Analysis of oxidation products of α-tocopherol in extra virgin olive oil using liquid chromatography–tandem mass spectrometry

Tanno, Rena; Kato, Shunji; Shimizu, Naoki; Ito, Junya; Sato, Shiu; Ogura, Yusuke; Sakaino, Masayoshi; Sano, Takashi; Eitsuka, Takahiro; Kuwahara, Shigefumi; Miyazawa, Teruo; Nakagawa, Kiyotaka

doi:10.1016/j.foodchem.2019.125582

Cited by 20 publications

(9 citation statements)

References 34 publications

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“…V E H also self‐oxidizes (Lampi et al, 1999; Tanno et al, 2020; Yamauchi et al, 1996), and therefore, the following multistep autocatalytic free‐radical chain reaction mechanism (step 9), previously reported in food systems (Takahashi et al, 2003), is also considered in the liposome system (Eqs. ).

V_{E} normalH \cdot + O_{2, normalL} \vec{false} V_{E} \cdot + {HO}_{2} \cdot

V_{E} \cdot + O_{2, normalL} \vec{false} V_{E} O_{2} \cdot

V_{E} O_{2} \cdot + V_{E} normalH \vec{false} V_{E} OOH + V_{E} \cdot

V_{E} O_{2} \cdot + V_{E} O_{2} \cdot \vec{false} NRP

V_{E} \cdot + V_{E} \cdot \vec{false} NRP

…”

Section: Resultsmentioning

confidence: 99%

Quantitative Evaluation of Oxidative Stability of Biomembrane Lipids in the Presence of Vitamin E

Takahashi

Hiromori

et al. 2021

J Americ Oil Chem Soc

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In this report, the oxidation of biomembrane lipids, phospholipid and cholesterol (ChH), was examined experimentally in the presence of vitamin E (VEH) by using a liposome system, which is widely used as a biomembrane model. A kinetic model was constructed by taking into account mechanisms of antioxidation and pro‐oxidation by VEH and the co‐oxidation mechanisms of biomembrane lipids reported previously. The model quantitatively described oxidation behavior in the liposome system under various VEH addition conditions. The model also predicted oxidation behavior in vivo under various oral ingestion conditions of VEH. The results suggest that ChH oxidation, which causes various diseases, can be suppressed effectively by taking a certain amount of VEH once a day to avoid a reduction in the VEH concentration present in the biomembrane. The proposed kinetic approach should be a useful tool for quantitatively characterizing complicated reaction systems, such as biomembrane oxidation.

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V_{E} normalH \cdot + O_{2, normalL} \vec{false} V_{E} \cdot + {HO}_{2} \cdot

V_{E} \cdot + O_{2, normalL} \vec{false} V_{E} O_{2} \cdot

V_{E} O_{2} \cdot + V_{E} normalH \vec{false} V_{E} OOH + V_{E} \cdot

V_{E} O_{2} \cdot + V_{E} O_{2} \cdot \vec{false} NRP

V_{E} \cdot + V_{E} \cdot \vec{false} NRP

…”

Section: Resultsmentioning

confidence: 99%

Quantitative Evaluation of Oxidative Stability of Biomembrane Lipids in the Presence of Vitamin E

Takahashi

Hiromori

et al. 2021

J Americ Oil Chem Soc

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“…Tocochromanols or tocols belong to the group of tocopherols and tocotrienols described as vitamin E. These chemical compounds are fat-soluble antioxidants which inhibit lipid oxidation in various plant food products [28,29]. The major tocopherol found in olive oil is α-tocopherol, representing around 90% all isomers [30].…”

Section: Resultsmentioning

confidence: 99%

Concentration of Potentially Bioactive Compounds in Italian Extra Virgin Olive Oils from Various Sources by Using LC-MS and Multivariate Data Analysis

Różańska

Russo

Cacciola

et al. 2020

Foods

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High quality extra virgin olive oils represent an optimal source of nutraceuticals. The European Union (EU) is the world’s leading olive oil producer, with the Mediterranean region as the main contributor. This makes the EU the greatest exporter and consumer of olive oil in the world. However, small olive oil producers also contribute to olive oil production. Beneficial effects on human health of extra virgin olive oil are well known, and these can be correlated to the presence of vitamin E and phenols. Together with the origin of the olives, extraction technology can influence the chemical composition of extra virgin olive oil. The aim of this study was to investigate the concentration of potentially bioactive compounds in Italian extra virgin olive oils from various sources. For this purpose, vitamin E and phenolic fractions were characterized using high-performance liquid chromatography (HPLC) coupled with fluorescence, photodiode array and mass spectrometry detection in fifty samples of oil pressed at industrial plants and sixty-six samples of oil produced in low-scale mills. Multivariate statistical data analysis was used to determine the applicability of selected phenolic compounds as potential quality indicators of extra virgin olive oils.

