How to boost antioxidants by lipophilization?

Laguerre, Mickaël; Bayrasy, Christelle; Lecomte, Jérôme; Chabi, Béatrice; Decker, Eric A.; Wrutniak‐Cabello, Chantal; Cabello, Gérard; Villeneuve, Pierre

doi:10.1016/j.biochi.2012.07.018

Cited by 105 publications

(106 citation statements)

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“…Using a broad range of homologous series of antioxidants in dispersed lipid models and cultured cells, it has been demonstrated that the antioxidant activity increases progressively with increasing chain length up to a critical point, beyond which the activity of the compounds decreases (Figure 4). Since its first mention (Laguerre et al 2009), this cut-off effect for antioxidants has been the subject of extensive research in lipid dispersions (Alemán et al 2015;Costa et al 2015;Laguerre et al 2010;Lee et al 2013;Losada-Barreiro et al 2013;Medina et al 2009;Panya et al 2012;Sørensen et al 2012Sørensen et al , 2014Sørensen et al , 2015 and cellular models , Laguerre et al 2011, Munoz-Marin et al 2013) as well as of review articles (Laguerre et al 2013a(Laguerre et al ,b, 2015Shahidi & Zhong 2011;Zhao et al 2015). Table 1 gives some examples of the experimental confirmations of the occurrence of a cut-off effect.…”

Section: Figurementioning

confidence: 99%

“…Antioxidant reactivity, which roughly consists of the potential to neutralize pro-oxidants by reduction or chelation, can be regarded as a virtual potential that needs to be physically expressed in a given system. A highly reactive antioxidant needs to be mobile and to diffuse easily to the site of action (Laguerre et al 2013a). It also needs to be properly positioned in compartmentalized systems to encounter pro-oxidants and protect unsaturated lipids.…”

Section: Introductionmentioning

confidence: 99%

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Mass Transport Phenomena in Lipid Oxidation and Antioxidation

Laguerre

Bily

Roller³

et al. 2017

Annu. Rev. Food Sci. Technol.

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In lipid dispersions, the ability of reactants to move from one lipid particle to another is an important, yet often ignored, determinant of lipid oxidation and its inhibition by antioxidants. This review describes three putative interparticle transfer mechanisms for oxidants and antioxidants: (a) diffusion, (b) collision-exchange-separation, and (c) micelle-assisted transfer. Mechanism a involves the diffusion of molecules from one particle to another through the intervening aqueous phase. Mechanism b involves the transfer of molecules from one particle to another when the particles collide with each other. Mechanism c involves the solubilization of molecules in micelles within the aqueous phase and then their transfer between particles. During lipid oxidation, the accumulation of surface-active lipid hydroperoxides (LOOHs) beyond their critical micelle concentration may shift their mass transport from the collision-exchange-separation pathway (slow transfer) to the micelle-assisted mechanism (fast transfer), which may account for the transition from the initiation to the propagation phase. Similarly, the cutoff effect governing antioxidant activity in lipid dispersions may be due to the fact that above a certain hydrophobicity, the transfer mechanism for antioxidants changes from diffusion to collision-exchange-separation. This hypothesis provides a simple model to rationalize the design and formulation of antioxidants and dispersed lipids.

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Section: Figurementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Mass Transport Phenomena in Lipid Oxidation and Antioxidation

Laguerre

Bily

Roller³

et al. 2017

Annu. Rev. Food Sci. Technol.

Self Cite

121

116

View full text Add to dashboard Cite

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“…In contrast, enzymatic synthesis is highly selective and is considered a more environmentally friendly process since it involves milder reaction conditions, fewer purification steps and lower waste production [2][3][4]. However, it is worth keeping in mind that enzymatic processes are often associated with longer reaction times, higher catalyst costs, and enzyme inhibition/deactivation issues related to reaction conditions (nature of substrates, products and solvents, pH, enzyme hydration state, etc.…”

Section: Lipophilization Of Phenolic Acidsmentioning

confidence: 99%

“…Based on this observation, lipophilization has been early considered to improve the surface-active properties of polar antioxidants, and thus their effectiveness in such dispersed lipid systems [1]. Basically, the modification consists of grafting a lipid moiety via different reactions (etherification, esterification, transesterification and amidation) and catalytic approaches (homogeneous vs heterogeneous, chemical vs enzymatic) according to the structure and the reactivity of starting molecules [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

From phenolics to phenolipids: Optimizing antioxidants in lipid dispersions

et al. 2013

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Natural non-polymeric phenolics are known to be powerful antioxidants, but their use for preventing lipid oxidation in unsaturated fatbased products, such as foodstuffs and cosmetics, is limited owing to their hydrophilic character. A promising technique - referred to as lipophilization - consists of covalently grafting a lipid moiety to the phenolic part to improve both surface activity and oil solubility of a given phenolic antioxidant. After being based on empiricism for decades, the lipophilization of phenolics is today more rationalized, as recent advances in the field have shown that the grafting of a medium chain-length is the best strategy to design powerful, custom-made phenolic antioxidants to protect lipid dispersion against oxidation. To illustrate, we report here the main strategies in the lipophilization of phenolic acids, the effect of such modification on the antioxidant properties, and current and potential applications of the resulting phenolipids. (Résumé d'auteur

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“…In a recent report, two water soluble antioxidants, chlorogenic acid and rosmarinic acid, were converted to amphipathic alkyl esters and found to acquire increased antioxidative potential. 8,9 Although amphipathic antioxidants are attracting more attention in food science and industry, it is difficult to measure amphipathic compounds including DHMBA by means of chromatographic separation. Amphipathic compounds are hardly retained on solid phases for conventional reversed-phase chromatography and hydrophilic interaction chromatography (HILIC).…”

Section: Introductionmentioning

confidence: 99%