Polar metabolites of polycyclic aromatic compounds from fungi are potential soil and groundwater contaminants
•The soil fungus Cunninghamella elegans transformed PACs into highly polar metabolites.•58 PAC metabolites were tentative identified.•A batch sorption experiment with polar PAC metabolites was performed in three soils.•Partition coefficients (Kd’s) of the PAC metabolites indicate high mobility in so...
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description | •The soil fungus Cunninghamella elegans transformed PACs into highly polar metabolites.•58 PAC metabolites were tentative identified.•A batch sorption experiment with polar PAC metabolites was performed in three soils.•Partition coefficients (Kd’s) of the PAC metabolites indicate high mobility in soil.
This study investigated the sorption to soil of water-soluble metabolites from polycyclic aromatic compounds (PACs). The soil fungus Cunninghamella elegans was used to produce PAC metabolites from two un-substituted PACs (phenanthrene, pyrene), three alkyl-substituted PACs (2-methylnaphthalene, 1-methylphenanthrene, 1-methylpyrene), and one sulfur-containing heterocyclic PAC (dibenzothiophene). Fifty-eight metabolites were tentatively identified; metabolites from the un-substituted PACs were hydroxylated and sulfate conjugated, whereas metabolites from alkyl-substituted PACs were sulfate conjugated and either hydroxylated or oxidized to carboxylic acids at the methyl group. The metabolism of the sulfur-containing heterocyclic PAC resulted in sulfate conjugates. The sorption of the PAC metabolites to three soils was determined using a batch equilibrium method, and partition coefficients (Kd’s) were calculated for fourteen representative metabolites. Sulfate conjugated metabolites displayed Kd’s below 70 whereas the metabolites with both a sulfate and a carboxylic acid group had Kd’s below 2.8. The low Kd’s of water-soluble PAC metabolites indicate high mobility in soil and a potential for leaching to surface- and groundwaters. |
doi_str_mv | 10.1016/j.chemosphere.2014.06.033 |
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This study investigated the sorption to soil of water-soluble metabolites from polycyclic aromatic compounds (PACs). The soil fungus Cunninghamella elegans was used to produce PAC metabolites from two un-substituted PACs (phenanthrene, pyrene), three alkyl-substituted PACs (2-methylnaphthalene, 1-methylphenanthrene, 1-methylpyrene), and one sulfur-containing heterocyclic PAC (dibenzothiophene). Fifty-eight metabolites were tentatively identified; metabolites from the un-substituted PACs were hydroxylated and sulfate conjugated, whereas metabolites from alkyl-substituted PACs were sulfate conjugated and either hydroxylated or oxidized to carboxylic acids at the methyl group. The metabolism of the sulfur-containing heterocyclic PAC resulted in sulfate conjugates. The sorption of the PAC metabolites to three soils was determined using a batch equilibrium method, and partition coefficients (Kd’s) were calculated for fourteen representative metabolites. Sulfate conjugated metabolites displayed Kd’s below 70 whereas the metabolites with both a sulfate and a carboxylic acid group had Kd’s below 2.8. The low Kd’s of water-soluble PAC metabolites indicate high mobility in soil and a potential for leaching to surface- and groundwaters.</description><identifier>ISSN: 0045-6535</identifier><identifier>EISSN: 1879-1298</identifier><identifier>DOI: 10.1016/j.chemosphere.2014.06.033</identifier><identifier>PMID: 25025602</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Adsorption ; Aromatic compounds ; Carboxylic acids ; Cunninghamella - metabolism ; Cunninghamella elegans ; Fungi ; Groundwater ; Kd coefficients ; Metabolites ; Phenanthrene ; Polycyclic aromatic compounds ; Polycyclic Aromatic Hydrocarbons - chemistry ; Polycyclic Aromatic Hydrocarbons - metabolism ; Soil (material) ; Soil - chemistry ; Soil Pollutants - chemistry ; Soil Pollutants - metabolism ; Soil sorption ; Sorption ; Sulfates ; Water Pollutants, Chemical - chemistry ; Water Pollutants, Chemical - metabolism</subject><ispartof>Chemosphere (Oxford), 2015-01, Vol.119, p.250-257</ispartof><rights>2014 Elsevier Ltd</rights><rights>Copyright © 2014 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c443t-9de6e1431018cd2ef288b25a584d4de597d3f4a42e58a7f75e49cb4c68f0408e3</citedby><cites>FETCH-LOGICAL-c443t-9de6e1431018cd2ef288b25a584d4de597d3f4a42e58a7f75e49cb4c68f0408e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0045653514007693$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25025602$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Boll, Esther S.</creatorcontrib><creatorcontrib>Johnsen, Anders R.</creatorcontrib><creatorcontrib>Christensen, Jan H.</creatorcontrib><title>Polar metabolites of polycyclic aromatic compounds from fungi are potential soil and groundwater contaminants</title><title>Chemosphere (Oxford)</title><addtitle>Chemosphere</addtitle><description>•The soil fungus Cunninghamella elegans transformed PACs into highly polar metabolites.•58 PAC metabolites were tentative identified.•A batch sorption experiment with polar PAC metabolites was performed in three soils.•Partition coefficients (Kd’s) of the PAC metabolites indicate high mobility in soil.
