Protective effects of synthetic hydroxytyrosol acetyl derivatives against oxidative stress in human cells.
Chemically stable di- and triacetyl derivatives of the natural o-diphenol antioxidant hydroxytyrosol were synthesized, and their chemical and biological antioxidant activities were assessed in comparison with that of the native synthetic compound. The chemical antioxidant activity of the selected compounds was evaluated by measuring the ferric reducing antioxidant power (FRAP). The data clearly indicate that, as expected, the hydroxytyrosol analogues, modified in the o-diphenolic ring, are devoid of any chemical antioxidant activity. On the contrary, both acetyl derivatives, at micromolar concentrations, equally protect against tert-butylhydroperoxide-induced oxidative damages in Caco-2 cells and human erythrocytes. This paper for the first time reports that chemically stable hydroxytyrosol acetyl derivatives, although devoid of chemical antioxidant activity, are as effective as the parent compound in protecting human cells from oxidative stress-induced cytotoxicity, after metabolization by esterases at the intestinal level, suggesting their possible utilization in either nutritional (functional food), cosmetic, or pharmaceutical preparations.
Manna
Caterina
C
Dipartimento di Biochimica e Biofisica F. Cedrangolo, Facoltà di Medicina e Chirurgia, Seconda Università degli Studi di Napoli, Via De Crecchio 7, 80138 Naples, Italy. caterina.manna@unina2.it
Migliardi
Valentina
V
Sannino
Filomena
F
De Martino
Antonio
A
Capasso
Renato
R
D000107:Acetylation; D000975:Antioxidants / Q000494:pharmacology*; D004912:Erythrocytes / Q000187:drug effects; D006801:Humans; D018384:Oxidative Stress / Q000187:drug effects*; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology
D000975:Antioxidants; C005975:3,4-dihydroxyphenylethanol; D010626:Phenylethyl Alcohol