Mechanism of the antioxidant action of silybin and 2,3-dehydrosilybin flavonolignans: a joint experimental and theoretical study

The Journal of Physical Chemistry. a
Patrick TrouillasDaniela Walterová

Abstract

Flavonolignans from silymarin, the standardized plant extract obtained from thistle, exhibit various antioxidant activities, which correlate with the other biological and therapeutic properties of that extract. To highlight the mode of action of flavonolignans as free radical scavengers and antioxidants, 10 flavonolignans, selectively methylated at different positions, were tested in vitro for their capacity to scavenge radicals (DPPH and superoxide) and to inhibit the lipid peroxidation induced on microsome membranes. The results are rationalized on the basis of (i) the oxidation potentials experimentally obtained by cyclic voltammetry and (ii) the theoretical redox properties obtained by quantum-chemical calculations (using a polarizable continuum model (PCM)-density functional theory (DFT) approach) of the ionization potentials and the O-H bond dissociation enthalpies (BDEs) of each OH group of the 10 compounds. We clearly establish the importance of the 3-OH and 20-OH groups as H donors, in the presence of the 2,3 double bond and the catechol moiety in the E-ring, respectively. For silybin derivatives (i.e., in the absence of the 2,3 double bond), secondary mechanisms (i.e., electron transfer (ET) mechanism and adduct forma...Continue Reading

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Citations

Nov 19, 2013·Journal of Computer-aided Molecular Design·El Hassane AnouarPatrick Trouillas
Dec 15, 2010·Journal of Bioenergetics and Biomembranes·Eva GabrielováMartin Modrianský
Jun 3, 2011·World Journal of Gastroenterology : WJG·Carmela Loguercio, Davide Festi
Mar 26, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anouar El HassaneJean-Frédéric F Weber
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