Myricetin, rosmarinic and carnosic acids as superior natural antioxidant alternatives to α-tocopherol for the preservation of omega-3 oils

Guitard, Romain; Paul, Jean‐François; Nardello‐Rataj, Véronique; Aubry, Jean‐Marie

doi:10.1016/j.foodchem.2016.06.038

Cited by 74 publications

(74 citation statements)

References 67 publications

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“…Reactive phenols ( 1 , 4 , 5 , 6 , 8 , 11 , 17 , 20 , 26 , 27 , 60 , 61 , 62 , 63 , 65 , 69 and 70 ) were mixed with DPPH • in stoichiometric amount leading to SOK (Equation (8)) [47]. Figure 2 shows an example of SOK reaction with hydroxytyrosol 62 in toluene.…”

Section: Resultsmentioning

confidence: 99%

Theoretical and Kinetic Tools for Selecting Effective Antioxidants: Application to the Protection of Omega-3 Oils with Natural and Synthetic Phenols

Guitard

Nardello‐Rataj

Aubry

2016

IJMS

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Radical-scavenging antioxidants play crucial roles in the protection of unsaturated oils against autoxidation and, especially, edible oils rich in omega-3 because of their high sensitivity to oxygen. Two complementary tools are employed to select, among a large set of natural and synthetic phenols, the most promising antioxidants. On the one hand, density functional theory (DFT) calculations provide bond dissociation enthalpies (BDEs) of 70 natural (i.e., tocopherols, hydroxybenzoic and cinnamic acids, flavonoids, stilbenes, lignans, and coumarins) and synthetic (i.e., 2,6-di-tert-butyl-4-methylphenol (BHT), 3-tert-butyl-4-hydroxyanisol (BHA), and tert-butylhydroquinone (TBHQ)) phenols. These BDEs are discussed on the basis of structure–activity relationships with regard to their potential antioxidant activities. On the other hand, the kinetic rate constants and number of hydrogen atoms released per phenol molecule are measured by monitoring the reaction of phenols with 2,2-diphenyl-1-picrylhydrazyl (DPPH•) radical. The comparison of the results obtained with these two complementary methods allows highlighting the most promising antioxidants. Finally, the antioxidant effectiveness of the best candidates is assessed by following the absorption of oxygen by methyl esters of linseed oil containing 0.5 mmol L−1 of antioxidant and warmed at 90 °C under oxygen atmosphere. Under these conditions, some natural phenols namely epigallocatechin gallate, myricetin, rosmarinic and carnosic acids were found to be more effective antioxidants than α-tocopherol.

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Section: Resultsmentioning

confidence: 99%

Theoretical and Kinetic Tools for Selecting Effective Antioxidants: Application to the Protection of Omega-3 Oils with Natural and Synthetic Phenols

Guitard

Nardello‐Rataj

Aubry

2016

IJMS

Self Cite

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“…Substitution with an additional hydroxyl group is even more efficient, since besides resonance stabilization, it stabilizes the phenoxy radical through intramolecular hydrogen bonding, if it is in the orto-position. A hydroxyl group in the para-position increases the stability of the phenoxy radical only by electron donation, while hydroxyl groups in the meta-position are electron withdrawing substituents with negligible impact on the stability of phenoxy radicals [76]. These relationships explain partially the results presented above.…”

Section: Application In Polymersmentioning

confidence: 67%

“…Bond dissociation enthalpies of different phenols are collected in Table 2. The values were derived from computational calculations [76] and they clearly show that the energy barrier required for hydrogen abstraction decreases considerably with increasing number of hydroxyl groups in the molecule, if they are in the orto-position, while the effect of additional hydroxyl groups is smaller, if they are located in the para-and meta-positions. …”

