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 Originalartikel i en vetenskaplig tidskrift (referentgranskad)


Interna författare/redaktörer


Publikationens författare: Roberta Bernini, Maurizio Barontini, Pasquale Mosesso, Gaetano Pepe, Stefan M. Willför, Rainer E. Sjöholm, Patrik C. Eklund and Raffaele Saladino
Förläggare: ROYAL SOC CHEMISTRY
Publiceringsår: 2009
Tidskrift: Organic and Biomolecular Chemistry
Tidskriftsakronym: ORG BIOMOL CHEM
Volym: 7
Nummer: 11
Artikelns första sida, sidnummer: 2367
Artikelns sista sida, sidnummer: 2377
Antal sidor: 11
ISSN: 1477-0520


Abstrakt

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.

Senast uppdaterad 2020-23-01 vid 03:22