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Metabolism of (R)- and (S)-3-(Phenylamino)propane-1,2-diol in C57BL/6- and A/J-Strain Mice. Identification of New Metabolites with Potential Toxicological Significance to the Toxic Oil Syndrome
The Toxic Oil Syndrome was a massive food-borne intoxication that occurred in Spain in 1981. Epidemiological studies point to 3-(phenylamino)propane-1,2-diol (PAP) derivatives as the putative toxic agents. We report further identification of metabolites cleared in urine of A/J and C57BL/6 mice in wh...
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| Published in: | Chemical research in toxicology 2001-08, Vol.14 (8), p.1097-1106 |
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| creator | Bujons, Jordi Ladona, Margarita G Messeguer, Angel Morató, Anna Ampurdanés, Coral |
| description | The Toxic Oil Syndrome was a massive food-borne intoxication that occurred in Spain in 1981. Epidemiological studies point to 3-(phenylamino)propane-1,2-diol (PAP) derivatives as the putative toxic agents. We report further identification of metabolites cleared in urine of A/J and C57BL/6 mice in which (R)- and (S)-3-(phenylamino)propane-1,2-diol were administered intraperitoneally. This investigation is an extension of previous studies carried out with the racemic compound [Ladona, M. G., Bujons, J., Messeguer, A., Ampurdanés, C., Morató, A., and Corbella, J. (1999) Chem. Res. Toxicol. 12, 1127−1137]. Both PAP enantiomers were extensively metabolized, and several metabolites were eliminated in urine. The HPLC profiles of the urine samples of both mouse strains treated with each enantiomer were qualitatively similar, but differences were found in a relatively higher proportion of several detected metabolites in mice treated with (R)-PAP compared with those treated with (S)-PAP. The main urine metabolite continues to be 2-hydroxy-3-(phenylamino)propanoic acid (1), which confirms our previous results obtained with rac-PAP. In addition to the detection of other metabolites already reported in our previous paper, interesting evidence is provided on the presence of 4-aminophenol and paracetamol conjugates in the urine samples from both mouse strains. The detection of these metabolites suggests the in vivo formation of quinoneimine PAP derivatives. Indeed, some quinoneimine species (11 and 12), as well as other PAP metabolites (13) that bear modifications in the alkyl chain, have been tentatively identified in mouse urine. These metabolic findings might imply a potential toxicological significance for the Toxic Oil Syndrome. |
| doi_str_mv | 10.1021/tx010001k |
| format | article |
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Identification of New Metabolites with Potential Toxicological Significance to the Toxic Oil Syndrome</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)</source><creator>Bujons, Jordi ; Ladona, Margarita G ; Messeguer, Angel ; Morató, Anna ; Ampurdanés, Coral</creator><creatorcontrib>Bujons, Jordi ; Ladona, Margarita G ; Messeguer, Angel ; Morató, Anna ; Ampurdanés, Coral</creatorcontrib><description>The Toxic Oil Syndrome was a massive food-borne intoxication that occurred in Spain in 1981. Epidemiological studies point to 3-(phenylamino)propane-1,2-diol (PAP) derivatives as the putative toxic agents. We report further identification of metabolites cleared in urine of A/J and C57BL/6 mice in which (R)- and (S)-3-(phenylamino)propane-1,2-diol were administered intraperitoneally. This investigation is an extension of previous studies carried out with the racemic compound [Ladona, M. G., Bujons, J., Messeguer, A., Ampurdanés, C., Morató, A., and Corbella, J. (1999) Chem. Res. Toxicol. 12, 1127−1137]. Both PAP enantiomers were extensively metabolized, and several metabolites were eliminated in urine. The HPLC profiles of the urine samples of both mouse strains treated with each enantiomer were qualitatively similar, but differences were found in a relatively higher proportion of several detected metabolites in mice treated with (R)-PAP compared with those treated with (S)-PAP. The main urine metabolite continues to be 2-hydroxy-3-(phenylamino)propanoic acid (1), which confirms our previous results obtained with rac-PAP. In addition to the detection of other metabolites already reported in our previous paper, interesting evidence is provided on the presence of 4-aminophenol and paracetamol conjugates in the urine samples from both mouse strains. The detection of these metabolites suggests the in vivo formation of quinoneimine PAP derivatives. Indeed, some quinoneimine species (11 and 12), as well as other PAP metabolites (13) that bear modifications in the alkyl chain, have been tentatively identified in mouse urine. These metabolic findings might imply a potential toxicological significance for the Toxic Oil Syndrome.