3,7-Dimethylpentadecane: a Novel Sex Pheromone Component from Leucoptera sinuella (Lepidoptera: Lyonetiidae).
Identifieur interne : 000615 ( Main/Exploration ); précédent : 000614; suivant : 0006163,7-Dimethylpentadecane: a Novel Sex Pheromone Component from Leucoptera sinuella (Lepidoptera: Lyonetiidae).
Auteurs : Wilson Barros-Parada [Chili] ; Jan Bergmann [Chili] ; Tomislav Curkovic [Chili] ; Cristian Espinosa [Chili] ; Eduardo Fuentes-Contreras [Chili] ; Jorge Guajardo [Chili] ; Heidy Herrera [Chili] ; Sebastián Morales [Chili] ; Abel F O. Queiroz [Chili, Brésil] ; Álvaro Vidal [Chili]Source :
- Journal of chemical ecology [ 1573-1561 ] ; 2020.
Abstract
Leucoptera sinuella is a leaf-miner moth present in several regions in the world, which has been recently introduced into Chile. The larvae feed exclusively on the leaves of poplar and willow trees, and the damage caused by the feeding behavior poses a threat to the wood-producing industry. Besides, L. sinuella larvae invade nearby orchards for pupation, causing rejections in Chilean fresh fruit for export. Here we report the identification of the female-produced sex pheromone of L. sinuella as a first step towards the development of pheromone-based methods for pest management of this species. First, we analyzed hexane extracts of the abdominal glands of virgin females by gas chromatography coupled with mass spectrometry and identified the major compound in these extracts to be 3,7-dimethylpentadecane, while minor compounds in the extracts proved to be 3,7-dimethyltetradecane and 7-methylpentadecane. Structure assignments were carried out by comparison of retention times and mass spectra of the natural products with those of authentic reference samples. Second, we conducted field tests, which showed that traps baited with synthetic 3,7-dimethylpentadecane were significantly attractive to males in a dose-dependent response. Our results also showed that a mixture of 3,7-dimethylpentadecane, 3,7-dimethyltetradecane, and 7-methylpentadecane in proportions similar to those found in gland extracts was the most attractive lure.
DOI: 10.1007/s10886-020-01208-z
PubMed: 32770448
Affiliations:
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Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso</wicri:regionArea><wicri:noRegion>Valparaíso</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2020">2020</date><idno type="RBID">pubmed:32770448</idno><idno type="pmid">32770448</idno><idno type="doi">10.1007/s10886-020-01208-z</idno><idno type="wicri:Area/Main/Corpus">000151</idno><idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Corpus" wicri:corpus="PubMed">000151</idno><idno type="wicri:Area/Main/Curation">000151</idno><idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Curation">000151</idno><idno type="wicri:Area/Main/Exploration">000151</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">3,7-Dimethylpentadecane: a Novel Sex Pheromone Component from Leucoptera sinuella (Lepidoptera: Lyonetiidae).</title><author><name sortKey="Barros Parada, Wilson" sort="Barros Parada, Wilson" uniqKey="Barros Parada W" first="Wilson" last="Barros-Parada">Wilson Barros-Parada</name><affiliation wicri:level="1"><nlm:affiliation>Escuela de Agronomía, Facultad de Ciencias Agronómicas y de los Alimentos, Pontificia Universidad Católica de Valparaíso, Quillota, Chile.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Escuela de Agronomía, Facultad de Ciencias Agronómicas y de los Alimentos, Pontificia Universidad Católica de Valparaíso, Quillota</wicri:regionArea><wicri:noRegion>Quillota</wicri:noRegion></affiliation></author><author><name sortKey="Bergmann, Jan" sort="Bergmann, Jan" uniqKey="Bergmann J" first="Jan" last="Bergmann">Jan Bergmann</name><affiliation wicri:level="1"><nlm:affiliation>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile. jan.bergmann@pucv.cl.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso</wicri:regionArea><wicri:noRegion>Valparaíso</wicri:noRegion></affiliation></author><author><name sortKey="Curkovic, Tomislav" sort="Curkovic, Tomislav" uniqKey="Curkovic T" first="Tomislav" last="Curkovic">Tomislav Curkovic</name><affiliation wicri:level="1"><nlm:affiliation>Facultad de Ciencias Agronómicas, Universidad de Chile, Santiago, Chile.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Facultad de Ciencias Agronómicas, Universidad de Chile, Santiago</wicri:regionArea><wicri:noRegion>Santiago</wicri:noRegion></affiliation></author><author><name sortKey="Espinosa, Cristian" sort="Espinosa, Cristian" uniqKey="Espinosa C" first="Cristian" last="Espinosa">Cristian Espinosa</name><affiliation wicri:level="1"><nlm:affiliation>Centro Tecnológico del Álamo (Poplar Technology Center), Universidad de Talca, Talca, Chile.