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Lupinacidin C, an Inhibitor of Tumor Cell Invasion from Micromonospora lupini
A new anthraquinone derivative, lupinacidin C (1), was isolated from the endophytic actinomycete Micromonospora lupini. The structure was elucidated on the basis of spectroscopic analyses, and the absolute configuration was determined by total synthesis. Lupinacidin C (1) exhibited the most potent i...
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| Published in: | Journal of natural products (Washington, D.C.) D.C.), 2011-04, Vol.74 (4), p.862-865 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a410t-3a51e66e97f65758302db0b2467604d19dea361ffeeb54fe03a10d081a3ea7453 |
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| cites | cdi_FETCH-LOGICAL-a410t-3a51e66e97f65758302db0b2467604d19dea361ffeeb54fe03a10d081a3ea7453 |
| container_end_page | 865 |
| container_issue | 4 |
| container_start_page | 862 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 74 |
| creator | Igarashi, Yasuhiro Yanase, Saeko Sugimoto, Kohei Enomoto, Masaru Miyanaga, Satoshi Trujillo, Martha E Saiki, Ikuo Kuwahara, Shigefumi |
| description | A new anthraquinone derivative, lupinacidin C (1), was isolated from the endophytic actinomycete Micromonospora lupini. The structure was elucidated on the basis of spectroscopic analyses, and the absolute configuration was determined by total synthesis. Lupinacidin C (1) exhibited the most potent inhibitory effects among the congeners on the invasion of murine colon carcinoma cells into the reconstituted basement membrane. |
| doi_str_mv | 10.1021/np100779t |
| format | article |
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The structure was elucidated on the basis of spectroscopic analyses, and the absolute configuration was determined by total synthesis. Lupinacidin C (1) exhibited the most potent inhibitory effects among the congeners on the invasion of murine colon carcinoma cells into the reconstituted basement membrane.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np100779t</identifier><identifier>PMID: 21226490</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Animals ; Anthraquinones - chemistry ; Anthraquinones - isolation & purification ; Anthraquinones - pharmacology ; Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Applied microbiology ; Basement Membrane - drug effects ; Biological and medical sciences ; Chemotherapic agents ; Colonic Neoplasms ; Drug Screening Assays, Antitumor ; Fundamental and applied biological sciences. Psychology ; Lupinus - microbiology ; Mice ; Microbiology ; Micromonospora - chemistry ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Root Nodules, Plant - microbiology ; Spain ; Stereoisomerism</subject><ispartof>Journal of natural products (Washington, D.C.), 2011-04, Vol.74 (4), p.862-865</ispartof><rights>Copyright © 2011 American Chemical Society and American Society of Pharmacognosy and American Society of Pharmacognosy</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a410t-3a51e66e97f65758302db0b2467604d19dea361ffeeb54fe03a10d081a3ea7453</citedby><cites>FETCH-LOGICAL-a410t-3a51e66e97f65758302db0b2467604d19dea361ffeeb54fe03a10d081a3ea7453</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24128428$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21226490$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Igarashi, Yasuhiro</creatorcontrib><creatorcontrib>Yanase, Saeko</creatorcontrib><creatorcontrib>Sugimoto, Kohei</creatorcontrib><creatorcontrib>Enomoto, Masaru</creatorcontrib><creatorcontrib>Miyanaga, Satoshi</creatorcontrib><creatorcontrib>Trujillo, Martha E</creatorcontrib><creatorcontrib>Saiki, Ikuo</creatorcontrib><creatorcontrib>Kuwahara, Shigefumi</creatorcontrib><title>Lupinacidin C, an Inhibitor of Tumor Cell Invasion from Micromonospora lupini</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>A new anthraquinone derivative, lupinacidin C (1), was isolated from the endophytic actinomycete Micromonospora lupini. The structure was elucidated on the basis of spectroscopic analyses, and the absolute configuration was determined by total synthesis. Lupinacidin C (1) exhibited the most potent inhibitory effects among the congeners on the invasion of murine colon carcinoma cells into the reconstituted basement membrane.