Neutral and acidic products derived from hydroxyl radical-induced oxidation of arabinotriose assessed by electrospray ionisation mass spectrometry
authors Moreira, ASP; da Costa, EV; Evtuguin, DV; Coimbra, MA; Nunes, FM; Domingues, MRM
nationality International
journal JOURNAL OF MASS SPECTROMETRY
author keywords Fenton reaction; hydroxyl radicals; oligosaccharides; electrospray ionisation; tandem mass spectrometry
keywords PARAMAGNETIC-RESONANCE SPECTROSCOPY; LIQUID-CHROMATOGRAPHY; COFFEE BEANS; STRUCTURAL-CHARACTERIZATION; HYDROGEN-PEROXIDE; POLYSACCHARIDES; DEGRADATION; IDENTIFICATION; OXYGEN; DISACCHARIDES
abstract The oxidation of -(15)-l-arabinotriose (Ara(3)), an oligosaccharide structurally related to side chains of coffee arabinogalactans, was studied in reaction with hydroxyl radicals generated under conditions of Fenton reaction (Fe2+/H2O2). The acidic and neutral oxidation products were separated by ligand exchange/size-exclusion chromatography, subsequently identified by electrospray ionisation mass spectrometry (ESI-MS) and structurally characterised by tandem MS (ESI-MS/MS). In acidic fraction were identified several oxidation products containing an acidic residue at the corresponding reducing end of Ara(3), namely arabinonic acid, and erythronic, glyceric and glycolic acids formed by oxidative scission of the furanose ring. In neutral fractions were identified derivatives containing keto, hydroxy and hydroperoxy moieties, as well as derivatives resulting from the ring scission at the reducing end of Ara(3). In both acidic and neutral fractions, beyond the trisaccharide derivatives, the corresponding di- and monosaccharide derivatives were identified indicating the occurrence of oxidative depolymerisation. The structural characterisation of these oxidation products by ESI-MS/MS allowed the differentiation of isobaric and isomeric species of acidic and neutral character. The species identified in this study may help in detection of roasting products associated with the free radical-mediated oxidation of coffee arabinogalactans. Copyright (c) 2014 John Wiley & Sons, Ltd.
publisher WILEY-BLACKWELL
issn 1076-5174
year published 2014
volume 49
issue 4
beginning page 280
ending page 290
digital object identifier (doi) 10.1002/jms.3339
web of science category Biochemical Research Methods; Chemistry, Analytical; Spectroscopy
subject category Biochemistry & Molecular Biology; Chemistry; Spectroscopy
unique article identifier WOS:000333950500004
link 24719343
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