Etnangien, a Macrolide-Polyene Antibiotic from Sorangium cellulosum That Inhibits Nucleic Acid Polymerases
Etnangien (1), a new macrolide antibiotic active against Gram-positive bacteria, was isolated from the culture broth of the myxobacterium Sorangium cellulosum, strains So ce750 and So ce1045. Spectroscopic structure elucidation of 1 revealed a complex macrocyclic lactone bearing a modified C21 carbo...
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Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2007-06, Vol.70 (6), p.1060-1063 |
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creator | Irschik, Herbert Schummer, Dietmar Höfle, Gerhard Reichenbach, Hans Steinmetz, Heinrich Jansen, Rolf |
description | Etnangien (1), a new macrolide antibiotic active against Gram-positive bacteria, was isolated from the culture broth of the myxobacterium Sorangium cellulosum, strains So ce750 and So ce1045. Spectroscopic structure elucidation of 1 revealed a complex macrocyclic lactone bearing a modified C21 carboxylic acid side chain. The latter contains two allylic hydroxyl groups and an all-E hexaene unit, which provides the characteristic UV chromophore of 1. Initial studies toward the mechanism of action showed that bacterial and viral nucleic acid polymerases are inhibited by etnangien (1). |
doi_str_mv | 10.1021/np070115h |
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Spectroscopic structure elucidation of 1 revealed a complex macrocyclic lactone bearing a modified C21 carboxylic acid side chain. The latter contains two allylic hydroxyl groups and an all-E hexaene unit, which provides the characteristic UV chromophore of 1. Initial studies toward the mechanism of action showed that bacterial and viral nucleic acid polymerases are inhibited by etnangien (1).</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np070115h</identifier><identifier>PMID: 17547459</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Antibiotics (antibacterial agents, antifungal agents) ; Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents ; Applied microbiology ; Biological and medical sciences ; Escherichia coli - drug effects ; Escherichia coli - enzymology ; Fundamental and applied biological sciences. Psychology ; Gram-Positive Bacteria - drug effects ; Leukemia Virus, Murine - drug effects ; Leukemia Virus, Murine - enzymology ; Macrolides - chemistry ; Macrolides - isolation & purification ; Macrolides - pharmacology ; Microbiology ; Molecular Structure ; Myxococcales - chemistry ; Nucleotidyltransferases - antagonists & inhibitors ; Polyenes - chemistry ; Polyenes - isolation & purification ; Polyenes - pharmacology ; Sorangium cellulosum</subject><ispartof>Journal of natural products (Washington, D.C.), 2007-06, Vol.70 (6), p.1060-1063</ispartof><rights>Copyright © 2007 American Chemical Society and American Society of Pharmacognosy</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-9966b897e7009c39f5ca964a778eac153c38758e93cd6a781c779f2e817336b63</citedby><cites>FETCH-LOGICAL-a381t-9966b897e7009c39f5ca964a778eac153c38758e93cd6a781c779f2e817336b63</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/np070115h$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np070115h$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18902809$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17547459$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Irschik, Herbert</creatorcontrib><creatorcontrib>Schummer, Dietmar</creatorcontrib><creatorcontrib>Höfle, Gerhard</creatorcontrib><creatorcontrib>Reichenbach, Hans</creatorcontrib><creatorcontrib>Steinmetz, Heinrich</creatorcontrib><creatorcontrib>Jansen, Rolf</creatorcontrib><title>Etnangien, a Macrolide-Polyene Antibiotic from Sorangium cellulosum That Inhibits Nucleic Acid Polymerases</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Etnangien (1), a new macrolide antibiotic active against Gram-positive bacteria, was isolated from the culture broth of the myxobacterium Sorangium cellulosum, strains So ce750 and So ce1045. Spectroscopic structure elucidation of 1 revealed a complex macrocyclic lactone bearing a modified C21 carboxylic acid side chain. The latter contains two allylic hydroxyl groups and an all-E hexaene unit, which provides the characteristic UV chromophore of 1. Initial studies toward the mechanism of action showed that bacterial and viral nucleic acid polymerases are inhibited by etnangien (1).