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Centro Tecnológico del Álamo (Poplar Technology Center), Universidad de Talca, Talca</wicri:regionArea><wicri:noRegion>Talca</wicri:noRegion></affiliation></author><author><name sortKey="Fuentes Contreras, Eduardo" sort="Fuentes Contreras, Eduardo" uniqKey="Fuentes Contreras E" first="Eduardo" last="Fuentes-Contreras">Eduardo Fuentes-Contreras</name><affiliation wicri:level="1"><nlm:affiliation>Centre for Molecular and Functional Ecology in Agroecosystems, Facultad de Ciencias Agrarias, Universidad de Talca, Talca, Chile.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Centre for Molecular and Functional Ecology in Agroecosystems, Facultad de Ciencias Agrarias, Universidad de Talca, Talca</wicri:regionArea><wicri:noRegion>Talca</wicri:noRegion></affiliation></author><author><name sortKey="Guajardo, Jorge" sort="Guajardo, Jorge" uniqKey="Guajardo J" first="Jorge" last="Guajardo">Jorge Guajardo</name><affiliation wicri:level="1"><nlm:affiliation>Centro Tecnológico del Álamo (Poplar Technology Center), Universidad de Talca, Talca, Chile.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Centro Tecnológico del Álamo (Poplar Technology Center), Universidad de Talca, Talca</wicri:regionArea><wicri:noRegion>Talca</wicri:noRegion></affiliation></author><author><name sortKey="Herrera, Heidy" sort="Herrera, Heidy" uniqKey="Herrera H" first="Heidy" last="Herrera">Heidy Herrera</name><affiliation wicri:level="1"><nlm:affiliation>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso</wicri:regionArea><wicri:noRegion>Valparaíso</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:affiliation>Núcleo de Química y Bioquímica, Facultad de Estudios Interdisciplinarios, Universidad Mayor, Santiago, Chile.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Núcleo de Química y Bioquímica, Facultad de Estudios Interdisciplinarios, Universidad Mayor, Santiago</wicri:regionArea><wicri:noRegion>Santiago</wicri:noRegion></affiliation></author><author><name sortKey="Morales, Sebastian" sort="Morales, Sebastian" uniqKey="Morales S" first="Sebastián" last="Morales">Sebastián Morales</name><affiliation wicri:level="1"><nlm:affiliation>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso</wicri:regionArea><wicri:noRegion>Valparaíso</wicri:noRegion></affiliation></author><author><name sortKey="Queiroz, Abel F O" sort="Queiroz, Abel F O" uniqKey="Queiroz A" first="Abel F O" last="Queiroz">Abel F O. Queiroz</name><affiliation wicri:level="1"><nlm:affiliation>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso</wicri:regionArea><wicri:noRegion>Valparaíso</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:affiliation>Instituto de Química e Biotecnologia, Universidade Federal de Alagoas, Maceió, Brazil.</nlm:affiliation><country xml:lang="fr">Brésil</country><wicri:regionArea>Instituto de Química e Biotecnologia, Universidade Federal de Alagoas, Maceió</wicri:regionArea><wicri:noRegion>Maceió</wicri:noRegion></affiliation></author><author><name sortKey="Vidal, Alvaro" sort="Vidal, Alvaro" uniqKey="Vidal A" first="Álvaro" last="Vidal">Álvaro Vidal</name><affiliation wicri:level="1"><nlm:affiliation>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso</wicri:regionArea><wicri:noRegion>Valparaíso</wicri:noRegion></affiliation></author></analytic><series><title level="j">Journal of chemical ecology</title><idno type="eISSN">1573-1561</idno><imprint><date when="2020" type="published">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Leucoptera sinuella is a leaf-miner moth present in several regions in the world, which has been recently introduced into Chile. The larvae feed exclusively on the leaves of poplar and willow trees, and the damage caused by the feeding behavior poses a threat to the wood-producing industry. Besides, L. sinuella larvae invade nearby orchards for pupation, causing rejections in Chilean fresh fruit for export. Here we report the identification of the female-produced sex pheromone of L. sinuella as a first step towards the development of pheromone-based methods for pest management of this species. First, we analyzed hexane extracts of the abdominal glands of virgin females by gas chromatography coupled with mass spectrometry and identified the major compound in these extracts to be 3,7-dimethylpentadecane, while minor compounds in the extracts proved to be 3,7-dimethyltetradecane and 7-methylpentadecane. Structure assignments were carried out by comparison of retention times and mass spectra of the natural products with those of authentic reference samples. Second, we conducted field tests, which showed that traps baited with synthetic 3,7-dimethylpentadecane were significantly attractive to males in a dose-dependent response. Our results also showed that a mixture of 3,7-dimethylpentadecane, 3,7-dimethyltetradecane, and 7-methylpentadecane in proportions similar to those found in gland extracts was the most attractive lure.