This study investigated the sorption to soil of water-soluble metabolites from polycyclic aromatic compounds (PACs). The soil fungus Cunninghamella elegans was used to produce PAC metabolites from two un-substituted PACs (phenanthrene, pyrene), three alkyl-substituted PACs (2-methylnaphthalene, 1-methylphenanthrene, 1-methylpyrene), and one sulfur-containing heterocyclic PAC (dibenzothiophene). Fifty-eight metabolites were tentatively identified; metabolites from the un-substituted PACs were hydroxylated and sulfate conjugated, whereas metabolites from alkyl-substituted PACs were sulfate conjugated and either hydroxylated or oxidized to carboxylic acids at the methyl group. The metabolism of the sulfur-containing heterocyclic PAC resulted in sulfate conjugates. The sorption of the PAC metabolites to three soils was determined using a batch equilibrium method, and partition coefficients (Kd’s) were calculated for fourteen representative metabolites. Sulfate conjugated metabolites displayed Kd’s below 70 whereas the metabolites with both a sulfate and a carboxylic acid group had Kd’s below 2.8. The low Kd’s of water-soluble PAC metabolites indicate high mobility in soil and a potential for leaching to surface- and groundwaters.</description><subject>Adsorption</subject><subject>Aromatic compounds</subject><subject>Carboxylic acids</subject><subject>Cunninghamella - metabolism</subject><subject>Cunninghamella elegans</subject><subject>Fungi</subject><subject>Groundwater</subject><subject>Kd coefficients</subject><subject>Metabolites</subject><subject>Phenanthrene</subject><subject>Polycyclic aromatic compounds</subject><subject>Polycyclic Aromatic Hydrocarbons - chemistry</subject><subject>Polycyclic Aromatic Hydrocarbons - metabolism</subject><subject>Soil (material)</subject><subject>Soil - chemistry</subject><subject>Soil Pollutants - chemistry</subject><subject>Soil Pollutants - metabolism</subject><subject>Soil sorption</subject><subject>Sorption</subject><subject>Sulfates</subject><subject>Water Pollutants, Chemical - chemistry</subject><subject>Water Pollutants, Chemical - metabolism</subject><issn>0045-6535</issn><issn>1879-1298</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkU2PFCEQhonRuOPqXzB489It300fzcSvZBM96JkwUOwy6W5aoDXz72Uyq_E4Jwj1vFSqHoTeUNJTQtW7Y-8eYE5lfYAMPSNU9ET1hPMnaEf1MHaUjfop2hEiZKcklzfoRSlHQlpYjs_RDZOESUXYDs3f0mQznqHaQ5pihYJTwGuaTu7kpuiwzWm2tV1cmte0Lb7g0J5w2Jb72KrQ4ApLjXbCJcUJ28Xj-3wmf9sKueWWaue42KWWl-hZsFOBV4_nLfrx8cP3_efu7uunL_v3d50Tgtdu9KCACt6G1c4zCEzrA5NWauGFBzkOngdhBQOp7RAGCWJ0B-GUDkQQDfwWvb38u-b0c4NSzRyLg2myC6StGKqGYeRcKXUFqjSTsq31CpSLgTFFaUPHC-pyKiVDMGuOs80nQ4k5OzRH859Dc3ZoiDLNYcu-fmyzHWbw_5J_pTVgfwGgrfBXhGyKi7A48DGDq8aneEWbP-c0tRs</recordid><startdate>201501</startdate><enddate>201501</enddate><creator>Boll, Esther S.</creator><creator>Johnsen, Anders R.</creator><creator>Christensen, Jan H.</creator><general>Elsevier Ltd</general><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><scope>7QH</scope><scope>7TG</scope><scope>7TV</scope><scope>7UA</scope><scope>C1K</scope><scope>F1W</scope><scope>H97</scope><scope>KL.</scope><scope>L.G</scope><scope>M7N</scope><scope>8FD</scope><scope>FR3</scope><scope>KR7</scope></search><sort><creationdate>201501</creationdate><title>Polar metabolites of polycyclic aromatic compounds from fungi are potential soil and groundwater contaminants</title><author>Boll, Esther S. ; Johnsen, Anders R. ; Christensen, Jan H.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c443t-9de6e1431018cd2ef288b25a584d4de597d3f4a42e58a7f75e49cb4c68f0408e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Adsorption</topic><topic>Aromatic compounds</topic><topic>Carboxylic acids</topic><topic>Cunninghamella - metabolism</topic><topic>Cunninghamella elegans</topic><topic>Fungi</topic><topic>Groundwater</topic><topic>Kd coefficients</topic><topic>Metabolites</topic><topic>Phenanthrene</topic><topic>Polycyclic aromatic compounds</topic><topic>Polycyclic Aromatic Hydrocarbons - chemistry</topic><topic>Polycyclic Aromatic Hydrocarbons - metabolism</topic><topic>Soil (material)</topic><topic>Soil - chemistry</topic><topic>Soil Pollutants - chemistry</topic><topic>Soil Pollutants - metabolism</topic><topic>Soil sorption</topic><topic>Sorption</topic><topic>Sulfates</topic><topic>Water Pollutants, Chemical - chemistry</topic><topic>Water Pollutants, Chemical - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Boll, Esther S.