Stachyflin and Acetylstachyflin, Novel Anti-influenza A Virus Substances, Produced by Stachybotrys sp. RF-7260: I. Isolation, Structure Elucidation and Biological Activities
Two novel compounds, stachyflin and acetylstachyflin, have been isolated by solid-state fermentation of Stachybotrys sp. RF-7260. The structures of both metabolites, determined by detailed NMR analyses and X-ray crystallographic analysis, are novel with a pentacyclic moiety including cis-fused decal...
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| Veröffentlicht in: | Journal of antibiotics 2002/02/25, Vol.55(2), pp.155-164 |
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| container_title | Journal of antibiotics |
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| creator | MINAGAWA, KAZUYUKI KOUZUKI, SHUICHI YOSHIMOTO, JUN KAWAMURA, YOSHIMI TANI, HIROYOSHI IWATA, TATSUO TERUI, YOSHIHIRO NAKAI, HIROSHI YAGI, SHIGENORI HATTORI, NAOHIKO FUJIWARA, TAMIO KAMIGAUCHI, TOSHIYUKI |
| description | Two novel compounds, stachyflin and acetylstachyflin, have been isolated by solid-state fermentation of Stachybotrys sp. RF-7260. The structures of both metabolites, determined by detailed NMR analyses and X-ray crystallographic analysis, are novel with a pentacyclic moiety including cis-fused decalin. The absolute stereochemistry of stachyflins was determined by circular dichroism analysis. Stachyflin showed antiviral activity against influenza A virus (H1N1) in vitro with an IC50 value of 0.003μM. Acetylstachyflin was about 77-fold less active than stachyflin. |
| doi_str_mv | 10.7164/antibiotics.55.155 |
| format | Article |
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The structures of both metabolites, determined by detailed NMR analyses and X-ray crystallographic analysis, are novel with a pentacyclic moiety including cis-fused decalin. The absolute stereochemistry of stachyflins was determined by circular dichroism analysis. Stachyflin showed antiviral activity against influenza A virus (H1N1) in vitro with an IC50 value of 0.003μM. Acetylstachyflin was about 77-fold less active than stachyflin.</description><identifier>ISSN: 0021-8820</identifier><identifier>EISSN: 1881-1469</identifier><identifier>DOI: 10.7164/antibiotics.55.155</identifier><identifier>PMID: 12002997</identifier><identifier>CODEN: JANTAJ</identifier><language>eng</language><publisher>Tokyo: JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</publisher><subject>Antibiotics. Antiinfectious agents. 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Drug treatments ; Sesquiterpenes - chemistry ; Sesquiterpenes - isolation & purification ; Sesquiterpenes - pharmacology ; Structure-Activity Relationship</subject><ispartof>The Journal of Antibiotics, 2002/02/25, Vol.55(2), pp.155-164</ispartof><rights>Japan Antibiotics Research Association</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c507t-6327252f1c172e5569ba562c22d8f43a8eed84237a57847e1ab7ce76e94353bd3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13624320$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12002997$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>MINAGAWA, KAZUYUKI</creatorcontrib><creatorcontrib>KOUZUKI, SHUICHI</creatorcontrib><creatorcontrib>YOSHIMOTO, JUN</creatorcontrib><creatorcontrib>KAWAMURA, YOSHIMI</creatorcontrib><creatorcontrib>TANI, HIROYOSHI</creatorcontrib><creatorcontrib>IWATA, TATSUO</creatorcontrib><creatorcontrib>TERUI, YOSHIHIRO</creatorcontrib><creatorcontrib>NAKAI, HIROSHI</creatorcontrib><creatorcontrib>YAGI, SHIGENORI</creatorcontrib><creatorcontrib>HATTORI, NAOHIKO</creatorcontrib><creatorcontrib>FUJIWARA, TAMIO</creatorcontrib><creatorcontrib>KAMIGAUCHI, TOSHIYUKI</creatorcontrib><title>Stachyflin and Acetylstachyflin, Novel Anti-influenza A Virus Substances, Produced by Stachybotrys sp. RF-7260: I. Isolation, Structure Elucidation and Biological Activities</title><title>Journal of antibiotics</title><addtitle>J. Antibiot.</addtitle><description>Two novel compounds, stachyflin and acetylstachyflin, have been isolated by solid-state fermentation of Stachybotrys sp. RF-7260. The structures of both metabolites, determined by detailed NMR analyses and X-ray crystallographic analysis, are novel with a pentacyclic moiety including cis-fused decalin. The absolute stereochemistry of stachyflins was determined by circular dichroism analysis. Stachyflin showed antiviral activity against influenza A virus (H1N1) in vitro with an IC50 value of 0.003μM. Acetylstachyflin was about 77-fold less active than stachyflin.