Absorption and effects of 3‐(N‐phenylamino)‐1,2‐propanediol esters in relation to toxic oil syndrome
Toxic Oil Syndrome (TOS) was an epidemic disease related to the consumption of rapessed oil denatured with aniline that made its sudden appearance in Spain in 1981. The fatty acid esters of 3‐(N‐phenylamino)‐1,2‐propanediol (PAP), which is a chemical class of by‐products resulting from the reaction...
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| Veröffentlicht in: | Lipids 2001-10, Vol.36 (10), p.1125-1133 |
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| creator | Closa, Daniel Folch, Emma Calaf, Rosa Elena Abián, Joaquin Roselló‐Catafau, Joan Gelpí, Emilio |
| description | Toxic Oil Syndrome (TOS) was an epidemic disease related to the consumption of rapessed oil denatured with aniline that made its sudden appearance in Spain in 1981. The fatty acid esters of 3‐(N‐phenylamino)‐1,2‐propanediol (PAP), which is a chemical class of by‐products resulting from the reaction of aniline with oil components, have shown a strong association with TOS‐related oils. These compounds also show some structural similarities to platelet‐activating factor (PAE). In search of a toxic agent that could explain the widespread systemic effects observed in TOS patients, we investigated the intestinal absorption and biotransformation of the different PAP esters found in TOS‐related oil samples and the possible pathophysiological effect of these mediators and their metabolic products if acting as PAF analogs. Results indicate that PAP esters are absorbed in the gastrointestinal tract and are distributed and stored in different organs, particularly in the liver and brown adipose tissue. PAP in these organs showed different patterns of fatty acids, indicating the ability of the gastrointestinal tract to modify the fatty acid composition of the parent PAP. Thus, the fatty acid profile of the PAP esters found in intestine appears to be related to the type of oil used as vehicle. Some of these PAP esters, when a long acyl chain was present in the sn‐1 position of the molecule, showed an inhibitory effect on the PAF synthesis. This is an important observation in line with the systemic nature of the disease. |
| doi_str_mv | 10.1007/s11745-001-0823-4 |
| format | Article |
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The fatty acid esters of 3‐(N‐phenylamino)‐1,2‐propanediol (PAP), which is a chemical class of by‐products resulting from the reaction of aniline with oil components, have shown a strong association with TOS‐related oils. These compounds also show some structural similarities to platelet‐activating factor (PAE). In search of a toxic agent that could explain the widespread systemic effects observed in TOS patients, we investigated the intestinal absorption and biotransformation of the different PAP esters found in TOS‐related oil samples and the possible pathophysiological effect of these mediators and their metabolic products if acting as PAF analogs. Results indicate that PAP esters are absorbed in the gastrointestinal tract and are distributed and stored in different organs, particularly in the liver and brown adipose tissue. PAP in these organs showed different patterns of fatty acids, indicating the ability of the gastrointestinal tract to modify the fatty acid composition of the parent PAP. Thus, the fatty acid profile of the PAP esters found in intestine appears to be related to the type of oil used as vehicle. Some of these PAP esters, when a long acyl chain was present in the sn‐1 position of the molecule, showed an inhibitory effect on the PAF synthesis. This is an important observation in line with the systemic nature of the disease.