1H NMR Study of the In Vitro Digestion of Highly Oxidized Soybean Oil and the Effect of the Presence of Ovalbumin

Oxidized lipids containing a wide variety of potentially toxic compounds can be ingested through diet. However, their transformations during digestion are little known, despite this knowledge being essential in understanding their impact on human health. Considering this, the in vitro digestion process of highly oxidized soybean oil, containing compounds bearing hydroperoxy, aldehyde, epoxy, keto- and hydroxy groups, among others, is studied by 1H nuclear magnetic resonance. Lipolysis extent, oxidation occurrence and the fate of oxidation products both present in the undigested oil and formed during digestion are analyzed. Furthermore, the effect during digestion of two different ovalbumin proportions on all the aforementioned issues is also addressed. It is proved that polyunsaturated group bioaccessibility is affected by both a decrease in lipolysis and oxidation occurrence during digestion. While hydroperoxide level declines throughout this process, epoxy-compounds, keto-dienes, hydroxy-compounds, furan-derivatives and n-alkanals persist to a great extent or even increase. Conversely, a,b-unsaturated aldehydes, especially the very reactive and toxic oxygenated ones, diminish, although part of them remains in the digestates. While a low ovalbumin proportion hardly affects oil evolution during digestion, at a high level it diminishes oxidation and reduces the concentration of potentially bioaccessible toxic oxidation compounds.

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In Vitro Digestion of Grape Seed Oil Inhibits Phospholipid-Regulating Effects of Oxidized Lipids

Biomolecules ◽

10.3390/biom10050708 ◽

2020 ◽

Vol 10 (5) ◽

pp. 708 ◽

Cited By ~ 2

Author(s):

Sarah Fruehwirth ◽

Sofie Zehentner ◽

Mohammed Salim ◽

Sonja Sterneder ◽

Johanna Tiroch ◽

...

Keyword(s):

Fatty Acids ◽

Seed Oil ◽

In Vitro Digestion ◽

Grape Seed ◽

Dietary Lipids ◽

Lipid Absorption ◽

Oxidized Lipids ◽

Grape Seed Oil ◽

Oxidized Triacylglycerols

The intake of dietary lipids is known to affect the composition of phospholipids in gastrointestinal cells, thereby influencing passive lipid absorption. However, dietary lipids rich in polyunsaturated fatty acids, such as vegetable oils, are prone to oxidation. Studies investigating the phospholipid-regulating effect of oxidized lipids are lacking. We aimed at identifying the effects of oxidized lipids from moderately (18.8 ± 0.39 meq O2/kg oil) and highly (28.2 ± 0.39 meq O2/kg oil) oxidized and in vitro digested cold-pressed grape seed oils on phospholipids in human gastric tumor cells (HGT-1). The oils were analyzed for their antioxidant constituents as well as their oxidized triacylglycerol profile by LC-MS/MS before and after a simulated digestion. The HGT-1 cells were treated with polar oil fractions containing epoxidized and hydroperoxidized triacylglycerols for up to six hours. Oxidized triacylglycerols from grape seed oil were shown to decrease during the in vitro digestion up to 40% in moderately and highly oxidized oil. The incubation of HGT-1 cells with oxidized lipids from non-digested oils induced the formation of cellular phospholipids consisting of unsaturated fatty acids, such as phosphocholines PC (18:1/22:6), PC (18:2/0:0), phosphoserine PS (42:8) and phosphoinositol PI (20:4/0:0), by about 40%–60%, whereas the incubation with the in vitro digested oils did not affect the phospholipid metabolism. Hence, the gastric conditions inhibited the phospholipid-regulating effect of oxidized triacylglycerols (oxTAGs), with potential implications in lipid absorption.

