A Novel Lepidopteran Sex Pheromone Produced by Females of a Lithosiinae Species, Lyclene dharma dharma, in the Family of Arctiidae
Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produced three pheromone components (I-III), which strongly stimulated male antennae. Using GC-MS analysis and chemical derivatizations, the following structures were estimated: 6-methyl-2-octadecanone (I), 14-methyl-2-octadecanone (II),...
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| Veröffentlicht in: | Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2007-11, Vol.71 (11), p.2860-2863 |
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| container_title | Bioscience, biotechnology, and biochemistry |
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| creator | YAMAMOTO, Masanobu KAMATA, Tomoya DO, Nguyen Duc ADACHI, Yasushi KINJO, Masakatsu ANDO, Tetsu |
| description | Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produced three pheromone components (I-III), which strongly stimulated male antennae. Using GC-MS analysis and chemical derivatizations, the following structures were estimated: 6-methyl-2-octadecanone (I), 14-methyl-2-octadecanone (II), and 6,14-dimethyl-2-octadecanone (III). While the stereochemistry of the chiral centers could not be determined because it was difficult to collect a sufficient amount of the natural pheromone, the plain structures of I and II were confirmed by synthesis of the racemic mixtures starting from diols. These methyl-branched ketones have not been identified as a natural product, indicating that they constitute a new chemical group of lepidopteran female sex pheromones. |
| doi_str_mv | 10.1271/bbb.70551 |
| format | Article |
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Using GC-MS analysis and chemical derivatizations, the following structures were estimated: 6-methyl-2-octadecanone (I), 14-methyl-2-octadecanone (II), and 6,14-dimethyl-2-octadecanone (III). While the stereochemistry of the chiral centers could not be determined because it was difficult to collect a sufficient amount of the natural pheromone, the plain structures of I and II were confirmed by synthesis of the racemic mixtures starting from diols. These methyl-branched ketones have not been identified as a natural product, indicating that they constitute a new chemical group of lepidopteran female sex pheromones.</description><identifier>ISSN: 0916-8451</identifier><identifier>EISSN: 1347-6947</identifier><identifier>DOI: 10.1271/bbb.70551</identifier><identifier>PMID: 17986763</identifier><language>eng</language><publisher>Tokyo: Japan Society for Bioscience, Biotechnology, and Agrochemistry</publisher><subject>Animals ; Arctiidae ; Biological and medical sciences ; chemical ecology ; Female ; female sex pheromone ; Fundamental and applied biological sciences. Psychology ; Gas Chromatography-Mass Spectrometry ; Ketones - analysis ; Ketones - chemistry ; Ketones - metabolism ; Lepidoptera ; methyl-branched 2-ketones ; methyloctadecanones ; Molecular Structure ; Moths - metabolism ; Sex Attractants - analysis ; Sex Attractants - chemistry ; Sex Attractants - metabolism</subject><ispartof>Bioscience, biotechnology, and biochemistry, 2007-11, Vol.71 (11), p.2860-2863</ispartof><rights>2007 by Japan Society for Bioscience, Biotechnology, and Agrochemistry 2007</rights><rights>2008 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 2007</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c609t-e472c1ee7bd689a131897f130b0ccfafd051a13dcc5bbd473e1832d4d860cc523</citedby><cites>FETCH-LOGICAL-c609t-e472c1ee7bd689a131897f130b0ccfafd051a13dcc5bbd473e1832d4d860cc523</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19949728$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17986763$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>YAMAMOTO, Masanobu</creatorcontrib><creatorcontrib>KAMATA, Tomoya</creatorcontrib><creatorcontrib>DO, Nguyen Duc</creatorcontrib><creatorcontrib>ADACHI, Yasushi</creatorcontrib><creatorcontrib>KINJO, Masakatsu</creatorcontrib><creatorcontrib>ANDO, Tetsu</creatorcontrib><title>A Novel Lepidopteran Sex Pheromone Produced by Females of a Lithosiinae Species, Lyclene dharma dharma, in the Family of Arctiidae</title><title>Bioscience, biotechnology, and biochemistry</title><addtitle>Biosci Biotechnol Biochem</addtitle><description>Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produced three pheromone components (I-III), which strongly stimulated male antennae. Using GC-MS analysis and chemical derivatizations, the following structures were estimated: 6-methyl-2-octadecanone (I), 14-methyl-2-octadecanone (II), and 6,14-dimethyl-2-octadecanone (III). While the stereochemistry of the chiral centers could not be determined because it was difficult to collect a sufficient amount of the natural pheromone, the plain structures of I and II were confirmed by synthesis of the racemic mixtures starting from diols. These methyl-branched ketones have not been identified as a natural product, indicating that they constitute a new chemical group of lepidopteran female sex pheromones.