Biosynthesis of (3Z,6Z,9Z)-3,6,9-Octadecatriene: The Main Component of the Pheromone Blend of Erannis bajaria
The hydrocarbons (3Z,6Z,9Z)-3,6,9-octadecatriene (3Z,6Z,9Z-18:H) and (3Z,6Z,9Z)-3,6,9-nonadecatriene (3Z,6Z,9Z-19:H) constitute the pheromone of the winter moth, Erannis bajaria. These compounds belong to a large group of lepidopteran pheromones which consist of unsaturated hydrocarbons and their co...
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| Veröffentlicht in: | Journal of chemical ecology 2007-08, Vol.33 (8), p.1505-1509 |
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| creator | Goller, Stephan Szöcs, Gabor Francke, Wittko Schulz, Stefan |
| description | The hydrocarbons (3Z,6Z,9Z)-3,6,9-octadecatriene (3Z,6Z,9Z-18:H) and (3Z,6Z,9Z)-3,6,9-nonadecatriene (3Z,6Z,9Z-19:H) constitute the pheromone of the winter moth, Erannis bajaria. These compounds belong to a large group of lepidopteran pheromones which consist of unsaturated hydrocarbons and their corresponding oxygenated derivatives. The biosynthesis of such hydrocarbons with an odd number of carbons in the chain is well understood. In contrast, knowledge about the biosynthesis of even numbered derivatives is lacking. We investigated the biosynthesis of 3Z,6Z,9Z-18:H by applying deuterium-labeled precursors to females of E. bajaria followed by gas chromatography-mass spectrometry analysis of extracts of the pheromone gland. A mixture of deuterium-labeled [17,17,18,18-²H₄]-3Z,6Z,9Z-18:H and the unlabeled 3Z,6Z,9Z-18:H was obtained after topical application and injection of (10Z,13Z,16Z)-[2,2,3,3-²H₄]-10,13,16-nonadecatrienoic acid ([2,2,3,3-²H₄]-10Z,13Z,16Z-19:acid) or (11Z,14Z,17Z)-[3,3,4,4-²H₄]-11,14,17-icosatrienoic acid ([3,3,4,4-²H₄]-11Z,14Z,17Z-20:acid). These results are consistent with a biosynthetic pathway that starts with α-linolenic acid (9Z,12Z,15Z-18:acid). Chain elongation leads to 11Z,14Z,17Z-20:acid, which is shortened by α-oxidation as the key step to yield 10Z,13Z,16Z-19:acid. This acid can be finally reduced to an aldehyde and decarbonylated or decarboxylated to furnish the pheromone component 3Z,6Z,9Z-18:H. A similar transformation of 11Z,14Z,17Z-20:acid yields the second pheromone component, 3Z,6Z,9Z-19:H. |
| doi_str_mv | 10.1007/s10886-007-9324-z |
| format | Article |
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These compounds belong to a large group of lepidopteran pheromones which consist of unsaturated hydrocarbons and their corresponding oxygenated derivatives. The biosynthesis of such hydrocarbons with an odd number of carbons in the chain is well understood. In contrast, knowledge about the biosynthesis of even numbered derivatives is lacking. We investigated the biosynthesis of 3Z,6Z,9Z-18:H by applying deuterium-labeled precursors to females of E. bajaria followed by gas chromatography-mass spectrometry analysis of extracts of the pheromone gland. A mixture of deuterium-labeled [17,17,18,18-²H₄]-3Z,6Z,9Z-18:H and the unlabeled 3Z,6Z,9Z-18:H was obtained after topical application and injection of (10Z,13Z,16Z)-[2,2,3,3-²H₄]-10,13,16-nonadecatrienoic acid ([2,2,3,3-²H₄]-10Z,13Z,16Z-19:acid) or (11Z,14Z,17Z)-[3,3,4,4-²H₄]-11,14,17-icosatrienoic acid ([3,3,4,4-²H₄]-11Z,14Z,17Z-20:acid). These results are consistent with a biosynthetic pathway that starts with α-linolenic acid (9Z,12Z,15Z-18:acid). Chain elongation leads to 11Z,14Z,17Z-20:acid, which is shortened by α-oxidation as the key step to yield 10Z,13Z,16Z-19:acid. This acid can be finally reduced to an aldehyde and decarbonylated or decarboxylated to furnish the pheromone component 3Z,6Z,9Z-18:H. A similar transformation of 11Z,14Z,17Z-20:acid yields the second pheromone component, 3Z,6Z,9Z-19:H.