Regioisomeric distribution of 9‐ and 13‐hydroperoxy linoleic acid in vegetable oils during storage and heating

Pignitter, Marc; Zaunschirm, Mathias; Lach, Judith; Unterberger, Laura; Kopic, Antonio; Kessler, Claudia; Kienesberger, Julia; Pischetsrieder, Monika; Eggersdorfer, Manfred; Riegger, Christoph; Somoza, Veronika

doi:10.1002/jsfa.8766

Cited by 12 publications

(17 citation statements)

References 38 publications

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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: 94%

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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Section: Introductionmentioning

confidence: 94%

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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“…Recently, Decker et al [ 4 ] pointed out various hurdles in predicting the effectiveness of antioxidants in real emulsions: the involvement in non-free radical scavenging reactions, the presence of different types of interfaces, inherent obstacles in studying lipid droplets properties, and varying oxidation kinetics in different droplets. Moreover, several contributions have recently suggested the expansion of traditional analytical patterns to a wider range of oxidation products to better understand oxidative phenomena [ 5 , 6 , 7 ]. Three distinct viewpoints by Paradiso, Villeneuve, and Laguerre discussed the need for a new step to study lipid oxidation in emulsified systems by focusing on different aspects [ 8 , 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Radical Scavenging Activity of Olive Oil Phenolic Antioxidants in Oil or Water Phase during the Oxidation of O/W Emulsions: An Oxidomics Approach

et al. 2020

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Omics approaches are recently being applied also in food lipid oxidation, to increase knowledge of oxidation and antioxidation mechanisms. The so-called oxidomics throws a wider spot of light on the complex patterns of reactions taking place in food lipids, especially in dispersed systems. This research aimed to investigate the radical scavenging activity of olive oil phenolic antioxidants (OPAs) in O/W emulsions, as affected by the phase in which they were added. This allowed one to assess whether different behaviors could be expected from antioxidants originally present in phenolic-rich olive oils compared to natural antioxidants added in the water phase during emulsion production. Hydroperoxide decomposition kinetics and the analysis of volatile pattern provided an outline of antioxidation mechanisms. Though being effective in slowing down oxidation when added both in the oil and water phase, OPAs interfered in different ways with oxidation pathways, based on the phase in which they were added. OPAs added to the water phase were more effective in slowing down hydroperoxide decomposition due to the hydrophilic radical initiator. On the other hand, OPAs present in the oil were more effective in preventing radical propagation, with relevant consequences on the volatile pattern.

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“…13-Hydroperoxy-9 Z ,11 E -octadecadienoic acid (13-HpODE, purity: 95.1%) and ( 13 C 18 )-13-hydroperoxy-9 Z ,11 E -octadecadienoic acid ([ 13 C 18 ]-13-HpODE, purity: 92.0%) were synthesized as described in a previous publication of our group [39]. (±)-13-Hydroxy-9 Z ,11 E -octadecadienoic acid (13-HODE, purity: ≥98%) was bought from Cayman Chemical (Cayman Europe, Tallinn, Estonia).…”

Section: Methodsmentioning

confidence: 99%

“…Afterwards, 500 µL of incubation solution (100 µM linoleic acid, 100 µM 13-HpODE or 100 µM hexanal in DMEM, respectively) were added to the apical compartment of the Snapwell insert, whereas 3 mL of medium (DMEM without FBS) was added to the basolateral compartment prior to sealing of the Snapwell plate. These concentrations for incubations were chosen for further assays because they represent oil-characteristic amounts of the test substances [39,43,44,45]. After an incubation of linoleic acid and 13-HpODE for six hours and an exposure to hexanal for 0.5 h (37 °C, 5% CO 2 , 95% humidity), which mimics relevant gastric retention time of food lipids, the supernatants from the basolateral and apical compartment were collected.…”

Section: Methodsmentioning

confidence: 99%

Exposure of Human Gastric Cells to Oxidized Lipids Stimulates Pathways of Amino Acid Biosynthesis on a Genomic and Metabolomic Level

et al. 2019

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The Western diet is characterized by a high consumption of heat-treated fats and oils. During deep-frying processes, vegetable oils are subjected to high temperatures which result in the formation of lipid peroxidation products. Dietary intake of oxidized vegetable oils has been associated with various biological effects, whereas knowledge about the effects of structurally-characterized lipid peroxidation products and their possible absorption into the body is scarce. This study investigates the impact of linoleic acid, one of the most abundant polyunsaturated fatty acids in vegetable oils, and its primary and secondary peroxidation products, 13-HpODE and hexanal, on genomic and metabolomic pathways in human gastric cells (HGT-1) in culture. The genomic and metabolomic approach was preceded by an up-to-six-hour exposure study applying 100 µM of each test compound to the apical compartment in order to quantitate the compounds’ recovery at the basolateral side. Exposure of HGT-1 cells to either 100 µM linoleic acid or 100 µM 13-HpODE resulted in the formation of approximately 1 µM of the corresponding hydroxy fatty acid, 13-HODE, in the basolateral compartment, whereas a mean concentration of 0.20 ± 0.13 µM hexanal was quantitated after an equivalent application of 100 µM hexanal. An integrated genomic and metabolomic pathway analysis revealed an impact of the linoleic acid peroxidation products, 13-HpODE and hexanal, primarily on pathways related to amino acid biosynthesis (p < 0.05), indicating that peroxidation of linoleic acid plays an important role in the regulation of intracellular amino acid biosynthesis.

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Regioisomeric distribution of 9‐ and 13‐hydroperoxy linoleic acid in vegetable oils during storage and heating

Cited by 12 publications

References 38 publications

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

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

Radical Scavenging Activity of Olive Oil Phenolic Antioxidants in Oil or Water Phase during the Oxidation of O/W Emulsions: An Oxidomics Approach

Exposure of Human Gastric Cells to Oxidized Lipids Stimulates Pathways of Amino Acid Biosynthesis on a Genomic and Metabolomic Level

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