Assessment of Soybean Oil Oxidative Stability from Rapid Analysis of its Minor Component Profile.

The minor components of vegetable oils are important for their oxidative stability. In order to know to what extent they can influence oil behaviour under oxidative conditions, two commercial soybean oils, one virgin and the other refined, both with very similar compositions in acyl groups but differing in their minor component profiles, were subjected to accelerated storage conditions. They were characterized by 1H nuclear magnetic resonance (NMR) and direct immersion solid-phase microextraction coupled to gas chromatography/mass spectrometry (DI-SPME-GC/MS), while oil oxidation was monitored by 1H-NMR. The lower levels of tocols and sterols in the virgin oil, together with its higher free fatty acid content when compared to the refined one, result in a lower oxidative stability. This is deduced from faster degradation of acyl groups and earlier generation of hydroperoxides, epoxides, and aldehydes in the virgin oil. These findings reveal that commercial virgin soybean oil quality is not necessarily higher than that of the refined type, and that a simple and rapid analysis of oil minor components by DI-SPME-GC/MS would enable one to establish quality levels within oils originating from the same plant species and similar unsaturation level regarding composition in potentially bioactive compounds and oxidative stability.

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

BACKGROUND: Minor components of edible oils could influence their evolution during in vitro digestion. This might affect the bioaccessibility of lipid nutrients and the safety of the ingested food. Bearing this in mind, the evolution of virgin and refined soybean oils, which are very similar in acyl group composition, has been studied throughout in vitro digestion using 1 H nuclear magnetic resonance (NMR) and solid-phase microextraction-gas chromatography /mass spectrometry, focusing on lipolysis and oxidation reactions. The fate of γ-tocopherol, the main antioxidant present in soybean oil, has also been analyzed with 1 H NMR. RESULTS: There were no noticeable differences in lipolysis between the two oils that were studied. The extent of oxidation during digestion, which was very low in both cases, was slightly higher in the virgin type, which showed lower tocopherols and squalene concentrations than the refined one, together with a considerable abundance of free fatty acids. This can be deduced both from the appearance after digestion of conjugated hydroperoxy- and hydroxy-dienes only in the virgin oil, and from its higher levels of volatile aldehydes and 2-pentyl-furan. Under in vitro digestion conditions, the formation of epoxides seemed to be favored over other oxidation products. Finally, although some soybean oil essential nutrients like polyunsaturated fatty acids exhibited no significant degradation after digestion, γ-tocopherol concentration diminished during this process, especially in the virgin oil. CONCLUSION: Although the minor component composition of the soybean oils did not affect lipolysis during in vitro digestion, it influenced the extent of their oxidation and γ-tocopherol bioaccessibility. © 2019 Society of Chemical Industry.

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, α,ß-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.

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.

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 position, with n-alkanals, malondialdehyde, (E)-2-alkenals, and toxic oxygenated α ß-unsaturated aldehydes. However, this latter finding does not seem enough to explain the antioxidant action of lysine.