</description><identifier>ISSN: 0024-4201</identifier><identifier>EISSN: 1558-9307</identifier><identifier>DOI: 10.1007/s11745-001-0823-4</identifier><identifier>PMID: 11768157</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer‐Verlag</publisher><subject>Absorption ; Adipose tissue ; Adipose Tissue - metabolism ; Adipose Tissue, Brown - metabolism ; Aniline Compounds - pharmacokinetics ; Aniline Compounds - pharmacology ; Animals ; Biotransformation ; Capillary Permeability - drug effects ; Carbon Radioisotopes ; Diglycerides - pharmacokinetics ; Diglycerides - pharmacology ; Esters ; Esters - pharmacokinetics ; Esters - pharmacology ; Fatty acids ; Fatty Acids, Monounsaturated ; Gastrointestinal tract ; Intestinal Absorption ; Lipopolysaccharides - pharmacology ; Liver - metabolism ; Macrophages, Alveolar - drug effects ; Macrophages, Alveolar - metabolism ; Male ; Plant Oils - toxicity ; Platelet Activating Factor - biosynthesis ; Platelet Aggregation Inhibitors - pharmacology ; Propylene Glycols - pharmacokinetics ; Propylene Glycols - pharmacology ; Rapeseed Oil ; Rats ; Rats, Wistar ; Syndrome ; Tissue Distribution ; Toxic oil syndrome ; Tritium</subject><ispartof>Lipids, 2001-10, Vol.36 (10), p.1125-1133</ispartof><rights>2001 American Oil Chemists' Society (AOCS)</rights><rights>AOCS Press 2001</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3725-649684be9cc97139631de86a12489d25da7443cc6ab914597f880cd8405423773</citedby><cites>FETCH-LOGICAL-c3725-649684be9cc97139631de86a12489d25da7443cc6ab914597f880cd8405423773</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1007%2Fs11745-001-0823-4$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1007%2Fs11745-001-0823-4$$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/11768157$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Closa, Daniel</creatorcontrib><creatorcontrib>Folch, Emma</creatorcontrib><creatorcontrib>Calaf, Rosa Elena</creatorcontrib><creatorcontrib>Abián, Joaquin</creatorcontrib><creatorcontrib>Roselló‐Catafau, Joan</creatorcontrib><creatorcontrib>Gelpí, Emilio</creatorcontrib><title>Absorption and effects of 3‐(N‐phenylamino)‐1,2‐propanediol esters in relation to toxic oil syndrome</title><title>Lipids</title><addtitle>Lipids</addtitle><description>Toxic Oil Syndrome (TOS) was an epidemic disease related to the consumption of rapessed oil denatured with aniline that made its sudden appearance in Spain in 1981. The fatty acid esters of 3‐(N‐phenylamino)‐1,2‐propanediol (PAP), which is a chemical class of by‐products resulting from the reaction of aniline with oil components, have shown a strong association with TOS‐related oils. These compounds also show some structural similarities to platelet‐activating factor (PAE). In search of a toxic agent that could explain the widespread systemic effects observed in TOS patients, we investigated the intestinal absorption and biotransformation of the different PAP esters found in TOS‐related oil samples and the possible pathophysiological effect of these mediators and their metabolic products if acting as PAF analogs. Results indicate that PAP esters are absorbed in the gastrointestinal tract and are distributed and stored in different organs, particularly in the liver and brown adipose tissue. PAP in these organs showed different patterns of fatty acids, indicating the ability of the gastrointestinal tract to modify the fatty acid composition of the parent PAP. Thus, the fatty acid profile of the PAP esters found in intestine appears to be related to the type of oil used as vehicle. Some of these PAP esters, when a long acyl chain was present in the sn‐1 position of the molecule, showed an inhibitory effect on the PAF synthesis. This is an important observation in line with the systemic nature of the disease.</description><subject>Absorption</subject><subject>Adipose tissue</subject><subject>Adipose Tissue - metabolism</subject><subject>Adipose Tissue, Brown - metabolism</subject><subject>Aniline Compounds - pharmacokinetics</subject><subject>Aniline Compounds - pharmacology</subject><subject>Animals</subject><subject>Biotransformation</subject><subject>Capillary Permeability - drug effects</subject><subject>Carbon Radioisotopes</subject><subject>Diglycerides - pharmacokinetics</subject><subject>Diglycerides - pharmacology</subject><subject>Esters</subject><subject>Esters - pharmacokinetics</subject><subject>Esters - pharmacology</subject><subject>Fatty acids</subject><subject>Fatty Acids, Monounsaturated</subject><subject>Gastrointestinal