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Molecules 2014, 19(4), 4115-4134; doi:10.3390/molecules19044115

Chemo-Enzymatic Synthesis of Silybin and 2,3-Dehydrosilybin Dimers

Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ-142 20 Prague 4, Czech Republic
Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 3, CZ-775 15 Olomouc, Czech Republic
Author to whom correspondence should be addressed.
Received: 12 February 2014 / Revised: 24 March 2014 / Accepted: 27 March 2014 / Published: 2 April 2014
(This article belongs to the Section Natural Products)
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Divalent or multivalent molecules often show enhanced biological activity relative to the simple monomeric units. Here we present enzymatically and chemically prepared dimers of the flavonolignans silybin and 2,3-dehydrosilybin. Their electrochemical behavior was studied by in situ and ex situ square wave voltammetry. The oxidation of monomers and dimers was similar, but adsorption onto the electrode and cell surfaces was different. A 1,1-diphenyl-2-picrylhydrazyl (DPPH) and an inhibition of microsomal lipoperoxidation assay were performed with same trend of results for silybin and 2,3-dehydrosilybin dimers. Silybin dimer showed better activity than the monomer, while on the contrary 2,3-dehydrosilybin dimer presented weaker antioxidant/antilipoperoxidant activity than its monomer. Cytotoxicity was evaluated on human umbilical vein endothelial cells, normal human adult keratinocytes, mouse fibroblasts (BALB/c 3T3) and human liver hepatocellular carcinoma cell line (HepG2). Silybin dimer was more cytotoxic than the parent compound and in the case of 2,3-dehydrosilybin its dimer showed weaker cytotoxicity than the monomer.
Keywords: flavonolignan; silybin; silibinin; dimerization; electrochemistry; antioxidant; microsomal lipid peroxidation; HUVEC; cytotoxicity flavonolignan; silybin; silibinin; dimerization; electrochemistry; antioxidant; microsomal lipid peroxidation; HUVEC; cytotoxicity

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Vavříková, E.; Vacek, J.; Valentová, K.; Marhol, P.; Ulrichová, J.; Kuzma, M.; Křen, V. Chemo-Enzymatic Synthesis of Silybin and 2,3-Dehydrosilybin Dimers. Molecules 2014, 19, 4115-4134.

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