</description><identifier>ISSN: 0893-228X</identifier><identifier>EISSN: 1520-5010</identifier><identifier>DOI: 10.1021/tx010001k</identifier><identifier>PMID: 11511184</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>acetaminophen ; Acetaminophen - chemistry ; Aminophenols - chemistry ; Aniline Compounds - metabolism ; Animals ; Canola Oil ; Chromatography, High Pressure Liquid ; Fatty Acids, Monounsaturated ; Food Contamination ; Mice ; Mice, Inbred C57BL ; p-Aminophenol ; Plant Oils - chemistry ; Propylene Glycols - metabolism ; Propylene Glycols - pharmacokinetics</subject><ispartof>Chemical research in toxicology, 2001-08, Vol.14 (8), p.1097-1106</ispartof><rights>Copyright © 2001 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a380t-b441efbd20be48ac8bce726ec601f0c949395377c63c35f70a0fb5e5d5d34fd93</citedby><cites>FETCH-LOGICAL-a380t-b441efbd20be48ac8bce726ec601f0c949395377c63c35f70a0fb5e5d5d34fd93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11511184$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bujons, Jordi</creatorcontrib><creatorcontrib>Ladona, Margarita G</creatorcontrib><creatorcontrib>Messeguer, Angel</creatorcontrib><creatorcontrib>Morató, Anna</creatorcontrib><creatorcontrib>Ampurdanés, Coral</creatorcontrib><title>Metabolism of (R)- and (S)-3-(Phenylamino)propane-1,2-diol in C57BL/6- and A/J-Strain Mice. Identification of New Metabolites with Potential Toxicological Significance to the Toxic Oil Syndrome</title><title>Chemical research in toxicology</title><addtitle>Chem. Res. Toxicol</addtitle><description>The Toxic Oil Syndrome was a massive food-borne intoxication that occurred in Spain in 1981. Epidemiological studies point to 3-(phenylamino)propane-1,2-diol (PAP) derivatives as the putative toxic agents. We report further identification of metabolites cleared in urine of A/J and C57BL/6 mice in which (R)- and (S)-3-(phenylamino)propane-1,2-diol were administered intraperitoneally. This investigation is an extension of previous studies carried out with the racemic compound [Ladona, M. G., Bujons, J., Messeguer, A., Ampurdanés, C., Morató, A., and Corbella, J. (1999) Chem. Res. Toxicol. 12, 1127−1137]. Both PAP enantiomers were extensively metabolized, and several metabolites were eliminated in urine. The HPLC profiles of the urine samples of both mouse strains treated with each enantiomer were qualitatively similar, but differences were found in a relatively higher proportion of several detected metabolites in mice treated with (R)-PAP compared with those treated with (S)-PAP. The main urine metabolite continues to be 2-hydroxy-3-(phenylamino)propanoic acid (1), which confirms our previous results obtained with rac-PAP. In addition to the detection of other metabolites already reported in our previous paper, interesting evidence is provided on the presence of 4-aminophenol and paracetamol conjugates in the urine samples from both mouse strains. The detection of these metabolites suggests the in vivo formation of quinoneimine PAP derivatives. Indeed, some quinoneimine species (11 and 12), as well as other PAP metabolites (13) that bear modifications in the alkyl chain, have been tentatively identified in mouse urine. These metabolic findings might imply a potential toxicological significance for the Toxic Oil Syndrome.</description><subject>acetaminophen</subject><subject>Acetaminophen - chemistry</subject><subject>Aminophenols - chemistry</subject><subject>Aniline Compounds - metabolism</subject><subject>Animals</subject><subject>Canola Oil</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Fatty Acids, Monounsaturated</subject><subject>Food Contamination</subject><subject>Mice</subject><subject>Mice, Inbred C57BL</subject><subject>p-Aminophenol</subject><subject>Plant Oils - chemistry</subject><subject>Propylene Glycols - metabolism</subject><subject>Propylene Glycols - pharmacokinetics</subject><issn>0893-228X</issn><issn>1520-5010</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><recordid>eNptkVFv0zAUhS0EYmXwwB9AfgG1El7tOG6Sx1EBG-pYRYqE9mI5zs3qLbFL7Grtz-Of4ZIyXniyru93zpXOQeg1o2eMJmwadpRRStn9EzRiIqFExPkpGtG84CRJ8h8n6IX3d5GIePYcnTAmGGN5OkK_riCoyrXGd9g1ePxtQrCyNR6XE8LJeLkGu29VZ6ybbHq3URYIe5-Q2rgWG4vnIvuwmM4Gzfn0CylDr-L_ldFwhi9rsME0RqtgnD34f4UH_PdiAI8fTFjjpQsHTrV45XZGu9bdRkmLS3Nr_6itBhwcDmsYCHxt4nZv69518BI9a1Tr4dXxPUXfP31czS_I4vrz5fx8QRTPaSBVmjJoqjqhFaS50nmlIUtmoGeUNVQXacELwbNMz7jmosmook0lQNSi5mlTF_wUvRt8Yw4_t-CD7IzX0LYxE7f1kuUJEzQTEZwMoO6d9z00ctObTvV7yag89CUf-4rsm6Pptuqg_kceC4oAGQDjA-we96q_l7OMZ0KulqW8uKH8hpdCssi_HXilvbxz297GTP5z-Dct8qrc</recordid><startdate>20010801</startdate><enddate>20010801</enddate><creator>Bujons, Jordi</creator><creator>Ladona, Margarita G</creator><creator>Messeguer, Angel</creator><creator>Morató, Anna</creator><creator>Ampurdanés, Coral</creator><general>American Chemical Society</general><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>7U7</scope><scope>C1K</scope></search><sort><creationdate>20010801</creationdate><title>Metabolism of (R)- and (S)-3-(Phenylamino)propane-1,2-diol