Hydroxytyrosol lipophilic analogues: enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection.
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.
Grasso
Salvatore
S
Dipartimento di Chimica Biologica, Chimica Medica e Biologia Molecolare, Università di Catania, Viale A. Doria 6, 95125 Catania, Italy.
Siracusa
Laura
L
Spatafora
Carmela
C
Renis
Marcella
M
Tringali
Corrado
C
D000107:Acetylation; D001419:Bacteria / Q000187:drug effects; D001713:Biphenyl Compounds; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D020552:Comet Assay; D004247:DNA / Q000187:drug effects*; D004249:DNA Damage; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D006801:Humans; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D008049:Lipase / Q000737:chemistry; D009153:Mutagens / Q000737:chemistry / Q000633:toxicity; D018384:Oxidative Stress / Q000187:drug effects / Q000502:physiology*; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D010851:Picrates / Q000737:chemistry; D012995:Solubility
D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D007202:Indicators and Reagents; D009153:Mutagens; D010851:Picrates; C005975:3,4-dihydroxyphenylethanol; D004247:DNA; C004931:1,1-diphenyl-2-picrylhydrazyl; D008049:Lipase; D010626:Phenylethyl Alcohol