Hydroxy-PCBs, Methoxy-PCBs and Hydroxy-Methoxy-PCBs: Metabolites of Polychlorinated Biphenyls Formed In Vitro by Tobacco Cells
While the metabolism of polychlorinated biphenyls (PCBs) in plant cells is a rarely studied field, hydroxy-PCBs have been detected in several studies involving the use of various plant species. The ability of the tobacco (Nicotiana tabacum) callus culture WSC-38 to metabolize six dichlorobiphenyls u...
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| Veröffentlicht in: | Environmental science & technology 2008-08, Vol.42 (15), p.5746-5751 |
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| creator | Rezek, Jan Macek, Tomas Mackova, Martina Triska, Jan Ruzickova, Kamila |
| description | While the metabolism of polychlorinated biphenyls (PCBs) in plant cells is a rarely studied field, hydroxy-PCBs have been detected in several studies involving the use of various plant species. The ability of the tobacco (Nicotiana tabacum) callus culture WSC-38 to metabolize six dichlorobiphenyls under aseptic conditions was studied, and the resulting PCB metabolites were analyzed. WSC-38 cultures were cultivated with individual dichlorinated PCB congeners. The metabolites were identified based on mass spectra characteristics after gas chromatography separation. In addition, metabolites of PCB 9 (2,5-dichlorobiphenyl) were identified by comparing their retention characteristics with the available standards. In most cases at least two hydroxy-PCBs were produced from each parent PCB. Methoxy-PCBs and hydroxy-methoxy-PCBs were other groups of metabolites produced. To the best of our knowledge, ours is the first report to determine the presence of methoxy- and hydroxy-methoxy-metabolites of PCBs in plants. The role of the O-methyltransferases (OMTs) in the methylation of hydroxy-PCBs is discussed. As methoxy-metabolites of acetophenone were found among our samples, we posit that the OMTs responsible for the methylation of these compounds are also involved in the metabolism of PCBs in cultures of WSC-38. |
| doi_str_mv | 10.1021/es800445h |
| format | Article |
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The ability of the tobacco (Nicotiana tabacum) callus culture WSC-38 to metabolize six dichlorobiphenyls under aseptic conditions was studied, and the resulting PCB metabolites were analyzed. WSC-38 cultures were cultivated with individual dichlorinated PCB congeners. The metabolites were identified based on mass spectra characteristics after gas chromatography separation. In addition, metabolites of PCB 9 (2,5-dichlorobiphenyl) were identified by comparing their retention characteristics with the available standards. In most cases at least two hydroxy-PCBs were produced from each parent PCB. Methoxy-PCBs and hydroxy-methoxy-PCBs were other groups of metabolites produced. To the best of our knowledge, ours is the first report to determine the presence of methoxy- and hydroxy-methoxy-metabolites of PCBs in plants. The role of the O-methyltransferases (OMTs) in the methylation of hydroxy-PCBs is discussed. As methoxy-metabolites of acetophenone were found among our samples, we posit that the OMTs responsible for the methylation of these compounds are also involved in the metabolism of PCBs in cultures of WSC-38.</description><identifier>ISSN: 0013-936X</identifier><identifier>EISSN: 1520-5851</identifier><identifier>DOI: 10.1021/es800445h</identifier><identifier>PMID: 18754503</identifier><identifier>CODEN: ESTHAG</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acetophenones - metabolism ; Applied sciences ; Biodegradation, Environmental ; Cell culture ; Cells ; Cells, Cultured ; Exact sciences and technology ; Gas Chromatography-Mass Spectrometry ; Mass spectrometry ; Metabolism ; Metabolites ; Methylation ; Nicotiana - chemistry ; Nicotiana - cytology ; Nicotiana - metabolism ; Nicotiana tabacum ; PCB ; Pollution ; Polychlorinated biphenyls ; Polychlorinated Biphenyls - analysis ; Polychlorinated Biphenyls - chemistry ; Polychlorinated Biphenyls - metabolism ; Remediation and Control Technologies ; Studies ; Tobacco</subject><ispartof>Environmental science & technology, 2008-08, Vol.42 (15), p.5746-5751</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><rights>Copyright American Chemical Society Aug 1, 