Uptake and Metabolic Fate of [14C]-2,4-Dichlorophenol and [14C]-2,4-Dichloroaniline in Wheat (Triticum aestivum) and Soybean (Glycine max)
The uptake and metabolism of [14C]-2,4-dichlorophenol (DCP) and [14C]-2,4-dichloroaniline (DCA) were investigated in wheat and soybean. Seeds were exposed to a nutrient solution containing 50 μM of one of two radiolabeled compounds, and plant organs were harvested separately after 18 days of growth....
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2003-07, Vol.51 (16), p.4712-4718 |
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| creator | Pascal-lorber, Sophie Rathahao, Estelle Cravedi, Jean-pierre Laurent, Francois |
| description | The uptake and metabolism of [14C]-2,4-dichlorophenol (DCP) and [14C]-2,4-dichloroaniline (DCA) were investigated in wheat and soybean. Seeds were exposed to a nutrient solution containing 50 μM of one of two radiolabeled compounds, and plant organs were harvested separately after 18 days of growth. In wheat, uptake of [14C]-2,4-DCP was 16.67 ± 2.65 and 15.50 ± 2.60% of [14C]-2,4-DCA. In soybean, uptake of [14C]-2,4-DCP was significantly higher than [14C]-2,4-DCA uptake, 38.39 ± 2.56 and 18.98 ± 1.64%, respectively. In the case of [14C]-2,4-DCP, the radioactivity absorbed by both species was found mainly associated with roots, whereas [14C]-2,4-DCA and related metabolites were associated with aerial parts, especially in soybean. In wheat, nonextractable residues represented 7.8 and 8.7% of the applied radioactivity in the case of [14C]-2,4-DCP and [14C]-2,4-DCA, respectively. In soybean, nonextractable residues amounted to 11.8 and 5.8% of the total radioactivity for [14C]-2,4-DCP and [14C]-2,4-DCA, respectively. In wheat, nonextractable residues were nearly equivalent to extractable residues for [14C]-2,4-DCP, whereas they were greater for [14C]-2,4-DCA. In soybean, the amount of extractable residues was significantly greater for both chemicals. However, in both species, nonextractable residues were mainly associated with roots. Isolation of soluble residues was next undertaken using excised shoots (wheat) or excised fully expanded leaves including petioles (soybean). Identification of metabolite structures was made by comparison with authentic standards, by enzymatic hydrolyses, and by electrospray ionization−mass spectrometric analyses. Both plant species shared a common metabolism for [14C]-2,4-DCP and [14C]-2,4-DCA since the malonylated glucoside conjugates were found as the final major metabolites. Keywords: Triticum aestivum; Glycine max; 2,4-dichlorophenol; 2,4-dichloroaniline; absorption; residues; metabolism; malonylated glycosides |
| doi_str_mv | 10.1021/jf034230j |
| format | Article |
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Seeds were exposed to a nutrient solution containing 50 μM of one of two radiolabeled compounds, and plant organs were harvested separately after 18 days of growth. In wheat, uptake of [14C]-2,4-DCP was 16.67 ± 2.65 and 15.50 ± 2.60% of [14C]-2,4-DCA. In soybean, uptake of [14C]-2,4-DCP was significantly higher than [14C]-2,4-DCA uptake, 38.39 ± 2.56 and 18.98 ± 1.64%, respectively. In the case of [14C]-2,4-DCP, the radioactivity absorbed by both species was found mainly associated with roots, whereas [14C]-2,4-DCA and related metabolites were associated with aerial parts, especially in soybean. In wheat, nonextractable residues represented 7.8 and 8.7% of the applied radioactivity in the case of [14C]-2,4-DCP and [14C]-2,4-DCA, respectively. In soybean, nonextractable residues amounted to 11.8 and 5.8% of the total radioactivity for [14C]-2,4-DCP and [14C]-2,4-DCA, respectively. In wheat, nonextractable residues were nearly equivalent to extractable residues for [14C]-2,4-DCP, whereas they were greater