Biosynthetic Studies on the Botcinolide Skeleton: New Hydroxylated Lactones from Botrytis cinerea
[reaction: see text] The biosynthetic origin of the botcinolide skeleton was investigated by means of feeding 13C- and 2H-labeled precursors to Botrytis cinerea. Three new compounds, two homobotcinolide derivatives, 3-O-acetylhomobotcinolide (5) and 8-methylhomobotcinolide (6), and a new 11-membered...
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| Veröffentlicht in: | Journal of organic chemistry 2006-01, Vol.71 (2), p.562-565 |
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| container_end_page | 565 |
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| container_issue | 2 |
| container_start_page | 562 |
| container_title | Journal of organic chemistry |
| container_volume | 71 |
| creator | REINO, José L. DURáN-PATRóN, Rosa M. DAOUBI, Mourad COLLADO, Isidro G. HERNáNDEZ-GALáN, Rosario |
| description | [reaction: see text] The biosynthetic origin of the botcinolide skeleton was investigated by means of feeding 13C- and 2H-labeled precursors to Botrytis cinerea. Three new compounds, two homobotcinolide derivatives, 3-O-acetylhomobotcinolide (5) and 8-methylhomobotcinolide (6), and a new 11-membered lactone (7), were isolated. Their structures were elucidated on the basis of spectroscopic data, including one-bond and long-range 1H-13C correlations. The relative stereochemistries were determined by combined analyses of NOE data and 1H-1H coupling constants. According to the results of feeding experiments with 13C- and 2H-labeled acetate and l-S-methylmethionine, 5 is an acetate-derived polyketide whose methyl groups originate from l-S-methylmethionine. This is a rare example of the incorporation of a methyl from methionine into a supposed C3 starter unit of the polyketide synthesis. |
| doi_str_mv | 10.1021/jo051993s |
| format | Article |
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Three new compounds, two homobotcinolide derivatives, 3-O-acetylhomobotcinolide (5) and 8-methylhomobotcinolide (6), and a new 11-membered lactone (7), were isolated. Their structures were elucidated on the basis of spectroscopic data, including one-bond and long-range 1H-13C correlations. The relative stereochemistries were determined by combined analyses of NOE data and 1H-1H coupling constants. According to the results of feeding experiments with 13C- and 2H-labeled acetate and l-S-methylmethionine, 5 is an acetate-derived polyketide whose methyl groups originate from l-S-methylmethionine. This is a rare example of the incorporation of a methyl from methionine into a supposed C3 starter unit of the polyketide synthesis.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo051993s</identifier><identifier>PMID: 16408965</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acetates ; Botrytis - chemistry ; Botrytis - growth & development ; Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Hydroxylation ; Lactones - chemistry ; Lactones - isolation & purification ; Methionine ; Models, Molecular ; Molecular Conformation ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2006-01, Vol.71 (2), p.562-565</ispartof><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17700509$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16408965$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>REINO, José L.</creatorcontrib><creatorcontrib>DURáN-PATRóN, Rosa M.</creatorcontrib><creatorcontrib>DAOUBI, Mourad</creatorcontrib><creatorcontrib>COLLADO, Isidro G.</creatorcontrib><creatorcontrib>HERNáNDEZ-GALáN, Rosario</creatorcontrib><title>Biosynthetic Studies on the Botcinolide Skeleton: New Hydroxylated Lactones from Botrytis cinerea</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>[reaction: see text] The biosynthetic origin of the botcinolide skeleton was investigated by means of feeding 13C- and 2H-labeled precursors to Botrytis cinerea. Three new compounds, two homobotcinolide derivatives, 3-O-acetylhomobotcinolide (5) and 8-methylhomobotcinolide (6), and a new 11-membered lactone (7), were isolated. Their structures were elucidated on the basis of spectroscopic data, including one-bond and long-range 1H-13C correlations. The relative stereochemistries were determined by combined analyses of NOE data and 1H-1H coupling constants. According to the results of feeding experiments with 13C- and 2H-labeled acetate and l-S-methylmethionine, 5 is an acetate-derived polyketide whose methyl groups originate from l-S-methylmethionine. This is a rare example of the incorporation of a methyl from methionine into a supposed C3 starter unit of the polyketide synthesis.