Formation of oligomeric alkenylperoxides during the oxidation of unsaturated fatty acids: an electrospray ionization tandem mass spectrometry study
authors Villaverde, JJ; Santos, SAO; Maciel, E; Simoes, MMQ; Neto, CP; Domingues, MRM; Silvestre, AJD
nationality International
journal JOURNAL OF MASS SPECTROMETRY
author keywords Fenton's and Fe2+; O2 systems; unsaturated fatty acids; oligomeric alkenylperoxides; oxidation; mass spectrometry
keywords EPOXIDIZED VEGETABLE-OILS; LIQUID-LIQUID SYSTEMS; OXIRANE RING; HYDROPEROXIDES; DEGRADATION; IDENTIFICATION; MECHANISMS; CHEMISTRY; PRODUCTS; HYDROXY
abstract This study reports the identification of oligomeric alkenylperoxides by electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (ESI-MS2), during the oxidation of oleic, linoleic and linolenic acids with Fenton's (Fe2+/H2O2) and Fe2+/O2 systems. The reactions were followed by ferrous oxidation-xylenol orange method together with GC-MS and GC-FID, allowing to observe that both oxidation systems are different in terms of hydroperoxide evolution, probably due to the presence of different intermediate reactive species: perferryl ion and OH radical responsible for the decomposition of lipid hydroperoxides and formation of new compounds. The analysis of ESI-MS in the negative mode, obtained after oxidation of each fatty acid, confirmed the presence of the monomeric oxidation products together with other compounds at high mass region above m/z 550. These new ions were attributed to oligomeric structures, identified by the fragmentation pathways observed in the tandem mass spectra. Copyright (C) 2012 John Wiley & Sons, Ltd.
publisher WILEY-BLACKWELL
issn 1076-5174
year published 2012
volume 47
issue 2
beginning page 163
ending page 172
digital object identifier (doi) 10.1002/jms.2047
web of science category Biochemical Research Methods; Chemistry, Analytical; Spectroscopy
subject category Biochemistry & Molecular Biology; Chemistry; Spectroscopy
unique article identifier WOS:000300694100003
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