Cardiolipin and oxidative stress: Identification of new short chain oxidation products of cardiolipin in in vitro analysis and in nephrotoxic drug-induced disturbances in rat kidney tissue

Maciel, Elisabete; Domingues, Pedro; Marques, Diane; Simões, Cláudia; Reis, Ana; Oliveira, Maria Manuel; Videira, Romeu A.; Peixoto, Francisco; Domingues, M. Rosário M.

doi:10.1016/j.ijms.2010.06.036

Cited by 11 publications

(14 citation statements)

References 33 publications

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“…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 . In contrast, in poly‐hydroxy derivatives, these products of fragmentation are absent and the MS/MS spectra are characterized by abundant losses of 1 H 2 O molecule (−18 Da) and losses of multiple H 2 O molecules (losses of n × 18 Da, such as loss of 36 Da and loss of 54 Da, that can occur in the case of more than 2 hydroxyl moieties) .…”

Section: Resultsmentioning

confidence: 81%

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: 81%

Electrochemical oxidation of phosphatidylethanolamines studied by mass spectrometry

Colombo

Coliva

Kraj³

et al. 2018

J Mass Spectrom

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“…These ions correspond to oxidation products with shortened acyl chain at C9 and a carboxylic acid terminal. Short chain oxidation products originated from cleavage of fatty acyl chains have been described for PS [13] and have been studied in phosphatidylcholine, phosphatidylserine, and cardiolipin phospholipids [27][28][29]. The shortened oxidation products are generated after abstraction of the bis-allylic hydrogen atoms by the hydroxyl radical, which through a β-scission mechanism, break down to short-chain phospholipid products with terminal aldehydic or carboxylic acid function.…”

Section: Resultsmentioning

confidence: 99%

“…In these spectra, we observe a major fragment ion formed by loss of 32 Da (−O 2 ), indicating the presence of a hydroperoxide [28,38]. Due to the fact that DPPS does not oxidize in the fatty acyl chain, the hydroperoxide moiety should be located in polar head group.…”

Section: Ms/ms Of These Ions [M -H -29]mentioning

confidence: 95%

Structural Characterization of Oxidized Glycerophosphatidylserine: Evidence of Polar Head Oxidation

Maciel

Silva

Simões

et al. 2011

J. Am. Soc. Mass Spectrom.

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Non-oxidized phosphatidylserine (PS) is known to play a key role in apoptosis but there is considerable research evidence suggesting that oxidized PS also plays a role in this event, leading to the increasing interest in studying PS oxidative modifications. In this work, different PS (1-palmitoyl-2-linoleoyl-sn-glycero-3-phospho-L-serine (PLPS), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-L-serine (POPS), and 1,2-dipalmitoyl-sn-glycero-3-phospho-L-serine (DPPS) were oxidized in vitro by hydroxyl radical, generated under Fenton reaction conditions, and the reactions were monitored by ESI-MS in negative mode. Oxidation products were then fractionated by thin layer chromatography (TLC) and characterized by tandem mass spectrometry (MS/MS). This approach allowed the identification of hydroxyl, peroxy, and keto derivatives due to oxidation of unsaturated fatty acyl chains. Oxidation products due to oxidation of serine polar head were also identified. These products, with lower molecular weight than the non-modified PS, were identified ashydroxyacetaldehyde plus hydroxy fatty acyl chain). Phosphatidic acid was also formed in these conditions. These findings confirm the oxidation of the serine polar head induced by the hydroxyl radical. The identification of these modifications may be a valuable tool to evaluate phosphatidylserine alteration under physiopathologic conditions and also to help understand the biological role of phosphatidylserine oxidation in the apoptotic process and other biological functions.

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“…In order to evaluate alterations in the PL profile of mice brain after stress stimuli, the total extracted PLs were fractionated by thin layer chromatography Short chain oxidation products of CL, were observed previously in vitro and in vivo and characterized by MS/MS analysis (Maciel et al, 2011). Figure 4 shows the MS/MS spectrum of the ion at m/z 697.8, which analysis and interpretation allowed the assignment of this ion as the short chain oxidation product CL- The CL hydroperoxy and hydroxy derivatives were already observed in CL oxidation in in vitro and in vivo studies (Tyurin et al, 2000, Tyurina et al, 2011.…”

Section: Effects Of Chronic Stress In Lipid Profiling Of Brainmentioning

confidence: 99%

Alterations in phospholipidomic profile in the brain of mouse model of depression induced by chronic unpredictable stress

et al. 2014

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This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. AbstractDepression is a worldwide disability disease associated with high morbidity and has increased dramatically in the last few years. The differential diagnosis and the definition of an individualized therapy for Depression is hampered by the absence of specific biomarkers. The aim of this study was to evaluate the phospholipdiomic profile of brain and myocardium in a mouse model of depression induced by chronic unpredictable stress. The lipidomic profile was evaluated by thin layer and liquid chromatography and mass spectrometry and lipid oxidation was estimated by FOX II assay. Antioxidant enzymes activity and the GSH/GSSG ratio were also evaluated.Results showed that chronic stress affect primarily the lipid profile of the brain, inducing an increased in lipid hydroperoxides, which was not detected in the myocardium. A significant decrease in phospahtidylinositol (PI) and in cardiolipin (CL) relative contents and also oxidation of cardiolipin and significant increase of phosphatidylcholine (PC) and phosphatidylethanolamine (PE) were observed in in brain from mice after unpredictable chronic stress conditions. In myocardium only an increase in PC content was observed. Nevertheless, both organs present a decreased GSH/GSSG ratio when compared to control groups, corroborating the occurrence of oxidative stress. The enzyme activities CAT and SOD were found to be decreased in the myocardium and increased in the brain, while glutathione reductase (GR) was decreased in brain. Our results indicate that in a mouse model for studying depression induced by chronic unpredictable stress, the modification of the expression of oxidative stress related enzymes did not prevent lipid oxidation in organs, particularly in the brain. These observations suggest that depression has an impact in the brain lipidome and that further studies are needed to better understand lipid role in depression and to evaluate their potential as future biomarkers.3

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Cardiolipin and oxidative stress: Identification of new short chain oxidation products of cardiolipin in in vitro analysis and in nephrotoxic drug-induced disturbances in rat kidney tissue

Cited by 11 publications

References 33 publications

Electrochemical oxidation of phosphatidylethanolamines studied by mass spectrometry

Electrochemical oxidation of phosphatidylethanolamines studied by mass spectrometry

Structural Characterization of Oxidized Glycerophosphatidylserine: Evidence of Polar Head Oxidation

Alterations in phospholipidomic profile in the brain of mouse model of depression induced by chronic unpredictable stress

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