Hydroxytyrosol lipophilic analogues: enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection

Bioorg Chem. 2007 Apr;35(2):137-52. doi: 10.1016/j.bioorg.2006.09.003. Epub 2006 Oct 31.

Abstract

The olive oil phenol hydroxytyrosol (3), as well its metabolite homovanillic alcohol (4), were subjected to chemoselective lipase-catalysed acylations, affording with good yield 10 derivatives (5-14) bearing C(2), C(3), C(4), C(10) and C(18) acyl chains at C-1. Hydroxytyrosol (3) and its lipophilic derivatives showed very good DPPH. radical scavenging activity. Compounds 3, 4 and their lipophilic analogues 5-14 were subjected to the atypical Comet test on whole blood cells: 3 and its analogues 5 and 6, with little hydrophobic character (logP<or=1.20), showed a good protective effect against H(2)O(2) induced oxidative DNA damage. The homovanillic alcohol 4 and its analogues 10-14 resulted scarcely effective both as radical scavengers and antioxidant agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Bacteria / drug effects
  • Biphenyl Compounds
  • Chemical Phenomena
  • Chemistry, Physical
  • Comet Assay
  • DNA / drug effects*
  • DNA Damage*
  • Free Radical Scavengers / chemical synthesis*
  • Free Radical Scavengers / pharmacology*
  • Fungi / drug effects
  • Humans
  • In Vitro Techniques
  • Indicators and Reagents
  • Lipase / chemistry
  • Mutagens / chemistry
  • Mutagens / toxicity
  • Oxidative Stress / drug effects
  • Oxidative Stress / physiology*
  • Phenylethyl Alcohol / analogs & derivatives*
  • Phenylethyl Alcohol / chemical synthesis
  • Phenylethyl Alcohol / pharmacology
  • Picrates / chemistry
  • Solubility

Substances

  • Biphenyl Compounds
  • Free Radical Scavengers
  • Indicators and Reagents
  • Mutagens
  • Picrates
  • 3,4-dihydroxyphenylethanol
  • DNA
  • 1,1-diphenyl-2-picrylhydrazyl
  • Lipase
  • Phenylethyl Alcohol