Structural and Stereochemical Studies of Hydroxyanthraquinone Derivatives from the Endophytic Fungus Coniothyrium sp
ABSTRACT Four known hydroxyanthraquinones (1–4) together with four new derivatives having a tetralone moiety, namely coniothyrinones A–D (5–8), were isolated from the culture of Coniothyrium sp., an endophytic fungus isolated from Salsola oppostifolia from Gomera in the Canary Islands. The structure...
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2013-02, Vol.25 (2), p.141-148 |
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| creator | Sun, Peng Huo, Juan Kurtán, Tibor Mándi, Attila Antus, Sándor Tang, Hua Draeger, Siegfried Schulz, Barbara Hussain, Hidayat Krohn, Karsten Pan, Weihua Yi, Yanghua Zhang, Wen |
| description | ABSTRACT
Four known hydroxyanthraquinones (1–4) together with four new derivatives having a tetralone moiety, namely coniothyrinones A–D (5–8), were isolated from the culture of Coniothyrium sp., an endophytic fungus isolated from Salsola oppostifolia from Gomera in the Canary Islands. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configurations of coniothyrinones A (5), B (6), and D (8) were determined by TDDFT calculations of CD spectra, allowing the determination of the absolute configuration of coniothyrinone C (7) as well. Coniothyrinones A (5), B (6), and D (8) could be used as ECD reference compounds in the determination of absolute configuration for related tetralone derivatives. This is the first report of anthraquinones and derivatives from an isolate of the genus Coniothyrium sp. These compounds showed inhibitory effects against the fungus Microbotryum violaceum, the alga Chlorella fusca, and the bacteria Escherichia coli and Bacillus megaterium. Chirality 25:141–148, 2013. © 2012 Wiley Periodicals, Inc. |
| doi_str_mv | 10.1002/chir.22128 |
| format | Article |
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Four known hydroxyanthraquinones (1–4) together with four new derivatives having a tetralone moiety, namely coniothyrinones A–D (5–8), were isolated from the culture of Coniothyrium sp., an endophytic fungus isolated from Salsola oppostifolia from Gomera in the Canary Islands. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configurations of coniothyrinones A (5), B (6), and D (8) were determined by TDDFT calculations of CD spectra, allowing the determination of the absolute configuration of coniothyrinone C (7) as well. Coniothyrinones A (5), B (6), and D (8) could be used as ECD reference compounds in the determination of absolute configuration for related tetralone derivatives. This is the first report of anthraquinones and derivatives from an isolate of the genus Coniothyrium sp. These compounds showed inhibitory effects against the fungus Microbotryum violaceum, the alga Chlorella fusca, and the bacteria Escherichia coli and Bacillus megaterium. Chirality 25:141–148, 2013. © 2012 Wiley Periodicals, Inc.</description><identifier>ISSN: 0899-0042</identifier><identifier>EISSN: 1520-636X</identifier><identifier>DOI: 10.1002/chir.22128</identifier><identifier>PMID: 23255384</identifier><language>eng</language><publisher>United States: Blackwell Publishing Ltd</publisher><subject>absolute configuration ; anthraquinone derivatives ; Anthraquinones - chemistry ; Anthraquinones - pharmacology ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Ascomycota - chemistry ; Bacillus megaterium ; Bacteria ; Chirality ; Chlorella - drug effects ; Chlorella fusca ; coniothyrinones ; Coniothyrium ; Coniothyrium sp ; Coniothyrium sp., coniothyrinones ; Culture ; Derivatives ; Endophytes - chemistry ; Escherichia coli ; Fungi ; Mathematical analysis ; Microbotryum violaceum ; Models, Molecular ; Molecular Conformation ; Salsola ; Spectra ; Stereoisomerism ; TDDFT ECD calculation ; tetralone</subject><ispartof>Chirality (New York, N.Y.), 2013-02, Vol.25 (2), p.141-148</ispartof><rights>Copyright © 2012 Wiley Periodicals, Inc</rights><rights>Copyright © 2012 Wiley Periodicals, Inc.