RK-1355A and B, novel quinomycin derivatives isolated from a microbial metabolites fraction library based on NPPlot screening
Two novel quinomycin derivatives, RK-1355A ( 1 ) and B ( 2 ), and one known quinomycin derivative, UK-63,598 ( 3 ), were isolated from a microbial metabolites fraction library of Streptomyces sp. RK88-1355 based on Natural Products Plot screening. The structural elucidation of 1 and 2 was establishe...
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| Veröffentlicht in: | Journal of antibiotics 2014-04, Vol.67 (4), p.323-329 |
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| container_title | Journal of antibiotics |
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| creator | Lim, Chung Liang Nogawa, Toshihiko Uramoto, Masakazu Okano, Akiko Hongo, Yayoi Nakamura, Takemichi Koshino, Hiroyuki Takahashi, Shunji Ibrahim, Darah Osada, Hiroyuki |
| description | Two novel quinomycin derivatives, RK-1355A (
1
) and B (
2
), and one known quinomycin derivative, UK-63,598 (
3
), were isolated from a microbial metabolites fraction library of
Streptomyces
sp. RK88-1355 based on Natural Products Plot screening. The structural elucidation of
1
and
2
was established through two-dimensional NMR and mass spectrometric measurements. They belong to a class of quinomycin antibiotics family having 3-hydroxyquinaldic acid and a sulfoxide moiety. They are the first examples for natural products as a quinoline type quinomycin having a sulfoxide on the intramolecular cross-linkage. They showed potent antiproliferative activities against various cancer cell lines and they were also found to exhibit moderate antibacterial activity. |
| doi_str_mv | 10.1038/ja.2013.144 |
| format | Article |
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1
) and B (
2
), and one known quinomycin derivative, UK-63,598 (
3
), were isolated from a microbial metabolites fraction library of
Streptomyces
sp. RK88-1355 based on Natural Products Plot screening. The structural elucidation of
1
and
2
was established through two-dimensional NMR and mass spectrometric measurements. They belong to a class of quinomycin antibiotics family having 3-hydroxyquinaldic acid and a sulfoxide moiety. They are the first examples for natural products as a quinoline type quinomycin having a sulfoxide on the intramolecular cross-linkage. They showed potent antiproliferative activities against various cancer cell lines and they were also found to exhibit moderate antibacterial activity.</description><identifier>ISSN: 0021-8820</identifier><identifier>EISSN: 1881-1469</identifier><identifier>DOI: 10.1038/ja.2013.144</identifier><identifier>PMID: 24496142</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject><![CDATA[631/154/1435 ; 631/326/22/1290 ; Animals ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - isolation & purification ; Anti-Bacterial Agents - metabolism ; Anti-Bacterial Agents - pharmacology ; Antibiotics ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - metabolism ; Antineoplastic Agents - pharmacology ; Bacteriology ; Biomedical and Life Sciences ; Bioorganic Chemistry ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Drug Discovery ; Echinomycin - analogs & derivatives ; Echinomycin - chemistry ; Echinomycin - isolation & purification ; Echinomycin - metabolism ; Echinomycin - pharmacology ; Escherichia coli - drug effects ; Escherichia coli - growth & development ; Humans ; Inhibitory Concentration 50 ; Life Sciences ; Medicinal Chemistry ; Metabolites ; Mice ; Microbial Sensitivity Tests ; Microbiology ; Molecular Structure ; Neoplasms - drug therapy ; Organic Chemistry ; original-article ; Small Molecule Libraries ; Staphylococcus aureus - drug effects ; Staphylococcus aureus - growth & development ; Streptomyces - metabolism]]></subject><ispartof>Journal of antibiotics, 2014-04, Vol.67 (4), p.323-329</ispartof><rights>Japan Antibiotics Research Association 2014</rights><rights>Copyright Nature Publishing Group Apr 