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Resveratrol inhibits metal ion-dependent and independent peroxidation of porcine low-density lipoproteins.
Biochem Pharmacol. 1997 May 09; 53(9):1347-55.BP

Abstract

Resveratrol, a phytoalexin (3, 4', 5, trihydroxystilbene) present in some red wines, has been reported to inhibit copper-mediated low-density lipoprotein (LDL) oxidation. In this study, we examined the efficiency of this compound in inhibiting metal ion-dependent and independent peroxidation of porcine LDL. At 0.5, 1, or 1.5 microM, transresveratrol prolonged the lag time preceding the onset of conjugated diene formation in a dose-dependent manner, with a slope of the propagation phase 5-fold greater in the presence of Cu SO4 (5 microM) than in the presence of the free radical generator, AAPH [2, 2'-azobis (2-amidinopropane) dihydrochloride] (1 mM). At 1 microM, transresveratrol prolonged the lag time 3.4- and 1.4-fold in the presence of copper and AAPH, respectively. Isomerisation into cisresveratrol significantly lowered the chelating capacity, but did not alter the free radical scavenging capacity. As compared to flavonoids and trolox, transresveratrol showed a much higher ability to prolong the lag time in copper, but not in AAPH-catalyzed oxidation. The kinetics of generation of degradative products in the presence of copper confirmed the strongest protective effects of transresveratrol, because the formation of thiobarbituric acid reactive substances and hydroperoxides was almost completely inhibited at 200 min. By contrast, transresveratrol was less potent than flavonoids (but more than trolox) as a scavenger of free radicals. Our data show that, like flavonoids, resveratrol protects LDL against peroxidative degradation by both chelating and free radical scavenging mechanisms. However, transresveratrol, which is by far the most potent chelator of copper, does not chelate iron. It might contribute to the protective effects of wine polyphenols by removing copper from LDL particles and arterial tissue and, thereby, delaying the consumption of flavonoids and endogenous antioxidants.

Authors+Show Affiliations

Laboratoire de Nutrition et Sécurité Alimentaire CRJ-INRA, Jouy-en-Josas, France.No affiliation info availableNo affiliation info available

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

9214696

Citation

Belguendouz, L, et al. "Resveratrol Inhibits Metal Ion-dependent and Independent Peroxidation of Porcine Low-density Lipoproteins." Biochemical Pharmacology, vol. 53, no. 9, 1997, pp. 1347-55.
Belguendouz L, Fremont L, Linard A. Resveratrol inhibits metal ion-dependent and independent peroxidation of porcine low-density lipoproteins. Biochem Pharmacol. 1997;53(9):1347-55.
Belguendouz, L., Fremont, L., & Linard, A. (1997). Resveratrol inhibits metal ion-dependent and independent peroxidation of porcine low-density lipoproteins. Biochemical Pharmacology, 53(9), 1347-55.
Belguendouz L, Fremont L, Linard A. Resveratrol Inhibits Metal Ion-dependent and Independent Peroxidation of Porcine Low-density Lipoproteins. Biochem Pharmacol. 1997 May 9;53(9):1347-55. PubMed PMID: 9214696.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Resveratrol inhibits metal ion-dependent and independent peroxidation of porcine low-density lipoproteins. AU - Belguendouz,L, AU - Fremont,L, AU - Linard,A, PY - 1997/5/9/pubmed PY - 1997/5/9/medline PY - 1997/5/9/entrez SP - 1347 EP - 55 JF - Biochemical pharmacology JO - Biochem. Pharmacol. VL - 53 IS - 9 N2 - Resveratrol, a phytoalexin (3, 4', 5, trihydroxystilbene) present in some red wines, has been reported to inhibit copper-mediated low-density lipoprotein (LDL) oxidation. In this study, we examined the efficiency of this compound in inhibiting metal ion-dependent and independent peroxidation of porcine LDL. At 0.5, 1, or 1.5 microM, transresveratrol prolonged the lag time preceding the onset of conjugated diene formation in a dose-dependent manner, with a slope of the propagation phase 5-fold greater in the presence of Cu SO4 (5 microM) than in the presence of the free radical generator, AAPH [2, 2'-azobis (2-amidinopropane) dihydrochloride] (1 mM). At 1 microM, transresveratrol prolonged the lag time 3.4- and 1.4-fold in the presence of copper and AAPH, respectively. Isomerisation into cisresveratrol significantly lowered the chelating capacity, but did not alter the free radical scavenging capacity. As compared to flavonoids and trolox, transresveratrol showed a much higher ability to prolong the lag time in copper, but not in AAPH-catalyzed oxidation. The kinetics of generation of degradative products in the presence of copper confirmed the strongest protective effects of transresveratrol, because the formation of thiobarbituric acid reactive substances and hydroperoxides was almost completely inhibited at 200 min. By contrast, transresveratrol was less potent than flavonoids (but more than trolox) as a scavenger of free radicals. Our data show that, like flavonoids, resveratrol protects LDL against peroxidative degradation by both chelating and free radical scavenging mechanisms. However, transresveratrol, which is by far the most potent chelator of copper, does not chelate iron. It might contribute to the protective effects of wine polyphenols by removing copper from LDL particles and arterial tissue and, thereby, delaying the consumption of flavonoids and endogenous antioxidants. SN - 0006-2952 UR - https://www.unboundmedicine.com/medline/citation/9214696/Resveratrol_inhibits_metal_ion_dependent_and_independent_peroxidation_of_porcine_low_density_lipoproteins_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0006-2952(96)00820-9 DB - PRIME DP - Unbound Medicine ER -