Hydroxylation of carbazoles by Aspergillus flavus VKM F-1024
Carbazole was metabolized by Aspergillus flavus VKM F-1024 forming few monohydroxylated products. The structure of metabolites was determined by TLC, GC, MS and 1H NMR analyses. 3-Hydroxycarbazole was revealed as a major bioconversion product, 1-hydroxy- and 2-hydroxycarbazoles were observed as mino...
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| Veröffentlicht in: | FEMS microbiology letters 2004-06, Vol.235 (1), p.51-56 |
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| container_title | FEMS microbiology letters |
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| creator | Lobastova, T.G Sukhodolskaya, G.V Nikolayeva, V.M Baskunov, B.P Turchin, K.F Donova, M.V |
| description | Carbazole was metabolized by Aspergillus flavus VKM F-1024 forming few monohydroxylated products. The structure of metabolites was determined by TLC, GC, MS and 1H NMR analyses. 3-Hydroxycarbazole was revealed as a major bioconversion product, 1-hydroxy- and 2-hydroxycarbazoles were observed as minor products. In the presence of 1-benzoylindole, the hydroxylation position shifted toward preferable accumulation of 2-hydroxycarbazole and the formation of 2,6- and 2,7-dihydroxycarbazoles. This effect and microbial formation of these metabolites have never been reported before. At the conversion of N-acetyl- and N-benzoylcarbazoles, carbazole was the major product, while 1-, 2- and 3-monohydroxycarbazoles were formed in small amounts. |
| doi_str_mv | 10.1111/j.1574-6968.2004.tb09566.x |
| format | Article |
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The structure of metabolites was determined by TLC, GC, MS and 1H NMR analyses. 3-Hydroxycarbazole was revealed as a major bioconversion product, 1-hydroxy- and 2-hydroxycarbazoles were observed as minor products. In the presence of 1-benzoylindole, the hydroxylation position shifted toward preferable accumulation of 2-hydroxycarbazole and the formation of 2,6- and 2,7-dihydroxycarbazoles. This effect and microbial formation of these metabolites have never been reported before. At the conversion of N-acetyl- and N-benzoylcarbazoles, carbazole was the major product, while 1-, 2- and 3-monohydroxycarbazoles were formed in small amounts.</description><identifier>ISSN: 0378-1097</identifier><identifier>EISSN: 1574-6968</identifier><identifier>DOI: 10.1111/j.1574-6968.2004.tb09566.x</identifier><identifier>PMID: 15158261</identifier><language>eng</language><publisher>Oxford, UK: Blackwell Publishing Ltd</publisher><subject>1‐, 2‐, 3‐hydroxycarbazole ; 2,6‐, 2,7‐dihydroxycarbazole ; Aspergillus ; Aspergillus flavus ; Aspergillus flavus - metabolism ; Bioconversion ; Biotransformation ; Carbazole ; Carbazoles ; Carbazoles - metabolism ; Hydroxylation ; Metabolites ; Microbiology ; Microorganisms ; Mycelium - metabolism ; NMR ; Nuclear magnetic resonance ; pollutants</subject><ispartof>FEMS microbiology letters, 2004-06, Vol.235 (1), p.51-56</ispartof><rights>2004 Federation of European Microbiological Societies 2004</rights><rights>2004 Federation of European Microbiological Societies</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3141-79bb0e101dd0df92a808b3efb7a90ab2fe39a7160974ebeb55bfc83ef9781fbe3</citedby><cites>FETCH-LOGICAL-c3141-79bb0e101dd0df92a808b3efb7a90ab2fe39a7160974ebeb55bfc83ef9781fbe3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1111%2Fj.1574-6968.2004.tb09566.x$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1111%2Fj.1574-6968.2004.tb09566.x$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15158261$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lobastova, T.G</creatorcontrib><creatorcontrib>Sukhodolskaya, G.V</creatorcontrib><creatorcontrib>Nikolayeva, V.M</creatorcontrib><creatorcontrib>Baskunov, B.P</creatorcontrib><creatorcontrib>Turchin, K.F</creatorcontrib><creatorcontrib>Donova, M.V</creatorcontrib><title>Hydroxylation of carbazoles by Aspergillus flavus VKM F-1024</title><title>FEMS microbiology letters</title><addtitle>FEMS Microbiol Lett</addtitle><description>Carbazole was metabolized by Aspergillus flavus VKM F-1024 forming few monohydroxylated products. The structure of metabolites was determined by TLC, GC, MS and 1H NMR analyses. 