Literature DB >> 19685263

Alkyldimethylpyrazines in the defensive spray of Phyllium westwoodii: a first for order Phasmatodea.

Aaron T Dossey1, Marco Gottardo, John M Whitaker, William R Roush, Arthur S Edison.   

Abstract

Phyllium westwoodii is a phasmid insect (Order Phasmatodea) belonging to the Family Phylliidae (leaf insects). These rather large and ornate creatures are known for their morphological resemblance to plant leaves for camouflage. Pyrazines are a common class of compounds used or produced by a wide variety of organisms, even humans. When an individual of P. westwoodii is disturbed, it sprays an opaque liquid from a pair of prothoracic glands, which are utilized by other phasmid species for defense. The current study has found that this liquid contains glucose and a mixture of 3-isobutyl-2,5-dimethylpyrazine, 2,5-dimethyl-3-(2-methylbutyl)pyrazine, and 2,5-dimethyl-3-(3-methylbutyl)pyrazine. This is the first report of pyrazines found in the defensive gland spray of phasmid insects, and the first chemical analysis of glandular material from family Phylliidae.

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Year:  2009        PMID: 19685263      PMCID: PMC3787517          DOI: 10.1007/s10886-009-9666-9

Source DB:  PubMed          Journal:  J Chem Ecol        ISSN: 0098-0331            Impact factor:   2.626


  20 in total

Review 1.  The FEMA GRAS assessment of pyrazine derivatives used as flavor ingredients. Flavor and Extract Manufacturers Association.

Authors:  T B Adams; J Doull; V J Feron; J I Goodman; L J Marnett; I C Munro; P M Newberne; P S Portoghese; R L Smith; W J Waddell; B M Wagner
Journal:  Food Chem Toxicol       Date:  2002-04       Impact factor: 6.023

2.  The first fossil leaf insect: 47 million years of specialized cryptic morphology and behavior.

Authors:  Sonja Wedmann; Sven Bradler; Jes Rust
Journal:  Proc Natl Acad Sci U S A       Date:  2006-12-29       Impact factor: 11.205

3.  4-methyl-l-hepten-3-one, the defensive compound from Agathemera elegans (Philippi) (Phasmatidae) Insecta.

Authors:  Guillermo Schmeda-Hirschmann
Journal:  Z Naturforsch C J Biosci       Date:  2006 Jul-Aug

4.  Strategy for automated analysis of dynamic metabolic mixtures by NMR. Application to an insect venom.

Authors:  Fengli Zhang; Aaron T Dossey; Cherian Zachariah; Arthur S Edison; Rafael Brüschweiler
Journal:  Anal Chem       Date:  2007-09-07       Impact factor: 6.986

5.  Design, construction, and validation of a 1-mm triple-resonance high-temperature-superconducting probe for NMR.

Authors:  William W Brey; Arthur S Edison; Robert E Nast; James R Rocca; Saikat Saha; Richard S Withers
Journal:  J Magn Reson       Date:  2006-01-19       Impact factor: 2.229

6.  Effects of milk fat, cocoa butter, or selected fat replacers on flavor volatiles of chocolate ice cream.

Authors:  W M Welty; R T Marshall; I U Grün; M R Ellersieck
Journal:  J Dairy Sci       Date:  2001-01       Impact factor: 4.034

7.  Iridoid biosynthesis in Chrysomelina larvae: Fat body produces early terpenoid precursors.

Authors:  Antje Burse; Axel Schmidt; Sindy Frick; Jürgen Kuhn; Jonathan Gershenzon; Wilhelm Boland
Journal:  Insect Biochem Mol Biol       Date:  2006-12-05       Impact factor: 4.714

8.  Alkylpyrazine alarm pheromones in ponerine ants.

Authors:  J W Wheeler; M S Blum
Journal:  Science       Date:  1973-11-02       Impact factor: 47.728

9.  Defensive production of quinoline by a phasmid insect (Oreophoetes peruana).

Authors:  T Eisner; R C Morgan; A B Attygalle; S R Smedley; K B Herath; J Meinwald
Journal:  J Exp Biol       Date:  1997-10       Impact factor: 3.312

10.  BioMagResBank.

Authors:  Eldon L Ulrich; Hideo Akutsu; Jurgen F Doreleijers; Yoko Harano; Yannis E Ioannidis; Jundong Lin; Miron Livny; Steve Mading; Dimitri Maziuk; Zachary Miller; Eiichi Nakatani; Christopher F Schulte; David E Tolmie; R Kent Wenger; Hongyang Yao; John L Markley
Journal:  Nucleic Acids Res       Date:  2007-11-04       Impact factor: 16.971

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  8 in total

1.  Defensive spiroketals from Asceles glaber (Phasmatodea): absolute configuration and effects on ants and mosquitoes.

Authors:  Aaron T Dossey; John M Whitaker; Maria Cristina A Dancel; Robert K Vander Meer; Ulrich R Bernier; Marco Gottardo; William R Roush
Journal:  J Chem Ecol       Date:  2012-09-14       Impact factor: 2.626

2.  Paralyzing action from a distance in an arboreal African ant species.

Authors:  Aline Rifflet; Nathan Tene; Jerome Orivel; Michel Treilhou; Alain Dejean; Angelique Vetillard
Journal:  PLoS One       Date:  2011-12-14       Impact factor: 3.240

3.  Volatile compound diversity and conserved alarm behaviour in Triatoma dimidiata.

Authors:  Irving May-Concha; Julio C Rojas; Leopoldo Cruz-López; Carlos N Ibarra-Cerdeña; Janine M Ramsey
Journal:  Parasit Vectors       Date:  2015-02-06       Impact factor: 3.876

4.  Pyrazines Attract Catocheilus Thynnine Wasps.

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

5.  Neurons of self-defence: neuronal innervation of the exocrine defence glands in stick insects.

Authors:  Konrad Stolz; Christoph-Rüdiger von Bredow; Yvette M von Bredow; Reinhard Lakes-Harlan; Tina E Trenczek; Johannes Strauß
Journal:  Front Zool       Date:  2015-10-24       Impact factor: 3.172

6.  Pyrazines from bacteria and ants: convergent chemistry within an ecological niche.

Authors:  Eduardo A Silva-Junior; Antonio C Ruzzini; Camila R Paludo; Fabio S Nascimento; Cameron R Currie; Jon Clardy; Mônica T Pupo
Journal:  Sci Rep       Date:  2018-02-07       Impact factor: 4.379

7.  De novo Synthesis of Chemical Defenses in an Aposematic Moth.

Authors:  Emily Burdfield-Steel; Hannu Pakkanen; Bibiana Rojas; Juan A Galarza; Johanna Mappes
Journal:  J Insect Sci       Date:  2018-03-01       Impact factor: 1.857

8.  Integrated phylogenomic and fossil evidence of stick and leaf insects (Phasmatodea) reveal a Permian-Triassic co-origination with insectivores.

Authors:  Erik Tihelka; Chenyang Cai; Mattia Giacomelli; Davide Pisani; Philip C J Donoghue
Journal:  R Soc Open Sci       Date:  2020-11-11       Impact factor: 2.963

  8 in total

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