Bioactive Dihydronaphthoquinone Derivatives from Fusarium solani
New dihydronaphthoquinone derivatives, karuquinone A (1), karuquinone B (2), and karuquinone C (3), were isolated from a fungal culture broth of Fusarium solani. The structures were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Three known compounds, javanicin (4), 2,3-...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2014-09, Vol.77 (9), p.1992-1996 |
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| container_end_page | 1996 |
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| container_issue | 9 |
| container_start_page | 1992 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 77 |
| creator | Takemoto, Kenji Kamisuki, Shinji Chia, Pei Thing Kuriyama, Isoko Mizushina, Yoshiyuki Sugawara, Fumio |
| description | New dihydronaphthoquinone derivatives, karuquinone A (1), karuquinone B (2), and karuquinone C (3), were isolated from a fungal culture broth of Fusarium solani. The structures were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Three known compounds, javanicin (4), 2,3-dihydro-5-hydroxy-8-methoxy-2,4-dimethylnaphtho[1,2-b]furan-6,9-dione (5), and 5-hydroxydihydrofusarubin C (6), were also isolated. The six isolated compounds were tested for cytotoxicity against three human cancer cell lines and a human umbilical vein endothelial cell (HUVEC) line. Of these, karuquinone A exhibited the strongest cytotoxic activity. Karuquinone B did not affect the proliferation of the cancer cell lines but did inhibit the proliferation of HUVEC. Additionally, we demonstrated that karuquinone A induces apoptosis in cancer cells through the generation of reactive oxygen species (ROS). |
| doi_str_mv | 10.1021/np500175j |
| format | Article |
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The structures were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Three known compounds, javanicin (4), 2,3-dihydro-5-hydroxy-8-methoxy-2,4-dimethylnaphtho[1,2-b]furan-6,9-dione (5), and 5-hydroxydihydrofusarubin C (6), were also isolated. The six isolated compounds were tested for cytotoxicity against three human cancer cell lines and a human umbilical vein endothelial cell (HUVEC) line. Of these, karuquinone A exhibited the strongest cytotoxic activity. Karuquinone B did not affect the proliferation of the cancer cell lines but did inhibit the proliferation of HUVEC. Additionally, we demonstrated that karuquinone A induces apoptosis in cancer cells through the generation of reactive oxygen species (ROS).</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np500175j</identifier><identifier>PMID: 25163667</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Apoptosis - drug effects ; Drug Screening Assays, Antitumor ; Fusarium - chemistry ; HeLa Cells ; Humans ; Molecular Structure ; Naphthoquinones - chemistry ; Naphthoquinones - isolation & purification ; Naphthoquinones - pharmacology ; Reactive Oxygen Species - metabolism</subject><ispartof>Journal of natural products (Washington, D.C.), 2014-09, Vol.77 (9), p.1992-1996</ispartof><rights>Copyright © 2014 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a414t-34b12348237ea6f76215427a1d75beb0efe80c5c77dc9f7ad34a01a7753776983</citedby><cites>FETCH-LOGICAL-a414t-34b12348237ea6f76215427a1d75beb0efe80c5c77dc9f7ad34a01a7753776983</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/np500175j$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np500175j$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25163667$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Takemoto, Kenji</creatorcontrib><creatorcontrib>Kamisuki, Shinji</creatorcontrib><creatorcontrib>Chia, Pei Thing</creatorcontrib><creatorcontrib>Kuriyama, Isoko</creatorcontrib><creatorcontrib>Mizushina, Yoshiyuki</creatorcontrib><creatorcontrib>Sugawara, Fumio</creatorcontrib><title>Bioactive Dihydronaphthoquinone Derivatives from Fusarium solani</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>New dihydronaphthoquinone derivatives, karuquinone A (1), karuquinone B (2), and karuquinone C (3), were isolated from a fungal culture broth of Fusarium solani. The structures were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Three known compounds, javanicin (4), 2,3-dihydro-5-hydroxy-8-methoxy-2,4-dimethylnaphtho[1,2-b]furan-6,9-dione (5), and 5-hydroxydihydrofusarubin C (6), were also isolated. The six isolated compounds were tested for cytotoxicity against three human cancer cell lines and a human umbilical vein endothelial cell (HUVEC) line. Of these, karuquinone A exhibited the strongest cytotoxic activity. Karuquinone B did not affect the proliferation of the cancer cell lines but did inhibit the proliferation of HUVEC. Additionally, we demonstrated that karuquinone A induces apoptosis in cancer cells through the generation of reactive oxygen species (ROS).