Identification of a sex pheromone component of Pseudococcus cryptus
A sex pheromone component of Pseudococcus cryptus has been isolated and identified. The crude pheromone extract obtained by airborne collection was fractionated by liquid chromatography (LC) on Florisil, and further purified by high performance liquid chromatography and preparative Gas Chromatograph...
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| Veröffentlicht in: | Journal of chemical ecology 2003-10, Vol.29 (10), p.2213-2223 |
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| container_title | Journal of chemical ecology |
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| creator | Arai, T Sugie, H Hiradate, S Kuwahara, S Itagaki, N Nakahata, T |
| description | A sex pheromone component of Pseudococcus cryptus has been isolated and identified. The crude pheromone extract obtained by airborne collection was fractionated by liquid chromatography (LC) on Florisil, and further purified by high performance liquid chromatography and preparative Gas Chromatography (GC). The pheromone component was shown to be an ester, the alcohol part of which was identical to the known alcohol moiety of the pheromone of Planococcus citri. The chemical structure was determined to be 3-isopropenyl-2,2-dimethylcyclobutylmethyl 3-methyl-3-butenoate by MS and 1H NMR analyses. The absolute configuration of the pheromone was assigned as (1R,3R) by comparison of the retention time of the alcohol derived from the P. cryptus pheromone with those of the alcohol derived from P. citri pheromone, and a synthetic sample of alcohol enriched in the (1R,3R)-enantiomer, using a chiral GC stationary phase. The structure of the pheromone was confirmed by synthesis, and by bioassays in a glasshouse. |
| doi_str_mv | 10.1023/a:1026214112242 |
| format | Article |
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The crude pheromone extract obtained by airborne collection was fractionated by liquid chromatography (LC) on Florisil, and further purified by high performance liquid chromatography and preparative Gas Chromatography (GC). The pheromone component was shown to be an ester, the alcohol part of which was identical to the known alcohol moiety of the pheromone of Planococcus citri. The chemical structure was determined to be 3-isopropenyl-2,2-dimethylcyclobutylmethyl 3-methyl-3-butenoate by MS and 1H NMR analyses. The absolute configuration of the pheromone was assigned as (1R,3R) by comparison of the retention time of the alcohol derived from the P. cryptus pheromone with those of the alcohol derived from P. citri pheromone, and a synthetic sample of alcohol enriched in the (1R,3R)-enantiomer, using a chiral GC stationary phase. The structure of the pheromone was confirmed by synthesis, and by bioassays in a glasshouse.</description><identifier>ISSN: 0098-0331</identifier><identifier>EISSN: 1573-1561</identifier><identifier>DOI: 10.1023/a:1026214112242</identifier><identifier>PMID: 14682507</identifier><identifier>CODEN: JCECD8</identifier><language>eng</language><publisher>New York, NY: Springer</publisher><subject>3-Isopropenyl-2,2-dimethylcyclobutylmethyl 3-methyl-3-butenoate ; Alcohols ; Analytical chemistry ; Animal and plant ecology ; Animal, plant and microbial ecology ; Animals ; Autoecology ; Bioassays ; Biological and medical sciences ; Biological Assay ; Butyrates - chemistry ; Butyrates - pharmacology ; chemical composition ; chemical structure ; Chromatography ; Chromatography, High Pressure Liquid ; Cyclobutanes - chemistry ; Cyclobutanes - pharmacology ; Female ; Fundamental and applied biological sciences. Psychology ; Gas chromatography ; Gas Chromatography-Mass Spectrometry ; General aspects ; insect control ; Insecta - chemistry ; Insecta - physiology ; Liquid chromatography ; Magnetic Resonance Spectroscopy ; Male ; Pheromones ; Pseudococcidae ; Pseudococcus ; Pseudococcus cryptus ; Retention time ; Sex Attractants - chemistry ; Sex Attractants - pharmacology ; sex pheromones ; stereochemistry</subject><ispartof>Journal of chemical ecology, 2003-10, Vol.29 (10), p.2213-2223</ispartof><rights>2004 INIST-CNRS</rights><rights>Plenum Publishing Corporation 2003</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c431t-1999b0674f897012cbb2c01e30c8c37bcd14905427c32a3f96992f6dea82d263</citedby></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=15291266$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14682507$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Arai, T</creatorcontrib><creatorcontrib>Sugie, H</creatorcontrib><creatorcontrib>Hiradate, S</creatorcontrib><creatorcontrib>Kuwahara, S</creatorcontrib><creatorcontrib>Itagaki, N</creatorcontrib><creatorcontrib>Nakahata, T</creatorcontrib><title>Identification of a sex pheromone component of Pseudococcus cryptus</title><title>Journal of chemical ecology</title><addtitle>J Chem Ecol</addtitle><description>A sex pheromone component of Pseudococcus cryptus has been isolated and identified. The crude pheromone extract obtained by airborne collection was fractionated by liquid chromatography (LC) on Florisil, and further purified by high performance liquid chromatography and preparative Gas Chromatography (GC). The pheromone component was shown to be an ester, the alcohol part of which was identical to the known alcohol moiety of the pheromone of Planococcus citri. The chemical structure was determined to be 3-isopropenyl-2,2-dimethylcyclobutylmethyl 3-methyl-3-butenoate by MS and 1H NMR analyses. The absolute configuration of the pheromone was assigned as (1R,3R) by comparison of the retention time of the alcohol derived from the P. cryptus pheromone with those of the alcohol derived from P. citri pheromone, and a synthetic sample of alcohol enriched in the (1R,3R)-enantiomer, using a chiral GC stationary phase. The structure of the pheromone was confirmed by synthesis, and by bioassays in a glasshouse.