tract</subject><subject>Intestinal Absorption</subject><subject>Lipopolysaccharides - pharmacology</subject><subject>Liver - metabolism</subject><subject>Macrophages, Alveolar - drug effects</subject><subject>Macrophages, Alveolar - metabolism</subject><subject>Male</subject><subject>Plant Oils - toxicity</subject><subject>Platelet Activating Factor - biosynthesis</subject><subject>Platelet Aggregation Inhibitors - pharmacology</subject><subject>Propylene Glycols - pharmacokinetics</subject><subject>Propylene Glycols - pharmacology</subject><subject>Rapeseed Oil</subject><subject>Rats</subject><subject>Rats, Wistar</subject><subject>Syndrome</subject><subject>Tissue Distribution</subject><subject>Toxic oil syndrome</subject><subject>Tritium</subject><issn>0024-4201</issn><issn>1558-9307</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</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>eNqFkM1KAzEUhYMotlYfwI0EVwqO5uZnkizF30JRF7oOaSaDU6aTmrRodz6Cz-iTmNqCS-GSyw3nnHv5EDoEcg6EyIsEILkoCIGCKMoKvoX6IIQqNCNyG_UJobzglEAP7aU0ySNwLXZRL_tKBUL2UXs5TiHO5k3osO0q7Ovau3nCocbs-_Pr5CE_s1ffLVs7bbpwmkc4o6vPGGa281UTWuzT3MeEmw5H39rfrHnI9dE4HJoWp2VXxTD1-2intm3yB5s-QC-3N89X98Xo8W54dTkqHJNUFCXXpeJjr53TEpguGVRelRYoV7qiorKSc-ZcaccauNCyVoq4SnEiOGVSsgE6XufmI98W-TozCYvY5ZVGKQUsYyizCNYiF0NK0ddmFpupjUsDxKzwmjVek_GaFV7Ds-doE7wYT33159jwzAK5Frw3rV_-n2hGw6drACrYD6x8iEk</recordid><startdate>200110</startdate><enddate>200110</enddate><creator>Closa, Daniel</creator><creator>Folch, Emma</creator><creator>Calaf, Rosa Elena</creator><creator>Abián, Joaquin</creator><creator>Roselló‐Catafau, Joan</creator><creator>Gelpí, Emilio</creator><general>Springer‐Verlag</general><general>Springer Nature B.V</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>3V.</scope><scope>7QL</scope><scope>7QP</scope><scope>7QR</scope><scope>7T7</scope><scope>7TK</scope><scope>7U9</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</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>BKSAR</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>PCBAR</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope></search><sort><creationdate>200110</creationdate><title>Absorption and effects of 3‐(N‐phenylamino)‐1,2‐propanediol esters in relation to toxic oil syndrome</title><author>Closa, Daniel ; Folch, Emma ; Calaf, Rosa Elena ; Abián, Joaquin ; Roselló‐Catafau, Joan ; Gelpí, Emilio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3725-649684be9cc97139631de86a12489d25da7443cc6ab914597f880cd8405423773</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Absorption</topic><topic>Adipose tissue</topic><topic>Adipose Tissue - metabolism</topic><topic>Adipose Tissue, Brown - metabolism</topic><topic>Aniline Compounds - pharmacokinetics</topic><topic>Aniline Compounds - pharmacology</topic><topic>Animals</topic><topic>Biotransformation</topic><topic>Capillary Permeability - drug effects</topic><topic>Carbon Radioisotopes</topic><topic>Diglycerides - pharmacokinetics</topic><topic>Diglycerides - pharmacology</topic><topic>Esters</topic><topic>Esters - pharmacokinetics</topic><topic>Esters - pharmacology</topic><topic>Fatty acids</topic><topic>Fatty Acids, Monounsaturated</topic><topic>Gastrointestinal tract</topic><topic>Intestinal Absorption</topic><topic>Lipopolysaccharides - pharmacology</topic><topic>Liver - metabolism</topic><topic>Macrophages, Alveolar - drug effects</topic><topic>Macrophages, Alveolar - metabolism</topic><topic>Male</topic><topic>Plant Oils - toxicity</topic><topic>Platelet Activating Factor - biosynthesis</topic><topic>Platelet Aggregation Inhibitors - pharmacology</topic><topic>Propylene Glycols - pharmacokinetics</topic><topic>Propylene Glycols - pharmacology</topic><topic>Rapeseed Oil</topic><topic>Rats</topic><topic>Rats, Wistar</topic><topic>Syndrome</topic><topic>Tissue Distribution</topic><topic>Toxic oil syndrome</topic><topic>Tritium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Closa, Daniel</creatorcontrib><creatorcontrib>Folch, Emma</creatorcontrib><creatorcontrib>Calaf, Rosa