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Formation of Lipid and Protein Oxidation Products during In Vitro Gastrointestinal Digestion of Dry-Cured Loins with Different Contents of Nitrate/Nitrite Added

Foods ◽

10.3390/foods10081748 ◽

2021 ◽

Vol 10 (8) ◽

pp. 1748

Author(s):

Guadalupe Lavado ◽

Nieves Higuero ◽

Manuel León-Camacho ◽

Ramón Cava

Keyword(s):

Protein Oxidation ◽

In Vitro Digestion ◽

Heme Iron ◽

Conjugated Dienes ◽

Oxidation Products ◽

Intestinal Phase ◽

Simulated Digestion ◽

Before And After ◽

Lipid And Protein Oxidation

The effect of nitrate/nitrite (0, 37.5, 75, and 150 mg/kg) in the dry-cured loin formulation on the formation of lipid and protein oxidation products during in vitro digestion was evaluated. Dry-cured loins formulated with nitrate/nitrite resulted in significantly less lipid and protein oxidation than uncured loins before and after simulated digestion. Compared to loins added with 0 mg/kg nitrate/nitrite, dry-cured loins with 37.5, 75, and 150 mg/kg contained a significantly lower content of conjugated dienes, malondialdehyde, carbonyls, and non-heme iron, and higher amounts of nitrosylmioglobin and thiols. During in vitro digestion, the content of conjugated dienes, malondialdehyde, and carbonyls increased, while thiol content decreased, indicating the development of lipid and protein oxidative processes. At the end of the intestinal phase, the 75 mg/kg digests had a significantly higher content of conjugated dienes, while no differences were found among the other digests. During the in vitro intestinal phase (180 and 240 min), nitrate/nitrite curing resulted in significantly lower malondialdehyde concentrations in the 37.5, 75, and 150 mg/kg loin digests than in the uncured loin digests. No significant differences were observed at the end of the intestinal digestion phase between the cured loin digests. Digests of dried loins without nitrate/nitrite addition showed higher carbonyl contents than the nitrate/nitrite cured counterparts. The loss of thiols was significantly higher in loin digests without added nitrate/nitrite than in loin digests with different amounts of curing salts. The addition of 37.5 mg/kg nitrate/nitrite in the cured loin formulation prevents the formation of lipid peroxidation products and carbonyls from protein oxidation and thiol loss during digestion

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After In Vitro Digestion, Jackfruit Flake Affords Protection against Acrylamide-Induced Oxidative Damage

Molecules ◽

10.3390/molecules24183322 ◽

2019 ◽

Vol 24 (18) ◽

pp. 3322 ◽

Cited By ~ 1

Author(s):

Daofeng Qu ◽

Chu Liu ◽

Mengxue Jiang ◽

Lifang Feng ◽

Yuewen Chen ◽

...

Keyword(s):

Oxidative Stress ◽

Oxidative Damage ◽

High Performance ◽

In Vitro Digestion ◽

Protective Effects ◽

Physical Damage ◽

Before And After ◽

High Content Analysis ◽

High Level

Some studies have demonstrated that acrylamide (AA) was correlated with oxidative stress, resulting in physical damage. The jackfruit flake was an immature pulp that contained a high level of antioxidant activity. This study aimed to assess the defensive efficacy of jackfruit flake in AA-induced oxidative stress before and after simulated gastrointestinal digestion. Our results indicate that the total polyphenol content of Jackfruit flake digest (Digestive products of jackfruit flake after gastrointestinal, JFG) was diminished; however, JFG had raised the relative antioxidant capacity compared to Jackfruit flake extract (JFE). Additionally, the results of High Performance Liquid Chromatography-Mass Spectrometry (HPLC-MS) implied that a proportion of compounds were degraded/converted into other unknown and/or undetected metabolites. Further, by high content analysis (HCA) techniques, JFG markedly reduced cytotoxicity and excessive production of reactive oxygen species (ROS) in cells, thereby alleviating mitochondrial disorders. In this study, it may be converted active compounds after digestion that had preferable protective effects against AA-induced oxidative damage.

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Influence of minor components on lipid bioaccessibility and oxidation during in vitro digestion of soybean oil

Journal of the Science of Food and Agriculture ◽

10.1002/jsfa.9734 ◽

2019 ◽

Vol 99 (10) ◽

pp. 4793-4800 ◽

Cited By ~ 4

Author(s):

Ana S Martin‐Rubio ◽

Patricia Sopelana ◽

María D Guillén

Keyword(s):

Soybean Oil ◽

In Vitro Digestion ◽

Minor Components

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A Dual Perspective of the Action of Lysine on Soybean Oil Oxidation Process Obtained by Combining 1H NMR and LC–MS: Antioxidant Effect and Generation of Lysine–Aldehyde Adducts

Antioxidants ◽

10.3390/antiox8090326 ◽

2019 ◽

Vol 8 (9) ◽

pp. 326 ◽

Cited By ~ 1

Author(s):

Ana S. Martin-Rubio ◽

Patricia Sopelana ◽

Fumie Nakashima ◽

Takahiro Shibata ◽

Koji Uchida ◽

...

