Synthesis and structure/antioxidant activity relationship of novel catecholic antioxidant structural analogues to hydroxytyrosol and its lipophilic esters.
A large panel of novel catecholic antioxidants and their fatty acid or methyl carbonate esters has been synthesized in satisfactory to good yields through a 2-iodoxybenzoic acid (IBX)-mediated aromatic hydroxylation as the key step. The new catechols are structural analogues of naturally occurring hydroxytyrosol (3,4-DHE). To evaluate structure/activity relationships, the antioxidant properties of all catecholic compounds were evaluated in vitro by ABTS assay and on whole cells by DCF fluorometric assay and compared with that of the corresponding already known hydroxytyrosyl derivatives. Results outline that all of the new catechols show antioxidant capacity in vitro higher than that of the corresponding hydroxytyrosyl derivatives. Less evident positive effects have been detected in whole cells experiments. Cytotoxicity experiments, using MTT assay, on a representative set of compounds evidenced no influence in cell survival.
Department of Agriculture, Forests, Nature and Energy (DAFNE), University of Tuscia , Via S. Camillo De Lellis, 01100 Viterbo, Italy.
Roberta
R
Bernini
Fernanda
F
Crisante
Maurizio
M
Barontini
Daniela
D
Tofani
Valentina
V
Balducci
Augusto
A
Gambacorta
D000818:Animals; D000975:Antioxidants / Q000494:pharmacology*; D052160:Benzothiazoles / Q000032:analysis; D002396:Catechols / Q000138:chemical synthesis* / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D004952:Esters / Q000737:chemistry; D005227:Fatty Acids / Q000737:chemistry; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry; D032446:Myoblasts / Q000166:cytology; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000032:analysis
D000975:Antioxidants; D052160:Benzothiazoles; D002396:Catechols; D004952:Esters; D005227:Fatty Acids; D007462:Iodobenzenes; D007463:Iodobenzoates; D013451:Sulfonic Acids; C005975:3,4-dihydroxyphenylethanol; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C476101:o-iodoxybenzoic acid; C034221:catechol; D010626:Phenylethyl Alcohol