Antioxidant constituents from rhubarb: Structural requirements of stilbenes for the activity and structures of two new anthraquinone glucosides

被引:153
作者
Matsuda, H [1 ]
Morikawa, T [1 ]
Toguchida, I [1 ]
Park, JY [1 ]
Harima, S [1 ]
Yoshikawa, M [1 ]
机构
[1] Kyoto Pharmaceut Univ, Yamashima Ku, Kyoto 6078412, Japan
关键词
D O I
10.1016/S0968-0896(00)00215-7
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
The methanolic extracts from five kinds of rhubarb were found to show scavenging activity for DPPH radical and .O-2(-). Two new anthraquinone glucosides were isolated from the rhizome of Rheum undulatum L. together with two anthraquinone glucosides, a naphthalene glucoside, and 10 stilbenes. In the screening test for radical scavenging activity of rhubarb constituents, stilbenes and a naphthalene glucoside showed activity, but anthraquinones and sennosides did not. In addition, most stilbenes inhibited lipid peroxidation of erythrocyte membrane by tert-butyl hydroperoxide. Detailed examination of the scavenging effect on various related compounds suggested the following structural requirements; 1) phenolic hydroxyl groups are essential to show the activity; 2) galloyl moiety enhances the activity; 3) glucoside moiety reduces the activity; 4) dihydrostilbene derivatives maintain the scavenging activity for the DPPH radical, but they show weak activity for .O-2(-) In addition, several stilbenes with both the 3-hydroxyl and 4'-methoxyl groups inhibited xanthine oxidase. (C) 2000 Elsevier Science Ltd. All rights reserved.
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页码:41 / 50
页数:10
相关论文
共 33 条
[1]   NEW NATURAL STILBENE GLUCOSIDE FROM RHEUM-RHAPONTICUM (POLYGONACEAE) [J].
BANKS, HJ ;
CAMERON, DW .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1971, 24 (11) :2427-&
[2]   ANTIOXIDANT DETERMINATIONS BY THE USE OF A STABLE FREE RADICAL [J].
BLOIS, MS .
NATURE, 1958, 181 (4617) :1199-1200
[3]   3,3',5'-TRI-0-METHYLPICEATANNOL AND 4,3',5'-TRI-0-METHYLPICEATANNOL - IMPROVEMENTS OVER PICEATANNOL IN BIOACTIVITY [J].
GILL, MT ;
BAJAJ, R ;
CHANG, CJ ;
NICHOLS, DE ;
MCLAUGHLIN, JL .
JOURNAL OF NATURAL PRODUCTS, 1987, 50 (01) :36-40
[4]  
GROSS SPA, 1999, FREE RADICAL RES, V31, P597
[5]  
HARA S, 1986, CHEM PHARM BULL, V34, P1843
[6]  
HATANO T, 1990, CHEM PHARM BULL, V38, P1224
[7]  
IMANARI T, 1977, IGAKU NO AYUMI, V101, P496
[8]  
KASHIWADA Y, 1984, CHEM PHARM BULL, V32, P3501
[9]  
KATO T, 1987, Shoyakugaku Zasshi, V41, P67
[10]   FREE-RADICALS AS MEDIATORS OF TISSUE-INJURY AND DISEASE [J].
KEHRER, JP .
CRITICAL REVIEWS IN TOXICOLOGY, 1993, 23 (01) :21-48