</description><subject>3-Isopropenyl-2,2-dimethylcyclobutylmethyl 3-methyl-3-butenoate</subject><subject>Alcohols</subject><subject>Analytical chemistry</subject><subject>Animal and plant ecology</subject><subject>Animal, plant and microbial ecology</subject><subject>Animals</subject><subject>Autoecology</subject><subject>Bioassays</subject><subject>Biological and medical sciences</subject><subject>Biological Assay</subject><subject>Butyrates - chemistry</subject><subject>Butyrates - pharmacology</subject><subject>chemical composition</subject><subject>chemical structure</subject><subject>Chromatography</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Cyclobutanes - chemistry</subject><subject>Cyclobutanes - pharmacology</subject><subject>Female</subject><subject>Fundamental and applied biological sciences. 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Psychology</topic><topic>Gas chromatography</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>General aspects</topic><topic>insect control</topic><topic>Insecta - chemistry</topic><topic>Insecta - physiology</topic><topic>Liquid chromatography</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Male</topic><topic>Pheromones</topic><topic>Pseudococcidae</topic><topic>Pseudococcus</topic><topic>Pseudococcus cryptus</topic><topic>Retention time</topic><topic>Sex Attractants - chemistry</topic><topic>Sex Attractants - pharmacology</topic><topic>sex pheromones</topic><topic>stereochemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Arai, T</creatorcontrib><creatorcontrib>Sugie, H</creatorcontrib><creatorcontrib>Hiradate, S</creatorcontrib><creatorcontrib>Kuwahara, S</creatorcontrib><creatorcontrib>Itagaki, N</creatorcontrib><creatorcontrib>Nakahata, T</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>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 Collection</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 Edition)</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>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 Korea</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</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>Medical Database</collection><collection>Science Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biological Science Database</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>Arai, T</au><au>Sugie, H</au><au>Hiradate, S</au><au>Kuwahara, S</au><au>Itagaki, N</au><au>Nakahata, T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of a sex pheromone component of Pseudococcus cryptus</atitle><jtitle>Journal of chemical ecology</jtitle><addtitle>J Chem Ecol</addtitle><date>2003-10-01</date><risdate>2003</risdate><volume>29</volume><issue>10</issue><spage>2213</spage><epage>2223</epage><pages>2213-2223</pages><issn>0098-0331</issn><eissn>1573-1561</eissn><coden>JCECD8</coden><abstract>A sex pheromone component of Pseudococcus cryptus has been isolated and identified. The crude pheromone extract obtained by airborne collection was fractionated by liquid chromatography (LC) on Florisil, and further purified by high performance liquid chromatography and preparative Gas Chromatography (GC). The pheromone component was shown to be an ester, the alcohol part of which was identical to the known alcohol moiety of the pheromone of Planococcus citri. The chemical structure was determined to be 3-isopropenyl-2,2-dimethylcyclobutylmethyl 3-methyl-3-butenoate by MS and 1H NMR analyses. The absolute configuration of the pheromone was assigned as (1R,3R) by comparison of the retention time of the alcohol derived from the P. cryptus pheromone with those of the alcohol derived from P. citri pheromone, and a synthetic sample of alcohol enriched in the (1R,3R)-enantiomer, using a chiral GC stationary phase. The structure of the pheromone was confirmed by synthesis, and by bioassays in a glasshouse.</abstract><cop>New York, NY</cop><pub>Springer</pub><pmid>14682507</pmid><doi>10.1023/a:1026214112242</doi><tpages>11</tpages></addata></record> |
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| subjects | 3-Isopropenyl-2,2-dimethylcyclobutylmethyl 3-methyl-3-butenoate Alcohols Analytical chemistry Animal and plant ecology Animal, plant and microbial ecology Animals Autoecology Bioassays Biological and medical sciences Biological Assay Butyrates - chemistry Butyrates - pharmacology chemical composition chemical structure Chromatography Chromatography, High Pressure Liquid Cyclobutanes - chemistry Cyclobutanes - pharmacology Female Fundamental and applied biological sciences. Psychology Gas chromatography Gas Chromatography-Mass Spectrometry General aspects insect control Insecta - chemistry Insecta - physiology Liquid chromatography Magnetic Resonance Spectroscopy Male Pheromones Pseudococcidae Pseudococcus Pseudococcus cryptus Retention time Sex Attractants - chemistry Sex Attractants - pharmacology sex pheromones stereochemistry |
| title | Identification of a sex pheromone component of Pseudococcus cryptus |
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