title: The discovery of 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine: a semiochemical in orchid pollination.
abstract: Drakaea livida (Orchidaceae) is pollinated by sexual deception of the wasp Zaspilothynnus nigripes (Thynnidae). It is shown that the orchid emits the same compound, 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine, that females emit when calling for mates. This novel pyrazine was isolated and identified by GC-EAD and GC-MS and confirmed by synthesis. This compound may represent the first known case of pyrazines as sex pheromones in Hymenoptera.
authors.affiliation: Research School of Chemistry, The Australian National University, Canberra ACT, 0200, Australia, Research School of Biology, The Australian National University, Canberra ACT, 0200, Australia, School of Chemistry and Biochemistry, The University of Western Australia, Crawley WA, 6009, Australia, Kings Park and Botanic Garden, The Botanic Garden and Parks Authority, West Perth WA, 6005, Australia, and School of Plant Biology, The University of Western Australia, Crawley, WA 6009, 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: 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; D005260:Female; D015394:Molecular Structure; D029595:Orchidaceae / Q000737:chemistry*; D054817:Pollination; D011719:Pyrazines / Q000737:chemistry* / Q000494:pharmacology; D012724:Sex Attractants / Q000737:chemistry* / Q000502:physiology; D014863:Wasps / Q000502:physiology*
chemical_list: C587755:2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine; D011719:Pyrazines; D012724:Sex Attractants