Decaspirones A−E, Bioactive Spirodioxynaphthalenes from the Freshwater Aquatic Fungus Decaisnella thyridioides
Decaspirones A−E (1−5), five new compounds related to the palmarumycins, were isolated from cultures of the freshwater aquatic fungal species Decaisnella thyridioides. The known compound palmarumycin CP1 (6) was also obtained. The structures of 1−5 were determined by analysis of NMR and MS data, and...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2006-12, Vol.69 (12), p.1667-1671 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Jiao, Ping Swenson, Dale C Gloer, James B Campbell, Jinx Shearer, Carol A |
| description | Decaspirones A−E (1−5), five new compounds related to the palmarumycins, were isolated from cultures of the freshwater aquatic fungal species Decaisnella thyridioides. The known compound palmarumycin CP1 (6) was also obtained. The structures of 1−5 were determined by analysis of NMR and MS data, and their relative configurations were assigned by analysis of 1H NMR J-values and NOESY data. The structure of the lead compound 1 was confirmed by X-ray crystallographic analysis. Compounds 1−5 possess a trans ring fusion not previously reported in members of this structural class. The absolute configuration of 1 was assigned using the modified Mosher method. Compounds 1−5 showed potent antifungal and antibacterial activity. |
| doi_str_mv | 10.1021/np060385k |
| format | Article |
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The known compound palmarumycin CP1 (6) was also obtained. The structures of 1−5 were determined by analysis of NMR and MS data, and their relative configurations were assigned by analysis of 1H NMR J-values and NOESY data. The structure of the lead compound 1 was confirmed by X-ray crystallographic analysis. Compounds 1−5 possess a trans ring fusion not previously reported in members of this structural class. The absolute configuration of 1 was assigned using the modified Mosher method. Compounds 1−5 showed potent antifungal and antibacterial activity.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np060385k</identifier><identifier>PMID: 17190439</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - isolation & purification ; Anti-Bacterial Agents - pharmacology ; Antifungal Agents - chemistry ; Antifungal Agents - isolation & purification ; Antifungal Agents - pharmacology ; Ascomycota - chemistry ; Aspergillus flavus - drug effects ; Biological and medical sciences ; Candida albicans - drug effects ; Crystallography, X-Ray ; Decaisnella thyridioides ; Dioxanes - chemistry ; Dioxanes - isolation & purification ; Escherichia coli - drug effects ; Fresh Water ; Fusarium - drug effects ; General pharmacology ; Medical sciences ; Molecular Conformation ; Molecular Structure ; Naphthalenes - chemistry ; Naphthalenes - isolation & purification ; Naphthalenes - pharmacology ; Nuclear Magnetic Resonance, Biomolecular ; Pharmacognosy. 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Nat. Prod</addtitle><description>Decaspirones A−E (1−5), five new compounds related to the palmarumycins, were isolated from cultures of the freshwater aquatic fungal species Decaisnella thyridioides. The known compound palmarumycin CP1 (6) was also obtained. The structures of 1−5 were determined by analysis of NMR and MS data, and their relative configurations were assigned by analysis of 1H NMR J-values and NOESY data. The structure of the lead compound 1 was confirmed by X-ray crystallographic analysis. Compounds 1−5 possess a trans ring fusion not previously reported in members of this structural class. The absolute configuration of 1 was assigned using the modified Mosher method. 