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
Author(s)
Date Issued
2009
Type
Article
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–H2O 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
Additional information
L'articolo è disponibile sul sito dell'editore: http://www.rsc.org
Citation
Bernini, R. et al. 2009. 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. "Organic & Biomolecular Chemistry" 7(11): 2367-2377
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