Vittatalactone, a beta-lactone from the striped cucumber beetle, Acalymma vittatum
A novel beta-lactone, vittatalactone (1), was isolated from collections of airborne volatile compounds from feeding male striped cucumber beetles, Acalymma vittatum. The structure of 1 was determined to be (3R,4R)-3-methyl-4-(1,3,5,7-tetramethyloctyl)oxetan-2-one by microderivatization, GC-MS, and N...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2005-01, Vol.68 (1), p.26-30 |
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| container_issue | 1 |
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| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 68 |
| creator | Morris, B.D Smyth, R.R Foster, S.P Hoffmann, M.P Roelofs, W.L Franke, S Francke, W |
| description | A novel beta-lactone, vittatalactone (1), was isolated from collections of airborne volatile compounds from feeding male striped cucumber beetles, Acalymma vittatum. The structure of 1 was determined to be (3R,4R)-3-methyl-4-(1,3,5,7-tetramethyloctyl)oxetan-2-one by microderivatization, GC-MS, and NMR studies. The absolute configurations at C-2 and C-3 on the beta-lactone ring were assigned by use of the modified Mosher method, applied to the beta-hydroxy acid methyl ester resulting from methanolysis of 1. Biological activity of 1, possibly as an aggregation pheromone for A. vittatum, was indicated by electrophysiological studies using beetle antennae and by the production of 1 by feeding male, and not female, beetles. |
| doi_str_mv | 10.1021/np049751v |
| format | Article |
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The structure of 1 was determined to be (3R,4R)-3-methyl-4-(1,3,5,7-tetramethyloctyl)oxetan-2-one by microderivatization, GC-MS, and NMR studies. The absolute configurations at C-2 and C-3 on the beta-lactone ring were assigned by use of the modified Mosher method, applied to the beta-hydroxy acid methyl ester resulting from methanolysis of 1. Biological activity of 1, possibly as an aggregation pheromone for A. vittatum, was indicated by electrophysiological studies using beetle antennae and by the production of 1 by feeding male, and not female, beetles.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np049751v</identifier><identifier>PMID: 15679312</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acalymma vittatum ; Animals ; Biochemistry. Physiology. Immunology ; Biological and medical sciences ; chemical structure ; Coleoptera ; Female ; Fundamental and applied biological sciences. Psychology ; Insecta ; Invertebrates ; lactones ; Lactones - chemistry ; Lactones - isolation & purification ; Lactones - pharmacology ; Male ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Physiology. Development ; Sex Attractants - chemistry ; Sex Attractants - isolation & purification ; Sex Attractants - pharmacology ; spectral analysis ; Stereoisomerism ; Vittatalactone ; volatile organic compounds</subject><ispartof>Journal of natural products (Washington, D.C.), 2005-01, Vol.68 (1), p.26-30</ispartof><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16477572$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15679312$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Morris, B.D</creatorcontrib><creatorcontrib>Smyth, R.R</creatorcontrib><creatorcontrib>Foster, S.P</creatorcontrib><creatorcontrib>Hoffmann, M.P</creatorcontrib><creatorcontrib>Roelofs, W.L</creatorcontrib><creatorcontrib>Franke, S</creatorcontrib><creatorcontrib>Francke, W</creatorcontrib><title>Vittatalactone, a beta-lactone from the striped cucumber beetle, Acalymma vittatum</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>A novel beta-lactone, vittatalactone (1), was isolated from collections of airborne volatile compounds from feeding male striped cucumber beetles, Acalymma vittatum. The structure of 1 was determined to be (3R,4R)-3-methyl-4-(1,3,5,7-tetramethyloctyl)oxetan-2-one by microderivatization, GC-MS, and NMR studies. The absolute configurations at C-2 and C-3 on the beta-lactone ring were assigned by use of the modified Mosher method, applied to the beta-hydroxy acid methyl ester resulting from methanolysis of 1. Biological activity of 1, possibly as an aggregation pheromone for A. vittatum, was indicated by electrophysiological studies using beetle antennae and by the production of 1 by feeding male, and not female, beetles.