</description><subject>Acetates</subject><subject>Botrytis - chemistry</subject><subject>Botrytis - growth & development</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Hydroxylation</subject><subject>Lactones - chemistry</subject><subject>Lactones - isolation & purification</subject><subject>Methionine</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkMFu1DAQhi1ERZeWAy-AfIFbysSO7ZgbrYBFrIBqW66RY0-E22zc2l7R3HrlNfskNeqWzmWk-b9vDj8hr2s4qoHV7y8CiFprnp6RRS0YVFJD85wsABirOJN8n7xM6QLKCCFekP1aNtBqKRbEHfuQ5in_xuwtXeet85homGi50OOQrZ_C6B3S9SWOmMP04e72L_2Of-hydjHczKPJ6OjK2JIVc4hh88-Lc_aJFhsjmkOyN5gx4avdPiDnnz-dnSyr1Y8vX08-rirPG54r1TPdcKy5GJxr-n7AQdpWGdSgmANrTSukkrZujWpagAZ5P_QwWM6UYhr4AXn38PcqhustptxtfLI4jmbCsE2dAtkyBrKAb3bgtt-g666i35g4d4-9FODtDjDJmnGIZrI-PXFKlSpBF6564HzKePM_N_Gyk4or0Z39XHfffjWnS6ZZx_g98i2BxA</recordid><startdate>20060120</startdate><enddate>20060120</enddate><creator>REINO, José L.</creator><creator>DURáN-PATRóN, Rosa M.</creator><creator>DAOUBI, Mourad</creator><creator>COLLADO, Isidro G.</creator><creator>HERNáNDEZ-GALáN, Rosario</creator><general>American Chemical Society</general><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>20060120</creationdate><title>Biosynthetic Studies on the Botcinolide Skeleton: New Hydroxylated Lactones from Botrytis cinerea</title><author>REINO, José L. ; DURáN-PATRóN, Rosa M. ; DAOUBI, Mourad ; COLLADO, Isidro G. ; HERNáNDEZ-GALáN, Rosario</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i343t-7b2943e135fdd4bbfef6c87ae9072d0cca85676c18a748004e3bfb0fc32772903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Acetates</topic><topic>Botrytis - chemistry</topic><topic>Botrytis - growth & development</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Hydroxylation</topic><topic>Lactones - chemistry</topic><topic>Lactones - isolation & purification</topic><topic>Methionine</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>REINO, José L.</creatorcontrib><creatorcontrib>DURáN-PATRóN, Rosa M.</creatorcontrib><creatorcontrib>DAOUBI, Mourad</creatorcontrib><creatorcontrib>COLLADO, Isidro G.</creatorcontrib><creatorcontrib>HERNáNDEZ-GALáN, Rosario</creatorcontrib><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 organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>REINO, José L.</au><au>DURáN-PATRóN, Rosa M.</au><au>DAOUBI, Mourad</au><au>COLLADO, Isidro G.</au><au>HERNáNDEZ-GALáN, Rosario</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biosynthetic Studies on the Botcinolide Skeleton: New Hydroxylated Lactones from Botrytis cinerea</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2006-01-20</date><risdate>2006</risdate><volume>71</volume><issue>2</issue><spage>562</spage><epage>565</epage><pages>562-565</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>[reaction: see text] The biosynthetic origin of the botcinolide skeleton was investigated by means of feeding 13C- and 2H-labeled precursors to Botrytis cinerea. Three new compounds, two homobotcinolide derivatives, 3-O-acetylhomobotcinolide (5) and 8-methylhomobotcinolide (6), and a new 11-membered lactone (7), were isolated. Their structures were elucidated on the basis of spectroscopic data, including one-bond and long-range 1H-13C correlations. The relative stereochemistries were determined by combined analyses of NOE data and 1H-1H coupling constants. According to the results of feeding experiments with 13C- and 2H-labeled acetate and l-S-methylmethionine, 5 is an acetate-derived polyketide whose methyl groups originate from l-S-methylmethionine. This is a rare example of the incorporation of a methyl from methionine into a supposed C3 starter unit of the polyketide synthesis.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16408965</pmid><doi>10.1021/jo051993s</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2006-01, Vol.71 (2), p.562-565 |
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| language | eng |
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| subjects | Acetates Botrytis - chemistry Botrytis - growth & development Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Hydroxylation Lactones - chemistry Lactones - isolation & purification Methionine Models, Molecular Molecular Conformation Organic chemistry Preparations and properties |
| title | Biosynthetic Studies on the Botcinolide Skeleton: New Hydroxylated Lactones from Botrytis cinerea |
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