for [14C]-2,4-DCA. In soybean, the amount of extractable residues was significantly greater for both chemicals. However, in both species, nonextractable residues were mainly associated with roots. Isolation of soluble residues was next undertaken using excised shoots (wheat) or excised fully expanded leaves including petioles (soybean). Identification of metabolite structures was made by comparison with authentic standards, by enzymatic hydrolyses, and by electrospray ionization−mass spectrometric analyses. Both plant species shared a common metabolism for [14C]-2,4-DCP and [14C]-2,4-DCA since the malonylated glucoside conjugates were found as the final major metabolites. Keywords: Triticum aestivum; Glycine max; 2,4-dichlorophenol; 2,4-dichloroaniline; absorption; residues; metabolism; malonylated glycosides</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf034230j</identifier><identifier>PMID: 14705901</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>aerial parts ; Aniline Compounds - metabolism ; Carbon Radioisotopes ; Chlorophenols - metabolism ; Chromatography, High Pressure Liquid ; Glycine max ; Glycine max - metabolism ; Life Sciences ; metabolism ; metabolites ; petioles ; plant organs ; roots ; seeds ; Seeds - metabolism ; shoots ; Solutions ; soybeans ; Spectrometry, Mass, Electrospray Ionization ; Triticum - metabolism ; Triticum aestivum ; wheat</subject><ispartof>Journal of agricultural and food chemistry, 2003-07, Vol.51 (16), p.4712-4718</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a407t-9b87addb359e1e84eba33f9978a0642e307c2be2dc894cbcad343dedf86ed4e63</citedby><cites>FETCH-LOGICAL-a407t-9b87addb359e1e84eba33f9978a0642e307c2be2dc894cbcad343dedf86ed4e63</cites><orcidid>0000-0003-0231-6394 ; 0000-0002-7271-7372 ; 0000-0003-2367-0202</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf034230j$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf034230j$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14705901$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-01763224$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Pascal-lorber, Sophie</creatorcontrib><creatorcontrib>Rathahao, Estelle</creatorcontrib><creatorcontrib>Cravedi, Jean-pierre</creatorcontrib><creatorcontrib>Laurent, Francois</creatorcontrib><title>Uptake and Metabolic Fate of [14C]-2,4-Dichlorophenol and [14C]-2,4-Dichloroaniline in Wheat (Triticum aestivum) and Soybean (Glycine max)</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The uptake and metabolism of [14C]-2,4-dichlorophenol (DCP) and [14C]-2,4-dichloroaniline (DCA) were investigated in wheat and soybean. Seeds were exposed to a nutrient solution containing 50 μM of one of two radiolabeled compounds, and plant organs were harvested separately after 18 days of growth. In wheat, uptake of [14C]-2,4-DCP was 16.67 ± 2.65 and 15.50 ± 2.60% of [14C]-2,4-DCA. In soybean, uptake of [14C]-2,4-DCP was significantly higher than [14C]-2,4-DCA uptake, 38.39 ± 2.56 and 18.98 ± 1.64%, respectively. In the case of [14C]-2,4-DCP, the radioactivity absorbed by both species was found mainly associated with roots, whereas [14C]-2,4-DCA and related metabolites were associated with aerial parts, especially in soybean. In wheat, nonextractable residues represented 7.8 and 8.7% of the applied radioactivity in the case of [14C]-2,4-DCP and [14C]-2,4-DCA, respectively. In soybean, nonextractable residues amounted to 11.8 and 5.8% of the total radioactivity for [14C]-2,4-DCP and [14C]-2,4-DCA, respectively. In wheat, nonextractable residues were nearly equivalent to extractable residues for [14C]-2,4-DCP, whereas they were greater for [14C]-2,4-DCA. In soybean, the amount of extractable residues was significantly greater for both chemicals. However, in both species, nonextractable