</div></front></TEI><pubmed><MedlineCitation Status="In-Process" Owner="NLM"><PMID Version="1">32770448</PMID><DateRevised><Year>2020</Year><Month>09</Month><Day>03</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1573-1561</ISSN><JournalIssue CitedMedium="Internet"><Volume>46</Volume><Issue>9</Issue><PubDate><Year>2020</Year><Month>Sep</Month></PubDate></JournalIssue><Title>Journal of chemical ecology</Title><ISOAbbreviation>J Chem Ecol</ISOAbbreviation></Journal><ArticleTitle>3,7-Dimethylpentadecane: a Novel Sex Pheromone Component from Leucoptera sinuella (Lepidoptera: Lyonetiidae).</ArticleTitle><Pagination><MedlinePgn>820-829</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1007/s10886-020-01208-z</ELocationID><Abstract><AbstractText>Leucoptera sinuella is a leaf-miner moth present in several regions in the world, which has been recently introduced into Chile. The larvae feed exclusively on the leaves of poplar and willow trees, and the damage caused by the feeding behavior poses a threat to the wood-producing industry. Besides, L. sinuella larvae invade nearby orchards for pupation, causing rejections in Chilean fresh fruit for export. Here we report the identification of the female-produced sex pheromone of L. sinuella as a first step towards the development of pheromone-based methods for pest management of this species. First, we analyzed hexane extracts of the abdominal glands of virgin females by gas chromatography coupled with mass spectrometry and identified the major compound in these extracts to be 3,7-dimethylpentadecane, while minor compounds in the extracts proved to be 3,7-dimethyltetradecane and 7-methylpentadecane. Structure assignments were carried out by comparison of retention times and mass spectra of the natural products with those of authentic reference samples. Second, we conducted field tests, which showed that traps baited with synthetic 3,7-dimethylpentadecane were significantly attractive to males in a dose-dependent response. Our results also showed that a mixture of 3,7-dimethylpentadecane, 3,7-dimethyltetradecane, and 7-methylpentadecane in proportions similar to those found in gland extracts was the most attractive lure.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Barros-Parada</LastName><ForeName>Wilson</ForeName><Initials>W</Initials><Identifier Source="ORCID">https://orcid.org/0000-0003-3015-4927</Identifier><AffiliationInfo><Affiliation>Escuela de Agronomía, Facultad de Ciencias Agronómicas y de los Alimentos, Pontificia Universidad Católica de Valparaíso, Quillota, Chile.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Bergmann</LastName><ForeName>Jan</ForeName><Initials>J</Initials><Identifier Source="ORCID">https://orcid.org/0000-0003-3566-1979</Identifier><AffiliationInfo><Affiliation>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile. jan.bergmann@pucv.cl.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Curkovic</LastName><ForeName>Tomislav</ForeName><Initials>T</Initials><Identifier Source="ORCID">https://orcid.org/0000-0003-3403-8800</Identifier><AffiliationInfo><Affiliation>Facultad de Ciencias Agronómicas, Universidad de Chile, Santiago, Chile.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Espinosa</LastName><ForeName>Cristian</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Centro Tecnológico del Álamo (Poplar Technology Center), Universidad de Talca, Talca, Chile.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Fuentes-Contreras</LastName><ForeName>Eduardo</ForeName><Initials>E</Initials><AffiliationInfo><Affiliation>Centre for Molecular and Functional Ecology in Agroecosystems, Facultad de Ciencias Agrarias, Universidad de Talca, Talca, Chile.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Guajardo</LastName><ForeName>Jorge</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>Centro Tecnológico del Álamo (Poplar Technology Center), Universidad de Talca, Talca, Chile.