Oxidised derivatives of silybin and their antiradical and antioxidant activity

被引：150

作者：

Gazák, R

Svobodová, A

Psotová, J

Sedmera, P

Prikrylová, V

Walterová, D

Kren, V

机构：

[1] Acad Sci Czech Republ, Inst Microbiol, Lab Biotransformat, CZ-14220 Prague, Czech Republic

[2] Palacky Univ, Fac Med, Inst Med Chem & Biochem, CZ-77515 Olomouc, Czech Republic

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2004年 / 12卷 / 21期

关键词：

silymarin; flavonoid; flavonolignan; antioxidant; radical scavenger;

D O I：

10.1016/j.bmc.2004.07.064

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5677 / 5687

页数：11

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