Structure-activity relationships in the fungistatic activity against Botrytis cinerea of clovanes modified on ring C
The preparation of clovanes 4, 5, 6, 8, and 9, which bear different levels of oxidation on ring C, is described for the first time. The biotransformation of compounds 5, 6, and 9 by the fungus Botrytis cinerea is investigated, yielding compounds 10, 11, and 12, which are described for the first time...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2004-05, Vol.67 (5), p.793-798 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Deligeorgopoulou, A Macias-Sanchez, A.J Mobbs, D.J Hitchcock, P.B Hanson, J.R Collado, I.G |
| description | The preparation of clovanes 4, 5, 6, 8, and 9, which bear different levels of oxidation on ring C, is described for the first time. The biotransformation of compounds 5, 6, and 9 by the fungus Botrytis cinerea is investigated, yielding compounds 10, 11, and 12, which are described for the first time, together with compounds 4-6, 8, and 9. The evaluation of the fungistatic activity against B. cinerea of compounds 6, 9, 12, 18, 19, 20, and 21 is reported. Comparison of these results with previously published data shows first that the inclusion of hydroxyl groups on ring C leads to a decrease in the biological activity and, second, that the presence of a 9alpha-hydroxyl group and an alkyl chain at C-2 plays an important role in the fungistatic activity against B. cinerea of compounds with a clovane skeleton. |
| doi_str_mv | 10.1021/np030404f |
| format | Article |
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The biotransformation of compounds 5, 6, and 9 by the fungus Botrytis cinerea is investigated, yielding compounds 10, 11, and 12, which are described for the first time, together with compounds 4-6, 8, and 9. The evaluation of the fungistatic activity against B. cinerea of compounds 6, 9, 12, 18, 19, 20, and 21 is reported. Comparison of these results with previously published data shows first that the inclusion of hydroxyl groups on ring C leads to a decrease in the biological activity and, second, that the presence of a 9alpha-hydroxyl group and an alkyl chain at C-2 plays an important role in the fungistatic activity against B. cinerea of compounds with a clovane skeleton.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np030404f</identifier><identifier>PMID: 15165139</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Biological and medical sciences ; Biotransformation ; Botrytis - drug effects ; Botrytis cinerea ; Bridged Bicyclo Compounds - chemical synthesis ; Bridged Bicyclo Compounds - chemistry ; Bridged Bicyclo Compounds - pharmacology ; Chemical control ; Control ; Crystallography, X-Ray ; Cyclization ; Fundamental and applied biological sciences. Psychology ; Fungal plant pathogens ; Fungicides, Industrial - chemical synthesis ; Fungicides, Industrial - chemistry ; Fungicides, Industrial - pharmacology ; Molecular Structure ; Oxidation-Reduction ; Phytopathology. Animal pests. Plant and forest protection ; Plant Diseases - microbiology ; Structure-Activity Relationship</subject><ispartof>Journal of natural products (Washington, D.C.), 2004-05, Vol.67 (5), p.793-798</ispartof><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15793305$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15165139$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Deligeorgopoulou, A</creatorcontrib><creatorcontrib>Macias-Sanchez, A.J</creatorcontrib><creatorcontrib>Mobbs, D.J</creatorcontrib><creatorcontrib>Hitchcock, P.B</creatorcontrib><creatorcontrib>Hanson, J.R</creatorcontrib><creatorcontrib>Collado, I.G</creatorcontrib><title>Structure-activity relationships in the fungistatic activity against Botrytis cinerea of clovanes modified on ring C</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>The preparation of clovanes 4, 5, 6, 8, and 9, which bear different levels of oxidation on ring C, is described for the first time. The biotransformation of compounds 5, 6, and 9 by the fungus Botrytis cinerea is investigated, yielding compounds 10, 11, and 12, which are described for the first time, together with compounds 4-6, 8, and 9. The evaluation of the fungistatic activity against B. cinerea of compounds 6, 9, 12, 18, 19, 20, and 21 is reported. Comparison of these results with previously published data shows first that the inclusion of hydroxyl groups on ring C leads to a decrease in the biological activity and, second, that the presence of a 9alpha-hydroxyl group and an alkyl chain at C-2 plays an important role in the fungistatic activity against B. cinerea of compounds with a clovane skeleton.