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
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetylation
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Bacteria / drug effects
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Biphenyl Compounds
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Chemical Phenomena
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Chemistry, Physical
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Comet Assay
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DNA / drug effects*
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DNA Damage*
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Free Radical Scavengers / chemical synthesis*
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Free Radical Scavengers / pharmacology*
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Fungi / drug effects
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Humans
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In Vitro Techniques
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Indicators and Reagents
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Lipase / chemistry
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Mutagens / chemistry
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Mutagens / toxicity
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Oxidative Stress / drug effects
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Oxidative Stress / physiology*
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Phenylethyl Alcohol / analogs & derivatives*
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Phenylethyl Alcohol / chemical synthesis
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Phenylethyl Alcohol / pharmacology
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Picrates / chemistry
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Solubility
Substances
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Biphenyl Compounds
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Free Radical Scavengers
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Indicators and Reagents
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Mutagens
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Picrates
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3,4-dihydroxyphenylethanol
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DNA
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1,1-diphenyl-2-picrylhydrazyl
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Lipase
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Phenylethyl Alcohol