</creatorcontrib><creatorcontrib>Johnsen, Anders R.</creatorcontrib><creatorcontrib>Christensen, Jan H.</creatorcontrib><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><collection>Aqualine</collection><collection>Meteorological & Geoastrophysical Abstracts</collection><collection>Pollution Abstracts</collection><collection>Water Resources Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Meteorological & Geoastrophysical Abstracts - Academic</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Civil Engineering Abstracts</collection><jtitle>Chemosphere (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Boll, Esther S.</au><au>Johnsen, Anders R.</au><au>Christensen, Jan H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Polar metabolites of polycyclic aromatic compounds from fungi are potential soil and groundwater contaminants</atitle><jtitle>Chemosphere (Oxford)</jtitle><addtitle>Chemosphere</addtitle><date>2015-01</date><risdate>2015</risdate><volume>119</volume><spage>250</spage><epage>257</epage><pages>250-257</pages><issn>0045-6535</issn><eissn>1879-1298</eissn><abstract>•The soil fungus Cunninghamella elegans transformed PACs into highly polar metabolites.•58 PAC metabolites were tentative identified.•A batch sorption experiment with polar PAC metabolites was performed in three soils.•Partition coefficients (Kd’s) of the PAC metabolites indicate high mobility in soil.
This study investigated the sorption to soil of water-soluble metabolites from polycyclic aromatic compounds (PACs). The soil fungus Cunninghamella elegans was used to produce PAC metabolites from two un-substituted PACs (phenanthrene, pyrene), three alkyl-substituted PACs (2-methylnaphthalene, 1-methylphenanthrene, 1-methylpyrene), and one sulfur-containing heterocyclic PAC (dibenzothiophene). Fifty-eight metabolites were tentatively identified; metabolites from the un-substituted PACs were hydroxylated and sulfate conjugated, whereas metabolites from alkyl-substituted PACs were sulfate conjugated and either hydroxylated or oxidized to carboxylic acids at the methyl group. The metabolism of the sulfur-containing heterocyclic PAC resulted in sulfate conjugates. The sorption of the PAC metabolites to three soils was determined using a batch equilibrium method, and partition coefficients (Kd’s) were calculated for fourteen representative metabolites. Sulfate conjugated metabolites displayed Kd’s below 70 whereas the metabolites with both a sulfate and a carboxylic acid group had Kd’s below 2.8. The low Kd’s of water-soluble PAC metabolites indicate high mobility in soil and a potential for leaching to surface- and groundwaters.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>25025602</pmid><doi>10.1016/j.chemosphere.2014.06.033</doi><tpages>8</tpages></addata></record> |
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subjects | Adsorption Aromatic compounds Carboxylic acids Cunninghamella - metabolism Cunninghamella elegans Fungi Groundwater Kd coefficients Metabolites Phenanthrene Polycyclic aromatic compounds Polycyclic Aromatic Hydrocarbons - chemistry Polycyclic Aromatic Hydrocarbons - metabolism Soil (material) Soil - chemistry Soil Pollutants - chemistry Soil Pollutants - metabolism Soil sorption Sorption Sulfates Water Pollutants, Chemical - chemistry Water Pollutants, Chemical - metabolism |
title | Polar metabolites of polycyclic aromatic compounds from fungi are potential soil and groundwater contaminants |
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