by populations of the warty hammer orchid, Drakaea livida, pollinated by a thynnine wasp in the genus Catocheilus were elucidated. With the exception of (2,5-dimethylpyrazin-3-yl)methyl 3-methylbutanoate (7), all active compounds were tetrasubstituted pyrazines, including hydroxymethyl (1) and ester (2 and 3) trimethylpyrazine derivatives. Male Catocheilus wasps were responsive to all of these compounds in GC-EAD experiments.
dc.identifier.issn0163-3864
dc.identifier.urihttp://hdl.handle.net/1885/67155
dc.publisherAmerican Chemical Society
dc.sourceJournal of Natural Products
dc.subjectKeywords: butyric acid derivative; ester derivative; hydroxyl group; methyl group; pyrazine derivative; sex pheromone; analytic method; article; electroantennographic detection; gas chromatography; heteronuclear multiple bond correlation; heteronuclear single quant
dc.titleDiscovery of tetrasubstituted pyrazines as semiochemicals in a sexually deceptive orchid
dc.typeJournal article
local.bibliographicCitation.issue9
local.bibliographicCitation.lastpage1594
local.bibliographicCitation.startpage1589
local.contributor.affiliationBohman, Bjorn, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationJeffares, Lynne, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationFlematti, Gavin, University of Western Australia
local.contributor.affiliationByrne, Lindsay T., University of Western Australia
local.contributor.affiliationSkelton, Brian, University of Western Australia
local.contributor.affiliationPhillips, Ryan, College of Medicine, Biology and Environment, ANU
local.contributor.affiliationDixon, Kingsley, Botanic Gardens & Parks Authority
local.contributor.affiliationPeakall, Rodney, College of Medicine, Biology and Environment, ANU
local.contributor.affiliationBarrow, Russell, College of Physical and Mathematical Sciences, ANU
local.contributor.authoruidBohman, Bjorn, u4778561
local.contributor.authoruidJeffares, Lynne, u4813224
local.contributor.authoruidPhillips, Ryan, u4906929
local.contributor.authoruidPeakall, Rodney, u9306248
local.contributor.authoruidBarrow, Russell, u9902002
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030502 - Natural Products Chemistry
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
local.identifier.ariespublicationf5625xPUB1407
local.identifier.citationvolume75
local.identifier.doi10.1021/np300388y
local.identifier.scopusID2-s2.0-84867024187
local.identifier.thomsonID000309199800012
local.type.statusPublished Version

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