Interactions between α-Tocopherol and Rosmarinic Acid and Its Alkyl Esters in Emulsions: Synergistic, Additive, or Antagonistic Effect?

Panya, Atikorn; Kittipongpittaya, Ketinun; Laguerre, Mickaël; Bayrasy, Christelle; Lecomte, Jérôme; Villeneuve, Pierre; McClements, David Julian; Decker, Eric A.

doi:10.1021/jf302673j

Cited by 58 publications

(79 citation statements)

References 47 publications

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“…Combinations of molecules in emulsion can often interact and synergistically or antagonistically impact lipid oxidation rates. 48 The impact of combinations of between WPI and DTAB or SDS on lipid oxidation rates in the W/O emulsion were tested at both pH 3.0 and 7.0 because the antioxidant activity of WPI was strongly influenced by pH.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Influence of Aqueous Phase Emulsifiers on Lipid Oxidation in Water-in-Walnut Oil Emulsions

Zhu

McClements

et al. 2014

J. Agric. Food Chem.

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Effects of selected aqueous phase emulsifiers on lipid oxidative stability of water-in-walnut oil (W/O) emulsions stabilized by polyglycerol polyricinoleate (PGPR) were evaluated. The formation of primary oxidation products (lipid hydroperoxides) and secondary oxidation products (headspace hexanal) increased with increasing dodecyltrimethylammonium bromide (DTAB) concentration (0.1−0.2 wt % of emulsions). In contrast, the addition of sodium dodecyl sulfate (SDS) in the aqueous phase reduced lipid hydroperoxide and hexanal formation. In addition, the presence of Tween 20 in the aqueous phase did not significantly influence lipid oxidation rates in W/O emulsions compared to the control (without Tween 20). Whey protein isolate (WPI) was observed to inhibit lipid oxidation in the W/O emulsions (0.05−0.2 wt % of emulsions). Aqueous phase pH had an important impact on the antioxidant capability of WPI, with higher pH improving its ability to inhibit lipid oxidation. The combination of WPI and DTAB in the aqueous phase suppressed the prooxidant effect of DTAB. The combination of WPI and SDS resulted in improved antioxidant activity, with inhibition being greater at pH 7.0 than at pH 3.0. These results suggest that the oxidative stability of W/O emulsions could be improved by the use of suitable emulsifiers in the aqueous phase.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Influence of Aqueous Phase Emulsifiers on Lipid Oxidation in Water-in-Walnut Oil Emulsions

Zhu

McClements

et al. 2014

J. Agric. Food Chem.

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“…This may indicate some interactions between tocopherol and caffeic acid/caffeates both for the antioxidative effect and localization in the emulsion system. The use of a combination of antioxidants to produce synergistic interaction has been reported earlier, e.g., tocopherol regeneration by ascorbic acid, polyphenols, and flavonoids . Panya et al carried out the only study investigating interactions between tocopherol and a phenol (rosmarinic acid) and its alkyl esters (rosmarinates, C4, C12, and C20) in Tween20 stabilized emulsions.…”

Section: Discussionmentioning

confidence: 99%

“…The use of a combination of antioxidants to produce synergistic interaction has been reported earlier, e.g., tocopherol regeneration by ascorbic acid, polyphenols, and flavonoids . Panya et al carried out the only study investigating interactions between tocopherol and a phenol (rosmarinic acid) and its alkyl esters (rosmarinates, C4, C12, and C20) in Tween20 stabilized emulsions. Rosmarinic acid exhibited strongest synergistic interaction with tocopherol, and C4 and C12 esters exhibited small synergistic interaction.…”

Section: Discussionmentioning

confidence: 99%

Alkyl caffeates as antioxidants in O/W emulsions: Impact of emulsifier type and endogenous tocopherols