in C57BL/6- and A/J-Strain Mice. Identification of New Metabolites with Potential Toxicological Significance to the Toxic Oil Syndrome</title><author>Bujons, Jordi ; Ladona, Margarita G ; Messeguer, Angel ; Morató, Anna ; Ampurdanés, Coral</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a380t-b441efbd20be48ac8bce726ec601f0c949395377c63c35f70a0fb5e5d5d34fd93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>acetaminophen</topic><topic>Acetaminophen - chemistry</topic><topic>Aminophenols - chemistry</topic><topic>Aniline Compounds - metabolism</topic><topic>Animals</topic><topic>Canola Oil</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Fatty Acids, Monounsaturated</topic><topic>Food Contamination</topic><topic>Mice</topic><topic>Mice, Inbred C57BL</topic><topic>p-Aminophenol</topic><topic>Plant Oils - chemistry</topic><topic>Propylene Glycols - metabolism</topic><topic>Propylene Glycols - pharmacokinetics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bujons, Jordi</creatorcontrib><creatorcontrib>Ladona, Margarita G</creatorcontrib><creatorcontrib>Messeguer, Angel</creatorcontrib><creatorcontrib>Morató, Anna</creatorcontrib><creatorcontrib>Ampurdanés, Coral</creatorcontrib><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>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>Chemical research in toxicology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bujons, Jordi</au><au>Ladona, Margarita G</au><au>Messeguer, Angel</au><au>Morató, Anna</au><au>Ampurdanés, Coral</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metabolism of (R)- and (S)-3-(Phenylamino)propane-1,2-diol in C57BL/6- and A/J-Strain Mice. Identification of New Metabolites with Potential Toxicological Significance to the Toxic Oil Syndrome</atitle><jtitle>Chemical research in toxicology</jtitle><addtitle>Chem. Res. Toxicol</addtitle><date>2001-08-01</date><risdate>2001</risdate><volume>14</volume><issue>8</issue><spage>1097</spage><epage>1106</epage><pages>1097-1106</pages><issn>0893-228X</issn><eissn>1520-5010</eissn><notes>ark:/67375/TPS-HZ03Z3S5-1</notes><notes>istex:9EBD20118CB8418151C04297B18F369C0B023C6F</notes><notes>ObjectType-Article-2</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-1</notes><notes>content type line 23</notes><abstract>The Toxic Oil Syndrome was a massive food-borne intoxication that occurred in Spain in 1981. Epidemiological studies point to 3-(phenylamino)propane-1,2-diol (PAP) derivatives as the putative toxic agents. We report further identification of metabolites cleared in urine of A/J and C57BL/6 mice in which (R)- and (S)-3-(phenylamino)propane-1,2-diol were administered intraperitoneally. This investigation is an extension of previous studies carried out with the racemic compound [Ladona, M. G., Bujons, J., Messeguer, A., Ampurdanés, C., Morató, A., and Corbella, J. (1999) Chem. Res. Toxicol. 12, 1127−1137]. Both PAP enantiomers were extensively metabolized, and several metabolites were eliminated in urine. The HPLC profiles of the urine samples of both mouse strains treated with each enantiomer were qualitatively similar, but differences were found in a relatively higher proportion of several detected metabolites in mice treated with (R)-PAP compared with those treated with (S)-PAP. The main urine metabolite continues to be 2-hydroxy-3-(phenylamino)propanoic acid (1), which confirms our previous results obtained with rac-PAP. In addition to the detection of other metabolites already reported in our previous paper, interesting evidence is provided on the presence of 4-aminophenol and paracetamol conjugates in the urine samples from both mouse strains. The detection of these metabolites suggests the in vivo formation of quinoneimine PAP derivatives. Indeed, some quinoneimine species (11 and 12), as well as other PAP metabolites (13) that bear modifications in the alkyl chain, have been tentatively identified in mouse urine. These metabolic findings might imply a potential toxicological significance for the Toxic Oil Syndrome.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11511184</pmid><doi>10.1021/tx010001k</doi><tpages>10</tpages></addata></record> |
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| ispartof | Chemical research in toxicology, 2001-08, Vol.14 (8), p.1097-1106 |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | acetaminophen Acetaminophen - chemistry Aminophenols - chemistry Aniline Compounds - metabolism Animals Canola Oil Chromatography, High Pressure Liquid Fatty Acids, Monounsaturated Food Contamination Mice Mice, Inbred C57BL p-Aminophenol Plant Oils - chemistry Propylene Glycols - metabolism Propylene Glycols - pharmacokinetics |
| title | Metabolism of (R)- and (S)-3-(Phenylamino)propane-1,2-diol in C57BL/6- and A/J-Strain Mice. Identification of New Metabolites with Potential Toxicological Significance to the Toxic Oil Syndrome |
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