title: Synthesis and Antioxidant Activity of Alkyl Nitroderivatives of Hydroxytyrosol.
abstract: 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.
authors.affiliation: Department of Organic and Pharmaceutical Chemistry, Faculty of Pharmacy, University of Seville, 41012 Seville, Spain. elegm@us.es.|Department of Metabolism and Nutrition, Institute of Food Science, Technology and Nutrition (ICTAN), Spanish National Research Council (CSIC), 28040 Madrid, Spain. elegm@us.es.
authors.forename: Elena
authors.initials: E
authors.lastname: Gallardo
authors.affiliation: Department of Organic and Pharmaceutical Chemistry, Faculty of Pharmacy, University of Seville, 41012 Seville, Spain. xiopalma@yahoo.es.
authors.forename: Rocío
authors.initials: R
authors.lastname: Palma-Valdés
authors.affiliation: Department of Metabolism and Nutrition, Institute of Food Science, Technology and Nutrition (ICTAN), Spanish National Research Council (CSIC), 28040 Madrid, Spain. beasarria@ictan.csic.es.
authors.forename: Beatriz
authors.initials: B
authors.lastname: Sarriá
authors.affiliation: Department of Organic and Pharmaceutical Chemistry, Faculty of Pharmacy, University of Seville, 41012 Seville, Spain. irenegalmar@hotmail.com.
authors.forename: Irene
authors.initials: I
authors.lastname: Gallardo
authors.affiliation: Department of Pharmacology, Faculty of Medicine, University of Malaga, 29071 Malaga, Spain. jpcruz@uma.es.
authors.forename: José P
authors.initials: JP
authors.lastname: de la Cruz
authors.affiliation: Department of Metabolism and Nutrition, Institute of Food Science, Technology and Nutrition (ICTAN), Spanish National Research Council (CSIC), 28040 Madrid, Spain. lbravo@ictan.csic.es.
authors.forename: Laura
authors.initials: L
authors.lastname: Bravo
authors.affiliation: Department of Metabolism and Nutrition, Institute of Food Science, Technology and Nutrition (ICTAN), Spanish National Research Council (CSIC), 28040 Madrid, Spain. raquel.mateos@ictan.csic.es.
authors.forename: Raquel
authors.initials: R
authors.lastname: Mateos
authors.affiliation: Department of Organic and Pharmaceutical Chemistry, Faculty of Pharmacy, University of Seville, 41012 Seville, Spain. jles@us.es.
authors.forename: José L
authors.initials: JL
authors.lastname: Espartero
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D052160:Benzothiazoles / Q000737:chemistry / Q000627:therapeutic use; D002244:Carbon / Q000737:chemistry; D036681:Fluorescence Recovery After Photobleaching; D016166:Free Radical Scavengers / Q000737:chemistry / Q000627:therapeutic use; D006801:Humans; D009585:Nitrogen Dioxide / Q000737:chemistry* / Q000627:therapeutic use; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry; D019800:Phenol / Q000737:chemistry; D010636:Phenols / Q000737:chemistry; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000627:therapeutic use; D017382:Reactive Oxygen Species / Q000737:chemistry*; D012715:Sesame Oil / Q000737:chemistry; D013451:Sulfonic Acids / Q000737:chemistry / Q000627:therapeutic use
chemical_list: D000975:Antioxidants; D052160:Benzothiazoles; D016166:Free Radical Scavengers; D010636:Phenols; D017382:Reactive Oxygen Species; D013451:Sulfonic Acids; C570629:carbol oil; C005975:3,4-dihydroxyphenylethanol; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; D019800:Phenol; D002244:Carbon; D012715:Sesame Oil; D010626:Phenylethyl Alcohol; D009585:Nitrogen Dioxide; D010100:Oxygen
keywords: Parkinson’s disease; alkyl nitrohydroxytyrosyl derivatives; antioxidant activity; hydroxytyrosol; nitrocatechol