Caulibugulones A−F, Novel Cytotoxic Isoquinoline Quinones and Iminoquinones from the Marine Bryozoan Caulibugula intermis
An extract of the marine bryozoan Caulibugula intermis, collected in the Indo-Pacific off Palau, produced a distinct pattern of differential cytotoxicity in the National Cancer Institute's 60 cell line antitumor screen. Bioactivity-directed fractionation of the extract provided six new compound...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2004-01, Vol.67 (1), p.70-73 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Milanowski, Dennis J Gustafson, Kirk R Kelley, James A McMahon, James B |
| description | An extract of the marine bryozoan Caulibugula intermis, collected in the Indo-Pacific off Palau, produced a distinct pattern of differential cytotoxicity in the National Cancer Institute's 60 cell line antitumor screen. Bioactivity-directed fractionation of the extract provided six new compounds, caulibugulones A−F (1−6). The structures of these novel metabolites were determined by spectrochemical analyses including LC-MS, HRFABMS, 1-D and 2-D NMR experiments, and by comparison with related compounds. The structures of compounds 2 and 3 were confirmed by chemical interconversion. The isolated compounds exhibited IC50's of 0.03−1.67 μg/mL against murine tumor cells in an in vitro cytotoxicity assay. |
| doi_str_mv | 10.1021/np030378l |
| format | Article |
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Bioactivity-directed fractionation of the extract provided six new compounds, caulibugulones A−F (1−6). The structures of these novel metabolites were determined by spectrochemical analyses including LC-MS, HRFABMS, 1-D and 2-D NMR experiments, and by comparison with related compounds. The structures of compounds 2 and 3 were confirmed by chemical interconversion. The isolated compounds exhibited IC50's of 0.03−1.67 μg/mL against murine tumor cells in an in vitro cytotoxicity assay.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np030378l</identifier><identifier>PMID: 14738389</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Bryozoa - chemistry ; Cell Line, Tumor ; Drug Screening Assays, Antitumor ; General pharmacology ; Isoquinolines - chemistry ; Isoquinolines - isolation & purification ; Isoquinolines - pharmacology ; Medical sciences ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Palau ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. 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Nat. Prod</addtitle><description>An extract of the marine bryozoan Caulibugula intermis, collected in the Indo-Pacific off Palau, produced a distinct pattern of differential cytotoxicity in the National Cancer Institute's 60 cell line antitumor screen. Bioactivity-directed fractionation of the extract provided six new compounds, caulibugulones A−F (1−6). The structures of these novel metabolites were determined by spectrochemical analyses including LC-MS, HRFABMS, 1-D and 2-D NMR experiments, and by comparison with related compounds. The structures of compounds 2 and 3 were confirmed by chemical interconversion. The isolated compounds exhibited IC50's of 0.03−1.67 μg/mL against murine tumor cells in an in vitro cytotoxicity assay.</description><subject>Animals</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Bryozoa - chemistry</subject><subject>Cell Line, Tumor</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General pharmacology</subject><subject>Isoquinolines - chemistry</subject><subject>Isoquinolines - isolation & purification</subject><subject>Isoquinolines - pharmacology</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Palau</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinones - chemistry</subject><subject>Quinones - isolation & purification</subject><subject>Quinones - pharmacology</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M1u1DAQB3ALUdGlcOAFwBeQkBoYx3HiHMuKlqXbAmorjtbUcYpLYm_tBHXLC3DmEXkSvNqle-Hkr59mxn9CnjF4wyBnb90COPBKdg_IhIkcshJy8ZBMgJU847IsdsnjGK8BEqvFI7LLiopLLusJ-TnFsbOX49XYeWciPfjz6_fhPj31P0xHp8vBD_7WajqL_ma0znfWGfpltVthdA2d9elw8--mDb6nwzdDTzCs6Luw9HceHd22QWrdYEJv4xOy02IXzdPNukcuDt-fTz9k809Hs-nBPMMC-JBVhZGmgFJCg23dgKmgKVoNrRaSC1ZrA0YIJkWVBGADDFn6eI265obnLd8jr9Z1FyFNauKgUnNtug6d8WNUEhgrhKwSfL2GOvgYg2nVItgew1IxUKuk1X3SyT7fFB0ve9Ns5SbaBF5uAEaNXRvQaRu3ThR5XeUiuWztbBzM7f07hu-qrHgl1PnnM5XPv348Pj0-UTL5F2vfold4FVLNi7McGAeWZkspbDujjuraj8GldP_zhb_Yyazi</recordid><startdate>20040101</startdate><enddate>20040101</enddate><creator>Milanowski, Dennis J</creator><creator>Gustafson, Kirk R</creator><creator>Kelley, James A</creator><creator>McMahon, James B</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><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>7X8</scope></search><sort><creationdate>20040101</creationdate><title>Caulibugulones A−F, Novel Cytotoxic Isoquinoline Quinones and Iminoquinones from the Marine Bryozoan Caulibugula intermis</title><author>Milanowski, Dennis J ; Gustafson, Kirk R ; Kelley, James A ; McMahon, James B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a403t-74e8e40680daf9d0e70d4fc0fc583519ce0e55185780d0ad01a11639ac93e32f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Animals</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Bryozoa - chemistry</topic><topic>Cell Line, Tumor</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General pharmacology</topic><topic>Isoquinolines - chemistry</topic><topic>Isoquinolines - isolation & purification</topic><topic>Isoquinolines - pharmacology</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Palau</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinones - chemistry</topic><topic>Quinones - isolation & purification</topic><topic>Quinones - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Milanowski, Dennis J</creatorcontrib><creatorcontrib>Gustafson, Kirk R</creatorcontrib><creatorcontrib>Kelley, James A</creatorcontrib><creatorcontrib>McMahon, James B</creatorcontrib><collection>AGRIS</collection><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>CrossRef</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>Milanowski, Dennis J</au><au>Gustafson, Kirk R</au><au>Kelley, James A</au><au>McMahon, James B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Caulibugulones A−F, Novel Cytotoxic Isoquinoline Quinones and Iminoquinones from the Marine Bryozoan Caulibugula intermis</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2004-01-01</date><risdate>2004</risdate><volume>67</volume><issue>1</issue><spage>70</spage><epage>73</epage><pages>70-73</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>An extract of the marine bryozoan Caulibugula intermis, collected in the Indo-Pacific off Palau, produced a distinct pattern of differential cytotoxicity in the National Cancer Institute's 60 cell line antitumor screen. Bioactivity-directed fractionation of the extract provided six new compounds, caulibugulones A−F (1−6). The structures of these novel metabolites were determined by spectrochemical analyses including LC-MS, HRFABMS, 1-D and 2-D NMR experiments, and by comparison with related compounds. The structures of compounds 2 and 3 were confirmed by chemical interconversion. The isolated compounds exhibited IC50's of 0.03−1.67 μg/mL against murine tumor cells in an in vitro cytotoxicity assay.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>14738389</pmid><doi>10.1021/np030378l</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2004-01, Vol.67 (1), p.70-73 |
| issn | 0163-3864 1520-6025 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Biological and medical sciences Bryozoa - chemistry Cell Line, Tumor Drug Screening Assays, Antitumor General pharmacology Isoquinolines - chemistry Isoquinolines - isolation & purification Isoquinolines - pharmacology Medical sciences Molecular Structure Nuclear Magnetic Resonance, Biomolecular Palau Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Quinones - chemistry Quinones - isolation & purification Quinones - pharmacology |
| title | Caulibugulones A−F, Novel Cytotoxic Isoquinoline Quinones and Iminoquinones from the Marine Bryozoan Caulibugula intermis |
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