</description><subject>Antibiotics (antibacterial agents, antifungal agents)</subject><subject>Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents</subject><subject>Applied microbiology</subject><subject>Biological and medical sciences</subject><subject>Escherichia coli - drug effects</subject><subject>Escherichia coli - enzymology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>Leukemia Virus, Murine - drug effects</subject><subject>Leukemia Virus, Murine - enzymology</subject><subject>Macrolides - chemistry</subject><subject>Macrolides - isolation & purification</subject><subject>Macrolides - pharmacology</subject><subject>Microbiology</subject><subject>Molecular Structure</subject><subject>Myxococcales - chemistry</subject><subject>Nucleotidyltransferases - antagonists & inhibitors</subject><subject>Polyenes - chemistry</subject><subject>Polyenes - isolation & purification</subject><subject>Polyenes - pharmacology</subject><subject>Sorangium cellulosum</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M1qGzEUBWBRWho36SIvELRpIJBppNHob-mGNA04randboUs34nlzEiuNAPN23cGm3jTlS7o43DvQeicks-UlPQm7IgklPLNGzShvCSFICV_iyaEClYwJaoT9CHnLSGEEc3foxMqeSUrridoe9cFG548hGts8aN1KTZ-DcU8Ni8QAE9D51c-dt7hOsUWL2Iaed9iB03TNzEP43JjO_wQNoPsMv7euwYGP3V-jcecFpLNkM_Qu9o2GT4e3lP06-vd8vZbMftx_3A7nRWWKdoVWguxUlqCJEQ7pmvurBaVlVKBdZQzx5TkCjRza2Glok5KXZegqGRMrAQ7RZf73F2Kf3rInWl9Hre1AWKfDdVKKSFGeLWHw9E5J6jNLvnWphdDiRmLNa_FDvbiENqvWlgf5aHJAXw6AJudbeqhJufz0SlNSkVGV-ydzx38ff236dkIySQ3y_nCPP78vZxVX-Zmccy1Lptt7FMYuvvPgv8A8JGbiA</recordid><startdate>20070601</startdate><enddate>20070601</enddate><creator>Irschik, Herbert</creator><creator>Schummer, Dietmar</creator><creator>Höfle, Gerhard</creator><creator>Reichenbach, Hans</creator><creator>Steinmetz, Heinrich</creator><creator>Jansen, Rolf</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><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>7QL</scope><scope>7T7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope></search><sort><creationdate>20070601</creationdate><title>Etnangien, a Macrolide-Polyene Antibiotic from Sorangium cellulosum That Inhibits Nucleic Acid Polymerases</title><author>Irschik, Herbert ; Schummer, Dietmar ; Höfle, Gerhard ; Reichenbach, Hans ; Steinmetz, Heinrich ; Jansen, Rolf</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-9966b897e7009c39f5ca964a778eac153c38758e93cd6a781c779f2e817336b63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Antibiotics (antibacterial agents, antifungal agents)</topic><topic>Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents</topic><topic>Applied microbiology</topic><topic>Biological and medical sciences</topic><topic>Escherichia coli - drug effects</topic><topic>Escherichia coli - enzymology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>Leukemia Virus, Murine - drug effects</topic><topic>Leukemia Virus, Murine - enzymology</topic><topic>Macrolides - chemistry</topic><topic>Macrolides - isolation & purification</topic><topic>Macrolides - pharmacology</topic><topic>Microbiology</topic><topic>Molecular Structure</topic><topic>Myxococcales - chemistry</topic><topic>Nucleotidyltransferases - antagonists & inhibitors</topic><topic>Polyenes - chemistry</topic><topic>Polyenes - isolation & purification</topic><topic>Polyenes - pharmacology</topic><topic>Sorangium cellulosum</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Irschik, Herbert</creatorcontrib><creatorcontrib>Schummer, Dietmar</creatorcontrib><creatorcontrib>Höfle, Gerhard</creatorcontrib><creatorcontrib>Reichenbach, Hans</creatorcontrib><creatorcontrib>Steinmetz, Heinrich</creatorcontrib><creatorcontrib>Jansen, Rolf</creatorcontrib><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>Bacteriology Abstracts (Microbiology B)</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Irschik, Herbert</au><au>Schummer, Dietmar</au><au>Höfle, Gerhard</au><au>Reichenbach, Hans</au><au>Steinmetz, Heinrich</au><au>Jansen, Rolf</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Etnangien, a Macrolide-Polyene Antibiotic from Sorangium cellulosum That Inhibits Nucleic Acid Polymerases</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2007-06-01</date><risdate>2007</risdate><volume>70</volume><issue>6</issue><spage>1060</spage><epage>1063</epage><pages>1060-1063</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Etnangien (1), a new macrolide antibiotic active against Gram-positive bacteria, was isolated from the culture broth of the myxobacterium Sorangium cellulosum, strains So ce750 and So ce1045. Spectroscopic structure elucidation of 1 revealed a complex macrocyclic lactone bearing a modified C21 carboxylic acid side chain. The latter contains two allylic hydroxyl groups and an all-E hexaene unit, which provides the characteristic UV chromophore of 1. Initial studies toward the mechanism of action showed that bacterial and viral nucleic acid polymerases are inhibited by etnangien (1).</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>17547459</pmid><doi>10.1021/np070115h</doi><tpages>4</tpages></addata></record> |
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subjects | Antibiotics (antibacterial agents, antifungal agents) Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents Applied microbiology Biological and medical sciences Escherichia coli - drug effects Escherichia coli - enzymology Fundamental and applied biological sciences. Psychology Gram-Positive Bacteria - drug effects Leukemia Virus, Murine - drug effects Leukemia Virus, Murine - enzymology Macrolides - chemistry Macrolides - isolation & purification Macrolides - pharmacology Microbiology Molecular Structure Myxococcales - chemistry Nucleotidyltransferases - antagonists & inhibitors Polyenes - chemistry Polyenes - isolation & purification Polyenes - pharmacology Sorangium cellulosum |
title | Etnangien, a Macrolide-Polyene Antibiotic from Sorangium cellulosum That Inhibits Nucleic Acid Polymerases |
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