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Herrera</LastName><ForeName>Heidy</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Núcleo de Química y Bioquímica, Facultad de Estudios Interdisciplinarios, Universidad Mayor, Santiago, Chile.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Morales</LastName><ForeName>Sebastián</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Queiroz</LastName><ForeName>Abel F O</ForeName><Initials>AFO</Initials><AffiliationInfo><Affiliation>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Instituto de Química e Biotecnologia, Universidade Federal de Alagoas, Maceió, Brazil.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Vidal</LastName><ForeName>Álvaro</ForeName><Initials>Á</Initials><AffiliationInfo><Affiliation>Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>EQM130154</GrantID><Agency>Fondo de Equipamiento Cientifico y Tecnologico</Agency><Country></Country></Grant><Grant><GrantID>039.399/2017</GrantID><Agency>Vicerrectoría de Investigación y Estudios Avanzados PUCV</Agency><Country></Country></Grant><Grant><GrantID>039.498/2018</GrantID><Agency>Vicerrectoría de Investigación y Estudios Avanzados</Agency><Country></Country></Grant><Grant><GrantID>IDI 40008896-0</GrantID><Agency>Fondo de Innovación para la Competitividad de la Región de O´Higgins</Agency><Country></Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2020</Year><Month>08</Month><Day>08</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Chem Ecol</MedlineTA><NlmUniqueID>7505563</NlmUniqueID><ISSNLinking>0098-0331</ISSNLinking></MedlineJournalInfo><CitationSubset>IM</CitationSubset><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Branched hydrocarbon</Keyword><Keyword MajorTopicYN="N">Invasive species</Keyword><Keyword MajorTopicYN="N">Leaf-miner</Keyword><Keyword MajorTopicYN="N">Poplar</Keyword><Keyword MajorTopicYN="N">Type III pheromone</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2020</Year><Month>05</Month><Day>27</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2020</Year><Month>07</Month><Day>30</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2020</Year><Month>07</Month><Day>13</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>8</Month><Day>10</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>8</Month><Day>10</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>8</Month><Day>10</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">32770448</ArticleId><ArticleId IdType="doi">10.1007/s10886-020-01208-z</ArticleId><ArticleId IdType="pii">10.1007/s10886-020-01208-z</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Brésil</li><li>Chili</li></country></list><tree><country name="Chili"><noRegion><name sortKey="Barros Parada, Wilson" sort="Barros Parada, Wilson" uniqKey="Barros Parada W" first="Wilson" last="Barros-Parada">Wilson Barros-Parada</name></noRegion><name sortKey="Bergmann, Jan" sort="Bergmann, Jan" uniqKey="Bergmann J" first="Jan" last="Bergmann">Jan Bergmann</name><name sortKey="Curkovic, Tomislav" sort="Curkovic, Tomislav" uniqKey="Curkovic T" first="Tomislav" last="Curkovic">Tomislav Curkovic</name><name sortKey="Espinosa, Cristian" sort="Espinosa, Cristian" uniqKey="Espinosa C" first="Cristian" last="Espinosa">Cristian Espinosa</name><name sortKey="Fuentes Contreras, Eduardo" sort="Fuentes Contreras, Eduardo" uniqKey="Fuentes Contreras E" first="Eduardo" last="Fuentes-Contreras">Eduardo Fuentes-Contreras</name><name sortKey="Guajardo, Jorge" sort="Guajardo, Jorge" uniqKey="Guajardo J" first="Jorge" last="Guajardo">Jorge Guajardo</name><name sortKey="Herrera, Heidy" sort="Herrera, Heidy" uniqKey="Herrera H" first="Heidy" last="Herrera">Heidy Herrera</name><name sortKey="Herrera, Heidy" sort="Herrera, Heidy" uniqKey="Herrera H" first="Heidy" last="Herrera">Heidy Herrera</name><name sortKey="Morales, Sebastian" sort="Morales, Sebastian" uniqKey="Morales S" first="Sebastián" last="Morales">Sebastián Morales</name><name sortKey="Queiroz, Abel F O" sort="Queiroz, Abel F O" uniqKey="Queiroz A" first="Abel F O" last="Queiroz">Abel F O. Queiroz</name><name sortKey="Vidal, Alvaro" sort="Vidal, Alvaro" uniqKey="Vidal A" first="Álvaro" last="Vidal">Álvaro Vidal</name></country><country name="Brésil"><noRegion><name sortKey="Queiroz, Abel F O" sort="Queiroz, Abel F O" uniqKey="Queiroz A" first="Abel F O" last="Queiroz">Abel F O. Queiroz</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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|texte= 3,7-Dimethylpentadecane: a Novel Sex Pheromone Component from Leucoptera sinuella (Lepidoptera: Lyonetiidae).
}}
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