residues were mainly associated with roots. Isolation of soluble residues was next undertaken using excised shoots (wheat) or excised fully expanded leaves including petioles (soybean). Identification of metabolite structures was made by comparison with authentic standards, by enzymatic hydrolyses, and by electrospray ionization−mass spectrometric analyses. Both plant species shared a common metabolism for [14C]-2,4-DCP and [14C]-2,4-DCA since the malonylated glucoside conjugates were found as the final major metabolites. Keywords: Triticum aestivum; Glycine max; 2,4-dichlorophenol; 2,4-dichloroaniline; absorption; residues; metabolism; malonylated glycosides</description><subject>aerial parts</subject><subject>Aniline Compounds - metabolism</subject><subject>Carbon Radioisotopes</subject><subject>Chlorophenols - metabolism</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Glycine max</subject><subject>Glycine max - metabolism</subject><subject>Life Sciences</subject><subject>metabolism</subject><subject>metabolites</subject><subject>petioles</subject><subject>plant organs</subject><subject>roots</subject><subject>seeds</subject><subject>Seeds - metabolism</subject><subject>shoots</subject><subject>Solutions</subject><subject>soybeans</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Triticum - metabolism</subject><subject>Triticum aestivum</subject><subject>wheat</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1u00AURi0EomlhwQuAN0WNhOHOjz32skppC6QCKYlYIDS6Hl-TSW1P8NhV8wo8NU4TpQtYjTTfuUcz9wuCVwzeM-Dsw6oEIbmA1ZNgxGIOUcxY-jQYwRBGaZywo-DY-xUApLGC58ERkwriDNgo-LNYd3hLITZFeEMd5q6yJrzEjkJXhj-YnPyM-DsZXVizrFzr1ktqXPWA_xtiYyvbUGib8PuSsAvP5q3trOnrEMl39q6vxw-jM7fJCZvw7KramO1EjffjF8GzEitPL_fnSbC4_DifXEfTr1efJufTCCWoLsryVGFR5CLOiFEqKUchyixTKUIiOQlQhufEC5Nm0uQGCyFFQUWZJlRISsRJMN55l1jpdWtrbDfaodXX51O9vQOmEsG5vGMD-3bHrlv3ux_-oGvrDVUVNuR6rxWLgYPKHqWmdd63VB7MDPS2JH0oaWBf76V9XlPxSO5bGYBoB1jf0f0hx_ZWJ0qoWM-_zTRPpsmXz9mNFgP_ZseX6DT-aq3XixkHJmGQsWENA3G6I9B4vXJ92wwb_s_T_gJx_a5y</recordid><startdate>20030730</startdate><enddate>20030730</enddate><creator>Pascal-lorber, Sophie</creator><creator>Rathahao, Estelle</creator><creator>Cravedi, Jean-pierre</creator><creator>Laurent, Francois</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</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><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-0231-6394</orcidid><orcidid>https://orcid.org/0000-0002-7271-7372</orcidid><orcidid>https://orcid.org/0000-0003-2367-0202</orcidid></search><sort><creationdate>20030730</creationdate><title>Uptake and Metabolic Fate of [14C]-2,4-Dichlorophenol and [14C]-2,4-Dichloroaniline in Wheat (Triticum aestivum) and Soybean (Glycine max)</title><author>Pascal-lorber, Sophie ; Rathahao, Estelle ; Cravedi, Jean-pierre ; Laurent, Francois</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a407t-9b87addb359e1e84eba33f9978a0642e307c2be2dc894cbcad343dedf86ed4e63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>aerial parts</topic><topic>Aniline Compounds - metabolism</topic><topic>Carbon Radioisotopes</topic><topic>Chlorophenols - metabolism</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Glycine max</topic><topic>Glycine max - metabolism</topic><topic>Life Sciences</topic><topic>metabolism</topic><topic>metabolites</topic><topic>petioles</topic><topic>plant organs</topic><topic>roots</topic><topic>seeds</topic><topic>Seeds - metabolism</topic><topic>shoots</topic><topic>Solutions</topic><topic>soybeans</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Triticum - metabolism</topic><topic>Triticum