Literature DB >> 22554451

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

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

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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Year:  2012        PMID: 22554451     DOI: 10.1021/ol300864u

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  12 in total

1.  Structure-Activity Relationships of Alkylpyrazine Analogs and Fear-Associated Behaviors in Mice.

Authors:  Kazumi Osada; Sadaharu Miyazono; Makoto Kashiwayanagi
Journal:  J Chem Ecol       Date:  2017-02-28       Impact factor: 2.626

2.  Drakolide Structure-activity Relationships for Sexual Attraction of Zeleboria Wasp Pollinator.

Authors:  Björn Bohman; Monica M Y Tan; Gavin R Flematti; Rod Peakall
Journal:  J Chem Ecol       Date:  2022-01-31       Impact factor: 2.626

3.  The production of a key floral volatile is dependent on UV light in a sexually deceptive orchid.

Authors:  Vasiliki Falara; Ranamalie Amarasinghe; Jacqueline Poldy; Eran Pichersky; Russell A Barrow; Rod Peakall
Journal:  Ann Bot       Date:  2012-10-22       Impact factor: 4.357

4.  Structure-Activity Studies of Semiochemicals from the Spider Orchid Caladenia plicata for Sexual Deception.

Authors:  Bjorn Bohman; Amir Karton; Gavin R Flematti; Adrian Scaffidi; Rod Peakall
Journal:  J Chem Ecol       Date:  2018-03-17       Impact factor: 2.626

5.  UV-B light contributes directly to the synthesis of chiloglottone floral volatiles.

Authors:  Ranamalie Amarasinghe; Jacqueline Poldy; Yuki Matsuba; Russell A Barrow; Jan M Hemmi; Eran Pichersky; Rod Peakall
Journal:  Ann Bot       Date:  2015-02-02       Impact factor: 4.357

6.  Caught in the act: pollination of sexually deceptive trap-flowers by fungus gnats in Pterostylis (Orchidaceae).

Authors:  Ryan D Phillips; Daniela Scaccabarozzi; Bryony A Retter; Christine Hayes; Graham R Brown; Kingsley W Dixon; Rod Peakall
Journal:  Ann Bot       Date:  2013-12-22       Impact factor: 4.357

7.  Parapheromones for Thynnine Wasps.

Authors:  Björn Bohman; Amir Karton; Ruby C M Dixon; Russell A Barrow; Rod Peakall
Journal:  J Chem Ecol       Date:  2015-12-14       Impact factor: 2.626

8.  Pyrazines Attract Catocheilus Thynnine Wasps.

Authors:  Bjorn Bohman; Rod Peakall
Journal:  Insects       Date:  2014-06-19       Impact factor: 2.769

Review 9.  The scent of wolves: pyrazine analogs induce avoidance and vigilance behaviors in prey.

Authors:  Kazumi Osada; Sadaharu Miyazono; Makoto Kashiwayanagi
Journal:  Front Neurosci       Date:  2015-10-07       Impact factor: 4.677

10.  Identification of (Z)-8-Heptadecene and n-Pentadecane as Electrophysiologically Active Compounds in Ophrys insectifera and Its Argogorytes Pollinator.

Authors:  Björn Bohman; Alyssa M Weinstein; Raimondas Mozuraitis; Gavin R Flematti; Anna-Karin Borg-Karlson
Journal:  Int J Mol Sci       Date:  2020-01-17       Impact factor: 5.923

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