Evaluation of the Mechanisms of Mayonnaise Phospholipid Oxidation

Kato, Shunji; Iseki, Tatsuya; Hanzawa, Yasuhiko; Otoki, Yurika; Ito, Junya; Kimura, Fumiko; Miyazawa, Teruo; Nakagawa, Kiyotaka

doi:10.5650/jos.ess16187

Cited by 13 publications

(9 citation statements)

References 21 publications

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“…As described in the Introduction, the isomerism of HpODE (i.e., hydroperoxide positional and cis-trans structural isomers) is essential to evaluate oxidation mechanisms in edible oil. 1,2,31,33,34,37 In this study, we aimed to discriminate these isomers using MS/MS and HPLC separation techniques. Because the selective analysis of HpODE isomers were achieved in the presence of sodium in previous studies, 31–37 OO-HpODE-TG references were dissolved in solvents containing sodium acetate.…”

Section: Resultsmentioning

confidence: 99%

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Determination of triacylglycerol oxidation mechanisms in canola oil using liquid chromatography–tandem mass spectrometry

et al. 2018

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Triacylglycerol (TG), the main component of edible oil, is oxidized by thermal-or photo-oxidation to form TG hydroperoxide (TGOOH) as the primary oxidation product. Since TGOOH and its subsequent oxidation products cause not only the deterioration of oil quality but also various toxicities, preventing the oxidation of edible oils is essential. Therefore understanding oxidation mechanisms that cause the formation of TGOOH is necessary. Since isomeric information of lipid hydroperoxide provides insights about oil oxidation mechanisms, we focused on dioleoyl-(hydroperoxy octadecadienoyl)-TG (OO-HpODE-TG) isomers, which are the primary oxidation products of the most abundant TG molecular species (dioleoyl-linoleoyl-TG) in canola oil. To secure highly selective and sensitive analysis, authentic OO-HpODE-TG isomer references (i.e., hydroperoxide positional/geometrical isomers) were synthesized and analyzed with HPLC-MS/MS. With the use of the method, photo-or thermal-oxidized edible oils were analyzed. While dioleoyl-(10-hydroperoxy-8E,12Z-octadecadienoyl)-TG (OO-(10-HpODE)-TG) and dioleoyl-(12-hydroperoxy-9Z,13E-octadecadienoyl)-TG (OO-(12-HpODE)-TG) were characteristically detected in photo-oxidized oils, dioleoyl-(9-hydroperoxy-10E,12E-octadecadienoyl)-TG and dioleoyl-(13-hydroperoxy-9E,11E-octadecadienoyl)-TG were found to increase depending on temperature in thermal-oxidized oils. These results prove that our methods not only evaluate oil oxidation in levels that are unquantifiable with peroxide value, but also allows for the determination of oil oxidation mechanisms. From the analysis of marketed canola oils, photooxidized products (i.e., OO-(10-HpODE)-TG and OO-(12-HpODE)-TG) were characteristically accumulated compared to the oil analyzed immediately after production. The method described in this paper is valuable in the understanding of oil and food oxidation mechanisms, and may be applied to the development of preventive methods against food deterioration.

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Section: Resultsmentioning

confidence: 99%

“…1). 1,2 Recently, we found that the use of alkali metals (e.g., sodium) on ESI tandem mass spectrometry (MS/MS) enables analysis of lipid hydroperoxide positional isomers, 31–37 and with the use of this technique, it was identified that the oxidation of phospholipids in mayonnaise was predominantly initiated by auto-oxidation. 37…”

Section: Introductionmentioning

confidence: 99%

Determination of triacylglycerol oxidation mechanisms in canola oil using liquid chromatography–tandem mass spectrometry

et al. 2018

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“…Our previous LC–MS/MS studies had extensively demonstrated the use of sodium ion to induce collision near the lipid hydroperoxides, which enabled distinctive identification of each TGOOH isomers 14 , 16 – 19 . In this study we expanded the use of the method to distinguish the TGOOH bearing OA, LA, and LnA hydroperoxide formed in the oxidized oils.…”

Section: Methodsmentioning

confidence: 99%

“…1 b). Such TGOOH isomers were high-selectively identified by our analytical method for lipid hydroperoxides with liquid chromatography tandem mass spectrometry (LC–MS/MS) 14 , 16 – 19 . Besides RBO, we measured and compared the target TG and TGOOH isomers in the oil with soybean oil (SO) and rapeseed oil (RPO) as those edible oils also have a different unique fatty acid profile 20 .…”