Sørensen

Villeneuve

Jacobsen

2017

Euro J Lipid Sci & Tech

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Antioxidant addition can be one strategy to limit lipid oxidation in emulsions. Research has proven that an important factor regarding the efficacy of antioxidants is their localization in the emulsion; however, other factors such as interactions with other components can also have an impact. Thus, the aim was to evaluate the impact of emulsifiers (Citrem and Tween80) and presence of endogenous tocopherols on the efficacies of caffeic acid and caffeates (C1–C20) as antioxidants in emulsions. Lipid oxidation was evaluated during storage and partitioning of caffeic acid and caffeates was estimated by measuring their concentrations in the aqueous phase. Partitioning of caffeic acid and caffeates was influenced by emulsifier type and the presence of endogenous tocopherols. Caffeic acid was the most efficient antioxidant in Citrem and Tween stabilized emulsions in the presence of endogenous tocopherol. In contrast, for Tween stabilized emulsions, caffeic acid acted as a prooxidant and the evaluated caffeates acted as strong antioxidants in the absence of endogenous tocopherol. Thus, when endogenous tocopherol was present lipophilization of caffeic acid did not increase its efficacy as an antioxidant. It is suggested that the differences observed in antioxidant efficiency with different emulsifiers and with and without endogenous tocopherols is due to emulsifier–antioxidant interactions and antioxidant–antioxidant interactions in the emulsions. Practical applications: Food emulsions contain endogenous tocopherols, thus, the impact of endogenous tocopherols on the efficacy of applied antioxidants is of interest to the industry. So far the hypotheses about antioxidant in emulsions are based on simple emulsions systems without the presence of tocopherols. The finding in this study revealed that both emulsifier type and the presence of endogenous tocopherol had an impact on the efficacy of caffeic acid and caffeates due to emulsifier–antioxidant and antioxidant–antioxidant interactions. This highlights the importance of evaluating the antioxidant in each emulsion system before selecting antioxidants for optimal protection against lipid oxidation. CAT value determined in oil-in-water micro emulsions with caffeic acid and caffeates (100 μM) and with and without endogenous tocopherol and lipid oxidation is initiated with the water soluble radical AAPH. (Résumé d'auteur

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“…3,4,6,[8][9][10]18,20 Much of this likely relates to the unique physical structure of low-moisture foods, which affects the physical location of the AOX. AOX should be most effective when they partition at the site of oxidation, which in both oilin-water emulsions and bulk oils containing association colloids is oil−water interfaces.…”

Section: ■ Discussionmentioning

confidence: 99%

Impact of Hydrophobicity on Antioxidant Efficacy in Low-Moisture Food

Barden

Barouh

Villeneuve

et al. 2015

J. Agric. Food Chem.

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The polarity and partitioning of antioxidants (AOX) in lipid dispersions and bulk oils have a large impact on efficacy, but this has not yet been studied in low-moisture foods. Using a homologous series of rosmarinic esters as AOX in crackers, we determined that efficacy increases with increasing hydrophobicity based on lipid hydroperoxide and hexanal generation. Confocal microscopy was used to determine the location of both lipids and AOX. Hydrophobic rosmarinic esters partitioned more closely with the lipid than rosmarinic acid, presumably placing the hydrophobic AOX at the site of oxidation reactions. Partitioning and efficacy of the intermediate polarity ester were affected by mode of incorporation (e.g., added to the water or to the lipid prior to dough formation). The synthetic AOXs propyl gallate, butylhydroxytoluene, and tert-butylhydroquinone gave similar results with the more hydrophobic BHT and TBHQ being more effective at reducing lipid hydroperoxide and hexanal generation than the more hydrophilic propyl gallate. These results provide important information on which AOX would be most effective in low-moisture foods.

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Interactions between α-Tocopherol and Rosmarinic Acid and Its Alkyl Esters in Emulsions: Synergistic, Additive, or Antagonistic Effect?

Cited by 58 publications

References 47 publications

Influence of Aqueous Phase Emulsifiers on Lipid Oxidation in Water-in-Walnut Oil Emulsions

Influence of Aqueous Phase Emulsifiers on Lipid Oxidation in Water-in-Walnut Oil Emulsions

Alkyl caffeates as antioxidants in O/W emulsions: Impact of emulsifier type and endogenous tocopherols

Impact of Hydrophobicity on Antioxidant Efficacy in Low-Moisture Food

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