LC-MS ion maps for the characterization of aniline derivatives of fatty acids and triglycerides in laboratory-denatured rapeseed oil
| Autor: | Rosa E. Calaf, Natalia Reig, Emilio Gelpí, Joaquín Abián, Angel Messeguer, Jordi Escabrós, Anna Morató |
|---|---|
| Rok vydání: | 2007 |
| Předmět: |
Glyceride
Phenylaminopropendiol esters Fatty Acids Monounsaturated chemistry.chemical_compound Aniline Liquid–liquid extraction Tandem Mass Spectrometry medicine Organic chemistry Plant Oils Anilides Solid phase extraction Carbon Radioisotopes Spectroscopy Chromatography High Pressure Liquid Triglycerides Tandem MS 2D ion maps chemistry.chemical_classification Fatty acid anilides Chromatography Aniline Compounds Extraction (chemistry) Fatty Acids Fatty acid medicine.disease LC-MS Vegetable oil chemistry Toxic oil syndrome Rapeseed Oil Chromatography Liquid |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname |
| Popis: | 15 pages, 8 figures. In 1981 Spain went through a unique epidemic associated with a food-borne vector, affecting more than 20.000 people with over 800 deaths, which came to be known as the Toxic Oil Syndrome (TOS). Early epidemiological studies showed a link between this illness and the ingestion of rapeseed oil denatured with 2% aniline. This oil, originally aniline-denatured for industrial use, was fraudulently processed in an attempt to remove free aniline, and marketed as edible oil. Fatty acid anilides (FAA), monoesters and diesters of 3-(N-phenylamino)-1,2-propanediol (PAP) are present in oil samples as they arise in the refining process from reactions of aniline with constituent fatty acids and triglycerides of the oil matrix and are the only extraneous compounds found in these samples. To expand the search for the causative agents in TOS-associated oils and to look for new aniline-related compounds, an exhaustive characterization of laboratory-processed oils was undertaken. These oils, in the presence of aniline doped with 14C labelled aniline, were submitted to the laboratory conditions required for the generation of PAPs and FAAs. Laboratory-generated oil samples were submitted to a liquid-liquid extraction procedure to remove the unreacted aniline. The extract was processed by double solid-phase extraction to improve detection limits forminor amine-containing compounds in oils. The extracts enriched in aniline derivatives were submitted to on-line HPLC-UV-APCI-MS. Using two-dimensional ion maps, the components of several families of derivatives were readily identified. Additionally, the extracts were also fractionated by HPLC-UV and the fractions were analyzed by HPLC-APCI-MS/MS to obtain structural information. Standards of some of these compounds were synthesized and analyzed to confirm the results. A total of 115 aniline derivatives from 9 aniline-related families were identified in these oil samples. These included fatty acid anilides and an extensive array of phenylaminopropanediol esters distributed in eight major compound classes. The authors thank Dr Montserrat Carrascal (EMEB Unit, IIBBIDIBAPS, CSIC, Barcelona) and Y.Castaño, R.Prieto and Juana Peña from the same Center for their technical support. Thanks are also due to the World Health Organization (WHO) for financial support through the Project EU/017025676. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|