Synthesis and Antioxidant Activity of Alkyl Nitroderivatives of Hydroxytyrosol
Elena Gallardo,
Rocío Palma-Valdés,
Beatriz Sarriá,
Irene Gallardo,
José P. de la Cruz,
Laura Bravo,
Raquel Mateos,
José L. Espartero
Affiliations
Elena Gallardo
Department of Organic and Pharmaceutical Chemistry, Faculty of Pharmacy, University of Seville, 41012 Seville, Spain
Rocío Palma-Valdés
Department of Organic and Pharmaceutical Chemistry, Faculty of Pharmacy, University of Seville, 41012 Seville, Spain
Beatriz Sarriá
Department of Metabolism and Nutrition, Institute of Food Science, Technology and Nutrition (ICTAN), Spanish National Research Council (CSIC), 28040 Madrid, Spain
Irene Gallardo
Department of Organic and Pharmaceutical Chemistry, Faculty of Pharmacy, University of Seville, 41012 Seville, Spain
José P. de la Cruz
Department of Pharmacology, Faculty of Medicine, University of Malaga, 29071 Malaga, Spain
Laura Bravo
Department of Metabolism and Nutrition, Institute of Food Science, Technology and Nutrition (ICTAN), Spanish National Research Council (CSIC), 28040 Madrid, Spain
Raquel Mateos
Department of Metabolism and Nutrition, Institute of Food Science, Technology and Nutrition (ICTAN), Spanish National Research Council (CSIC), 28040 Madrid, Spain
José L. Espartero
Department of Organic and Pharmaceutical Chemistry, Faculty of Pharmacy, University of Seville, 41012 Seville, Spain
A series of alkyl nitrohydroxytyrosyl ether derivatives has been synthesized from free hydroxytyrosol (HT), the natural olive oil phenol, in order to increase the assortment of compounds with potential neuroprotective activity in Parkinson’s disease. In this work, the antioxidant activity of these novel compounds has been evaluated using Ferric Reducing Antioxidant Power (FRAP), 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS), and Oxygen Radical Scavenging Capacity (ORAC) assays compared to that of nitrohydroxytyrosol (NO2HT) and free HT. New compounds showed variable antioxidant activity depending on the alkyl side chain length; compounds with short chains (2–4 carbon atoms) maintained or even improved the antioxidant activity compared to NO2HT and/or HT, whereas those with longer side chains (6–8 carbon atoms) showed lower activity than NO2HT but higher than HT.