aestivum</topic><topic>wheat</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pascal-lorber, Sophie</creatorcontrib><creatorcontrib>Rathahao, Estelle</creatorcontrib><creatorcontrib>Cravedi, Jean-pierre</creatorcontrib><creatorcontrib>Laurent, Francois</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><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>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pascal-lorber, Sophie</au><au>Rathahao, Estelle</au><au>Cravedi, Jean-pierre</au><au>Laurent, Francois</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Uptake and Metabolic Fate of [14C]-2,4-Dichlorophenol and [14C]-2,4-Dichloroaniline in Wheat (Triticum aestivum) and Soybean (Glycine max)</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2003-07-30</date><risdate>2003</risdate><volume>51</volume><issue>16</issue><spage>4712</spage><epage>4718</epage><pages>4712-4718</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>The uptake and metabolism of [14C]-2,4-dichlorophenol (DCP) and [14C]-2,4-dichloroaniline (DCA) were investigated in wheat and soybean. Seeds were exposed to a nutrient solution containing 50 μM of one of two radiolabeled compounds, and plant organs were harvested separately after 18 days of growth. In wheat, uptake of [14C]-2,4-DCP was 16.67 ± 2.65 and 15.50 ± 2.60% of [14C]-2,4-DCA. In soybean, uptake of [14C]-2,4-DCP was significantly higher than [14C]-2,4-DCA uptake, 38.39 ± 2.56 and 18.98 ± 1.64%, respectively. In the case of [14C]-2,4-DCP, the radioactivity absorbed by both species was found mainly associated with roots, whereas [14C]-2,4-DCA and related metabolites were associated with aerial parts, especially in soybean. In wheat, nonextractable residues represented 7.8 and 8.7% of the applied radioactivity in the case of [14C]-2,4-DCP and [14C]-2,4-DCA, respectively. In soybean, nonextractable residues amounted to 11.8 and 5.8% of the total radioactivity for [14C]-2,4-DCP and [14C]-2,4-DCA, respectively. In wheat, nonextractable residues were nearly equivalent to extractable residues for [14C]-2,4-DCP, whereas they were greater for [14C]-2,4-DCA. In soybean, the amount of extractable residues was significantly greater for both chemicals. However, in both species, nonextractable residues were mainly associated with roots. Isolation of soluble residues was next undertaken using excised shoots (wheat) or excised fully expanded leaves including petioles (soybean). Identification of metabolite structures was made by comparison with authentic standards, by enzymatic hydrolyses, and by electrospray ionization−mass spectrometric analyses. Both plant species shared a common metabolism for [14C]-2,4-DCP and [14C]-2,4-DCA since the malonylated glucoside conjugates were found as the final major metabolites. Keywords: Triticum aestivum; Glycine max; 2,4-dichlorophenol; 2,4-dichloroaniline; absorption; residues; metabolism; malonylated glycosides</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>14705901</pmid><doi>10.1021/jf034230j</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-0231-6394</orcidid><orcidid>https://orcid.org/0000-0002-7271-7372</orcidid><orcidid>https://orcid.org/0000-0003-2367-0202</orcidid></addata></record> |
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| ispartof | Journal of agricultural and food chemistry, 2003-07, Vol.51 (16), p.4712-4718 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | aerial parts Aniline Compounds - metabolism Carbon Radioisotopes Chlorophenols - metabolism Chromatography, High Pressure Liquid Glycine max Glycine max - metabolism Life Sciences metabolism metabolites petioles plant organs roots seeds Seeds - metabolism shoots Solutions soybeans Spectrometry, Mass, Electrospray Ionization Triticum - metabolism Triticum aestivum wheat |
| title | Uptake and Metabolic Fate of [14C]-2,4-Dichlorophenol and [14C]-2,4-Dichloroaniline in Wheat (Triticum aestivum) and Soybean (Glycine max) |
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