Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier Beetle Chauliognathus fallax (Coleoptera: Cantharidae)

Detalhes bibliográficos
Autor(a) principal: Vidal,Diogo M.
Data de Publicação: 2016
Outros Autores: Fávaro,Carla F., Guimarães,Matheus M., Zarbin,Paulo H. G.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000801506
Resumo: Chauliognathus fallax Germar 1824 (Coleoptera: Cantharidae) occurs in North and South America and Australia. Gas chromatographic (GC) analyses of volatiles released by adults showed the presence of a male specific compound. GC coupled with electroantennographic detection (GC-EAD) showed that this compound is exclusively bioactive on female antennae, suggesting it to be a sex pheromone. GC coupled with mass spectrometry (GC-MS) and Fourier transform infrared spectroscopy (GC-FTIR), as well as dimethyl disulfide (DMDS) derivatization and hydrogenation, suggested the target compound to be (Z)-tricos-11-ene. Unambiguous structural proof was achieved by independent synthesis, whereas the biological significance of the compound as a sex pheromone was confirmed by field bioassays.
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spelling Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier Beetle Chauliognathus fallax (Coleoptera: Cantharidae)soldier beetleGC-MSGC-FTIRpheromone synthesis(Z)-tricos-11-eneChauliognathus fallax Germar 1824 (Coleoptera: Cantharidae) occurs in North and South America and Australia. Gas chromatographic (GC) analyses of volatiles released by adults showed the presence of a male specific compound. GC coupled with electroantennographic detection (GC-EAD) showed that this compound is exclusively bioactive on female antennae, suggesting it to be a sex pheromone. GC coupled with mass spectrometry (GC-MS) and Fourier transform infrared spectroscopy (GC-FTIR), as well as dimethyl disulfide (DMDS) derivatization and hydrogenation, suggested the target compound to be (Z)-tricos-11-ene. Unambiguous structural proof was achieved by independent synthesis, whereas the biological significance of the compound as a sex pheromone was confirmed by field bioassays.Sociedade Brasileira de Química2016-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000801506Journal of the Brazilian Chemical Society v.27 n.8 2016reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20160199info:eu-repo/semantics/openAccessVidal,Diogo M.Fávaro,Carla F.Guimarães,Matheus M.Zarbin,Paulo H. G.eng2016-08-19T00:00:00Zoai:scielo:S0103-50532016000801506Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2016-08-19T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier Beetle Chauliognathus fallax (Coleoptera: Cantharidae)
title Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier Beetle Chauliognathus fallax (Coleoptera: Cantharidae)
spellingShingle Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier Beetle Chauliognathus fallax (Coleoptera: Cantharidae)
Vidal,Diogo M.
soldier beetle
GC-MS
GC-FTIR
pheromone synthesis
(Z)-tricos-11-ene
title_short Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier Beetle Chauliognathus fallax (Coleoptera: Cantharidae)
title_full Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier Beetle Chauliognathus fallax (Coleoptera: Cantharidae)
title_fullStr Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier Beetle Chauliognathus fallax (Coleoptera: Cantharidae)
title_full_unstemmed Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier Beetle Chauliognathus fallax (Coleoptera: Cantharidae)
title_sort Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier Beetle Chauliognathus fallax (Coleoptera: Cantharidae)
author Vidal,Diogo M.
author_facet Vidal,Diogo M.
Fávaro,Carla F.
Guimarães,Matheus M.
Zarbin,Paulo H. G.
author_role author
author2 Fávaro,Carla F.
Guimarães,Matheus M.
Zarbin,Paulo H. G.
author2_role author
author
author
dc.contributor.author.fl_str_mv Vidal,Diogo M.
Fávaro,Carla F.
Guimarães,Matheus M.
Zarbin,Paulo H. G.
dc.subject.por.fl_str_mv soldier beetle
GC-MS
GC-FTIR
pheromone synthesis
(Z)-tricos-11-ene
topic soldier beetle
GC-MS
GC-FTIR
pheromone synthesis
(Z)-tricos-11-ene
description Chauliognathus fallax Germar 1824 (Coleoptera: Cantharidae) occurs in North and South America and Australia. Gas chromatographic (GC) analyses of volatiles released by adults showed the presence of a male specific compound. GC coupled with electroantennographic detection (GC-EAD) showed that this compound is exclusively bioactive on female antennae, suggesting it to be a sex pheromone. GC coupled with mass spectrometry (GC-MS) and Fourier transform infrared spectroscopy (GC-FTIR), as well as dimethyl disulfide (DMDS) derivatization and hydrogenation, suggested the target compound to be (Z)-tricos-11-ene. Unambiguous structural proof was achieved by independent synthesis, whereas the biological significance of the compound as a sex pheromone was confirmed by field bioassays.
publishDate 2016
dc.date.none.fl_str_mv 2016-08-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000801506
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000801506
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20160199
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.27 n.8 2016
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
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institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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