</description><identifier>ISSN: 0098-0331</identifier><identifier>EISSN: 1573-1561</identifier><identifier>DOI: 10.1007/s10886-007-9324-z</identifier><identifier>PMID: 17610118</identifier><identifier>CODEN: JCECD8</identifier><language>eng</language><publisher>New York, NY: New York : Springer-Verlag</publisher><subject>Alkenes - metabolism ; Animals ; biochemical pathways ; Biochemistry. Physiology. Immunology ; Biological and medical sciences ; Biosynthesis ; chemical composition ; Deuterium ; Erannis ; Fundamental and applied biological sciences. Psychology ; Gas chromatography ; Gas Chromatography-Mass Spectrometry ; Geometridae ; hydrocarbons ; Insecta ; Invertebrates ; Lepidoptera ; Mass spectrometry ; Moths - metabolism ; pheromone biosynthesis ; pheromone blends ; pheromone glands ; pheromone precursors ; Pheromones ; Pheromones - metabolism ; Physiology. Development ; radiolabeling ; sex pheromones ; Unsaturated hydrocarbons</subject><ispartof>Journal of chemical ecology, 2007-08, Vol.33 (8), p.1505-1509</ispartof><rights>2008 INIST-CNRS</rights><rights>Springer Science+Business Media, LLC 2007</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c411t-934f8139539d46dc8b59a99aefa73d9980b3764fa3deceea47dca71f7b6523a13</citedby><cites>FETCH-LOGICAL-c411t-934f8139539d46dc8b59a99aefa73d9980b3764fa3deceea47dca71f7b6523a13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27929,27930</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18991117$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17610118$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Goller, Stephan</creatorcontrib><creatorcontrib>Szöcs, Gabor</creatorcontrib><creatorcontrib>Francke, Wittko</creatorcontrib><creatorcontrib>Schulz, Stefan</creatorcontrib><title>Biosynthesis of (3Z,6Z,9Z)-3,6,9-Octadecatriene: The Main Component of the Pheromone Blend of Erannis bajaria</title><title>Journal of chemical ecology</title><addtitle>J Chem Ecol</addtitle><description>The hydrocarbons (3Z,6Z,9Z)-3,6,9-octadecatriene (3Z,6Z,9Z-18:H) and (3Z,6Z,9Z)-3,6,9-nonadecatriene (3Z,6Z,9Z-19:H) constitute the pheromone of the winter moth, Erannis bajaria. These compounds belong to a large group of lepidopteran pheromones which consist of unsaturated hydrocarbons and their corresponding oxygenated derivatives. The biosynthesis of such hydrocarbons with an odd number of carbons in the chain is well understood. In contrast, knowledge about the biosynthesis of even numbered derivatives is lacking. We investigated the biosynthesis of 3Z,6Z,9Z-18:H by applying deuterium-labeled precursors to females of E. bajaria followed by gas chromatography-mass spectrometry analysis of extracts of the pheromone gland. A mixture of deuterium-labeled [17,17,18,18-²H₄]-3Z,6Z,9Z-18:H and the unlabeled 3Z,6Z,9Z-18:H was obtained after topical application and injection of (10Z,13Z,16Z)-[2,2,3,3-²H₄]-10,13,16-nonadecatrienoic acid ([2,2,3,3-²H₄]-10Z,13Z,16Z-19:acid) or (11Z,14Z,17Z)-[3,3,4,4-²H₄]-11,14,17-icosatrienoic acid ([3,3,4,4-²H₄]-11Z,14Z,17Z-20:acid). These results are consistent with a biosynthetic pathway that starts with α-linolenic acid (9Z,12Z,15Z-18:acid). Chain elongation leads to 11Z,14Z,17Z-20:acid, which is shortened by α-oxidation as the key step to yield 10Z,13Z,16Z-19:acid. This acid can be finally reduced to an aldehyde and decarbonylated or decarboxylated to furnish the pheromone component 3Z,6Z,9Z-18:H. A similar transformation of 11Z,14Z,17Z-20:acid yields the second pheromone component, 3Z,6Z,9Z-19:H.