</description><subject>Animals</subject><subject>Anthraquinones - chemistry</subject><subject>Anthraquinones - isolation & purification</subject><subject>Anthraquinones - pharmacology</subject><subject>Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Applied microbiology</subject><subject>Basement Membrane - drug effects</subject><subject>Biological and medical sciences</subject><subject>Chemotherapic agents</subject><subject>Colonic Neoplasms</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Lupinus - microbiology</subject><subject>Mice</subject><subject>Microbiology</subject><subject>Micromonospora - chemistry</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Root Nodules, Plant - microbiology</subject><subject>Spain</subject><subject>Stereoisomerism</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNptkE1Lw0AQhhdRtH4c_AOSi4hgdPYjm-QoxY9Ci5d6DpNkF7cku3G3Efz3bmm1F0_vMDy8MzyEXFK4p8Dogx0oQJ6X6wMyoRmDVALLDskEqOQpL6Q4IachrACAQ5kdkxNGGZOihAlZzMfBWGxMa2wyvUvQJjP7YWqzdj5xOlmOfRymquvi_guDcTbR3vXJwjQxnHVhcB6TblNjzsmRxi6oi12ekffnp-X0NZ2_vcymj_MUBYV1yjGjSkpV5lpmeVZwYG0NNRMylyBaWrYKuaRaK1VnQivgSKGFgiJXmIuMn5Gbbe_g3eeowrrqTWjik2iVG0NVSC445JRH8nZLxm9D8EpXgzc9-u-KQrWRV_3Ji-zVrnWse9X-kb-2InC9AzA02GmPtjFhzwnKCsGKPYdNqFZu9DbK-OfgD0MBgbo</recordid><startdate>20110425</startdate><enddate>20110425</enddate><creator>Igarashi, Yasuhiro</creator><creator>Yanase, Saeko</creator><creator>Sugimoto, Kohei</creator><creator>Enomoto, Masaru</creator><creator>Miyanaga, Satoshi</creator><creator>Trujillo, Martha E</creator><creator>Saiki, Ikuo</creator><creator>Kuwahara, Shigefumi</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>7X8</scope></search><sort><creationdate>20110425</creationdate><title>Lupinacidin C, an Inhibitor of Tumor Cell Invasion from Micromonospora lupini</title><author>Igarashi, Yasuhiro ; Yanase, Saeko ; Sugimoto, Kohei ; Enomoto, Masaru ; Miyanaga, Satoshi ; Trujillo, Martha E ; Saiki, Ikuo ; Kuwahara, Shigefumi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-3a51e66e97f65758302db0b2467604d19dea361ffeeb54fe03a10d081a3ea7453</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Animals</topic><topic>Anthraquinones - chemistry</topic><topic>Anthraquinones - isolation & purification</topic><topic>Anthraquinones - pharmacology</topic><topic>Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Applied microbiology</topic><topic>Basement Membrane - drug effects</topic><topic>Biological and medical sciences</topic><topic>Chemotherapic agents</topic><topic>Colonic Neoplasms</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Lupinus - microbiology</topic><topic>Mice</topic><topic>Microbiology</topic><topic>Micromonospora - chemistry</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Root Nodules, Plant - microbiology</topic><topic>Spain</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Igarashi, Yasuhiro</creatorcontrib><creatorcontrib>Yanase, Saeko</creatorcontrib><creatorcontrib>Sugimoto, Kohei</creatorcontrib><creatorcontrib>Enomoto, Masaru</creatorcontrib><creatorcontrib>Miyanaga, Satoshi</creatorcontrib><creatorcontrib>Trujillo, Martha E</creatorcontrib><creatorcontrib>Saiki, Ikuo</creatorcontrib><creatorcontrib>Kuwahara, Shigefumi</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>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>Igarashi, Yasuhiro</au><au>Yanase, Saeko</au><au>Sugimoto, Kohei</au><au>Enomoto, Masaru</au><au>Miyanaga, Satoshi</au><au>Trujillo, Martha E</au><au>Saiki, Ikuo</au><au>Kuwahara, Shigefumi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lupinacidin C, an Inhibitor of Tumor Cell Invasion from Micromonospora lupini</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2011-04-25</date><risdate>2011</risdate><volume>74</volume><issue>4</issue><spage>862</spage><epage>865</epage><pages>862-865</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>A new anthraquinone derivative, lupinacidin C (1), was isolated from the endophytic actinomycete Micromonospora lupini. The structure was elucidated on the basis of spectroscopic analyses, and the absolute configuration was determined by total synthesis. Lupinacidin C (1) exhibited the most potent inhibitory effects among the congeners on the invasion of murine colon carcinoma cells into the reconstituted basement membrane.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>21226490</pmid><doi>10.1021/np100779t</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2011-04, Vol.74 (4), p.862-865 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_863430713 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Animals Anthraquinones - chemistry Anthraquinones - isolation & purification Anthraquinones - pharmacology Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Applied microbiology Basement Membrane - drug effects Biological and medical sciences Chemotherapic agents Colonic Neoplasms Drug Screening Assays, Antitumor Fundamental and applied biological sciences. Psychology Lupinus - microbiology Mice Microbiology Micromonospora - chemistry Molecular Structure Nuclear Magnetic Resonance, Biomolecular Root Nodules, Plant - microbiology Spain Stereoisomerism |
| title | Lupinacidin C, an Inhibitor of Tumor Cell Invasion from Micromonospora lupini |
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