</description><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - isolation & purification</subject><subject>Antiviral Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Fermentation</subject><subject>Heterocyclic Compounds, 4 or More Rings - chemistry</subject><subject>Heterocyclic Compounds, 4 or More Rings - isolation & purification</subject><subject>Heterocyclic Compounds, 4 or More Rings - pharmacology</subject><subject>Indoles - chemistry</subject><subject>Indoles - isolation & purification</subject><subject>Indoles - pharmacology</subject><subject>Influenza A virus - drug effects</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0021-8820</issn><issn>1881-1469</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpNkEtP3DAURi3UCobHH2BRedOuyOBH_MhyhAqtilrEaxs5zk0x8jiDnVRKfz1GGQ1sbMk-9_uuDkKnlCwVleW5CYNrXD84m5ZCLKkQe2hBtaYFLWX1CS0IYbTQmpEDdJjSMyFccaX30QFl-auq1AKFu8HYp6nzLmATWryyMEw-7R7P8O_-H3i8yl2FC50fIfw3eIUfXRwTvhubzAYL6QzfxL4dLbS4mfCc2vRDnBJOmyW-vSwUk-QYfe6MT3CyvY_Qw-X3-4sfxfWfq58Xq-vCCqKGQnKmmGAdtVQxEEJWjRGSWcZa3ZXcaIBWl4wrI5QuFVDTKAtKQlVywZuWH6Fvc-4m9i8jpKFeu2TBexOgH1Od_SlJqMggm0Eb-5QidPUmurWJU03JG1XWHyzXQtTZch76sk0fmzW07yNbrRn4ugVMssZ3MSty6Z3jkpWckcz9mrnnbPEv7AATc52Hj920kvqtn81HXmNH2ScTawj8FRTto2o</recordid><startdate>20020201</startdate><enddate>20020201</enddate><creator>MINAGAWA, KAZUYUKI</creator><creator>KOUZUKI, SHUICHI</creator><creator>YOSHIMOTO, JUN</creator><creator>KAWAMURA, YOSHIMI</creator><creator>TANI, HIROYOSHI</creator><creator>IWATA, TATSUO</creator><creator>TERUI, YOSHIHIRO</creator><creator>NAKAI, HIROSHI</creator><creator>YAGI, SHIGENORI</creator><creator>HATTORI, NAOHIKO</creator><creator>FUJIWARA, TAMIO</creator><creator>KAMIGAUCHI, TOSHIYUKI</creator><general>JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</general><general>Japan Antibiotics Research Association</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>20020201</creationdate><title>Stachyflin and Acetylstachyflin, Novel Anti-influenza A Virus Substances, Produced by Stachybotrys sp. RF-7260</title><author>MINAGAWA, KAZUYUKI ; KOUZUKI, SHUICHI ; YOSHIMOTO, JUN ; KAWAMURA, YOSHIMI ; TANI, HIROYOSHI ; IWATA, TATSUO ; TERUI, YOSHIHIRO ; NAKAI, HIROSHI ; YAGI, SHIGENORI ; HATTORI, NAOHIKO ; FUJIWARA, TAMIO ; KAMIGAUCHI, TOSHIYUKI</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c507t-6327252f1c172e5569ba562c22d8f43a8eed84237a57847e1ab7ce76e94353bd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Antibiotics. Antiinfectious agents. 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RF-7260: I. Isolation, Structure Elucidation and Biological Activities</atitle><jtitle>Journal of antibiotics</jtitle><addtitle>J. Antibiot.</addtitle><date>2002-02-01</date><risdate>2002</risdate><volume>55</volume><issue>2</issue><spage>155</spage><epage>164</epage><pages>155-164</pages><issn>0021-8820</issn><eissn>1881-1469</eissn><coden>JANTAJ</coden><abstract>Two novel compounds, stachyflin and acetylstachyflin, have been isolated by solid-state fermentation of Stachybotrys sp. RF-7260. The structures of both metabolites, determined by detailed NMR analyses and X-ray crystallographic analysis, are novel with a pentacyclic moiety including cis-fused decalin. The absolute stereochemistry of stachyflins was determined by circular dichroism analysis. Stachyflin showed antiviral activity against influenza A virus (H1N1) in vitro with an IC50 value of 0.003μM. 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| fulltext | fulltext |
| identifier | ISSN: 0021-8820 |
| ispartof | The Journal of Antibiotics, 2002/02/25, Vol.55(2), pp.155-164 |
| issn | 0021-8820 1881-1469 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_71676015 |
| source | MEDLINE; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese |
| subjects | Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Antiviral Agents - chemistry Antiviral Agents - isolation & purification Antiviral Agents - pharmacology Biological and medical sciences Fermentation Heterocyclic Compounds, 4 or More Rings - chemistry Heterocyclic Compounds, 4 or More Rings - isolation & purification Heterocyclic Compounds, 4 or More Rings - pharmacology Indoles - chemistry Indoles - isolation & purification Indoles - pharmacology Influenza A virus - drug effects Medical sciences Molecular Structure Pharmacology. Drug treatments Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - pharmacology Structure-Activity Relationship |
| title | Stachyflin and Acetylstachyflin, Novel Anti-influenza A Virus Substances, Produced by Stachybotrys sp. RF-7260: I. Isolation, Structure Elucidation and Biological Activities |
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