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Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Spiro Compounds - chemistry</subject><subject>Spiro Compounds - isolation & purification</subject><subject>Spiro Compounds - pharmacology</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Wisconsin</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0cFu1DAQBmALgehSOPACKBcqITUwjmM7OW5LtyAqUWiRuFkTZ8K6zSapndDuG_TMI_IkJOyqe0HiNNLMp1-jGcZecnjLIeHvmg4UiExeP2IzLhOIFSTyMZsBVyIWmUr32LMQrgBAQC6fsj2ueQ6pyGese08WQ-d821CI5r_vf50cRkeuRdu7nxRdTJPStXfrBrtlv8SaJlf5dhX1S4oWnsLyFnvy0fxmwN7ZaDE0P4YQTbkuNFTXOMq1d2OKKyk8Z08qrAO92NZ99m1xcnn8IT77fPrxeH4Wo-Sij0srM1WS0kioqVCcl5XNKw2pHLsSrC6o4kWuSiwBEoRc6RK00gBZyotU7LODTW7n25uBQm9WLthpnYbaIRiVJUqlufwvTIDnKhdT4psNtL4NwVNlOu9W6NeGg5n-YB7-MNpX29ChWFG5k9vDj-D1FmCwWFceG-vCzmWjyf66eONc6OnuYY7-2igttDSX5xfm6_dPPJVHX8z5LhdtMFft4JvxyP9Y8A-oUK2s</recordid><startdate>20061201</startdate><enddate>20061201</enddate><creator>Jiao, Ping</creator><creator>Swenson, Dale C</creator><creator>Gloer, James B</creator><creator>Campbell, Jinx</creator><creator>Shearer, Carol A</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</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>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>F1W</scope><scope>FR3</scope><scope>H99</scope><scope>L.F</scope><scope>L.G</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20061201</creationdate><title>Decaspirones A−E, Bioactive Spirodioxynaphthalenes from the Freshwater Aquatic Fungus Decaisnella thyridioides</title><author>Jiao, Ping ; Swenson, Dale C ; Gloer, James B ; Campbell, Jinx ; Shearer, Carol A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a513t-dc586de67aea7eb611dfc9f7045de650c7bef1b96dad002a0967d076700841b43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - isolation & purification</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - isolation & purification</topic><topic>Antifungal Agents - pharmacology</topic><topic>Ascomycota - chemistry</topic><topic>Aspergillus flavus - drug effects</topic><topic>Biological and medical sciences</topic><topic>Candida albicans - drug effects</topic><topic>Crystallography, X-Ray</topic><topic>Decaisnella thyridioides</topic><topic>Dioxanes - chemistry</topic><topic>Dioxanes - isolation & purification</topic><topic>Escherichia coli - drug effects</topic><topic>Fresh Water</topic><topic>Fusarium - drug effects</topic><topic>General pharmacology</topic><topic>Medical sciences</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Naphthalenes - chemistry</topic><topic>Naphthalenes - isolation & purification</topic><topic>Naphthalenes - pharmacology</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Pharmacognosy. 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Nat. Prod</addtitle><date>2006-12-01</date><risdate>2006</risdate><volume>69</volume><issue>12</issue><spage>1667</spage><epage>1671</epage><pages>1667-1671</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Decaspirones A−E (1−5), five new compounds related to the palmarumycins, were isolated from cultures of the freshwater aquatic fungal species Decaisnella thyridioides. The known compound palmarumycin CP1 (6) was also obtained. The structures of 1−5 were determined by analysis of NMR and MS data, and their relative configurations were assigned by analysis of 1H NMR J-values and NOESY data. The structure of the lead compound 1 was confirmed by X-ray crystallographic analysis. Compounds 1−5 possess a trans ring fusion not previously reported in members of this structural class. The absolute configuration of 1 was assigned using the modified Mosher method. Compounds 1−5 showed potent antifungal and antibacterial activity.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>17190439</pmid><doi>10.1021/np060385k</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - isolation & purification Anti-Bacterial Agents - pharmacology Antifungal Agents - chemistry Antifungal Agents - isolation & purification Antifungal Agents - pharmacology Ascomycota - chemistry Aspergillus flavus - drug effects Biological and medical sciences Candida albicans - drug effects Crystallography, X-Ray Decaisnella thyridioides Dioxanes - chemistry Dioxanes - isolation & purification Escherichia coli - drug effects Fresh Water Fusarium - drug effects General pharmacology Medical sciences Molecular Conformation Molecular Structure Naphthalenes - chemistry Naphthalenes - isolation & purification Naphthalenes - pharmacology Nuclear Magnetic Resonance, Biomolecular Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Spiro Compounds - chemistry Spiro Compounds - isolation & purification Spiro Compounds - pharmacology Staphylococcus aureus - drug effects Wisconsin |
| title | Decaspirones A−E, Bioactive Spirodioxynaphthalenes from the Freshwater Aquatic Fungus Decaisnella thyridioides |
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