2014</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c444t-c2096c49945a524c542475050f8fa16dabbb88f1ad3c4cd0eb04e5d5b0caddfb3</citedby><cites>FETCH-LOGICAL-c444t-c2096c49945a524c542475050f8fa16dabbb88f1ad3c4cd0eb04e5d5b0caddfb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24496142$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lim, Chung Liang</creatorcontrib><creatorcontrib>Nogawa, Toshihiko</creatorcontrib><creatorcontrib>Uramoto, Masakazu</creatorcontrib><creatorcontrib>Okano, Akiko</creatorcontrib><creatorcontrib>Hongo, Yayoi</creatorcontrib><creatorcontrib>Nakamura, Takemichi</creatorcontrib><creatorcontrib>Koshino, Hiroyuki</creatorcontrib><creatorcontrib>Takahashi, Shunji</creatorcontrib><creatorcontrib>Ibrahim, Darah</creatorcontrib><creatorcontrib>Osada, Hiroyuki</creatorcontrib><title>RK-1355A and B, novel quinomycin derivatives isolated from a microbial metabolites fraction library based on NPPlot screening</title><title>Journal of antibiotics</title><addtitle>J Antibiot</addtitle><addtitle>J Antibiot (Tokyo)</addtitle><description>Two novel quinomycin derivatives, RK-1355A (
1
) and B (
2
), and one known quinomycin derivative, UK-63,598 (
3
), were isolated from a microbial metabolites fraction library of
Streptomyces
sp. RK88-1355 based on Natural Products Plot screening. The structural elucidation of
1
and
2
was established through two-dimensional NMR and mass spectrometric measurements. They belong to a class of quinomycin antibiotics family having 3-hydroxyquinaldic acid and a sulfoxide moiety. They are the first examples for natural products as a quinoline type quinomycin having a sulfoxide on the intramolecular cross-linkage. They showed potent antiproliferative activities against various cancer cell lines and they were also found to exhibit moderate antibacterial activity.</description><subject>631/154/1435</subject><subject>631/326/22/1290</subject><subject>Animals</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - isolation & purification</subject><subject>Anti-Bacterial Agents - metabolism</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibiotics</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - metabolism</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Bacteriology</subject><subject>Biomedical and Life Sciences</subject><subject>Bioorganic Chemistry</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Drug Discovery</subject><subject>Echinomycin - analogs & derivatives</subject><subject>Echinomycin - chemistry</subject><subject>Echinomycin - isolation & purification</subject><subject>Echinomycin - metabolism</subject><subject>Echinomycin - pharmacology</subject><subject>Escherichia coli - drug effects</subject><subject>Escherichia coli - growth & development</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Life Sciences</subject><subject>Medicinal Chemistry</subject><subject>Metabolites</subject><subject>Mice</subject><subject>Microbial Sensitivity Tests</subject><subject>Microbiology</subject><subject>Molecular Structure</subject><subject>Neoplasms - drug therapy</subject><subject>Organic Chemistry</subject><subject>original-article</subject><subject>Small Molecule Libraries</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Staphylococcus aureus - growth & development</subject><subject>Streptomyces - metabolism</subject><issn>0021-8820</issn><issn>1881-1469</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNptkd1rFTEQxYMo9rb65LsEfBHsXvO5m32sxapYtIg-h8nHllyySZvsXuiD_7spt4qITwMzvzkzh4PQC0q2lHD1dgdbRijfUiEeoQ1VinZU9ONjtCGE0U4pRo7Qca07QvjAB_UUHTEhxp4KtkE_v33uKJfyDENy-N0pTnnvI75dQ8rznQ0JO1_CHpaw9xWHmiMs3uGp5BkDnoMt2QSIePYLmBzD0qipgF1CTjgGU6DcYQO17bTGl6urmBdcbfE-hXT9DD2ZIFb__KGeoB8X77-ff-wuv374dH522VkhxNJZRsbeinEUEiQTVgomBkkkmdQEtHdgjFFqouC4FdYRb4jw0klDLDg3GX6CXh90b0q-XX1d9Byq9TFC8nmtmko6Kq5YTxv66h90l9eS2neaDmpopxlXjXpzoJr_Wouf9E0Jc_OqKdH3qegd6PtUdEul0S8fNFcze_eH_R1DA04PQG2jdO3LX0f_o_cLbdOWbw</recordid><startdate>20140401</startdate><enddate>20140401</enddate><creator>Lim, Chung Liang</creator><creator>Nogawa, Toshihiko</creator><creator>Uramoto, Masakazu</creator><creator>Okano, Akiko</creator><creator>Hongo, Yayoi</creator><creator>Nakamura, Takemichi</creator><creator>Koshino, Hiroyuki</creator><creator>Takahashi, Shunji</creator><creator>Ibrahim, Darah</creator><creator>Osada, Hiroyuki</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</general><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>3V.