Oxidised derivatives of silybin and their antiradical and antioxidant activity

[Display omitted] Carboxylic acids derived from silybin ( 1) and 2,3-dehydrosilybin ( 2) with improved water solubility were prepared by selective oxidation of parent compounds and a new inexpensive method for preparation of 2,3-dehydrosilybin from silybin was developed and optimised. The antioxidat...

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Published in:Bioorganic & medicinal chemistry 2004-11, Vol.12 (21), p.5677-5687
Main Authors: Gažák, Radek, Svobodová, Alena, Psotová, Jitka, Sedmera, Petr, Přikrylová, Věra, Walterová, Daniela, Křen, Vladimı́r
Format: Article
Language:English
Subjects:
Animals
Antioxidant
Antioxidants - chemistry
Antioxidants - pharmacology
Biological and medical sciences
Flavonoid
Flavonolignan
Free Radical Scavengers - chemistry
Free Radical Scavengers - pharmacology
General and cellular metabolism. Vitamins
Medical sciences
Microsomes, Liver - drug effects
Microsomes, Liver - metabolism
Oxidation-Reduction - drug effects
Pharmacology. Drug treatments
Radical scavenger
Rats
Silymarin
Silymarin - chemistry
Silymarin - pharmacology
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Summary:[Display omitted] Carboxylic acids derived from silybin ( 1) and 2,3-dehydrosilybin ( 2) with improved water solubility were prepared by selective oxidation of parent compounds and a new inexpensive method for preparation of 2,3-dehydrosilybin from silybin was developed and optimised. The antioxidative properties of the above-mentioned compounds and of side product 3a from oxidation of compound 1 were determined by cyclic voltammetry, free radical scavenging (DPPH, superoxide) assays, and by inhibition of in vitro generated liver microsomal lipid peroxidation. Dehydrogenation at C (2)–C (3) in flavonolignans (silybin vs 2,3-dehydrosilybin; silybinic acid vs 2,3-dehydrosilybinic acid) strongly improved antioxidative properties (analogously as in flavonoids taxifolin vs quercetin). Thus, in antioxidative properties, dehydrosilybin was superior to silybin by one order, but its water solubility is too low for application in aqueous milieu. On the other hand, 2,3-dehydrosilybinic acid is a fairly soluble derivative with antilipoperoxidation and antiradical activities better than that of silybin.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2004.07.064