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

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Roberta Bernini, Maurizio Barontini, Pasquale Mosesso, Gaetano Pepe, Stefan M. Willför, Rainer E. Sjöholm, Patrik C. Eklund and Raffaele Saladino
Publisher: ROYAL SOC CHEMISTRY
Publication year: 2009
Journal: Organic and Biomolecular Chemistry
Journal acronym: ORG BIOMOL CHEM
Volume number: 7
Issue number: 11
Start page: 2367
End page: 2377
Number of pages: 11
ISSN: 1477-0520


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.

Last updated on 2019-19-11 at 05:02