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Open AccessFeature PaperArticle

Profile of Phosphatidylserine Modifications under Nitroxidative Stress Conditions Using a Liquid Chromatography-Mass Spectrometry Based Approach

1
Mass Spectrometry Centre, UI QOPNA, Chemistry Department, University of Aveiro, 3810-193 Aveiro, Portugal
2
Chemistry Department, University of Trás-os-Montes e Alto Douro, 5000-801 Vila Real, Portugal
3
Biology Department & CESAM & ECOMARE, University of Aveiro, 3810-193 Aveiro, Portugal
*
Author to whom correspondence should be addressed.
Academic Editors: Nicola Marchetti and Anna Laura Capriotti
Molecules 2019, 24(1), 107; https://doi.org/10.3390/molecules24010107
Received: 9 November 2018 / Revised: 19 December 2018 / Accepted: 24 December 2018 / Published: 29 December 2018
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PDF [1629 KB, uploaded 29 December 2018]
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Abstract

Nitrated lipids have been detected in vitro and in vivo, usually associated with a protective effect. While nitrated fatty acids have been widely studied, few studies reported the nitration and nitroxidation of the phospholipid classes phosphatidylcholine, and phosphatidylethanolamine. However, no information regarding nitrated and nitroxidized phosphatidylserine can be found in the literature. This work aims to identify and characterize the nitrated and nitroxidized derivatives of 1-palmitoyl-2-oleoyl-sn-3-glycero-phosphoserine (POPS), obtained after incubation with nitronium tetrafluoroborate, by liquid chromatography (LC) coupled to mass spectrometry (MS) and tandem MS (MS/MS). Several nitrated and nitroxidized products were identified, namely, nitro, nitroso, nitronitroso, and dinitro derivatives, as well as some nitroxidized species such as nitrosohydroxy, nitrohydroxy, and nitrohydroperoxy. The fragmentation pathways identified were structure-dependent and included the loss of HNO and HNO2 for nitroso and nitro derivatives, respectively. Combined losses of PS polar head group plus HNO or HNO2 and carboxylate anions of modified fatty acyl chain were also observed. The nitrated POPS also showed antiradical potential, demonstrated by the ability to scavenge the ABTS●+ and DPPH radicals. Overall, this in vitro model of nitration based on LC-MS/MS provided additional insights into the nitrated and nitroxidized derivatives of PS and their fragmentation fingerprinting. This information is a valuable tool for targeted analysis of these modified PS in complex biological samples, to further explore the new clues on the antioxidant potential of nitrated POPS. View Full-Text
Keywords: lipidomic; nitration; nitroxidative stress; phosphatidylserine; tandem mass spectrometry; LC-MS lipidomic; nitration; nitroxidative stress; phosphatidylserine; tandem mass spectrometry; LC-MS
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Neves, B.; Domingues, P.; Oliveira, M.M.; Domingues, M.R.; Melo, T. Profile of Phosphatidylserine Modifications under Nitroxidative Stress Conditions Using a Liquid Chromatography-Mass Spectrometry Based Approach. Molecules 2019, 24, 107.

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