Antioxidant properties of silybin glycosides

Authors

  • Pavel Kosina,

    1. Centre for Bioanalytical Research, Palacký University, Hněvotínská 3, 775 15 Olomouc, Czech Republic
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  • Vladimír Křen,

    1. Institute of Microbiology, Laboratory of Biotransformation, Academy of Sciences of the Czech Republic, Videňská 1083, 142 00 Prague 4, Czech Republic
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  • Rolf Gebhardt,

    1. Department of Biochemistry, Faculty of Medicine, University Leipzig, Liebigstr. 16, 04103 Leipzig, Germany
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  • František Grambal,

    1. Department of Inorganic and Physical Chemistry, Faculty of Natural Sciences, Palacký University, Tř. Svobody 8, 771 00 Olomouc, Czech Republic
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  • Jitka Ulrichová,

    1. Institute of Medical Chemistry and Biochemistry, Medical Faculty, Palacký University, Hněvotínská 3, 775 15 Olomouc, Czech Republic
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  • Daniela Walterová

    Corresponding author
    1. Institute of Medical Chemistry and Biochemistry, Medical Faculty, Palacký University, Hněvotínská 3, 775 15 Olomouc, Czech Republic
    • Institute of Medical Chemistry, Medical Faculty, Palacký University, Hněvotínská 3, 775 15 Olomouc, Czech Republic
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Abstract

New soluble derivatives of the hepatoprotective flavonolignan silybin (1), namely silybin galactoside (2), glucoside (3), lactoside (4) and maltoside (5) were investigated for their radical scavenging and antilipoperoxidation properties. According to cyclic voltammetry the results show that glycosides are weaker electron donors than silybin, although it was of interest that they were found to be more potent scavengers of the 1,1-diphenyl-2-picrylhydrazyl and the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid)-derived radicals. The glycosides (2)–(5) were more efficient than silybin in preventing tert-butylhydroperoxide-induced lipoperoxidation of rat liver mitochondrial membranes. Furthermore, glycosides (2)–(5) were significantly more cytoprotective than silybin in tert-butylhydroperoxide-damaged rat erythrocytes and primary hepatocyte cultures. Glycosylation of silybin substantially reduced its toxic effects in primary cultured hepatocytes observed during prolonged incubation. These results suggest that silybin glycosides are suitable soluble derivatives of silybin for experimental studies and may have therapeutic potential. Copyright © 2002 John Wiley & Sons, Ltd.

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