In Vitro Antibacterial Activity of Sphaeropsidins and Chemical Derivatives toward Xanthomonas oryzae pv. oryzae, the Causal Agent of Rice Bacterial Blight
Sphaeropsidin A, the main phytotoxin produced by Diplodia cupressi, as well as the two natural analogues sphaeropsidins B and C and 14 derivatives obtained by chemical modifications were assayed for antibacterial activity against Xanthomonas oryzae pv. oryzae, Pseudomonas fuscovaginae, and Burkholde...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2011-12, Vol.74 (12), p.2520-2525 |
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| creator | Evidente, Antonio Venturi, Vittorio Masi, Marco Degrassi, Giuliano Cimmino, Alessio Maddau, Lucia Andolfi, Anna |
| description | Sphaeropsidin A, the main phytotoxin produced by Diplodia cupressi, as well as the two natural analogues sphaeropsidins B and C and 14 derivatives obtained by chemical modifications were assayed for antibacterial activity against Xanthomonas oryzae pv. oryzae, Pseudomonas fuscovaginae, and Burkholderia glumae, the causal agents of severe bacterial rice diseases. The results showed a strong and specific activity of sphaeropsidin A against X. oryzae pv. oryzae, while no activity was observed against the other two pathogens. The results of structure–activity relationship studies showed that structural features important to impart this antibacterial activity are the presence of the C-7 carbonyl group and the hemiketalic lactone functionality. The C-13 vinyl group, the double bond of ring C, and/or the tertiary C-9 hydroxy group, as well as the pimarane arrangement of the tricylic carbon skeleton, were also important for the antibacterial activity. These findings may be useful in designing novel compounds for practical applications in agriculture. |
| doi_str_mv | 10.1021/np200625m |
| format | Article |
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The results showed a strong and specific activity of sphaeropsidin A against X. oryzae pv. oryzae, while no activity was observed against the other two pathogens. The results of structure–activity relationship studies showed that structural features important to impart this antibacterial activity are the presence of the C-7 carbonyl group and the hemiketalic lactone functionality. The C-13 vinyl group, the double bond of ring C, and/or the tertiary C-9 hydroxy group, as well as the pimarane arrangement of the tricylic carbon skeleton, were also important for the antibacterial activity. These findings may be useful in designing novel compounds for practical applications in agriculture.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np200625m</identifier><identifier>PMID: 22124378</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - isolation & purification ; Anti-Bacterial Agents - pharmacology ; Antibiotics (antibacterial agents, antifungal agents) ; Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents ; Applied microbiology ; Bacteria ; Biological and medical sciences ; Burkholderia - drug effects ; Burkholderia glumae ; Diplodia ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Diterpenes - pharmacology ; Fundamental and applied biological sciences. Psychology ; Gene Expression Regulation, Bacterial ; Microbial Sensitivity Tests ; Microbiology ; Molecular Structure ; Netherlands ; Oryza - metabolism ; Oryza - microbiology ; Oryza sativa ; Plant Diseases - etiology ; Plant Diseases - genetics ; Plant Diseases - microbiology ; Pseudomonas - drug effects ; Pseudomonas fuscovaginae ; Structure-Activity Relationship ; Xanthomonas - drug effects ; Xanthomonas oryzae</subject><ispartof>Journal of natural products (Washington, D.C.), 2011-12, Vol.74 (12), p.2520-2525</ispartof><rights>Copyright © 2011 American Chemical Society and American Society of Pharmacognosy</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a377t-1fb61e3fc58a71f7ea26f870c70e84db0a733903272d635d166b0691353c49d63</citedby><cites>FETCH-LOGICAL-a377t-1fb61e3fc58a71f7ea26f870c70e84db0a733903272d635d166b0691353c49d63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np200625m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np200625m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25339356$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22124378$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Evidente, Antonio</creatorcontrib><creatorcontrib>Venturi, Vittorio</creatorcontrib><creatorcontrib>Masi, Marco</creatorcontrib><creatorcontrib>Degrassi, Giuliano</creatorcontrib><creatorcontrib>Cimmino, Alessio</creatorcontrib><creatorcontrib>Maddau, Lucia</creatorcontrib><creatorcontrib>Andolfi, Anna</creatorcontrib><title>In