The discovery of 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine: a semiochemical in orchid pollination

Björn Bohman; Lynne Jeffares; Gavin Flematti; Ryan D Phillips; Kingsley W Dixon; Rod Peakall; Russell A Barrow

doi:10.1021/ol300864u

The discovery of 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine: a semiochemical in orchid pollination

Org Lett. 2012 May 18;14(10):2576-8. doi: 10.1021/ol300864u. Epub 2012 May 3.

Authors

Björn Bohman¹, Lynne Jeffares, Gavin Flematti, Ryan D Phillips, Kingsley W Dixon, Rod Peakall, Russell A Barrow

Affiliation

¹ 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.

PMID: 22554451
DOI: 10.1021/ol300864u

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Female
Molecular Structure
Orchidaceae / chemistry*
Pollination*
Pyrazines / chemistry*
Pyrazines / pharmacology
Sex Attractants / chemistry*
Sex Attractants / physiology
Wasps / physiology*

Substances

2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine
Pyrazines
Sex Attractants