Antioxidant activity evaluation of alkyl hydroxytyrosyl ethers, a new class of hydroxytyrosol derivatives

Pereira-Caro, Gema; Madrona, Andrés; Bravo, Laura; Espartero, José L.; Alcudia, Felipe; Cert, Arturo; Mateos, Raquel

doi:10.1016/j.foodchem.2008.11.069

Cited by 72 publications

(70 citation statements)

References 40 publications

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“…25,26 The acetylation of the primary alcoholic group of HTy significantly increases its transport across the small intestinal epithelial barrier, enhancing its bioavailability. 28 The antioxidant activities of these compounds were evaluated by several methods, 29 and again, similar behavior to that of HTy was found. 27 To avoid this hydrolysis process, a series of lipophilic alkyl hydroxytyrosyl ethers (HTy ethers, 3) ( Fig.…”

Section: Introductionmentioning

confidence: 63%

Antioxidant activity of alkyl hydroxytyrosyl ethers in unsaturated lipids

et al. 2015

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The antioxidant activity of ethyl and octyl hydroxytyrosyl ethers toward lipids was determined using the Rancimat and open cup methods at high temperatures and 50 °C, respectively. The effect of the unsaturation of the matrix was evaluated using sunflower, soya, and fish refined oils. The antioxidant activities of alkyl hydroxytyrosyl ethers (HTy ethers), hydroxytyrosyl esters, and free hydroxytyrosol are similar, and are much higher than that of α-tocopherol at the same millimolar concentration. The relationship between the induction period and the concentration of the HTy ethers is a sigmoidal curve; an accurate concentration of HTy ethers is necessary to achieve maximum activity, as it increases with the level of matrix unsaturation. The presence of tocopherols in commercial oils affects the antioxidant effect of HTy ethers. Thus, the addition of a low concentration of HTy ethers results in a positive effect, whereas the effect of the addition of high amounts of ethers is slightly less than that of the phenol alone. The addition of HTy ethers to commercial refined oils increases the stability of the oils and preserves tocopherols and polyunsaturated fatty acids from oxidation, enabling the oils to maintain their nutritional properties for longer periods of time.

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Section: Introductionmentioning

confidence: 63%

Antioxidant activity of alkyl hydroxytyrosyl ethers in unsaturated lipids

et al. 2015

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“…8 However, experiments of tissue damage induced by chemical agents (t-BOOH) indicated that HT ether derivatives prevented the decrease in glutathione concentration after chemical damage. 23,25,26 The in vitro design of these experiments as well as the type of cell used may be the main explanations for the differences in the results. However, the effect of HT ether derivatives on lipid peroxidation showed a direct relationship with its neuroprotective action, as demonstrated by the linear correlation between the levels of TBARS and LDH in the experimental groups ( Figure 3).…”

Section: ■ Discussionmentioning

confidence: 99%

Cytoprotective Effect of Hydroxytyrosyl Alkyl Ether Derivatives after Oral Administration to Rats in a Model of Glucose–Oxygen Deprivation in Brain Slices

Muñoz‐Marín

Cruz

Guerrero

et al. 2012

J. Agric. Food Chem.

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This study was designed to determine whether the oral administration of hydroxytyrosol (HT) alkyl ether derivatives has a neuroprotective effect in rats. The animals were treated for 7 days with HT or ethyl, butyl, hexyl, octyl, and dodecyl HT ether. A method of in vitro hypoxia-reoxygenation in brain slices was used. Hexyl, octyl, and dodecyl HT derivatives reduced brain cell death (LDH efflux). Lipid peroxidation and nitrite concentrations were inhibited most by hexyl, octyl, and dodecyl derivatives. Concentrations of 3-nitrotyrosine were reduced by HT butyl, hexyl, octyl, and dodecyl ether derivatives. Interleukin-1β was significantly reduced in brain slices from rats treated with all HT ether derivatives. LDH efflux showed a linear correlation with brain concentrations of lipid peroxides, nitrites plus nitrates, and interleukin 1β. The reduction in oxidative and nitrosative stress and decreased production of pro-inflammatory interleukins may be the basis for the observed neuroprotective effects.

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“…Results were expressed as the induction time (IT) corresponding to the stability of the lipid matrix. Considering that minimal differences in fatty acid composition of lipid matrixes critically determine stability and consequently induction time, the antioxidant activity of the references (1, 8 and 9) was analysed in order to carry out a more accurate comparison with that of isochromans (2-7), although the former data had been published previously (Pereira-Caro et al, 2009). Figure 2 shows the IT values of purified matrices of sunflower oil spiked with increasing concentrations of the studied compounds (1-9).…”

Section: Antioxidant Activity In Lipid Matricesmentioning

confidence: 99%