Keyword(s):

Soybean Oil ◽

1H Nmr ◽

Oxidation Process ◽

Edible Oils ◽

Oxidation Products ◽

Oil Oxidation ◽

Liquid Chromatography Mass Spectrometry ◽

Action Mechanism ◽

1H Nuclear Magnetic Resonance ◽

Dual Perspective

Little is still known about both the effect of amino acids on the oxidation course of edible oils and the modifications that the former may undergo during this process. Bearing this in mind, the objective of this work was to study the evolution of a system consisting of soybean oil with 2% of l-lysine under heating at 70 °C and stirring conditions, analyzing how the co-oxidation of the oil and of the amino acid affects their respective evolutions, and trying to obtain information about the action mechanism of lysine on soybean oil oxidation. The study of the oil progress by 1H Nuclear Magnetic Resonance (1H NMR) showed that the presence of lysine noticeably delays oil degradation and oxidation products generation in comparison with a reference oil without lysine. Regarding lysine evolution, the analysis by 1H NMR and Liquid Chromatography–Mass Spectrometry of a series of aqueous extracts obtained from the oil containing lysine over time revealed the formation of lysine adducts, most of them at the ε position, with n-alkanals, malondialdehyde, (E)-2-alkenals, and toxic oxygenated α β-unsaturated aldehydes. However, this latter finding does not seem enough to explain the antioxidant action of lysine.

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Malondialdehyde and 4-hydroxy-2-hexenal are formed during dynamic gastrointestinal in vitro digestion of cod liver oils

Food & Function ◽

10.1039/c6fo00635c ◽

2016 ◽

Vol 7 (8) ◽

pp. 3458-3467 ◽

Cited By ~ 16

Author(s):

Karin Larsson ◽

Cecilia Tullberg ◽

Marie Alminger ◽

Robert Havenaar ◽

Ingrid Undeland

Keyword(s):

Lipid Oxidation ◽

In Vitro Digestion ◽

Oxidation Products ◽

Cod Liver Oil ◽

Lipid Oxidation Products

Lipid oxidation products are formed during dynamicin vitrodigestion of cod liver oil.

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In Vitro Study for Lipolysis of Soybean Oil, Pomegranate Oil, and Their Blended and Interesterified Oils under a pH-Stat Model and a Simulated Model of Small Intestinal Digestion

Nutrients ◽

10.3390/nu11030678 ◽

2019 ◽

Vol 11 (3) ◽

pp. 678 ◽

Cited By ~ 2

Author(s):

Chenming Ji ◽

Jung-Ah Shin ◽

Soon Hong ◽

Ki-Teak Lee

Keyword(s):

Soybean Oil ◽

In Vitro Study ◽

In Vitro Digestion ◽

Molar Ratio ◽

Simulated Model ◽

Interesterified Oil ◽

Intestinal Digestion ◽

Ph Stat ◽

Small Intestinal

In this study, two in vitro digestion models were employed to compare the rate of lipolysis in soybean oil (SBO), pomegranate oil (PGO), a physical blend (PHY, 1:1 molar ratio of SBO:PGO, w/w), and their enzymatically interesterified oil (IO). In the pH-stat digestion model (emulsified oils with bile salts), PGO emulsion containing 74.7% conjugated form of linolenic acid (CLn) showed a significantly lower release rate of free fatty acid (FFA) than the other oil emulsions (p < 0.05). In FFA release rates and oil droplet sizes between PHY and IO emulsions, no significant differences were observed (p > 0.05). In a simulated model of small intestinal digestion, the lipolysis rates of SBO, PGO, PHY, and IO after digestion for 30 min in digestion fluids were 80.4%, 66.5%, 74.8%, and 77.0%, respectively. The rate of lipolysis in PGO was significantly lower than that in SBO (p < 0.05), and the lowest lipolysis rate was observed in the conjugated form of trilinolenoyl glycerol (CLn-CLn-CLn).

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