Micellar catalysis in the oxidation of lipids

Касаикина, О. Т.; Golyavin, A. A.; Krugovov, D. A.; Kartasheva, Z. S.; Pisarenko, L. M.

doi:10.3103/s0027131410030193

Cited by 17 publications

(7 citation statements)

References 3 publications

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“…Kasaikina et al [86] Primary amphiphilic products of the oxidation of LOOH and lipids, and cationic surfactants form mixed micelles, which accelerated the decomposition of LOOH and other polar components (e.g., metalcontaining compounds, inhibitors etc. )…”

Section: Lipophilic Compounds Do Not Affect the Oxidation In Bulk Oilsmentioning

confidence: 99%

The supramolecular chemistry of lipid oxidation and antioxidation in bulk oils

Budilarto

Kamal‐Eldin

2015

Euro J Lipid Sci & Tech

149

119

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The microenvironment formed by surface active compounds is being recognized as the active site of lipid oxidation. Trace amounts of water occupy the core of micro micelles and several amphiphilic minor components (e.g., phospholipids, monoacylglycerols, free fatty acids, etc.) act as surfactants and affect lipid oxidation in a complex fashion dependent on the structure and stability of the microemulsions in a continuous lipid phase such as bulk oil. The structures of the triacylglycerols and other lipid-soluble molecules affect their organization and play important roles during the course of the oxidation reactions. Antioxidant head groups, variably located near the water-oil colloidal interfaces, trap and scavenge radicals according to their location and concentration. According to this scenario, antioxidants inhibit lipid oxidation not only by scavenging radicals via hydrogen donation but also by physically stabilizing the micelles at the microenvironments of the reaction sites. There is a cut-off effect (optimum value) governing the inhibitory effects of antioxidants depending inter alias on their hydrophilic/lipophilic balance and their concentrations. These complex effects, previously considered as paradoxes in antioxidants research, are now better explained by the supramolecular chemistry of lipid oxidation and antioxidants, which is discussed in this review.

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Section: Lipophilic Compounds Do Not Affect the Oxidation In Bulk Oilsmentioning

confidence: 99%

The supramolecular chemistry of lipid oxidation and antioxidation in bulk oils

Budilarto

Kamal‐Eldin

2015

Euro J Lipid Sci & Tech

149

119

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“…Reverse micelles can act as nano‐reactors that can alter chemical reaction rates by bringing hydrophilic and lipophilic compounds into close contact, allowing increased interactions . Kasaikina and co‐workers used different surfactants in non‐aqueous media, including bulk oil, as a simple self‐assembling model to investigate the impact of physical structures on lipid oxidation. They indicated that surfactants in heterogeneous systems could spontaneously group into micro/nano‐structures such as reverse micelles and that lipid hydroperoxides could act as co‐surfactants.…”

Section: Phospholipids In Lipid Oxidationmentioning

confidence: 99%

Phospholipids in foods: prooxidants or antioxidants?

2015

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Lipid oxidation is one of the major causes of quality deterioration in natural and processed foods and thus a large economic concern in the food industry. Phospholipids, especially lecithins, are already widely used as natural emulsifiers and have been gaining increasing interest as natural antioxidants to control lipid oxidation. This review summarizes the fatty acid composition and content of phospholipids naturally occurring in several foods. The role of phospholipids as substrates for lipid oxidation is discussed, with a focus on meats and dairy products. Prooxidant and antioxidant mechanisms of phospholipids are also discussed to get a better understanding of the possible opportunities for using phospholipids as food antioxidants.

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“…The phenomenon of micellar catalysis (any reaction promotion in the presence of surfactants) was known for a rather long time and applied in many processes . Significant influence of surfactants and multiphase system formation on the lipid and hydrocarbon oxidation has been found and studied only in recent decades . The micellar catalysis in the lipid oxidation has specific features due to several reasons: (1) Hydroperoxides (LOOH), the primary oxidation products, are amphiphilic and surface active compounds, in contrast to initial lipids ; in the presence of surfactants (S) hydroperoxides form mixed micelles {nLOOH…mS} , in which LOOH plays the role of a co‐surfactant.…”

Section: Micellar Effects In Liquid‐phase Oxidationmentioning

confidence: 99%

“…Significant influence of surfactants and multiphase system formation on the lipid and hydrocarbon oxidation has been found and studied only in recent decades . The micellar catalysis in the lipid oxidation has specific features due to several reasons: (1) Hydroperoxides (LOOH), the primary oxidation products, are amphiphilic and surface active compounds, in contrast to initial lipids ; in the presence of surfactants (S) hydroperoxides form mixed micelles {nLOOH…mS} , in which LOOH plays the role of a co‐surfactant. (2) The comparison of the effects of different surfactants on lipid and hydrocarbon oxidation reveals that cationic surfactants (S + ) promote hydroperoxide destruction resulting in the formation of free radicals and thus S + accelerate the oxidation as a whole .…”

Section: Micellar Effects In Liquid‐phase Oxidationmentioning

confidence: 99%

“…The micellar catalysis in the lipid oxidation has specific features due to several reasons: (1) Hydroperoxides (LOOH), the primary oxidation products, are amphiphilic and surface active compounds, in contrast to initial lipids ; in the presence of surfactants (S) hydroperoxides form mixed micelles {nLOOH…mS} , in which LOOH plays the role of a co‐surfactant. (2) The comparison of the effects of different surfactants on lipid and hydrocarbon oxidation reveals that cationic surfactants (S + ) promote hydroperoxide destruction resulting in the formation of free radicals and thus S + accelerate the oxidation as a whole . It must be noted that in organic solvents, the well‐known neuromediator acetylcholine (ACh) forms mixed micelles {mLOOH…nACh}, accelerates lipid oxidation and hydroperoxide decomposition into free radicals similarly to cationic surfactants .…”

Section: Micellar Effects In Liquid‐phase Oxidationmentioning

confidence: 99%

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Unusual antioxidant effects in multiphase and complex systems

Касаикина

Krugovov

Mengele

2017

Euro J Lipid Sci & Tech

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In recent years, a number of studies have produced evidence that the multiphase and boundary effects in the systems containing surfactants, have to be taken into account for the development of innovative antioxidant technologies of lipid containing products. This report presents some unusual antioxidant effects, which occur only in multiphase complex systems due to the influence of surfactants (S).Hydroperoxides (LOOH), the primary oxidation products, form mixed micelles with surfactants (S) {nLOOHmS}. In the case of cationic surfactants (S + ), an accelerated hydroperoxide decomposition resulted in free radical generation occurs. Moderate magnetic field affects the free radical escape from mixed micelles {nLOOHmS + } into bulk solution; it can result in inhibiting of lipid oxidation in micellar system. Nonionic S can inhibit the catalyzed lipid oxidation by solubilization of the hydrophilic catalyst and spatial separation of the catalyst and substrate. Anionic surfactants alkylsulfates and alkylphosphates are effective antioxidants for alkylaromatic hydrocarbons due to the catalytic heterolytic decomposition of hydroperoxides into carbonyl compound and phenol which scavenges peroxyl radicals.

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Micellar catalysis in the oxidation of lipids

Cited by 17 publications

References 3 publications

The supramolecular chemistry of lipid oxidation and antioxidation in bulk oils

The supramolecular chemistry of lipid oxidation and antioxidation in bulk oils

Phospholipids in foods: prooxidants or antioxidants?

Unusual antioxidant effects in multiphase and complex systems

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