title: A selective de-O-methylation of guaiacyl lignans to corresponding catechol derivatives by 2-iodoxybenzoic acid (IBX). The role of the catechol moiety on the toxicity of lignans.
abstract: We report here the first selective de-O-methylation of a large panel of guaiacyl lignans to the corresponding catechol derivatives by using IBX as primary oxidant under green conditions (dimethyl carbonate-H(2)O solvent) through an in situ reduction procedure. The influence of the catechol moiety on the cytotoxicity and genotoxicity of new lignan derivatives has been investigated. The results obtained indicated that the presence of the catechol moiety sharply enhances the clastogenic potential (e.g. induction of chromosomal aberrations), the cytotoxicity and the modulation of cell cycle progression with respect to the parent compounds. Thus, despite the in vitro antioxidant activity usually described for catechol derivatives, our results show for the first time the generation of a clastogenic potential, highly indicative of a long-term genetic and cancer risk.
authors.affiliation: Department of Agrobiology and Agrochemistry, University of Tuscia, 01100, Viterbo, Italy. berninir@unitus.it
authors.forename: Roberta
authors.initials: R
authors.lastname: Bernini
authors.forename: Maurizio
authors.initials: M
authors.lastname: Barontini
authors.forename: Pasquale
authors.initials: P
authors.lastname: Mosesso
authors.forename: Gaetano
authors.initials: G
authors.lastname: Pepe
authors.forename: Stefan M
authors.initials: SM
authors.lastname: Willför
authors.forename: Rainer E
authors.initials: RE
authors.lastname: Sjöholm
authors.forename: Patrik C
authors.initials: PC
authors.lastname: Eklund
authors.forename: Raffaele
authors.initials: R
authors.lastname: Saladino
mesh_terms: D000818:Animals; D002396:Catechols / Q000737:chemistry* / Q000633:toxicity*; D002455:Cell Division / Q000187:drug effects; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D006224:Cricetinae; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry; D017705:Lignans / Q000737:chemistry* / Q000633:toxicity*; D008745:Methylation; D009152:Mutagenicity Tests; D010084:Oxidation-Reduction
chemical_list: D002396:Catechols; D007462:Iodobenzenes; D007463:Iodobenzoates; D017705:Lignans; C476101:o-iodoxybenzoic acid; C034221:catechol