</rights><rights>Copyright © 2013 Wiley Periodicals, Inc., A Wiley Company</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4978-fc3f049a4f2c6c4e5962fa0f49ef4fda0bb687e4eb127af310b1f5553e96b31a3</citedby><cites>FETCH-LOGICAL-c4978-fc3f049a4f2c6c4e5962fa0f49ef4fda0bb687e4eb127af310b1f5553e96b31a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchir.22128$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchir.22128$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23255384$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sun, Peng</creatorcontrib><creatorcontrib>Huo, Juan</creatorcontrib><creatorcontrib>Kurtán, Tibor</creatorcontrib><creatorcontrib>Mándi, Attila</creatorcontrib><creatorcontrib>Antus, Sándor</creatorcontrib><creatorcontrib>Tang, Hua</creatorcontrib><creatorcontrib>Draeger, Siegfried</creatorcontrib><creatorcontrib>Schulz, Barbara</creatorcontrib><creatorcontrib>Hussain, Hidayat</creatorcontrib><creatorcontrib>Krohn, Karsten</creatorcontrib><creatorcontrib>Pan, Weihua</creatorcontrib><creatorcontrib>Yi, Yanghua</creatorcontrib><creatorcontrib>Zhang, Wen</creatorcontrib><title>Structural and Stereochemical Studies of Hydroxyanthraquinone Derivatives from the Endophytic Fungus Coniothyrium sp</title><title>Chirality (New York, N.Y.)</title><addtitle>Chirality</addtitle><description>ABSTRACT
Four known hydroxyanthraquinones (1–4) together with four new derivatives having a tetralone moiety, namely coniothyrinones A–D (5–8), were isolated from the culture of Coniothyrium sp., an endophytic fungus isolated from Salsola oppostifolia from Gomera in the Canary Islands. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configurations of coniothyrinones A (5), B (6), and D (8) were determined by TDDFT calculations of CD spectra, allowing the determination of the absolute configuration of coniothyrinone C (7) as well. Coniothyrinones A (5), B (6), and D (8) could be used as ECD reference compounds in the determination of absolute configuration for related tetralone derivatives. This is the first report of anthraquinones and derivatives from an isolate of the genus Coniothyrium sp. These compounds showed inhibitory effects against the fungus Microbotryum violaceum, the alga Chlorella fusca, and the bacteria Escherichia coli and Bacillus megaterium. Chirality 25:141–148, 2013. © 2012 Wiley Periodicals, Inc.</description><subject>absolute configuration</subject><subject>anthraquinone derivatives</subject><subject>Anthraquinones - chemistry</subject><subject>Anthraquinones - pharmacology</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Ascomycota - chemistry</subject><subject>Bacillus megaterium</subject><subject>Bacteria</subject><subject>Chirality</subject><subject>Chlorella - drug effects</subject><subject>Chlorella fusca</subject><subject>coniothyrinones</subject><subject>Coniothyrium</subject><subject>Coniothyrium sp</subject><subject>Coniothyrium sp., coniothyrinones</subject><subject>Culture</subject><subject>Derivatives</subject><subject>Endophytes - chemistry</subject><subject>Escherichia coli</subject><subject>Fungi</subject><subject>Mathematical analysis</subject><subject>Microbotryum violaceum</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Salsola</subject><subject>Spectra</subject><subject>Stereoisomerism</subject><subject>TDDFT ECD calculation</subject><subject>tetralone</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0U1rFDEYB_Agil2rFz-ABLyIMDVvk5kcZe12C4uCW1G8hEwmcVJnJtu8tJ1v32m37cGDPQUefs8_PPwBeIvREUaIfNKdC0eEYFI_AwtcElRwyn89BwtUC1EgxMgBeBXjOUJIcMpeggNCSVnSmi1A2qaQdcpB9VCNLdwmE4zXnRmcnkfblFtnIvQWrqc2-OtJjakL6iK70Y8GfjHBXarkLmdjgx9g6gw8Hlu_66bkNFzl8U-OcOlH51M3BZcHGHevwQur-mje3L-H4Mfq-Gy5LjbfTk6XnzeFZqKqC6upRUwoZonmmplScGIVskwYy2yrUNPwujLMNJhUylKMGmzL-TAjeEOxoofgwz53F_xFNjHJwUVt-l6NxucoccVYhTgl_GnKqCC0Jqh-mpKK1hhjymb6_h967nMY55slpvPvFRJ3gR_3SgcfYzBW7oIbVJgkRvK2YXnbsLxreMbv7iNzM5j2kT5UOgO8B1euN9N_ouRyffr9IbTY77iYzPXjjgp_Ja9oVcqfX0_kCokt-S028ozeAJFqwTE</recordid><startdate>201302</startdate><enddate>201302</enddate><creator>Sun, Peng</creator><creator>Huo, Juan</creator><creator>Kurtán, Tibor</creator><creator>Mándi, Attila</creator><creator>Antus, Sándor</creator><creator>Tang, Hua</creator><creator>Draeger, Siegfried</creator><creator>Schulz, Barbara</creator><creator>Hussain, Hidayat</creator><creator>Krohn, Karsten</creator><creator>Pan, Weihua</creator><creator>Yi, Yanghua</creator><creator>Zhang, Wen</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>7QO</scope><scope>7QR</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><scope>M7N</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>201302</creationdate><title>Structural and Stereochemical Studies of Hydroxyanthraquinone Derivatives from the Endophytic Fungus Coniothyrium sp</title><author>Sun, Peng ; Huo, Juan ; Kurtán, Tibor ; Mándi, Attila ; Antus, Sándor ; Tang, Hua ; Draeger, Siegfried ; Schulz, Barbara ; Hussain, Hidayat ; Krohn, Karsten ; Pan, Weihua ; Yi, Yanghua ; Zhang, Wen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4978-fc3f049a4f2c6c4e5962fa0f49ef4fda0bb687e4eb127af310b1f5553e96b31a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>absolute configuration</topic><topic>anthraquinone derivatives</topic><topic>Anthraquinones - chemistry</topic><topic>Anthraquinones - pharmacology</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Ascomycota - chemistry</topic><topic>Bacillus megaterium</topic><topic>Bacteria</topic><topic>Chirality</topic><topic>Chlorella - drug effects</topic><topic>Chlorella fusca</topic><topic>coniothyrinones</topic><topic>Coniothyrium</topic><topic>Coniothyrium sp</topic><topic>Coniothyrium sp., coniothyrinones</topic><topic>Culture</topic><topic>Derivatives</topic><topic>Endophytes - chemistry</topic><topic>Escherichia coli</topic><topic>Fungi</topic><topic>Mathematical analysis</topic><topic>Microbotryum violaceum</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Salsola</topic><topic>Spectra</topic><topic>Stereoisomerism</topic><topic>TDDFT ECD calculation</topic><topic>tetralone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sun, Peng</creatorcontrib><creatorcontrib>Huo, Juan</creatorcontrib><creatorcontrib>Kurtán, Tibor</creatorcontrib><creatorcontrib>Mándi, Attila</creatorcontrib><creatorcontrib>Antus, Sándor</creatorcontrib><creatorcontrib>Tang, Hua</creatorcontrib><creatorcontrib>Draeger, Siegfried</creatorcontrib><creatorcontrib>Schulz, Barbara</creatorcontrib><creatorcontrib>Hussain, Hidayat</creatorcontrib><creatorcontrib>Krohn, Karsten</creatorcontrib><creatorcontrib>Pan, Weihua</creatorcontrib><creatorcontrib>Yi, Yanghua</creatorcontrib><creatorcontrib>Zhang, Wen</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sun, Peng</au><au>Huo, Juan</au><au>Kurtán, Tibor</au><au>Mándi, Attila</au><au>Antus, Sándor</au><au>Tang, Hua</au><au>Draeger, Siegfried</au><au>Schulz, Barbara</au><au>Hussain, Hidayat</au><au>Krohn, Karsten</au><au>Pan, Weihua</au><au>Yi, Yanghua</au><au>Zhang, Wen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structural and Stereochemical Studies of Hydroxyanthraquinone Derivatives from the Endophytic Fungus Coniothyrium sp</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>2013-02</date><risdate>2013</risdate><volume>25</volume><issue>2</issue><spage>141</spage><epage>148</epage><pages>141-148</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>ABSTRACT
Four known hydroxyanthraquinones (1–4) together with four new derivatives having a tetralone moiety, namely coniothyrinones A–D (5–8), were isolated from the culture of Coniothyrium sp., an endophytic fungus isolated from Salsola oppostifolia from Gomera in the Canary Islands. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configurations of coniothyrinones A (5), B (6), and D (8) were determined by TDDFT calculations of CD spectra, allowing the determination of the absolute configuration of coniothyrinone C (7) as well. Coniothyrinones A (5), B (6), and D (8) could be used as ECD reference compounds in the determination of absolute configuration for related tetralone derivatives. This is the first report of anthraquinones and derivatives from an isolate of the genus Coniothyrium sp. These compounds showed inhibitory effects against the fungus Microbotryum violaceum, the alga Chlorella fusca, and the bacteria Escherichia coli and Bacillus megaterium. Chirality 25:141–148, 2013. © 2012 Wiley Periodicals, Inc.</abstract><cop>United States</cop><pub>Blackwell Publishing Ltd</pub><pmid>23255384</pmid><doi>10.1002/chir.22128</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | absolute configuration anthraquinone derivatives Anthraquinones - chemistry Anthraquinones - pharmacology Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antifungal Agents - chemistry Antifungal Agents - pharmacology Ascomycota - chemistry Bacillus megaterium Bacteria Chirality Chlorella - drug effects Chlorella fusca coniothyrinones Coniothyrium Coniothyrium sp Coniothyrium sp., coniothyrinones Culture Derivatives Endophytes - chemistry Escherichia coli Fungi Mathematical analysis Microbotryum violaceum Models, Molecular Molecular Conformation Salsola Spectra Stereoisomerism TDDFT ECD calculation tetralone |
| title | Structural and Stereochemical Studies of Hydroxyanthraquinone Derivatives from the Endophytic Fungus Coniothyrium sp |
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