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

Björn Bohman, Lynne Jeffares, Gavin Flematti, Ryan D. Phillips, Kingsley W. Dixon, Rod Peakall, Russell A. Barrow^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

49 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2576-2578
Number of pages	3
Journal	Organic Letters
Volume	14
Issue number	10
DOIs	https://doi.org/10.1021/ol300864u
Publication status	Published - 18 May 2012

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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.",

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T1 - The discovery of 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine

T2 - A semiochemical in orchid pollination

AU - Bohman, Björn

AU - Jeffares, Lynne

AU - Flematti, Gavin

AU - Phillips, Ryan D.

AU - Dixon, Kingsley W.

AU - Peakall, Rod

AU - Barrow, Russell A.

PY - 2012/5/18

Y1 - 2012/5/18

N2 - 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.

AB - 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.

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JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

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

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