Synthesis and Antioxidant Activity of Alkyl Nitroderivatives of Hydroxytyrosol

Molecules. 2016 May 18;21(5):656. doi: 10.3390/molecules21050656.

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.

Keywords: Parkinson’s disease; alkyl nitrohydroxytyrosyl derivatives; antioxidant activity; hydroxytyrosol; nitrocatechol.

MeSH terms

  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry*
  • Antioxidants / therapeutic use
  • Benzothiazoles / chemistry
  • Benzothiazoles / therapeutic use
  • Carbon / chemistry
  • Fluorescence Recovery After Photobleaching
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / therapeutic use
  • Humans
  • Nitrogen Dioxide / chemistry*
  • Nitrogen Dioxide / therapeutic use
  • Oxidation-Reduction
  • Oxygen / chemistry
  • Phenol / chemistry
  • Phenols / chemistry
  • Phenylethyl Alcohol / analogs & derivatives*
  • Phenylethyl Alcohol / chemical synthesis
  • Phenylethyl Alcohol / chemistry
  • Phenylethyl Alcohol / therapeutic use
  • Reactive Oxygen Species / chemistry*
  • Sesame Oil / chemistry
  • Sulfonic Acids / chemistry
  • Sulfonic Acids / therapeutic use

Substances

  • Antioxidants
  • Benzothiazoles
  • Free Radical Scavengers
  • Phenols
  • Reactive Oxygen Species
  • Sulfonic Acids
  • carbol oil
  • 3,4-dihydroxyphenylethanol
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • Phenol
  • Carbon
  • Sesame Oil
  • Phenylethyl Alcohol
  • Nitrogen Dioxide
  • Oxygen