Determination of Aniline Derivatives in Oils Related to the Toxic Oil Syndrome by Atmospheric Pressure Ionization-Tandem Mass Spectrometry

Calaf, Rosa E.; Peña, J.; Paytubi, Sònia; Blount, Benjamin C.; Paz, Manuel Posada de la; Gelpí, E.; Abian, Joaquín

doi:10.1021/ac0101712

Cited by 25 publications

(20 citation statements)

References 21 publications

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“…Although several chemical markers of the toxic oil are known nowadays (anilines, phenylaminopropanediols), the actual toxic factor(s) remain obscure [4]. A further understanding of those factors is of prime importance to prevent the occurrence of any other related episode such as the Eosinophilia Myalgia Syndrome that appeared in 1989 in the USA [5].…”

Section: Introductionmentioning

confidence: 99%

Determination of protein markers in human serum: Analysis of protein expression in toxic oil syndrome studies

et al. 2004

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Toxic oil syndrome (TOS) is a disease that appeared in Spain in 1981. It affected more than 20 000 people and produced over 300 deaths in the first 2 years. In this paper, a prospective study on the differences in gene expression in sera between a control versus a TOS-affected population, both originally exposed to the toxic oil, is presented. Differential protein expression was analyzed by two-dimensional electrophoresis (2-DE). Several problems related with serum analysis by 2-DE were addressed in order to improve protein detection in the gel images. Three new commercial systems for albumin depletion were tested to optimize the detection of minor proteins that can be obscured by the presence of a few families of high abundance proteins (albumin, immunoglobulins). Other factors, such as the use of nonionic reductants or the presence of thiourea in the gels, were also tested. From these optimized images, a group of 329 major gel spots was located, matched and compared in serum samples. Thirty-five of these protein spots were found to be under- or overexpressed in TOS patients (> three-fold increase or decrease). Proteins in the differential spots were identified by matrix-assisted laser desorption/ionization-time of flight peptide map fingerprinting and database search. Several haptoglobin isoforms were found to be differentially expressed, showing expression phenotypes that could be related with TOS affection. Haptoglobin phenotypes have been previously reported to have important biological and clinical consequences and have been described as risk factors for several diseases.

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Section: Introductionmentioning

confidence: 99%

Determination of protein markers in human serum: Analysis of protein expression in toxic oil syndrome studies

et al. 2004

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“…31,69 Biomarkers The analysis of contaminated oil was complicated by poor identifi cation markers on cooking oil bottles during the recall process. 31,69 Biomarkers The analysis of contaminated oil was complicated by poor identifi cation markers on cooking oil bottles during the recall process.…”

Section: Methodsmentioning

confidence: 99%

Food Contamination

Barceloux

Faact²,

Facmt³

2008

Medical Toxicology of Natural Substances

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“…Many years after, Cravatt et al (1995) verified that similar compounds belonging to the class of fatty acid amides had pharmacological effects (Cravatt et al 1996). On the other hand, in past years several authors (Posada de la Schurz et al 1996;Calaf et al 2001) related aniline derivatives with the toxic oil syndrome.…”

Section: Introductionmentioning

confidence: 95%

Instability of an aromatic amine in fatty food and fatty food simulant: characterisation of reaction products and prediction of their toxicity

Paseiro-Cerrato

Quirós

Sendón

et al. 2014

Food Additives & Contaminants: Part A

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It is a well-known fact that amines are not stable in food of a fatty nature. In this study the synthesis and characterisation of the products obtained as a result of the reaction of amines in a fatty medium are reported. Based on the well-known reactions among amines and acid and esters groups, two novel compounds were synthesised using m-xylylenediamine (mXDA), a primary diamine widely used as monomer in the manufacture of food contact materials and two fatty acids, oleic acid and palmitic acid, which occur in most fats. The resulting compounds were two molecules belonging to the family of fatty acid amides, dioleamide and dipalmitamide. A complete characterisation of both products was carried out employing several techniques such as infrared spectroscopy, (1)H- and (13)C-NMR spectroscopy, electron ionisation mass spectrometry, LC-MS/MS and UV spectrometry. The results obtained by the different techniques were well correlated. In the second part of the work, the formation of these compounds in real samples was evaluated. For this purpose a certain volume of olive oil was spiked with a known amount of mXDA. Olive oil was selected as a fatty medium since it is a widely consumed food and additionally is used as a fatty food simulant in migration studies of food contact materials. A method was developed to extract the fatty acid amides from the fatty matrix, which were then identified by LC-MS/MS. The toxicity of the synthesised compounds was predicted using a toxicity estimation software tool.

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Determination of Aniline Derivatives in Oils Related to the Toxic Oil Syndrome by Atmospheric Pressure Ionization-Tandem Mass Spectrometry

Cited by 25 publications

References 21 publications

Determination of protein markers in human serum: Analysis of protein expression in toxic oil syndrome studies

Determination of protein markers in human serum: Analysis of protein expression in toxic oil syndrome studies

Food Contamination

Instability of an aromatic amine in fatty food and fatty food simulant: characterisation of reaction products and prediction of their toxicity

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