Section: Introductionmentioning

confidence: 99%

Revealing the thermal oxidation stability and its mechanism of rice bran oil

Rahmania

Kato

Sawada

et al. 2020

Sci Rep

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Although the stability of rice bran oil (RBo) has been showed on several studies, the factors which make it capable on maintaining its stability under thermal oxidation has not been sure yet. We hypothesized that its fatty acid composition [high composition of oleic acid (oA), lower composition of linoleic acid (LA) and α-linolenic acid (LnA)] and/or its antioxidant agents [γ-oryzanol (OZ)] and vitamin E [tocopherol (Toc), tocotrienol (T3)] might be the biggest factor. To prove the hypothesis, we thermally oxidized RBO under 40 °C for 17 days to mimic the harsh daily storage condition, and compared it with soybean oil (So) and rapeseed oil (Rpo) then monitoring their primary oxidation products [triacylglycerol hydroperoxide (TGOOH)] from easily oxidized fatty acid contained in triacylglycerol (tG) and the amount loss of antioxidant agents. As a result, RBo showed the lowest TGOOH/TG ratio, followed by RPO and SO. The superior stability RPO compared SO might occur due to because of the influence of the fatty acid profile (higher OA and lower LA). For RBO's case, besides its fatty acid profile, the existence of OZ and the synergistic effect of OZ and vitamin E might have a greater contribution in maintaining its stability under thermal oxidation. One of the best things about rice bran oil (RBO), an oil extracted from the bran layer of the rice kernel, would be its stability, which secures the value of RBO and its related products 1-3. Indeed, some studies have shown the higher thermal-oxidation stability of RBO compared to other edible oils 4-7 , nevertheless the mechanism of the stability of RBO is still speculative. Its fatty acid profile and/or its antioxidant agents might be one of the biggest reasons; namely, contents of easily oxidized fatty acids [i.e. poly-unsaturated fatty acid such as linoleic acid (LA) and α-linolenic acid (LnA)], stable fatty acid [i.e. mono-unsaturated fatty acid such as oleic acid (OA)] and/ or antioxidants [tocopherol (Toc), tocotrienol (T3), and γ-oryzanol (OZ)] in RBO have been hypothesized as possible factors that made RBO showed a stability under thermal oxidation 8-13. However, verification of the above hypothesis has been severely hampered, because of the fact that the common methods used to determine the oils' stability [e.g., peroxide value (POV), rancimat method, and spectrophotometry] cannot provide enough information, especially about which and how much fatty acids are actually oxidized 14 and whether the antioxidant agents can affect/improve RBO's stability during the thermal oxidation 13. Overcoming this issue will lead to developing more quality and confident RBO and its related products. In this study, for evaluating the contribution of individual fatty acids of RBO, we explored the use of the twodimensional (2D) profiling method with liquid chromatography time-of-flight mass spectrometry (LC-TOF/ MS) 15 to determine the most suitable target of triacylglycerol (TG) contained in fresh RBO which structurally composed either OA, LA or LnA in one of fatty acid composition ...

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“…In general, the mechanisms of lipid oxidation have been well known including photo-oxidation (singlet-oxygen induced oxidation) and auto-oxidation (radical oxidation), and it has been found that each mechanism forms different characteristic lipid hydroperoxides (LOOH) with different regio and geometric ( cis/trans ) isomers 10–12 . Based on this knowledge, some studies, including our studies, have proposed that the oxidation mechanisms of lipids can be deduced according to its characteristic isomers of LOOH 13–18 .…”

Section: Introductionmentioning

confidence: 95%

Evaluation of lipid oxidation mechanisms in beverages and cosmetics via analysis of lipid hydroperoxide isomers

Ito

Komuro

Parida

et al. 2019

Sci Rep

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Understanding of lipid oxidation mechanisms (e.g., auto-oxidation and photo-oxidation) in foods and cosmetics is deemed essential to maintain the quality of such products. In this study, the oxidation mechanisms in foods and cosmetics were evaluated through analysis of linoleic acid hydroperoxide (LAOOH) and linoleic acid ethyl ester hydroperoxide (ELAOOH) isomers. Based on our previous method for analysis of LAOOH isomers, in this study, we developed a new HPLC-MS/MS method that enables analysis of ELAOOH isomers. The HPLC-MS/MS methods to analyze LAOOH and ELOOH isomers were applied to food (liquor) and cosmetic (skin cream) samples. As a result, LAOOH and ELAOOH isomers specific to photo-oxidation, and ELAOOH isomers characteristic to auto-oxidation were detected in some marketed liquor samples, suggesting that lipid oxidation of marketed liquor proceeds by both photo- and auto-oxidation during the manufacturing process and/or sales. In contrast, because only LAOOH and ELAOOH isomers specific to auto-oxidation were detected in skin cream stored under dark at different temperatures (−5 °C–40 °C) for different periods (2–15 months), auto-oxidation was considered to be the major oxidation mechanism in such samples. Therefore, our HPLC-MS/MS methods appear to be powerful tools to elucidate lipid oxidation mechanisms in food and cosmetic products.

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Evaluation of the Mechanisms of Mayonnaise Phospholipid Oxidation

Cited by 13 publications

References 21 publications

Determination of triacylglycerol oxidation mechanisms in canola oil using liquid chromatography–tandem mass spectrometry

Determination of triacylglycerol oxidation mechanisms in canola oil using liquid chromatography–tandem mass spectrometry

Revealing the thermal oxidation stability and its mechanism of rice bran oil

Evaluation of lipid oxidation mechanisms in beverages and cosmetics via analysis of lipid hydroperoxide isomers

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