Chemo-enzymatic synthesis of silybin and 2,3-dehydrosilybin dimers

0428380 - MBÚ 2015 RIV CH eng J - Článek v odborném periodiku
Vavříková, Eva - Vacek, J. - Valentová, Kateřina - Marhol, Petr - Ulrichová, J. - Kuzma, Marek - Křen, Vladimír
Chemo-enzymatic synthesis of silybin and 2,3-dehydrosilybin dimers.
Molecules. Roč. 19, č. 4 (2014), s. 4115-4134. E-ISSN 1420-3049
Grant CEP: GA MŠMT(CZ) LD13041
Institucionální podpora: RVO:61388971
Klíčová slova: flavonolignan * silybin * silibinin
Kód oboru RIV: CE - Biochemie
Impakt faktor: 2.416, rok: 2014

Divalent or multivalent molecules often show enhanced biological aktivity 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
Trvalý link: http://hdl.handle.net/11104/0233765