title: Discovery of tetrasubstituted pyrazines as semiochemicals in a sexually deceptive orchid.
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.
authors.affiliation: Research School of Chemistry, The Australian National University, Canberra ACT 0200, Australia.
authors.forename: Björn
authors.initials: B
authors.lastname: Bohman
authors.forename: Lynne
authors.initials: L
authors.lastname: Jeffares
authors.forename: Gavin
authors.initials: G
authors.lastname: Flematti
authors.forename: Lindsay T
authors.initials: LT
authors.lastname: Byrne
authors.forename: Brian W
authors.initials: BW
authors.lastname: Skelton
authors.forename: Ryan D
authors.initials: RD
authors.lastname: Phillips
authors.forename: Kingsley W
authors.initials: KW
authors.lastname: Dixon
authors.forename: Rod
authors.initials: R
authors.lastname: Peakall
authors.forename: Russell A
authors.initials: RA
authors.lastname: Barrow
mesh_terms: D000818:Animals; D001315:Australia; D018360:Crystallography, X-Ray; D004578:Electron Spin Resonance Spectroscopy; D006801:Humans; D008297:Male; D015394:Molecular Structure; D029595:Orchidaceae / Q000737:chemistry* / Q000235:genetics / Q000502:physiology; D054817:Pollination; D011719:Pyrazines / Q000737:chemistry* / Q000494:pharmacology*; D012724:Sex Attractants / Q000737:chemistry*; D014863:Wasps / Q000235:genetics*
chemical_list: D011719:Pyrazines; D012724:Sex Attractants