Study on the inhibitory effect of tannins and flavonoids against the 1,1-diphenyl-2-picrylhydrazyl radical

被引:473
作者
Yokozawa, T [1 ]
Chen, CP
Dong, E
Tanaka, T
Nonaka, GI
Nishioka, I
机构
[1] Toyama Med & Pharmaceut Univ, Res Inst Wakan Yaku, Sugitani, Toyama 9300194, Japan
[2] Nagasaki Univ, Fac Pharmaceut Sci, Nagasaki 8528131, Japan
[3] Kyushu Univ, Fac Pharmaceut Sci, Fukuoka 8128582, Japan
关键词
tannin; flavonoid; 1,1-diphenyl-2-picrylhydrazyl; radical; structure-activity relationship;
D O I
10.1016/S0006-2952(98)00128-2
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
Fifty-one tannins and forty-one flavonoids isolated from Oriental medicinal herbs were evaluated for their antioxidant ability with a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-generating system. The results showed that tannins and certain flavonoids are potential free-radical scavengers, and that their activity against the DPPH radical is closely associated with their chemical structure. A comparison of the two classes of compounds showed that tannins have more potential than flavonoids because almost all the tannins demonstrated significant scavenging action within a low concentration range, whereas the activity of flavonoids varied distinctively among the different compounds. An increase of galloyl groups, molecular weight, and ortho-hydroxyl structure enhanced the activity of tannins, whereas the number and position of hydroxyl groups were important features for the scavenging of free radicals by flavonoids, Moreover, it appeared that when the free hydroxyl group was methoxylated or glycosylated, the inhibitory activity was obviously decreased or even abolished. (C) 1998 Elsevier Science Inc.
引用
收藏
页码:213 / 222
页数:10
相关论文
共 49 条
[1]  
[Anonymous], 1991, EC MED PLANT RES PLA
[2]   Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships [J].
Cao, GH ;
Sofic, E ;
Prior, RL .
FREE RADICAL BIOLOGY AND MEDICINE, 1997, 22 (05) :749-760
[3]  
DEBY C, 1970, CR SOC BIOL, V164, P267
[4]  
HALLIWELL B, 1990, METHOD ENZYMOL, V186, P1
[5]  
HATANO T, 1989, CHEM PHARM BULL, V37, P2016
[6]   RADICAL SCAVENGER ACTIVITY OF DIFFERENT 3',4'-DIHYDROXYFLAVONOLS AND 1,5-DICAFFEOYLQUINIC ACID STUDIED BY INHIBITION OF CHEMILUMINESCENCE [J].
HEILMANN, J ;
MERFORT, I ;
WEISS, M .
PLANTA MEDICA, 1995, 61 (05) :435-438
[7]   THE INHIBITORY EFFECT OF TANNINS ON LIPID-PEROXIDATION OF RAT-HEART MITOCHONDRIA [J].
HONG, CY ;
WANG, CP ;
HUANG, SS ;
HSU, FL .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 1995, 47 (02) :138-142
[8]   STRUCTURE-ACTIVITY RELATIONSHIP OF FLAVONOIDS WITH SUPEROXIDE SCAVENGING ACTIVITY [J].
HU, JP ;
CALOMME, M ;
LASURE, A ;
DEBRUYNE, T ;
PIETERS, L ;
VLIETINCK, A ;
VANDENBERGHE, DA .
BIOLOGICAL TRACE ELEMENT RESEARCH, 1995, 47 (1-3) :327-331
[9]   TANNINS AND RELATED-COMPOUNDS .57. GALLIC ACID-ESTERS OF PROTO-QUERCITOL, QUINIC ACID AND (-)-SHIKIMIC ACID FROM QUERCUS-MONGOLICA AND QUERCUS-MYRSINAEFOLIA [J].
ISHIMARU, K ;
NONAKA, G ;
NISHIOKA, I .
PHYTOCHEMISTRY, 1987, 26 (05) :1501-1504
[10]  
KASHIWADA Y, 1986, CHEM PHARM BULL, V34, P4083