</description><subject>Alkenes - metabolism</subject><subject>Animals</subject><subject>biochemical pathways</subject><subject>Biochemistry. Physiology. Immunology</subject><subject>Biological and medical sciences</subject><subject>Biosynthesis</subject><subject>chemical composition</subject><subject>Deuterium</subject><subject>Erannis</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gas chromatography</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Geometridae</subject><subject>hydrocarbons</subject><subject>Insecta</subject><subject>Invertebrates</subject><subject>Lepidoptera</subject><subject>Mass spectrometry</subject><subject>Moths - metabolism</subject><subject>pheromone biosynthesis</subject><subject>pheromone blends</subject><subject>pheromone glands</subject><subject>pheromone precursors</subject><subject>Pheromones</subject><subject>Pheromones - metabolism</subject><subject>Physiology. Development</subject><subject>radiolabeling</subject><subject>sex pheromones</subject><subject>Unsaturated hydrocarbons</subject><issn>0098-0331</issn><issn>1573-1561</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNqFkU1v1DAQhi0EokvhB3CBqBJVkTbgiRN_cKOr8iEVFYn2shdrkjhsVom92NlD--uZaFeqxAVfPBo9845fv4y9Bv4BOFcfE3CtZU5lbkRR5g9P2AIqJXKoJDxlC86NzrkQcMJepLTlnBdSV8_ZCSgJHEAv2HjZh3Tvp41LfcpCl12I9VKul2b9PhdLuTT5TTNh6xqcYu-8-5Tdblz2A3ufrcK4C975aR4jgeznxsUwUiu7HJxv5_ZVRO9JuMYtxh5fsmcdDsm9Ot6n7O7L1e3qW3598_X76vN13pQAE5kpOw3CVMK0pWwbXVcGjUHXoRKtMZrXQsmyQ0EPcw5L1TaooFO1rAqBIE7Z-UF3F8OfvUuTHfvUuGFA78I-WcUVgVr_Fyy4KCs6BJ79A27DPnoyYZUQRJWFIQgOUBNDStF1dhf7EeO9BW7nxOwhMTuXc2L2gWbeHIX39ejax4ljRAS8OwKYGhw6-tGmT4-cNgYAFHFvD1yHweLvSMzdr4KDoGWmKMnsX3JvpMo</recordid><startdate>20070801</startdate><enddate>20070801</enddate><creator>Goller, Stephan</creator><creator>Szöcs, Gabor</creator><creator>Francke, Wittko</creator><creator>Schulz, Stefan</creator><general>New York : Springer-Verlag</general><general>Springer</general><general>Springer Nature B.V</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7QG</scope><scope>7QR</scope><scope>7SN</scope><scope>7SS</scope><scope>7U7</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>C1K</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7N</scope><scope>M7P</scope><scope>P64</scope><scope>PCBAR</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>RC3</scope><scope>7X8</scope></search><sort><creationdate>20070801</creationdate><title>Biosynthesis of (3Z,6Z,9Z)-3,6,9-Octadecatriene: The Main Component of the Pheromone Blend of Erannis bajaria</title><author>Goller, Stephan ; Szöcs, Gabor ; Francke, Wittko ; Schulz, Stefan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c411t-934f8139539d46dc8b59a99aefa73d9980b3764fa3deceea47dca71f7b6523a13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Alkenes - metabolism</topic><topic>Animals</topic><topic>biochemical pathways</topic><topic>Biochemistry. Physiology. Immunology</topic><topic>Biological and medical sciences</topic><topic>Biosynthesis</topic><topic>chemical composition</topic><topic>Deuterium</topic><topic>Erannis</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gas chromatography</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Geometridae</topic><topic>hydrocarbons</topic><topic>Insecta</topic><topic>Invertebrates</topic><topic>Lepidoptera</topic><topic>Mass spectrometry</topic><topic>Moths - metabolism</topic><topic>pheromone biosynthesis</topic><topic>pheromone blends</topic><topic>pheromone glands</topic><topic>pheromone precursors</topic><topic>Pheromones</topic><topic>Pheromones - metabolism</topic><topic>Physiology. Development</topic><topic>radiolabeling</topic><topic>sex pheromones</topic><topic>Unsaturated hydrocarbons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Goller, Stephan</creatorcontrib><creatorcontrib>Szöcs, Gabor</creatorcontrib><creatorcontrib>Francke, Wittko</creatorcontrib><creatorcontrib>Schulz, Stefan</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Animal Behavior Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Ecology Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Toxicology Abstracts</collection><collection>Health & Medical Complete (ProQuest)</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>Public Health Database</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Earth, Atmospheric & Aquatic Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection (Proquest) (PQ_SDU_P3)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>PML(ProQuest Medical Library)</collection><collection>ProQuest Science Journals</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>ProQuest Biological Science Journals</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Earth, Atmospheric & Aquatic Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central Basic</collection><collection>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of chemical ecology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Goller, Stephan</au><au>Szöcs, Gabor</au><au>Francke, Wittko</au><au>Schulz, Stefan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biosynthesis of (3Z,6Z,9Z)-3,6,9-Octadecatriene: The Main Component of the Pheromone Blend of Erannis bajaria</atitle><jtitle>Journal of chemical ecology</jtitle><addtitle>J Chem Ecol</addtitle><date>2007-08-01</date><risdate>2007</risdate><volume>33</volume><issue>8</issue><spage>1505</spage><epage>1509</epage><pages>1505-1509</pages><issn>0098-0331</issn><eissn>1573-1561</eissn><coden>JCECD8</coden><abstract>The hydrocarbons (3Z,6Z,9Z)-3,6,9-octadecatriene (3Z,6Z,9Z-18:H) and (3Z,6Z,9Z)-3,6,9-nonadecatriene (3Z,6Z,9Z-19:H) constitute the pheromone of the winter moth, Erannis bajaria. These compounds belong to a large group of lepidopteran pheromones which consist of unsaturated hydrocarbons and their corresponding oxygenated derivatives. The biosynthesis of such hydrocarbons with an odd number of carbons in the chain is well understood. In contrast, knowledge about the biosynthesis of even numbered derivatives is lacking. We investigated the biosynthesis of 3Z,6Z,9Z-18:H by applying deuterium-labeled precursors to females of E. bajaria followed by gas chromatography-mass spectrometry analysis of extracts of the pheromone gland. A mixture of deuterium-labeled [17,17,18,18-²H₄]-3Z,6Z,9Z-18:H and the unlabeled 3Z,6Z,9Z-18:H was obtained after topical application and injection of (10Z,13Z,16Z)-[2,2,3,3-²H₄]-10,13,16-nonadecatrienoic acid ([2,2,3,3-²H₄]-10Z,13Z,16Z-19:acid) or (11Z,14Z,17Z)-[3,3,4,4-²H₄]-11,14,17-icosatrienoic acid ([3,3,4,4-²H₄]-11Z,14Z,17Z-20:acid). These results are consistent with a biosynthetic pathway that starts with α-linolenic acid (9Z,12Z,15Z-18:acid). Chain elongation leads to 11Z,14Z,17Z-20:acid, which is shortened by α-oxidation as the key step to yield 10Z,13Z,16Z-19:acid. This acid can be finally reduced to an aldehyde and decarbonylated or decarboxylated to furnish the pheromone component 3Z,6Z,9Z-18:H. A similar transformation of 11Z,14Z,17Z-20:acid yields the second pheromone component, 3Z,6Z,9Z-19:H.</abstract><cop>New York, NY</cop><pub>New York : Springer-Verlag</pub><pmid>17610118</pmid><doi>10.1007/s10886-007-9324-z</doi><tpages>5</tpages></addata></record> |
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| subjects | Alkenes - metabolism Animals biochemical pathways Biochemistry. Physiology. Immunology Biological and medical sciences Biosynthesis chemical composition Deuterium Erannis Fundamental and applied biological sciences. Psychology Gas chromatography Gas Chromatography-Mass Spectrometry Geometridae hydrocarbons Insecta Invertebrates Lepidoptera Mass spectrometry Moths - metabolism pheromone biosynthesis pheromone blends pheromone glands pheromone precursors Pheromones Pheromones - metabolism Physiology. Development radiolabeling sex pheromones Unsaturated hydrocarbons |
| title | Biosynthesis of (3Z,6Z,9Z)-3,6,9-Octadecatriene: The Main Component of the Pheromone Blend of Erannis bajaria |
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