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« Previous AbstractThe discovery of 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine: a semiochemical in orchid pollination    Next AbstractAlkylations and hydroxymethylations of pyrazines via green Minisci-type reactions »

J Nat Prod


Title:Discovery of tetrasubstituted pyrazines as semiochemicals in a sexually deceptive orchid
Author(s):Bohman B; Jeffares L; Flematti G; Byrne LT; Skelton BW; Phillips RD; Dixon KW; Peakall R; Barrow RA;
Address:"Research School of Chemistry, The Australian National University, Canberra ACT 0200, Australia"
Journal Title:J Nat Prod
Year:2012
Volume:20120918
Issue:9
Page Number:1589 - 1594
DOI: 10.1021/np300388y
ISSN/ISBN:1520-6025 (Electronic) 0163-3864 (Linking)
Abstract:"Sexually 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"
Keywords:"Animals Australia Crystallography, X-Ray Electron Spin Resonance Spectroscopy Humans Male Molecular Structure Orchidaceae/*chemistry/genetics/physiology *Pollination Pyrazines/*chemistry/*pharmacology Sex Attractants/*chemistry Wasps/*genetics;"
Notes:"MedlineBohman, Bjorn Jeffares, Lynne Flematti, Gavin Byrne, Lindsay T Skelton, Brian W Phillips, Ryan D Dixon, Kingsley W Peakall, Rod Barrow, Russell A eng Research Support, Non-U.S. Gov't 2012/09/20 J Nat Prod. 2012 Sep 28; 75(9):1589-94. doi: 10.1021/np300388y. Epub 2012 Sep 18"

 
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