Vitro Antibacterial Activity of Sphaeropsidins and Chemical Derivatives toward Xanthomonas oryzae pv. oryzae, the Causal Agent of Rice Bacterial Blight</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Sphaeropsidin A, the main phytotoxin produced by Diplodia cupressi, as well as the two natural analogues sphaeropsidins B and C and 14 derivatives obtained by chemical modifications were assayed for antibacterial activity against Xanthomonas oryzae pv. oryzae, Pseudomonas fuscovaginae, and Burkholderia glumae, the causal agents of severe bacterial rice diseases. The results showed a strong and specific activity of sphaeropsidin A against X. oryzae pv. oryzae, while no activity was observed against the other two pathogens. The results of structure–activity relationship studies showed that structural features important to impart this antibacterial activity are the presence of the C-7 carbonyl group and the hemiketalic lactone functionality. The C-13 vinyl group, the double bond of ring C, and/or the tertiary C-9 hydroxy group, as well as the pimarane arrangement of the tricylic carbon skeleton, were also important for the antibacterial activity. 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Psychology</subject><subject>Gene Expression Regulation, Bacterial</subject><subject>Microbial Sensitivity Tests</subject><subject>Microbiology</subject><subject>Molecular Structure</subject><subject>Netherlands</subject><subject>Oryza - metabolism</subject><subject>Oryza - microbiology</subject><subject>Oryza sativa</subject><subject>Plant Diseases - etiology</subject><subject>Plant Diseases - genetics</subject><subject>Plant Diseases - microbiology</subject><subject>Pseudomonas - drug effects</subject><subject>Pseudomonas fuscovaginae</subject><subject>Structure-Activity Relationship</subject><subject>Xanthomonas - drug effects</subject><subject>Xanthomonas oryzae</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp90ctu1DAUBmALgehQWPACyBsESKT4EtvJcjrcKlVC4iZ20YnjNK4SO7WdQcOj8LR41GG6QaxsWZ_OL58foaeUnFHC6Bs3M0IkE9M9tKKCkUISJu6jFaGSF7yS5Ql6FOM1IYSTWjxEJ4xRVnJVrdDvC4e_2xQ8XrtkW9DJBAsjXutktzbtsO_xl3kAE_wcbWddxOA6vBnMZHV2bzPfQrYm4uR_QujwD3Bp8JN3ELEPu19g8Lw9O1xf4zQYvIEl7kOujEv7hM9WG3x-DD8f7dWQHqMHPYzRPDmcp-jb-3dfNx-Ly08fLjbrywK4UqmgfSup4b0WFSjaKwNM9pUiWhFTlV1LQHFeE84U6yQXHZWyJbKmXHBd1vnpFL24nTsHf7OYmJrJRm3GEZzxS2xqympaiZJl-fK_Mu--LIkgVZnpq1uqg48xmL6Zg50g7BpKmn1pzbG0bJ8dxi7tZLqj_NtSBs8PAGJeeh_AaRvvnMgf5ELeOdCxufZLcHlv_wj8A6ldq1E</recordid><startdate>20111227</startdate><enddate>20111227</enddate><creator>Evidente, Antonio</creator><creator>Venturi, Vittorio</creator><creator>Masi, Marco</creator><creator>Degrassi, Giuliano</creator><creator>Cimmino, Alessio</creator><creator>Maddau, Lucia</creator><creator>Andolfi, Anna</creator><general>American Chemical Society and American Society of Pharmacognosy</general><general>American Society of Pharmacognosy</general><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>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20111227</creationdate><title>In Vitro Antibacterial Activity of Sphaeropsidins and Chemical Derivatives toward Xanthomonas oryzae pv. oryzae, the Causal Agent of Rice Bacterial Blight</title><author>Evidente, Antonio ; Venturi, Vittorio ; Masi, Marco ; Degrassi, Giuliano ; Cimmino, Alessio ; Maddau, Lucia ; Andolfi, Anna</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a377t-1fb61e3fc58a71f7ea26f870c70e84db0a733903272d635d166b0691353c49d63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - isolation & purification</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibiotics (antibacterial agents, antifungal agents)</topic><topic>Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents</topic><topic>Applied microbiology</topic><topic>Bacteria</topic><topic>Biological and medical sciences</topic><topic>Burkholderia - drug