2008</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a505t-7dfb17a52c39229ad090bb76ae754e66512ebf14bd1aaf546d7068a67ae93b673</citedby><cites>FETCH-LOGICAL-a505t-7dfb17a52c39229ad090bb76ae754e66512ebf14bd1aaf546d7068a67ae93b673</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/es800445h$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/es800445h$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20548121$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18754503$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rezek, Jan</creatorcontrib><creatorcontrib>Macek, Tomas</creatorcontrib><creatorcontrib>Mackova, Martina</creatorcontrib><creatorcontrib>Triska, Jan</creatorcontrib><creatorcontrib>Ruzickova, Kamila</creatorcontrib><title>Hydroxy-PCBs, Methoxy-PCBs and Hydroxy-Methoxy-PCBs: Metabolites of Polychlorinated Biphenyls Formed In Vitro by Tobacco Cells</title><title>Environmental science & technology</title><addtitle>Environ. Sci. Technol</addtitle><description>While the metabolism of polychlorinated biphenyls (PCBs) in plant cells is a rarely studied field, hydroxy-PCBs have been detected in several studies involving the use of various plant species. The ability of the tobacco (Nicotiana tabacum) callus culture WSC-38 to metabolize six dichlorobiphenyls under aseptic conditions was studied, and the resulting PCB metabolites were analyzed. WSC-38 cultures were cultivated with individual dichlorinated PCB congeners. The metabolites were identified based on mass spectra characteristics after gas chromatography separation. In addition, metabolites of PCB 9 (2,5-dichlorobiphenyl) were identified by comparing their retention characteristics with the available standards. In most cases at least two hydroxy-PCBs were produced from each parent PCB. Methoxy-PCBs and hydroxy-methoxy-PCBs were other groups of metabolites produced. To the best of our knowledge, ours is the first report to determine the presence of methoxy- and hydroxy-methoxy-metabolites of PCBs in plants. The role of the O-methyltransferases (OMTs) in the methylation of hydroxy-PCBs is discussed. As methoxy-metabolites of acetophenone were found among our samples, we posit that the OMTs responsible for the methylation of these compounds are also involved in the metabolism of PCBs in cultures of WSC-38.</description><subject>Acetophenones - metabolism</subject><subject>Applied sciences</subject><subject>Biodegradation, Environmental</subject><subject>Cell culture</subject><subject>Cells</subject><subject>Cells, Cultured</subject><subject>Exact sciences and technology</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Mass spectrometry</subject><subject>Metabolism</subject><subject>Metabolites</subject><subject>Methylation</subject><subject>Nicotiana - chemistry</subject><subject>Nicotiana - cytology</subject><subject>Nicotiana - metabolism</subject><subject>Nicotiana tabacum</subject><subject>PCB</subject><subject>Pollution</subject><subject>Polychlorinated biphenyls</subject><subject>Polychlorinated Biphenyls - analysis</subject><subject>Polychlorinated Biphenyls - chemistry</subject><subject>Polychlorinated Biphenyls - metabolism</subject><subject>Remediation and Control Technologies</subject><subject>Studies</subject><subject>Tobacco</subject><issn>0013-936X</issn><issn>1520-5851</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNplkV9r2zAUxcXYWNNuD_sCQww2KMzrlWxZ9t6WsP6BlAaalb6JK1km7hwrlRyoX_rZp5A0GduTuDo_DveeQ8gHBt8YcHZmQwGQZWLxioyY4JCIQrDXZATA0qRM8_sjchzCAwDwFIq35IgVUmQC0hF5vhwq756GZDYZh6_02vaLl4liV9EX-W_h-wZD7dqmt4G6ms5cO5hF63zTYW8rOm5WC9sNbaDnzi_jx1VH75reO6oHOncajXF0Yts2vCNvamyDfb97T8iv85_zyWUyvbm4mvyYJihA9Imsas0kCm7SkvMSKyhBa5mjjXfYPBeMW12zTFcMsRZZXknIC8wl2jLVuUxPyJet78q7x7UNvVo2wcQNsLNuHRQrhZSSlxH89A_44Na-i7upmB1LY7Ibt9MtZLwLwdtarXyzRD8oBmrTiNo3EtmPO8O1jlEcyF0FEfi8AzAYbGuPnWnCnuMgsoJxFrlkyzWht097Hf1vFQ-UQs1nt0pMx3fX5f2tmh980YTDEf8v-Afcsq3q</recordid><startdate>20080801</startdate><enddate>20080801</enddate><creator>Rezek, Jan</creator><creator>Macek, Tomas</creator><creator>Mackova, Martina</creator><creator>Triska, Jan</creator><creator>Ruzickova, Kamila</creator><general>American Chemical Society</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>7QO</scope><scope>7ST</scope><scope>7T7</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>SOI</scope><scope>7TV</scope></search><sort><creationdate>20080801</creationdate><title>Hydroxy-PCBs, Methoxy-PCBs and Hydroxy-Methoxy-PCBs: Metabolites of Polychlorinated Biphenyls Formed In Vitro by Tobacco Cells</title><author>Rezek, Jan ; Macek, Tomas ; Mackova, Martina ; Triska, Jan ; Ruzickova, Kamila</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a505t-7dfb17a52c39229ad090bb76ae754e66512ebf14bd1aaf546d7068a67ae93b673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Acetophenones - metabolism</topic><topic>Applied sciences</topic><topic>Biodegradation, Environmental</topic><topic>Cell culture</topic><topic>Cells</topic><topic>Cells, Cultured</topic><topic>Exact sciences and technology</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Mass spectrometry</topic><topic>Metabolism</topic><topic>Metabolites</topic><topic>Methylation</topic><topic>Nicotiana - chemistry</topic><topic>Nicotiana - cytology</topic><topic>Nicotiana - metabolism</topic><topic>Nicotiana tabacum</topic><topic>PCB</topic><topic>Pollution</topic><topic>Polychlorinated biphenyls</topic><topic>Polychlorinated Biphenyls - analysis</topic><topic>Polychlorinated Biphenyls - chemistry</topic><topic>Polychlorinated Biphenyls - metabolism</topic><topic>Remediation and Control Technologies</topic><topic>Studies</topic><topic>Tobacco</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rezek, Jan</creatorcontrib><creatorcontrib>Macek, Tomas</creatorcontrib><creatorcontrib>Mackova, Martina</creatorcontrib><creatorcontrib>Triska, Jan</creatorcontrib><creatorcontrib>Ruzickova, Kamila</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>Biotechnology Research Abstracts</collection><collection>Environment Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Environment Abstracts</collection><collection>Pollution Abstracts</collection><jtitle>Environmental science & technology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rezek, Jan</au><au>Macek, Tomas</au><au>Mackova, Martina</au><au>Triska, Jan</au><au>Ruzickova, Kamila</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hydroxy-PCBs, Methoxy-PCBs and Hydroxy-Methoxy-PCBs: Metabolites of Polychlorinated Biphenyls Formed In Vitro by Tobacco Cells</atitle><jtitle>Environmental science & technology</jtitle><addtitle>Environ. Sci. Technol</addtitle><date>2008-08-01</date><risdate>2008</risdate><volume>42</volume><issue>15</issue><spage>5746</spage><epage>5751</epage><pages>5746-5751</pages><issn>0013-936X</issn><eissn>1520-5851</eissn><coden>ESTHAG</coden><abstract>While the metabolism of polychlorinated biphenyls (PCBs) in plant cells is a rarely studied field, hydroxy-PCBs have been detected in several studies involving the use of various plant species. The ability of the tobacco (Nicotiana tabacum) callus culture WSC-38 to metabolize six dichlorobiphenyls under aseptic conditions was studied, and the resulting PCB metabolites were analyzed. WSC-38 cultures were cultivated with individual dichlorinated PCB congeners. The metabolites were identified based on mass spectra characteristics after gas chromatography separation. In addition, metabolites of PCB 9 (2,5-dichlorobiphenyl) were identified by comparing their retention characteristics with the available standards. In most cases at least two hydroxy-PCBs were produced from each parent PCB. Methoxy-PCBs and hydroxy-methoxy-PCBs were other groups of metabolites produced. To the best of our knowledge, ours is the first report to determine the presence of methoxy- and hydroxy-methoxy-metabolites of PCBs in plants. The role of the O-methyltransferases (OMTs) in the methylation of hydroxy-PCBs is discussed. As methoxy-metabolites of acetophenone were found among our samples, we posit that the OMTs responsible for the methylation of these compounds are also involved in the metabolism of PCBs in cultures of WSC-38.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18754503</pmid><doi>10.1021/es800445h</doi><tpages>6</tpages></addata></record> |
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| ispartof | Environmental science & technology, 2008-08, Vol.42 (15), p.5746-5751 |
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| source | MEDLINE; ACS Publications |
| subjects | Acetophenones - metabolism Applied sciences Biodegradation, Environmental Cell culture Cells Cells, Cultured Exact sciences and technology Gas Chromatography-Mass Spectrometry Mass spectrometry Metabolism Metabolites Methylation Nicotiana - chemistry Nicotiana - cytology Nicotiana - metabolism Nicotiana tabacum PCB Pollution Polychlorinated biphenyls Polychlorinated Biphenyls - analysis Polychlorinated Biphenyls - chemistry Polychlorinated Biphenyls - metabolism Remediation and Control Technologies Studies Tobacco |
| title | Hydroxy-PCBs, Methoxy-PCBs and Hydroxy-Methoxy-PCBs: Metabolites of Polychlorinated Biphenyls Formed In Vitro by Tobacco Cells |
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