</description><subject>Biological and medical sciences</subject><subject>Biotransformation</subject><subject>Botrytis - drug effects</subject><subject>Botrytis cinerea</subject><subject>Bridged Bicyclo Compounds - chemical synthesis</subject><subject>Bridged Bicyclo Compounds - chemistry</subject><subject>Bridged Bicyclo Compounds - pharmacology</subject><subject>Chemical control</subject><subject>Control</subject><subject>Crystallography, X-Ray</subject><subject>Cyclization</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Fungal plant pathogens</subject><subject>Fungicides, Industrial - chemical synthesis</subject><subject>Fungicides, Industrial - chemistry</subject><subject>Fungicides, Industrial - pharmacology</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Phytopathology. Animal pests. Plant and forest protection</subject><subject>Plant Diseases - microbiology</subject><subject>Structure-Activity Relationship</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpN0U2LFDEQBuAgijuuHvwDmoveWitJ56OPOvgFA4qzi-AlpNPJbLQnmU3Si_PvDcy4eKrD-1AUbyH0nMAbApS8jQdg0EPvH6AV4RQ6AZQ_RCsggnVMif4CPSnlF0BjA3-MLggnghM2rFDd1rzYumTXGVvDXahHnN1sakix3IRDwSHieuOwX-IulNoCi--l2ZkQS8XvU83HGgq2IbrsDE4e2zndmegK3qcp-OAmnCLOIe7w-il65M1c3LPzvETXHz9crT93m6-fvqzfbTrPGNRO-IGoXhEu7CAEWGvHiRCQnnshqJUDTHJiYz8SodwkaS8soXK0Shk_cOHZJXp92nvI6XZxpep9KNbNc7srLUUTBYIqSht8cYbLuHeTPuSwN_mo__XUwKszMMWa2WcTbSj_OTm0k3lz3cm1qtyf-9zk31pIJrm--rbVP-T3DduIn1o1__LkvUna7HLbeb2lQBi0xyquOPsLe1eQMw</recordid><startdate>20040501</startdate><enddate>20040501</enddate><creator>Deligeorgopoulou, A</creator><creator>Macias-Sanchez, A.J</creator><creator>Mobbs, D.J</creator><creator>Hitchcock, P.B</creator><creator>Hanson, J.R</creator><creator>Collado, I.G</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>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope></search><sort><creationdate>20040501</creationdate><title>Structure-activity relationships in the fungistatic activity against Botrytis cinerea of clovanes modified on ring C</title><author>Deligeorgopoulou, A ; Macias-Sanchez, A.J ; Mobbs, D.J ; Hitchcock, P.B ; Hanson, J.R ; Collado, I.G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f330t-6f91848156c9660cccbd1107f5f662c790d7d3b4b168ed7246c127bc88af956f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Biological and medical sciences</topic><topic>Biotransformation</topic><topic>Botrytis - drug effects</topic><topic>Botrytis cinerea</topic><topic>Bridged Bicyclo Compounds - chemical synthesis</topic><topic>Bridged Bicyclo Compounds - chemistry</topic><topic>Bridged Bicyclo Compounds - pharmacology</topic><topic>Chemical control</topic><topic>Control</topic><topic>Crystallography, X-Ray</topic><topic>Cyclization</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Fungal plant pathogens</topic><topic>Fungicides, Industrial - chemical synthesis</topic><topic>Fungicides, Industrial - chemistry</topic><topic>Fungicides, Industrial - pharmacology</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><topic>Phytopathology. Animal pests. 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Nat. Prod</addtitle><date>2004-05-01</date><risdate>2004</risdate><volume>67</volume><issue>5</issue><spage>793</spage><epage>798</epage><pages>793-798</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>The preparation of clovanes 4, 5, 6, 8, and 9, which bear different levels of oxidation on ring C, is described for the first time. The biotransformation of compounds 5, 6, and 9 by the fungus Botrytis cinerea is investigated, yielding compounds 10, 11, and 12, which are described for the first time, together with compounds 4-6, 8, and 9. The evaluation of the fungistatic activity against B. cinerea of compounds 6, 9, 12, 18, 19, 20, and 21 is reported. Comparison of these results with previously published data shows first that the inclusion of hydroxyl groups on ring C leads to a decrease in the biological activity and, second, that the presence of a 9alpha-hydroxyl group and an alkyl chain at C-2 plays an important role in the fungistatic activity against B. cinerea of compounds with a clovane skeleton.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>15165139</pmid><doi>10.1021/np030404f</doi><tpages>6</tpages></addata></record> |
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| subjects | Biological and medical sciences Biotransformation Botrytis - drug effects Botrytis cinerea Bridged Bicyclo Compounds - chemical synthesis Bridged Bicyclo Compounds - chemistry Bridged Bicyclo Compounds - pharmacology Chemical control Control Crystallography, X-Ray Cyclization Fundamental and applied biological sciences. Psychology Fungal plant pathogens Fungicides, Industrial - chemical synthesis Fungicides, Industrial - chemistry Fungicides, Industrial - pharmacology Molecular Structure Oxidation-Reduction Phytopathology. Animal pests. Plant and forest protection Plant Diseases - microbiology Structure-Activity Relationship |
| title | Structure-activity relationships in the fungistatic activity against Botrytis cinerea of clovanes modified on ring C |
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