Bioconversion of silybin to phase I and II microbial metabolites with retained antioxidant activity

被引：37

作者：

Abourashed, Ehab A. ^{[1
]}

Mikell, Julie R. ^{[2
]}

Khan, Ikhlas A. ^{[3
]}

机构：

[1] Chicago State Univ, Dept Pharmaceut Sci, Coll Pharm, Chicago, IL 60628 USA

[2] Univ Mississippi, Natl Ctr Nat Prod Res, Coll Pharm, University, MS 38677 USA

[3] Univ Mississippi, Natl Ctr Nat Prod Res, Dept Pharmacognosy, Res Inst Pharmaceut Sci,Sch Pharm, University, MS 38677 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2012年 / 20卷 / 09期

基金：

美国国家科学基金会;

关键词：

Microbial transformation; Biotransformation; Bioconversion; Milk thistle; Flavonolignan; Silybin; Silibinin; Antioxidant; Free-radical scavenging; CELL-GROWTH; SILIBININ; SILYMARIN; CANCER; CARCINOMA; COMPLEX;

D O I：

10.1016/j.bmc.2012.03.046

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

Microbial transformation of silybin (1), the major flavonolignan of milk thistle (Silybum marianum, Asteraceae), resulted in the isolation of four metabolites. The structures of the isolated metabolites were determined by spectroscopic methods. One phase I metabolite was produced by Beauveria bassiana and was characterized as 8-hydroxysilybin (2). Three phase II metabolites were produced by two Cunninghamella species and were identified as 2,3-dehydrosilybin-3-O-beta-D-glucoside (3), obtained from Cunninghamella species; and silybin-7-sulfate (4) and 2,3-dehydrosilybin-7-sulfate (5), obtained from Cunninghamella blakesleana. Compared to 1 (IC50 284 mu g/mL), the generated metabolites displayed varying levels of antioxidant activities in the DPPH free-radical scavenging assay. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2784 / 2788

页数：5

共 24 条

[1]

Abourashed E.A., 1996, CHEM PHARM BULL, V2000, P48

[2]

Thin-layer densitometry as an alternative tool in the quantitative evaluation of the free radical scavenging activity of natural antioxidants [J].

Abourashed, EA .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2005, 60 (11) :1212-1218

[3]

Abourashed EA, 1999, CURR MED CHEM, V6, P359

[4]

Avila JR, 1999, COMPLEMENTARY ALTERN

[5]

Azerad R, 1999, Adv Biochem Eng Biotechnol, V63, P169

[6]

Inhibition of human carcinoma cell growth and DNA synthesis by silibinin, an active constituent of milk thistle: comparison with silymarin [J].

Bhatia, N ;

Zhao, JF ;

Wolf, DM ;

Agarwal, R .

CANCER LETTERS, 1999, 147 (1-2) :77-84

[7]

Identifying the differential effects of silymarin constituents on cell growth and cell cycle regulatory molecules in human prostate cancer cells [J].

Deep, Gagan ;

Oberlies, Nicholas H. ;

Kro, David J. ;

Agarwal, Rajesh .

INTERNATIONAL JOURNAL OF CANCER, 2008, 123 (01) :41-50

[8]

Antitumour activity of the silybin-phosphatidylcholine complex, 1dB 1016, against human ovarian cancer [J].

Gallo, D ;

Giacomelli, S ;

Ferlini, C ;

Raspaglio, G ;

Apollonio, P ;

Prislei, S ;

Riva, A ;

Morazzoni, P ;

Bombardelli, E ;

Scambia, G .

EUROPEAN JOURNAL OF CANCER, 2003, 39 (16) :2403-2410

[9]

Oxidised derivatives of silybin and their antiradical and antioxidant activity [J].

Gazák, R ;

Svobodová, A ;

Psotová, J ;

Sedmera, P ;

Prikrylová, V ;

Walterová, D ;

Kren, V .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (21) :5677-5687

[10]

Silybin and silymarin -: New and emerging applications in medicine [J].

Gazak, Radek ;

Walterova, Daniela ;

Kren, Vladimir .

CURRENT MEDICINAL CHEMISTRY, 2007, 14 (03) :315-338

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