effects</topic><topic>Burkholderia glumae</topic><topic>Diplodia</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Diterpenes - pharmacology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gene Expression Regulation, Bacterial</topic><topic>Microbial Sensitivity Tests</topic><topic>Microbiology</topic><topic>Molecular Structure</topic><topic>Netherlands</topic><topic>Oryza - metabolism</topic><topic>Oryza - microbiology</topic><topic>Oryza sativa</topic><topic>Plant Diseases - etiology</topic><topic>Plant Diseases - genetics</topic><topic>Plant Diseases - microbiology</topic><topic>Pseudomonas - drug effects</topic><topic>Pseudomonas fuscovaginae</topic><topic>Structure-Activity Relationship</topic><topic>Xanthomonas - drug effects</topic><topic>Xanthomonas oryzae</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Evidente, Antonio</creatorcontrib><creatorcontrib>Venturi, Vittorio</creatorcontrib><creatorcontrib>Masi, Marco</creatorcontrib><creatorcontrib>Degrassi, Giuliano</creatorcontrib><creatorcontrib>Cimmino, Alessio</creatorcontrib><creatorcontrib>Maddau, Lucia</creatorcontrib><creatorcontrib>Andolfi, Anna</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</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><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Evidente, Antonio</au><au>Venturi, Vittorio</au><au>Masi, Marco</au><au>Degrassi, Giuliano</au><au>Cimmino, Alessio</au><au>Maddau, Lucia</au><au>Andolfi, Anna</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>In Vitro Antibacterial Activity of Sphaeropsidins and Chemical Derivatives toward Xanthomonas oryzae pv. oryzae, the Causal Agent of Rice Bacterial Blight</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2011-12-27</date><risdate>2011</risdate><volume>74</volume><issue>12</issue><spage>2520</spage><epage>2525</epage><pages>2520-2525</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Sphaeropsidin A, the main phytotoxin produced by Diplodia cupressi, as well as the two natural analogues sphaeropsidins B and C and 14 derivatives obtained by chemical modifications were assayed for antibacterial activity against Xanthomonas oryzae pv. oryzae, Pseudomonas fuscovaginae, and Burkholderia glumae, the causal agents of severe bacterial rice diseases. The results showed a strong and specific activity of sphaeropsidin A against X. oryzae pv. oryzae, while no activity was observed against the other two pathogens. The results of structure–activity relationship studies showed that structural features important to impart this antibacterial activity are the presence of the C-7 carbonyl group and the hemiketalic lactone functionality. The C-13 vinyl group, the double bond of ring C, and/or the tertiary C-9 hydroxy group, as well as the pimarane arrangement of the tricylic carbon skeleton, were also important for the antibacterial activity. These findings may be useful in designing novel compounds for practical applications in agriculture.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>22124378</pmid><doi>10.1021/np200625m</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2011-12, Vol.74 (12), p.2520-2525 |
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| subjects | Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - isolation & purification Anti-Bacterial Agents - pharmacology Antibiotics (antibacterial agents, antifungal agents) Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents Applied microbiology Bacteria Biological and medical sciences Burkholderia - drug effects Burkholderia glumae Diplodia Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology Fundamental and applied biological sciences. Psychology Gene Expression Regulation, Bacterial Microbial Sensitivity Tests Microbiology Molecular Structure Netherlands Oryza - metabolism Oryza - microbiology Oryza sativa Plant Diseases - etiology Plant Diseases - genetics Plant Diseases - microbiology Pseudomonas - drug effects Pseudomonas fuscovaginae Structure-Activity Relationship Xanthomonas - drug effects Xanthomonas oryzae |
| title | In Vitro Antibacterial Activity of Sphaeropsidins and Chemical Derivatives toward Xanthomonas oryzae pv. oryzae, the Causal Agent of Rice Bacterial Blight |
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