title: In vitro assessment of antioxidant activity of tyrosol, resveratrol and their acetylated derivatives.
abstract: Consumption of phenolic compounds is associated with beneficial effects in humans even though many of them are poorly absorbed. The aim of this study was to investigate the in vitro antioxidant activity of tyrosol (T), resveratrol (R) and their acetylated derivatives (AcD), as increased lipophilicity has been reported to improve absorption. The chemically synthesized AcDs were evaluated by their ability to scavenge DPPH radicals, inhibit non-enzymatic linoleic acid peroxidation, inhibit human serum oxidation in the presence of copper ions and inhibit lipoxygenase activity. T showed an inhibitory effect only in serum oxidation, where the T-acetylated at aromatic-OH was the most active. The T-acetylated at aliphatic-OH and 3,5-diacetyl-R exhibited the most powerful effect in non-enzymatic linoleic acid peroxidation with IC50 values 2.4 mM ± 0.21 and 0.055 mM ± 0.0018, respectively. In all other tests R was the most potent among all its AcD and T. Increasing lipophilicity by acetylation improves antioxidant activity of phenolic compounds in non-enzymatic lipid peroxidation assays.
authors: Department of Nutritional Science and Dietetics, Harokopio University, Athens, Greece.
authors: Ioanna C
authors: IC
authors: Vlachogianni
authors: Department of Nutritional Science and Dietetics, Harokopio University, Athens, Greece.
authors: Elizabeth
authors: E
authors: Fragopoulou
authors: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, National and Kapodistrian University of Athens, Greece.
authors: Ioannis K
authors: IK
authors: Kostakis
authors: Department of Nutritional Science and Dietetics, Harokopio University, Athens, Greece. Electronic address: antonop@hua.gr.
authors: Smaragdi
authors: S
authors: Antonopoulou
mesh_terms: D000107:Acetylation; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000737:chemistry / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D066298:In Vitro Techniques; D019787:Linoleic Acid / Q000737:chemistry; D015227:Lipid Peroxidation / Q000187:drug effects; D016859:Lipoxygenase Inhibitors / Q000737:chemistry / Q000494:pharmacology; D010084:Oxidation-Reduction; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology; D010851:Picrates / Q000737:chemistry / Q000494:pharmacology; D000077185:Resveratrol; D044967:Serum; D013025:Glycine max / Q000201:enzymology; D013267:Stilbenes / Q000032:analysis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000975:Antioxidants; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D016859:Lipoxygenase Inhibitors; D010851:Picrates; D013267:Stilbenes; C011867:4-hydroxyphenylethanol; D019787:Linoleic Acid; C004931:1,1-diphenyl-2-picrylhydrazyl; D010626:Phenylethyl Alcohol; D000077185:Resveratrol
keywords: Acetylation; Antioxidant; Lipophilicity; Resveratrol; Synthesis; Tyrosol