</description><subject>Animals</subject><subject>Arctiidae</subject><subject>Biological and medical sciences</subject><subject>chemical ecology</subject><subject>Female</subject><subject>female sex pheromone</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Ketones - analysis</subject><subject>Ketones - chemistry</subject><subject>Ketones - metabolism</subject><subject>Lepidoptera</subject><subject>methyl-branched 2-ketones</subject><subject>methyloctadecanones</subject><subject>Molecular Structure</subject><subject>Moths - metabolism</subject><subject>Sex Attractants - analysis</subject><subject>Sex Attractants - chemistry</subject><subject>Sex Attractants - metabolism</subject><issn>0916-8451</issn><issn>1347-6947</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0V9r1TAYBvAgijubXvgFJCAOhHUmbZo_l4fhUaHoYHpd0uQtJyNtjkk77a2f3MxTGeiFVy-8_J43hAehF5Rc0lLQt13XXQpS1_QR2tCKiYIrJh6jDVGUF5LV9ASdpnRLSF7U9Ck6oUJJLni1QT-3-FO4A48bODgbDhNEPeIb-IGv9xDDEEbA1zHY2YDF3YJ3MGgPCYcea9y4aR-Sc6MGfHMA4yBd4GYxHnLK7nUc9DousBvxtAe804Pzy318G83knNXwDD3ptU_wfJ1n6Ovu3ZerD0Xz-f3Hq21TGE7UVAATpaEAorNcKk0rKpXoaUU6Ykyve0tqmrfWmLrrLBMVUFmVllnJM6jL6gydH-8eYvg2Q5rawSUD3usRwpxaLmsmS8n-C0tCScVLleGrv-BtmOOYP9FSxpSknJA6qzdHZWJIKULfHqIbdFxaStr7_trcX_u7v2xfrhfnbgD7INfCMni9Ap2M9n1uy7j04JRiSpQyO3Z0buxDLuB7iN62k158iH9C1b_v_wKd47P8</recordid><startdate>20071101</startdate><enddate>20071101</enddate><creator>YAMAMOTO, Masanobu</creator><creator>KAMATA, Tomoya</creator><creator>DO, Nguyen Duc</creator><creator>ADACHI, Yasushi</creator><creator>KINJO, Masakatsu</creator><creator>ANDO, Tetsu</creator><general>Japan Society for Bioscience, Biotechnology, and Agrochemistry</general><general>Japan Society for Bioscience Biotechnology and Agrochemistry</general><general>Oxford University Press</general><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>7QR</scope><scope>7SN</scope><scope>7SS</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20071101</creationdate><title>A Novel Lepidopteran Sex Pheromone Produced by Females of a Lithosiinae Species, Lyclene dharma dharma, in the Family of Arctiidae</title><author>YAMAMOTO, Masanobu ; KAMATA, Tomoya ; DO, Nguyen Duc ; ADACHI, Yasushi ; KINJO, Masakatsu ; ANDO, Tetsu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c609t-e472c1ee7bd689a131897f130b0ccfafd051a13dcc5bbd473e1832d4d860cc523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Animals</topic><topic>Arctiidae</topic><topic>Biological and medical sciences</topic><topic>chemical ecology</topic><topic>Female</topic><topic>female sex pheromone</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Ketones - analysis</topic><topic>Ketones - chemistry</topic><topic>Ketones - metabolism</topic><topic>Lepidoptera</topic><topic>methyl-branched 2-ketones</topic><topic>methyloctadecanones</topic><topic>Molecular Structure</topic><topic>Moths - metabolism</topic><topic>Sex Attractants - analysis</topic><topic>Sex Attractants - chemistry</topic><topic>Sex Attractants - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>YAMAMOTO, Masanobu</creatorcontrib><creatorcontrib>KAMATA, Tomoya</creatorcontrib><creatorcontrib>DO, Nguyen Duc</creatorcontrib><creatorcontrib>ADACHI, Yasushi</creatorcontrib><creatorcontrib>KINJO, Masakatsu</creatorcontrib><creatorcontrib>ANDO, Tetsu</creatorcontrib><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>Chemoreception Abstracts</collection><collection>Ecology Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioscience, biotechnology, and biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>YAMAMOTO, Masanobu</au><au>KAMATA, Tomoya</au><au>DO, Nguyen Duc</au><au>ADACHI, Yasushi</au><au>KINJO, Masakatsu</au><au>ANDO, Tetsu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Novel Lepidopteran Sex Pheromone Produced by Females of a Lithosiinae Species, Lyclene dharma dharma, in the Family of Arctiidae</atitle><jtitle>Bioscience, biotechnology, and biochemistry</jtitle><addtitle>Biosci Biotechnol Biochem</addtitle><date>2007-11-01</date><risdate>2007</risdate><volume>71</volume><issue>11</issue><spage>2860</spage><epage>2863</epage><pages>2860-2863</pages><issn>0916-8451</issn><eissn>1347-6947</eissn><abstract>Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produced three pheromone components (I-III), which strongly stimulated male antennae. Using GC-MS analysis and chemical derivatizations, the following structures were estimated: 6-methyl-2-octadecanone (I), 14-methyl-2-octadecanone (II), and 6,14-dimethyl-2-octadecanone (III). While the stereochemistry of the chiral centers could not be determined because it was difficult to collect a sufficient amount of the natural pheromone, the plain structures of I and II were confirmed by synthesis of the racemic mixtures starting from diols. These methyl-branched ketones have not been identified as a natural product, indicating that they constitute a new chemical group of lepidopteran female sex pheromones.</abstract><cop>Tokyo</cop><pub>Japan Society for Bioscience, Biotechnology, and Agrochemistry</pub><pmid>17986763</pmid><doi>10.1271/bbb.70551</doi><tpages>4</tpages></addata></record> |
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| source | J-STAGE Free; MEDLINE; Oxford University Press Journals All Titles (1996-Current); Freely Accessible Japanese Titles; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Animals Arctiidae Biological and medical sciences chemical ecology Female female sex pheromone Fundamental and applied biological sciences. Psychology Gas Chromatography-Mass Spectrometry Ketones - analysis Ketones - chemistry Ketones - metabolism Lepidoptera methyl-branched 2-ketones methyloctadecanones Molecular Structure Moths - metabolism Sex Attractants - analysis Sex Attractants - chemistry Sex Attractants - metabolism |
| title | A Novel Lepidopteran Sex Pheromone Produced by Females of a Lithosiinae Species, Lyclene dharma dharma, in the Family of Arctiidae |
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