Discovery of tetrasubstituted pyrazines as semiochemicals in a sexually deceptive orchid

Björn Bohman; Lynne Jeffares; Gavin Flematti; Lindsay T. Byrne; Brian W. Skelton; Ryan D. Phillips; Kingsley W. Dixon; Rod Peakall; Russell A. Barrow

doi:10.1021/np300388y

Discovery of tetrasubstituted pyrazines as semiochemicals in a sexually deceptive orchid

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

^*Corresponding author for this work

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

48 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1589-1594
Number of pages	6
Journal	Journal of Natural Products
Volume	75
Issue number	9
DOIs	https://doi.org/10.1021/np300388y
Publication status	Published - 28 Sept 2012

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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.",

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AU - Bohman, Björn

AU - Jeffares, Lynne

AU - Flematti, Gavin

AU - Byrne, Lindsay T.

AU - Skelton, Brian W.

AU - Phillips, Ryan D.

AU - Dixon, Kingsley W.

AU - Peakall, Rod

AU - Barrow, Russell A.

PY - 2012/9/28

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N2 - 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.

AB - 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.

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U2 - 10.1021/np300388y

DO - 10.1021/np300388y

M3 - Article

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SP - 1589

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JO - Journal of Natural Products

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Discovery of tetrasubstituted pyrazines as semiochemicals in a sexually deceptive orchid

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