Radical peroxidation of palmitoyl-lineloyl-glycerophosphocholine liposomes: Identification of long-chain oxidised products by liquid chromatography–tandem mass spectrometry

Reis, Ana; Domingues, M. Rosário M.; Amado, Francisco; Ferrer‐Correia, A. J.; Domingues, Pedro

doi:10.1016/j.jchromb.2007.05.006

Cited by 50 publications

(44 citation statements)

References 48 publications

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“…In the context of the analysis of PLPE bearing 2 oxygen insertions (PLPE + 2O), it was previously observed that the typical fragmentation of hydroperoxide moieties under MS/MS displays abundant ions due to loss of H 2 O 2 (−34 Da) and/or O 2 (−32 Da) . The neutral loss of H 2 O 2 from the oxidized parent ion was also correlated with the insertion of hydroperoxide in several works reporting MS/MS analyses of oxidized PCs . Additionally, the neutral loss of O 2 had already been proposed as a characteristic fingerprint of hydroperoxide moieties, in other studies focused on the structural characterization of oxidized phospholipids by MS/MS .…”

Section: Resultsmentioning

confidence: 89%

Electrochemical oxidation of phosphatidylethanolamines studied by mass spectrometry

Colombo

Coliva

Kraj³

et al. 2018

J Mass Spectrom

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Phosphatidylethanolamines (PEs) are widely present in cellular membranes and lipoproteins. Oxidation of PE fatty acyl chains generates several oxidized products, exerting a vast number of biological functions, not totally unveiled yet. In vitro biomimetic models have been used to identify oxidized PEs and to develop analytical strategies for their targeted detection in vivo. Most of the models are based on oxidation by reactive oxygen species (ROS), but the oxidative metabolism of PE also relies on controlled reactions catalyzed by enzymes as lipoxygenase, which can be mimicked by electrochemical (EC) oxidation. In this study, 3 PE standards (1‐palmitoyl‐2‐oleoyl‐sn‐glycero‐3‐phosphoethanolamine (POPE), 1‐palmitoyl‐2‐linoleoyl‐sn‐glycero‐3‐phosphoethanolamine (PLPE), and 1‐palmitoyl‐2‐arachidonoyl‐sn‐glycero‐3‐phosphoethanolamine (PAPE)) were oxidized by EC oxidation, using an EC flow‐through cell system as a biomimetic model of oxidative injury. The new oxidation products were identified by online EC electrospray ionization mass spectrometry (EC‐ESI‐MS and MS/MS). Long‐chain and short‐chain oxidation products were identified, bearing modifications in the sn‐2 acyl chains, whereas the oxidation pattern was dependent on the unsaturation level. Long‐chain oxidation products of PEs (keto, hydroxy, hydroperoxy, poly‐hydroperoxy derivatives) were identified, bearing up to 5, 7, and 10 oxygens for POPE, PLPE, and PAPE, respectively. Fourteen short‐chain oxidation products, 7 from PLPE, and 7 from PAPE, including aldehydes, γ‐hydroxy‐α,β‐aldehydes, and dicarboxylic acids were characterized. Some of these oxidized species were previously reported during the oxidative metabolism of PEs driven by ROS. The EC‐ESI‐MS platform was, therefore, able to mimic the oxidative metabolism of PEs mediated by ROS.

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Section: Resultsmentioning

confidence: 89%

Electrochemical oxidation of phosphatidylethanolamines studied by mass spectrometry

Colombo

Coliva

Kraj³

et al. 2018

J Mass Spectrom

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“…This opens the possibility to identify novel OxPLs that may have detrimental effects in photoageing and UV-induced pathologies as well as photoproducts that mediate benefi cial effects of UVA radiation, which is used for therapy of infl ammatory skin diseases. This task, which was outside of the scope of this work, can be pursued using other modes of HPLC-MS/MS ( 47,48,50 ), high-resolution mass spectrometry ( 51 ), group-specifi c reagents ( 27,31 ), and other approaches demonstrated here identifi cation by MS/MS fragmentation studies in the negative ion mode of four molecular species of endogenously formed OxPCs accumulating in UVA-irradiated fi broblasts.…”

Section: Discussionmentioning

confidence: 99%

A simplified procedure for semi-targeted lipidomic analysis of oxidized phosphatidylcholines induced by UVA irradiation

Грубер¹,

Bicker²,

Oskolkova³

et al. 2012

Journal of Lipid Research

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“…Moreover, considering that structurally similar OxPC exhibit different biological activity, knowledge on the exact structural details in OxPC is crucial. Mass spectrometry (MS) combined with liquid chromatography (LC) is the most suitable approach for the sensitive detection of OxPC in mixtures with the advantage to retrieve information at the molecular level . In extracts profiled by targeted scanning approaches the identification of exact structural features of OxPC is fairly easy for truncated OxPC based on parameters such as m/z value and retention time (rt) including the distinction of isomeric and isobaric structures.…”

Section: Introductionmentioning

confidence: 99%

Structural motifs in primary oxidation products of palmitoyl‐arachidonoyl‐phosphatidylcholines by LC‐MS/MS

Reis

Domingues

2013

J. Mass Spectrom.

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Oxidative modifications to phospholipids (OxPL) play a major role in modulating signaling events in inflammation and infection, and complete understanding on the induced biological effects can only be understood based on knowledge of the oxidative motifs present. Specific neutral losses observed in tandem mass spectrometry data (LC-MS/MS) of primary peroxidation products in oxidized palmitoyl-arachidonoyl-phosphatidylcholines (OxPAPC) provide information on the prevailing structural motifs regarding the oxidized acyl carbon chain, the nature of oxidized group and the site of carbon oxidation. The higher hydrophobicity of hydroperoxides compared to di-hydroxy derivatives under reverse-phase conditions together with specific fragmentation patterns enabled the identification of 12 structurally different OxPAPC structural (di-hydroxy and hydroperoxide derivatives) and positional isomers as well as the presence of poly-hydroxy together with isoprostanes derivatives. The fragmentation patterns described in quadrupole time-of-flight and linear ion trap instruments complement the m/z value and retention time parameters in the identification of oxidative composition in OxPAPC products becoming a valuable tool for the exploratory screening of oxidized phosphatidylcholines in OxPAPC extracts, distinction of native and modified PC isobaric structures in complex samples contributing to the increased understanding of redox lipidomics in inflammation and infection.

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Radical peroxidation of palmitoyl-lineloyl-glycerophosphocholine liposomes: Identification of long-chain oxidised products by liquid chromatography–tandem mass spectrometry

Cited by 50 publications

References 48 publications

Electrochemical oxidation of phosphatidylethanolamines studied by mass spectrometry

Electrochemical oxidation of phosphatidylethanolamines studied by mass spectrometry

A simplified procedure for semi-targeted lipidomic analysis of oxidized phosphatidylcholines induced by UVA irradiation

Structural motifs in primary oxidation products of palmitoyl‐arachidonoyl‐phosphatidylcholines by LC‐MS/MS

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