Elena</creatorcontrib><creatorcontrib>Abián, Joaquin</creatorcontrib><creatorcontrib>Roselló‐Catafau, Joan</creatorcontrib><creatorcontrib>Gelpí, Emilio</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Neurosciences Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>Public Health Database</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Natural Science Collection</collection><collection>Earth, Atmospheric & Aquatic Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biological Science Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Earth, Atmospheric & Aquatic Science Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><jtitle>Lipids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Closa, Daniel</au><au>Folch, Emma</au><au>Calaf, Rosa Elena</au><au>Abián, Joaquin</au><au>Roselló‐Catafau, Joan</au><au>Gelpí, Emilio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Absorption and effects of 3‐(N‐phenylamino)‐1,2‐propanediol esters in relation to toxic oil syndrome</atitle><jtitle>Lipids</jtitle><addtitle>Lipids</addtitle><date>2001-10</date><risdate>2001</risdate><volume>36</volume><issue>10</issue><spage>1125</spage><epage>1133</epage><pages>1125-1133</pages><issn>0024-4201</issn><eissn>1558-9307</eissn><abstract>Toxic Oil Syndrome (TOS) was an epidemic disease related to the consumption of rapessed oil denatured with aniline that made its sudden appearance in Spain in 1981. The fatty acid esters of 3‐(N‐phenylamino)‐1,2‐propanediol (PAP), which is a chemical class of by‐products resulting from the reaction of aniline with oil components, have shown a strong association with TOS‐related oils. These compounds also show some structural similarities to platelet‐activating factor (PAE). In search of a toxic agent that could explain the widespread systemic effects observed in TOS patients, we investigated the intestinal absorption and biotransformation of the different PAP esters found in TOS‐related oil samples and the possible pathophysiological effect of these mediators and their metabolic products if acting as PAF analogs. Results indicate that PAP esters are absorbed in the gastrointestinal tract and are distributed and stored in different organs, particularly in the liver and brown adipose tissue. PAP in these organs showed different patterns of fatty acids, indicating the ability of the gastrointestinal tract to modify the fatty acid composition of the parent PAP. Thus, the fatty acid profile of the PAP esters found in intestine appears to be related to the type of oil used as vehicle. Some of these PAP esters, when a long acyl chain was present in the sn‐1 position of the molecule, showed an inhibitory effect on the PAF synthesis. This is an important observation in line with the systemic nature of the disease.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer‐Verlag</pub><pmid>11768157</pmid><doi>10.1007/s11745-001-0823-4</doi><tpages>9</tpages></addata></record> |
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| ispartof | Lipids, 2001-10, Vol.36 (10), p.1125-1133 |
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| source | MEDLINE; Access via Wiley Online Library; SpringerLink Journals - AutoHoldings |
| subjects | Absorption Adipose tissue Adipose Tissue - metabolism Adipose Tissue, Brown - metabolism Aniline Compounds - pharmacokinetics Aniline Compounds - pharmacology Animals Biotransformation Capillary Permeability - drug effects Carbon Radioisotopes Diglycerides - pharmacokinetics Diglycerides - pharmacology Esters Esters - pharmacokinetics Esters - pharmacology Fatty acids Fatty Acids, Monounsaturated Gastrointestinal tract Intestinal Absorption Lipopolysaccharides - pharmacology Liver - metabolism Macrophages, Alveolar - drug effects Macrophages, Alveolar - metabolism Male Plant Oils - toxicity Platelet Activating Factor - biosynthesis Platelet Aggregation Inhibitors - pharmacology Propylene Glycols - pharmacokinetics Propylene Glycols - pharmacology Rapeseed Oil Rats Rats, Wistar Syndrome Tissue Distribution Toxic oil syndrome Tritium |
| title | Absorption and effects of 3‐(N‐phenylamino)‐1,2‐propanediol esters in relation to toxic oil syndrome |
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