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“…In total, 150 µL of this fraction was evaporated then dissolved in methanol for the analysis of the new SQ secondary oxidation product, while the remaining 800 µL was used to analyze SQ-OOH isomers using a previously reported HPLC-MS/MS method [ 42 ]. The concentrations of individual SQ-OOH standards and the secondary oxidation product were determined prior to HPLC-MS/MS analyses using the ferrous oxidation-xylenol orange (FOX) assay as described previously [ 43 , 44 , 45 ], except in the case of 10-OOH-SQ where it was gravimetrically weighed due to its extreme lability to the assay.…”

Section: Methodsmentioning

confidence: 99%

“…were determined prior to HPLC-MS/MS analyses using the ferrous oxidation-xylenol orange (FOX) assay as described previously [43][44][45], except in the case of 10-OOH-SQ where it was gravimetrically weighed due to its extreme lability to the assay.…”

Section: Preparation Of Total and Individual Sq-ooh Isomersmentioning

confidence: 99%

Novel Photoinduced Squalene Cyclic Peroxide Identified, Detected, and Quantified in Human Skin Surface Lipids

et al. 2021

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Skin surface lipids (SSLs) form the first barrier that protects the human organism from external stressors, disruption of the homeostasis of SSLs can result in severe skin abnormalities. One of the main causes of this disruption is oxidative stress that is primarily due to SSLs oxidation. Squalene (SQ), the most abundant lipid among SSLs, was shown to first undergo singlet molecular oxygen (1O2) oxidation to yield 6 SQ-monohydroperoxide (SQ-OOH) isomers as the primary oxidation products. However, due to the instability and lability of hydroperoxides, we found that when total SQ-OOH isomers are further photooxidized, they form a unique higher molecular weight secondary oxidation product. To generate the compound, we photooxidized total SQ-OOH isomers in the presence of ground state molecular oxygen (3O2), after its isolation and purification, we studied its structure using MS/MS, NMR, derivatization reactions, and chemical calculations. The compound was identified as 2-OOH-3-(1,2-dioxane)-SQ. Photooxidation of individual SQ-OOH isomers revealed that 6-OOH-SQ is the precursor of 2-OOH-3-(1,2-dioxane)-SQ and indicated the possibility of the formation of similar cyclic peroxides from each isomer following the same photoinduced chain reaction mechanism. An HPLC-MS/MS method was developed for the analysis of 2-OOH-3-(1,2-dioxane)-SQ and its presence on the skin was confirmed in SSLs of six healthy individuals. Its quantity on the skin correlated directly to that of SQ and was not inversely proportional to its precursor, indicating the possibility of its accumulation on the skin surface and the constant regeneration of 6-OOH-SQ from SQ’s oxidation. In general, research on lipid cyclic peroxides in the human organism is very limited, and especially on the skin. This study shows for the first time the identification and presence of a novel SQ cyclic peroxide “2-OOH-3-(1,2-dioxane)-SQ” in SSLs, shedding light on the importance of further studying its effect and role on the skin.

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Analysis of oxidation products of α-tocopherol in extra virgin olive oil using liquid chromatography–tandem mass spectrometry

Cited by 20 publications

References 34 publications

Quantitative Evaluation of Oxidative Stability of Biomembrane Lipids in the Presence of Vitamin E

Quantitative Evaluation of Oxidative Stability of Biomembrane Lipids in the Presence of Vitamin E

Concentration of Potentially Bioactive Compounds in Italian Extra Virgin Olive Oils from Various Sources by Using LC-MS and Multivariate Data Analysis

Novel Photoinduced Squalene Cyclic Peroxide Identified, Detected, and Quantified in Human Skin Surface Lipids

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