Understanding the nitrolipidome: From chemistry to mass spectrometry and biological significance of modified complex lipids

Neves, Bruno Miguel; Ferreira, Helena Beatriz; Guerra, Inês M S; Moreira, Ana S. P.; Domingues, Pedro; Domingues, M. Rosário; Melo, Tânia

doi:10.1016/j.plipres.2022.101176

Cited by 6 publications

(8 citation statements)

References 70 publications

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“…POPI was selected as a standard to study the nitration of the PI class since oleic acid (18:1, OA) has been described as one of the main targets of nitration in free-FAs and PLs containing unsaturated FAs. , Indeed, nitro-oleic acid (NO 2 -OA) has been reported as an important bioactive lipid with anti-inflammatory , and antioxidant properties …”

Section: Resultsmentioning

confidence: 99%

Analysis of Phosphatidylinositol Modifications by Reactive Nitrogen Species Using LC-MS: Coming to Grips with Their Nitroxidative Susceptibility

Bonciarelli

Neves

Domingues

et al. 2023

J. Am. Soc. Mass Spectrom.

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Phosphatidylinositols (PIs) are complex lipids that play a key role in cell signaling. Like other phospholipids, they are esterified with unsaturated fatty acyl residues (FAs), making them susceptible to modification by reactive oxygen and nitrogen species (RNS). Recent studies using mass spectrometry (MS)-based lipidomics approaches have revealed that lipid nitration results in a plethora of structurally and chemically modified lipids (epilipids), including nitrated and nitroxidized derivatives of phosphatidylcholines, phosphatidylethanolamines, phosphatidylserines, and cardiolipins. However, there is a notable lack of knowledge regarding the characterization of RNS-modified PI derivatives. In this study, we used C18 high-resolution liquid chromatography−tandem MS approaches to describe the fragmentation signature of nitrated and nitroxidized PIs, bearing different fatty acyl chains. Using this approach and accurate mass measurements, we were able to identify nitro-PI derivatives, dinitro-and nitrohydroxy-derivatives for a few PI species. The data showed the typical neutral loss of nitrous acid (HNO 2 ) as well as the fragmentation patterns corresponding to modified fatty acyl chains (such as NOmaking it possible to identify these epilipids. The susceptibility of PIs to nitration was also investigated, revealing that it depends exclusively on the chains of unsaturated FAs esterified in PI, showing a higher conversion rate for those with C18:1. Overall, the knowledge gathered in this study will contribute to the precise characterization of these epilipids in complex biological samples, offering new opportunities to unveil the pathophysiological roles of nitrated and nitroxidized PI derivatives at the cellular and tissue levels.

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Section: Resultsmentioning

confidence: 99%

Analysis of Phosphatidylinositol Modifications by Reactive Nitrogen Species Using LC-MS: Coming to Grips with Their Nitroxidative Susceptibility

Bonciarelli

Neves

Domingues

et al. 2023

J. Am. Soc. Mass Spectrom.

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“…Such uncommon (rare) FAs are usually found at low concentrations; however they exert interesting bioactivities. These uncommon FAs include odd-chain, branched and cyclic FAs [ 8 ] and FAs bearing functional groups such as hydroxy [ 9 , 10 , 11 , 12 ], oxo [ 13 , 14 ], epoxy [ 15 , 16 ] and nitro [ 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

Liquid Chromatography-Mass Spectrometry (LC-MS) Derivatization-Based Methods for the Determination of Fatty Acids in Biological Samples

Mantzourani

Kokotou

2022

Molecules

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Fatty acids (FAs) play pleiotropic roles in living organisms, acting as signaling molecules and gene regulators. They are present in plants and foods and may affect human health by food ingestion. As a consequence, analytical methods for their determination in biological fluids, plants and foods have attracted high interest. Undoubtedly, mass spectrometry (MS) has become an indispensable technique for the analysis of FAs. Due to the inherent poor ionization efficiency of FAs, their chemical derivatization prior to analysis is often employed. Usually, the derivatization of the FA carboxyl group aims to charge reversal, allowing detection and quantification in positive ion mode, thus, resulting in an increase in sensitivity in determination. Another approach is the derivatization of the double bond of unsaturated FAs, which aims to identify the double bond location. The present review summarizes the various classes of reagents developed for FA derivatization and discusses their applications in the liquid chromatography-MS (LC-MS) analysis of FAs in various matrices, including plasma and feces. In addition, applications for the determination of eicosanoids and fatty acid esters of hydroxy fatty acids (FAHFAs) are discussed.

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“…In addition, separation techniques such as liquid chromatography (LC) can be conveniently coupled to the MS analyzers to attain a prior sample separation that reduces ion suppression phenomena and increases signal-to-noise ratio for low-abundance analytes. , Moreover, the recent development of MS devices with ion mobility spectrometry (IMS) can support further characterization of the measured lipid species and increase the identification confidence in untargeted studies . Despite these technological advances, only a few epilipid classes (e.g., eicosanoids and docosanoids) , have been extensively studied over the past decade, and our global understanding of the “epilipidome” (bio)chemistry is still very limited. , The main obstacle to a comprehensive epilipidome analysis and annotation arguably lies in its intrinsic chemical complexity, which causes a series of both analytical- and computational-related challenges:…”

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confidence: 99%

“… 22 Despite these technological advances, only a few epilipid classes (e.g., eicosanoids and docosanoids) 8 , 23 have been extensively studied over the past decade, and our global understanding of the “epilipidome” (bio)chemistry is still very limited. 15 , 24 The main obstacle to a comprehensive epilipidome analysis and annotation arguably lies in its intrinsic chemical complexity, which causes a series of both analytical- and computational-related challenges:…”

mentioning

confidence: 99%

“…Alterations of the lipid composition in cells, tissues, or organelles have been associated with a large number of diseases, including inflammation, cancer, and degenerative or metabolic disorders. − Within biological systems, lipids can undergo a range of enzymatic and nonenzymatic reactions (e.g., oxidation, nitration, sulfation, and halogenation) that introduce structural modifications and/or new functional groups to the native molecule . The resulting modified lipid species, generally referred to as “epilipids”, are known to be heavily involved in the regulation of physiological and pathological conditions. − …”

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confidence: 99%

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Software and Computational Tools for LC-MS-Based Epilipidomics: Challenges and Solutions

et al. 2023

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Understanding the nitrolipidome: From chemistry to mass spectrometry and biological significance of modified complex lipids

Cited by 6 publications

References 70 publications

Analysis of Phosphatidylinositol Modifications by Reactive Nitrogen Species Using LC-MS: Coming to Grips with Their Nitroxidative Susceptibility

Analysis of Phosphatidylinositol Modifications by Reactive Nitrogen Species Using LC-MS: Coming to Grips with Their Nitroxidative Susceptibility

Liquid Chromatography-Mass Spectrometry (LC-MS) Derivatization-Based Methods for the Determination of Fatty Acids in Biological Samples

Software and Computational Tools for LC-MS-Based Epilipidomics: Challenges and Solutions

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