Section: Natural Polyphenolsmentioning

confidence: 99%

“…The efficiency of vitamin E can be further increased by the synergistic interaction of phosphite type secondary stabilizers, like The structure and characteristics of a few natural antioxidants are presented in Table 3 without any attempt of being comprehensive. Besides their structure also the number of active phenolic hydroxyl groups and their smallest hydrogen bond dissociation enthalpy (BDE) are also listed in the table, the latter was calculated by time-dependent functional density theory methods by various authors [76,[110][111][112][113]. The solubility of the compounds in polyethylene was estimated from changes in the color of the polymer as a function of antioxidant content.…”

Section: Application In Polymersmentioning

confidence: 99%

“…The limited solubility of polar, small molecular weight stabilizers affects homogeneity and efficiency negatively and eventually leads to their migration from the polymer matrix. The application of α-tocopherol as primary stabilizer in UHMWPE clearly shows the importance of both low BDE (289.1 kJ/mol [76]) and sufficient solubility in the polymer matrix, which is enhanced by the saturated hydrocarbon chain. Considerable effort is put into the chemical modification, even polymerization of phenolic antioxidants in order to increase their solubility in and slow down their migration from the matrix [124], but such a modification increases price and chances for potential health issues.…”

Section: Application In Polymersmentioning

confidence: 99%

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Enhancing Lipid Oxidative Stability of Cooked‐Chilled Lamb Meat through Dietary Rosemary Diterpenes

Ortuño

Inchingolo

Delgado

et al. 2019

Euro J Lipid Sci & Tech

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A dietary rosemary extract (DRE) containing carnosic acid and carnosol at 1:1 (w/w) for enhancing the lipid oxidative stability in cooked‐chilled lamb meat, is evaluated. Three diets for fattening lambs are tested: i) a cereal‐based concentrate (C‐diet); ii) the C‐diet plus 600 mg vitamin E per kg feed (E‐diet); and iii) the C‐diet plus 600 mg rosemary diterpenes per kg feed (R‐diet). Griddled‐chilled lamb patties are kept at 4 °C and lighting for 2 days, simulating catering conditions. Diterpenes have a lower deposition rate than vitamin E in lamb muscle and are completely degraded during cooking. DRE is thus less effective than dietary vitamin E in enhancing the oxidative stability of the patties. After 2‐day storage, the R‐diet shows lower (p < 0.01) peroxide values and thiobarbituric acid reactive substances than the C‐diet, while, in contrast to the E‐diet, it does not inhibit (p > 0.05) the formation of cholesterol oxidation products. The R‐diet increases (p < 0.05) the proportion of polyunsaturated fatty acids and decreases (p < 0.05) the n‐6/n‐3 ratio. These findings suggest antioxidant protection by dietary bioactive compounds beyond the direct radical scavenging activity that is able to stabilize lipids during the meat shelf‐life. Practical Applications: Cooked‐chilled meat lipids strongly oxidize in ready‐to‐eat dishes kept in retailing conditions, which may negatively affect their levels of polyunsaturated fatty acids (PUFA), cholesterol oxidation products (COP), and other lipid oxidation products. Dietary rosemary diterpenes can be used as a clean alternative to feed additives to enhance the oxidative stability of cooked‐chilled meat. Improved health and antioxidant status of the animal might be able to reduce oxidative spoilage during meat shelf‐life. Diterpenes provide lesser antioxidant protection than dietary vitamin E but may improve the PUFA content, with positive implications for the nutritional quality of lamb fat. The use of dietary antioxidants with different properties may contribute to improving the efficacy of animal feeds to improve meat quality.

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Myricetin, rosmarinic and carnosic acids as superior natural antioxidant alternatives to α-tocopherol for the preservation of omega-3 oils

Cited by 74 publications

References 67 publications

Theoretical and Kinetic Tools for Selecting Effective Antioxidants: Application to the Protection of Omega-3 Oils with Natural and Synthetic Phenols

Theoretical and Kinetic Tools for Selecting Effective Antioxidants: Application to the Protection of Omega-3 Oils with Natural and Synthetic Phenols

Natural antioxidants as stabilizers for polymers

Enhancing Lipid Oxidative Stability of Cooked‐Chilled Lamb Meat through Dietary Rosemary Diterpenes

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