Investigation of Lipoproteins Oxidation Mechanisms by the Analysis of Lipid Hydroperoxide Isomers

Kato, Shunji; Osuka, Yusuke; Khalifa, Saoussane; Obama, Takashi; Itabe, Hiroyuki; Nakagawa, Kiyotaka

doi:10.3390/antiox10101598

Cited by 7 publications

(8 citation statements)

References 35 publications

(66 reference statements)

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“…Kato et al [ 90 ] in order to determine the oxidation mechanisms of human plasma lipoproteins before illness, developed novel analytical methods using LC-MS/MS for 1-palmitoyl-2-linoleoyl- sn -glycero-3-phosphocholine hydroperoxide (PC 16:0/18:2;OOH) and cholesteryl linoleate hydroperoxide (CE 18:2;OOH) isomers (partially including the cis–trans isomer) without any derivatizations ( Figure 18 ). The predominant PC 16:0/18:2;OOH and CE 18:2;OOH isomers in LDL and HDL were found to be PC 16:0/18:2;9OOH, PC 16:0/18:2;13OOH, CE 18:2;9OOH, and CE 18:2;13OOH, which means that PC and CE in LDL and HDL are mainly oxidized by radical and/or enzymatic oxidation.…”

Section: Hyphenated Methodsmentioning

confidence: 99%

“… 1-Palmitoyl-2-linoleoyl- sn -glycero-3-phosphocholine (PC 16:0/18:2) and cholesteryl linoleate (CE 18:2) peroxidation mechanisms and the structures of their hydroperoxide isomers. PC 16:0/18:2 and CE 18:2 were oxidized to 1-palmitoyl-2-linoleoyl- sn -glycero-3-phosphocholine hydroperoxide (PC 16:0/18:2;OOH) and cholesteryl linoleate hydroperoxide (CE 18:2;OOH) isomers, respectively, by radical, enzymatic, and singlet-oxygen ( 1 O 2 ) oxidation [ 90 ]. …”

Section: Figurementioning

confidence: 99%

“… MRM chromatograms of PC 16:0/18:2;OOH isomers ( A , B ) and CE 18:2;OOH isomers ( C , D ). LOOH extracted from LDL ( A , C ) and HDL ( B , D ) [ 90 ]. …”

Section: Figurementioning

confidence: 99%

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Analytical and Structural Tools of Lipid Hydroperoxides: Present State and Future Perspectives

Kontogianni

Gerothanassis

2022

Molecules

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Mono- and polyunsaturated lipids are particularly susceptible to peroxidation, which results in the formation of lipid hydroperoxides (LOOHs) as primary nonradical-reaction products. LOOHs may undergo degradation to various products that have been implicated in vital biological reactions, and thus in the pathogenesis of various diseases. The structure elucidation and qualitative and quantitative analysis of lipid hydroperoxides are therefore of great importance. The objectives of the present review are to provide a critical analysis of various methods that have been widely applied, and more specifically on volumetric methods, applications of UV-visible, infrared, Raman/surface-enhanced Raman, fluorescence and chemiluminescence spectroscopies, chromatographic methods, hyphenated MS techniques, NMR and chromatographic methods, NMR spectroscopy in mixture analysis, structural investigations based on quantum chemical calculations of NMR parameters, applications in living cells, and metabolomics. Emphasis will be given to analytical and structural methods that can contribute significantly to the molecular basis of the chemical process involved in the formation of lipid hydroperoxides without the need for the isolation of the individual components. Furthermore, future developments in the field will be discussed.

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Section: Hyphenated Methodsmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

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Analytical and Structural Tools of Lipid Hydroperoxides: Present State and Future Perspectives

Kontogianni

Gerothanassis

2022

Molecules

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“…The extraction of TG 18:1/18:1/18:1; OOH from the collected samples ( i.e., lymph and emulsion) was conducted using the modified Folch method [ 23 , 24 ]. Each sample (200 μL) was diluted with 0.9% (w/v) potassium chloride–1 mM ethylenediaminetetraacetic acid (200 μL).…”

Section: Methodsmentioning

confidence: 99%

Dietary triacylglycerol hydroperoxide is not absorbed, yet it induces the formation of other triacylglycerol hydroperoxides in the gastrointestinal tract

et al. 2022

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“…That could account for the predominance of FA 18:2-OOH species in serum and our analysis results are consistent with this report. The intact LOOHs such as cholesterol hydroperoxide (CE-OOH) and phospholipid (PL-OOH) were characterized in intact as well as oxidized HDL and LDL [ 30 , 34 , 35 ] However, there are no reports on total FAOOH levels in HDL and LDL. Our results demonstrated the occurrence of a large amount of FA18:1-OOH and FA 22:1-OOH in both oxHDL and oxLDL respectively.…”

Section: Discussionmentioning

confidence: 99%

Simple and Sensitive Method for the Quantitative Determination of Lipid Hydroperoxides by Liquid Chromatography/Mass Spectrometry

Liang

Gowda

et al. 2022

Antioxidants

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Lipid hydroperoxides (LOOH) are the initial products of the peroxidation of unsaturated lipids and play a crucial role in lipid oxidation due to their ability to decompose into free radicals and cause adverse effects on human health. Thus, LOOHs are commonly considered biomarkers of oxidative stress-associated pathological conditions. Despite their importance, the sensitive and selective analytical method for determination is limited, due to their low abundance, poor stability, and low ionizing efficiency. To overcome these limitations, in this study, we chemically synthesized eight fatty acid hydroperoxides (FAOOH), including FA 18:1-OOH, FA 18:2-OOH, FA 18:3-OOH, FA 20:4-OOH, FA 20:5-OOH, FA 22:1-OOH, FA 22:6-OOH as analytes, and FA 19:1-OOH as internal standard. Then, they were chemically labeled with 2-methoxypropene (2-MxP) to obtain FAOOMxP by one-step derivatization (for 10 min). A selected reaction monitoring assisted targeted analytical method was developed using liquid chromatography/tandem mass spectrometry (LC-MS/MS). The MxP-labelling improved the stability and enhanced the ionization efficiency in positive mode. Application of reverse-phase chromatography allowed coelution of analytes and internal standards with a short analysis time of 6 min. The limit of detection and quantification for FAOOH ranged from 0.1–1 pmol/µL and 1–2.5 pmol/µL, respectively. The method was applied to profile total FAOOHs in chemically oxidized human serum samples (n = 5) and their fractions of low and high-density lipoproteins (n = 4). The linoleic acid hydroperoxide (FA 18:2-OOH) and oleic acid hydroperoxide (FA 18:1-OOH) were the most abundant FAOOHs in human serum and lipoproteins. Overall, our validated LC-MS/MS methodology features enhanced detection and rapid separation that enables facile quantitation of multiple FAOOHs, therefore providing a valuable tool for determining the level of lipid peroxidation with potential diagnostic applications.

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Investigation of Lipoproteins Oxidation Mechanisms by the Analysis of Lipid Hydroperoxide Isomers

Cited by 7 publications

References 35 publications

Analytical and Structural Tools of Lipid Hydroperoxides: Present State and Future Perspectives

Analytical and Structural Tools of Lipid Hydroperoxides: Present State and Future Perspectives

Dietary triacylglycerol hydroperoxide is not absorbed, yet it induces the formation of other triacylglycerol hydroperoxides in the gastrointestinal tract

Simple and Sensitive Method for the Quantitative Determination of Lipid Hydroperoxides by Liquid Chromatography/Mass Spectrometry

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