Discovery of tetrasubstituted pyrazines as semiochemicals in a sexually deceptive orchid

J Nat Prod. 2012 Sep 28;75(9):1589-94. doi: 10.1021/np300388y. Epub 2012 Sep 18.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Australia
  • Crystallography, X-Ray
  • Electron Spin Resonance Spectroscopy
  • Humans
  • Male
  • Molecular Structure
  • Orchidaceae / chemistry*
  • Orchidaceae / genetics
  • Orchidaceae / physiology
  • Pollination*
  • Pyrazines / chemistry*
  • Pyrazines / pharmacology*
  • Sex Attractants / chemistry*
  • Wasps / genetics*

Substances

  • Pyrazines
  • Sex Attractants