</description><subject>Acalymma vittatum</subject><subject>Animals</subject><subject>Biochemistry. Physiology. Immunology</subject><subject>Biological and medical sciences</subject><subject>chemical structure</subject><subject>Coleoptera</subject><subject>Female</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Insecta</subject><subject>Invertebrates</subject><subject>lactones</subject><subject>Lactones - chemistry</subject><subject>Lactones - isolation & purification</subject><subject>Lactones - pharmacology</subject><subject>Male</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Physiology. Development</subject><subject>Sex Attractants - chemistry</subject><subject>Sex Attractants - isolation & purification</subject><subject>Sex Attractants - pharmacology</subject><subject>spectral analysis</subject><subject>Stereoisomerism</subject><subject>Vittatalactone</subject><subject>volatile organic compounds</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpF0EtPxCAQB3BiNLquHvwC2ouerA5QynL0rYnx_Tg2Qxe02m5XoBv324vuqhcImR__yQwhGxT2KDC6PxpDpqSgkwXSo4JBmgMTi6QHNOcpH-TZCln1_g0AOCixTFaoyKXilPXI3VMVAgassQztyOwmmGgTMJ2_E-vaJgmvJvHBVWMzTMqu7BptXGQm1PHDQYn1tGkwmfwkdc0aWbJYe7M-v_vk8fTk4eg8vbw-uzg6uEwtBxpSylWulWFSKakVCCHNYKhVaTOtrbAglIktQKO1gmY4LJnWwmqNnA6ospT3yc4sd-zaj874UDSVL01d48i0nS9yyRXL4tknm3PY6cYMi7GrGnTT4ncLEWzPAfo4jXU4Kiv_7_JMSiG_XTpzlQ_m86-O7v27mRTFw819cZyd8sPnW1VcRb818xbbAl9czHy8Z0Dj_ABywAT_AtZohBQ</recordid><startdate>20050101</startdate><enddate>20050101</enddate><creator>Morris, B.D</creator><creator>Smyth, R.R</creator><creator>Foster, S.P</creator><creator>Hoffmann, M.P</creator><creator>Roelofs, W.L</creator><creator>Franke, S</creator><creator>Francke, W</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20050101</creationdate><title>Vittatalactone, a beta-lactone from the striped cucumber beetle, Acalymma vittatum</title><author>Morris, B.D ; Smyth, R.R ; Foster, S.P ; Hoffmann, M.P ; Roelofs, W.L ; Franke, S ; Francke, W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f301t-1396b9e27997b90557e8db9cf4bbf5f059ebee0baff514adc2bb5fbba31819f13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Acalymma vittatum</topic><topic>Animals</topic><topic>Biochemistry. Physiology. Immunology</topic><topic>Biological and medical sciences</topic><topic>chemical structure</topic><topic>Coleoptera</topic><topic>Female</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Insecta</topic><topic>Invertebrates</topic><topic>lactones</topic><topic>Lactones - chemistry</topic><topic>Lactones - isolation & purification</topic><topic>Lactones - pharmacology</topic><topic>Male</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Physiology. Development</topic><topic>Sex Attractants - chemistry</topic><topic>Sex Attractants - isolation & purification</topic><topic>Sex Attractants - pharmacology</topic><topic>spectral analysis</topic><topic>Stereoisomerism</topic><topic>Vittatalactone</topic><topic>volatile organic compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Morris, B.D</creatorcontrib><creatorcontrib>Smyth, R.R</creatorcontrib><creatorcontrib>Foster, S.P</creatorcontrib><creatorcontrib>Hoffmann, M.P</creatorcontrib><creatorcontrib>Roelofs, W.L</creatorcontrib><creatorcontrib>Franke, S</creatorcontrib><creatorcontrib>Francke, W</creatorcontrib><collection>AGRIS</collection><collection>Istex</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>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Morris, B.D</au><au>Smyth, R.R</au><au>Foster, S.P</au><au>Hoffmann, M.P</au><au>Roelofs, W.L</au><au>Franke, S</au><au>Francke, W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Vittatalactone, a beta-lactone from the striped cucumber beetle, Acalymma vittatum</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2005-01-01</date><risdate>2005</risdate><volume>68</volume><issue>1</issue><spage>26</spage><epage>30</epage><pages>26-30</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>A novel beta-lactone, vittatalactone (1), was isolated from collections of airborne volatile compounds from feeding male striped cucumber beetles, Acalymma vittatum. The structure of 1 was determined to be (3R,4R)-3-methyl-4-(1,3,5,7-tetramethyloctyl)oxetan-2-one by microderivatization, GC-MS, and NMR studies. The absolute configurations at C-2 and C-3 on the beta-lactone ring were assigned by use of the modified Mosher method, applied to the beta-hydroxy acid methyl ester resulting from methanolysis of 1. Biological activity of 1, possibly as an aggregation pheromone for A. vittatum, was indicated by electrophysiological studies using beetle antennae and by the production of 1 by feeding male, and not female, beetles.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>15679312</pmid><doi>10.1021/np049751v</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2005-01, Vol.68 (1), p.26-30 |
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| source | ACS Publications; MEDLINE |
| subjects | Acalymma vittatum Animals Biochemistry. Physiology. Immunology Biological and medical sciences chemical structure Coleoptera Female Fundamental and applied biological sciences. Psychology Insecta Invertebrates lactones Lactones - chemistry Lactones - isolation & purification Lactones - pharmacology Male Molecular Structure Nuclear Magnetic Resonance, Biomolecular Physiology. Development Sex Attractants - chemistry Sex Attractants - isolation & purification Sex Attractants - pharmacology spectral analysis Stereoisomerism Vittatalactone volatile organic compounds |
| title | Vittatalactone, a beta-lactone from the striped cucumber beetle, Acalymma vittatum |
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