</scope><scope>7QL</scope><scope>7T5</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7P</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>7X8</scope></search><sort><creationdate>20140401</creationdate><title>RK-1355A and B, novel quinomycin derivatives isolated from a microbial metabolites fraction library based on NPPlot screening</title><author>Lim, Chung Liang ; Nogawa, Toshihiko ; Uramoto, Masakazu ; Okano, Akiko ; Hongo, Yayoi ; Nakamura, Takemichi ; Koshino, Hiroyuki ; Takahashi, Shunji ; Ibrahim, Darah ; Osada, Hiroyuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c444t-c2096c49945a524c542475050f8fa16dabbb88f1ad3c4cd0eb04e5d5b0caddfb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>631/154/1435</topic><topic>631/326/22/1290</topic><topic>Animals</topic><topic>Anti-Bacterial Agents - 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Academic</collection><jtitle>Journal of antibiotics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lim, Chung Liang</au><au>Nogawa, Toshihiko</au><au>Uramoto, Masakazu</au><au>Okano, Akiko</au><au>Hongo, Yayoi</au><au>Nakamura, Takemichi</au><au>Koshino, Hiroyuki</au><au>Takahashi, Shunji</au><au>Ibrahim, Darah</au><au>Osada, Hiroyuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>RK-1355A and B, novel quinomycin derivatives isolated from a microbial metabolites fraction library based on NPPlot screening</atitle><jtitle>Journal of antibiotics</jtitle><stitle>J Antibiot</stitle><addtitle>J Antibiot (Tokyo)</addtitle><date>2014-04-01</date><risdate>2014</risdate><volume>67</volume><issue>4</issue><spage>323</spage><epage>329</epage><pages>323-329</pages><issn>0021-8820</issn><eissn>1881-1469</eissn><abstract>Two novel quinomycin derivatives, RK-1355A (
1
) and B (
2
), and one known quinomycin derivative, UK-63,598 (
3
), were isolated from a microbial metabolites fraction library of
Streptomyces
sp. RK88-1355 based on Natural Products Plot screening. The structural elucidation of
1
and
2
was established through two-dimensional NMR and mass spectrometric measurements. They belong to a class of quinomycin antibiotics family having 3-hydroxyquinaldic acid and a sulfoxide moiety. They are the first examples for natural products as a quinoline type quinomycin having a sulfoxide on the intramolecular cross-linkage. They showed potent antiproliferative activities against various cancer cell lines and they were also found to exhibit moderate antibacterial activity.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>24496142</pmid><doi>10.1038/ja.2013.144</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-8820 |
| ispartof | Journal of antibiotics, 2014-04, Vol.67 (4), p.323-329 |
| issn | 0021-8820 1881-1469 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1519838261 |
| source | MEDLINE; EZB-FREE-00999 freely available EZB journals |
| subjects | 631/154/1435 631/326/22/1290 Animals Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - isolation & purification Anti-Bacterial Agents - metabolism Anti-Bacterial Agents - pharmacology Antibiotics Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - metabolism Antineoplastic Agents - pharmacology Bacteriology Biomedical and Life Sciences Bioorganic Chemistry Cell Line, Tumor Cell Proliferation - drug effects Drug Discovery Echinomycin - analogs & derivatives Echinomycin - chemistry Echinomycin - isolation & purification Echinomycin - metabolism Echinomycin - pharmacology Escherichia coli - drug effects Escherichia coli - growth & development Humans Inhibitory Concentration 50 Life Sciences Medicinal Chemistry Metabolites Mice Microbial Sensitivity Tests Microbiology Molecular Structure Neoplasms - drug therapy Organic Chemistry original-article Small Molecule Libraries Staphylococcus aureus - drug effects Staphylococcus aureus - growth & development Streptomyces - metabolism |
| title | RK-1355A and B, novel quinomycin derivatives isolated from a microbial metabolites fraction library based on NPPlot screening |
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