3-Hydroxycarbazole was revealed as a major bioconversion product, 1-hydroxy- and 2-hydroxycarbazoles were observed as minor products. In the presence of 1-benzoylindole, the hydroxylation position shifted toward preferable accumulation of 2-hydroxycarbazole and the formation of 2,6- and 2,7-dihydroxycarbazoles. This effect and microbial formation of these metabolites have never been reported before. At the conversion of N-acetyl- and N-benzoylcarbazoles, carbazole was the major product, while 1-, 2- and 3-monohydroxycarbazoles were formed in small amounts.</description><subject>1‐, 2‐, 3‐hydroxycarbazole</subject><subject>2,6‐, 2,7‐dihydroxycarbazole</subject><subject>Aspergillus</subject><subject>Aspergillus flavus</subject><subject>Aspergillus flavus - metabolism</subject><subject>Bioconversion</subject><subject>Biotransformation</subject><subject>Carbazole</subject><subject>Carbazoles</subject><subject>Carbazoles - metabolism</subject><subject>Hydroxylation</subject><subject>Metabolites</subject><subject>Microbiology</subject><subject>Microorganisms</subject><subject>Mycelium - metabolism</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>pollutants</subject><issn>0378-1097</issn><issn>1574-6968</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNqVkEFv0zAYhi0EYmXwF1jEJG7JPttxHE9wmKaVoXXaYYyrZSf2lMqtO7sZDb9-jlKBhLYDvnwHP8_n1y9CnzAUOJ2TZYEZL_NKVHVBAMpiq0Gwqip2r9Dsz9VrNAPK6xyD4AfoXYxLSCyB6i06wAyzmlR4hr5cDm3wu8GpbefXmbdZo4JWv70zMdNDdhY3Jtx3zvUxs049pvHz6jqbp7WkfI_eWOWi-bCfh-hufvHj_DJf3Hz7fn62yBuKS5xzoTUYDLhtobWCqBpqTY3VXAlQmlhDheK4SkFLo41mTNumToDgNbba0EP0edq7Cf6hN3ErV11sjHNqbXwfJceCsZrzBB7_Ay59H9YpmyQU-PjtSiTqdKKa4GMMxspN6FYqDBKDHBuWSznWKMca5diw3Dcsd0n-uH-i1yvT_lX3lSbg6wT86pwZ_mO1nF8v2Oizyff95gU7fz7Y0eRZ5aW6D12Ud7cEMAUQtBSE0yfKA6LI</recordid><startdate>200406</startdate><enddate>200406</enddate><creator>Lobastova, T.G</creator><creator>Sukhodolskaya, G.V</creator><creator>Nikolayeva, V.M</creator><creator>Baskunov, B.P</creator><creator>Turchin, K.F</creator><creator>Donova, M.V</creator><general>Blackwell Publishing Ltd</general><general>Oxford University Press</general><scope>FBQ</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>3V.</scope><scope>7QL</scope><scope>7T7</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7N</scope><scope>M7P</scope><scope>P64</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>RC3</scope><scope>7X8</scope></search><sort><creationdate>200406</creationdate><title>Hydroxylation of carbazoles by Aspergillus flavus VKM F-1024</title><author>Lobastova, T.G ; 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| identifier | ISSN: 0378-1097 |
| ispartof | FEMS microbiology letters, 2004-06, Vol.235 (1), p.51-56 |
| issn | 0378-1097 1574-6968 |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete; Oxford University Press Journals All Titles (1996-Current); Alma/SFX Local Collection |
| subjects | 1‐, 2‐, 3‐hydroxycarbazole 2,6‐, 2,7‐dihydroxycarbazole Aspergillus Aspergillus flavus Aspergillus flavus - metabolism Bioconversion Biotransformation Carbazole Carbazoles Carbazoles - metabolism Hydroxylation Metabolites Microbiology Microorganisms Mycelium - metabolism NMR Nuclear magnetic resonance pollutants |
| title | Hydroxylation of carbazoles by Aspergillus flavus VKM F-1024 |
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