</description><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Apoptosis - drug effects</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fusarium - chemistry</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Molecular Structure</subject><subject>Naphthoquinones - chemistry</subject><subject>Naphthoquinones - isolation & purification</subject><subject>Naphthoquinones - pharmacology</subject><subject>Reactive Oxygen Species - metabolism</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0E1Lw0AQBuBFFFurB_-A5CLoITqT_UpuarUqFLzoOWySDd3SZONuUui_d0trT4KngZmHl-El5BLhDiHB-7bjACj58oiMkScQC0j4MRkDChrTVLAROfN-CQAUMn5KRgkPFyHkmDw8GavK3qx19GwWm8rZVnWLfmG_B9PaNmy1M2u1BT6qnW2i2eCVM0MTebtSrTknJ7VaeX2xnxPyNXv5nL7F84_X9-njPFYMWR9TVmBCWZpQqZWopUiQs0QqrCQvdAG61imUvJSyKrNaqooyBaik5FRKkaV0Qm52uZ0Lv2nf543xpV6FH7QdfI5SAqYsY_A_5UIgpJiJQG93tHTWe6frvHOmUW6TI-TbbvNDt8Fe7WOHotHVQf6WGcD1DqjS50s7uDYU8kfQD235fyk</recordid><startdate>20140926</startdate><enddate>20140926</enddate><creator>Takemoto, Kenji</creator><creator>Kamisuki, Shinji</creator><creator>Chia, Pei Thing</creator><creator>Kuriyama, Isoko</creator><creator>Mizushina, Yoshiyuki</creator><creator>Sugawara, Fumio</creator><general>American Chemical Society and American Society of Pharmacognosy</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>7X8</scope></search><sort><creationdate>20140926</creationdate><title>Bioactive Dihydronaphthoquinone Derivatives from Fusarium solani</title><author>Takemoto, Kenji ; Kamisuki, Shinji ; Chia, Pei Thing ; Kuriyama, Isoko ; Mizushina, Yoshiyuki ; Sugawara, Fumio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a414t-34b12348237ea6f76215427a1d75beb0efe80c5c77dc9f7ad34a01a7753776983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Apoptosis - drug effects</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fusarium - chemistry</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Molecular Structure</topic><topic>Naphthoquinones - chemistry</topic><topic>Naphthoquinones - isolation & purification</topic><topic>Naphthoquinones - pharmacology</topic><topic>Reactive Oxygen Species - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Takemoto, Kenji</creatorcontrib><creatorcontrib>Kamisuki, Shinji</creatorcontrib><creatorcontrib>Chia, Pei Thing</creatorcontrib><creatorcontrib>Kuriyama, Isoko</creatorcontrib><creatorcontrib>Mizushina, Yoshiyuki</creatorcontrib><creatorcontrib>Sugawara, Fumio</creatorcontrib><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>Takemoto, Kenji</au><au>Kamisuki, Shinji</au><au>Chia, Pei Thing</au><au>Kuriyama, Isoko</au><au>Mizushina, Yoshiyuki</au><au>Sugawara, Fumio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bioactive Dihydronaphthoquinone Derivatives from Fusarium solani</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2014-09-26</date><risdate>2014</risdate><volume>77</volume><issue>9</issue><spage>1992</spage><epage>1996</epage><pages>1992-1996</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>New dihydronaphthoquinone derivatives, karuquinone A (1), karuquinone B (2), and karuquinone C (3), were isolated from a fungal culture broth of Fusarium solani. The structures were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Three known compounds, javanicin (4), 2,3-dihydro-5-hydroxy-8-methoxy-2,4-dimethylnaphtho[1,2-b]furan-6,9-dione (5), and 5-hydroxydihydrofusarubin C (6), were also isolated. The six isolated compounds were tested for cytotoxicity against three human cancer cell lines and a human umbilical vein endothelial cell (HUVEC) line. Of these, karuquinone A exhibited the strongest cytotoxic activity. Karuquinone B did not affect the proliferation of the cancer cell lines but did inhibit the proliferation of HUVEC. 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| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2014-09, Vol.77 (9), p.1992-1996 |
| issn | 0163-3864 1520-6025 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Apoptosis - drug effects Drug Screening Assays, Antitumor Fusarium - chemistry HeLa Cells Humans Molecular Structure Naphthoquinones - chemistry Naphthoquinones - isolation & purification Naphthoquinones - pharmacology Reactive Oxygen Species - metabolism |
| title | Bioactive Dihydronaphthoquinone Derivatives from Fusarium solani |
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