ESR study on the structure and hydroxyl radical-scavenging activity relationships of ginsenosides isolated from Panax ginseng C. A.!MEYER

被引:58
作者
Kang, Ki Sung
Yokozawa, Takako
Yamabe, Noriko
Kim, Hyun Young
Park, Jeong Hill
机构
[1] Toyama Univ, Inst Nat Med, Sugitani, Toyama 9300194, Japan
[2] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea
关键词
panax ginseng; hydroxyl radical; electron spin resonance; 20(S)-Rg(3); 20(S)-protopanaxadiol;
D O I
10.1248/bpb.30.917
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
Ginsenosides have been regarded as the main active components of Panax ginseng C. A. MEYER, and the antioxidant activity of ginsenosides in vivo is well described. However, there has been virtually no report describing the direct free radical-scavenging activities of ginsenosides through the long history of ginseng research. The hydroxyl radical (center dot OH)-scavenging activity test using an electron spin resonance spectrometer (ESR) is suggested to be the most appropriate to measure the antioxidant activities of ginsenosides. Therefore, we investigated the center dot OH-scavenging and ferrous metal ion-chelating activities of several ginsenosides of Panax ginseng using ESR for the identification of active ginsenosides and its structure and activity relationships. As a result, 20(S)-Rg(3) showed the strongest activity, and the next were in the decreasing order of Rb-1, Rg(1), Rc, Rb-2, and Rd when dissolved with water. The center dot OH-scavenging activities of ginsenosides were related to the ferrous metal ion-chelating activities of their aglycone, 20(S)-protopanaxadiol. In addition, the ferrous metal ion-chelating activities of ginsenosides were thought to be influenced by their types of hydrophilic sugar moieties.
引用
收藏
页码:917 / 921
页数:5
相关论文
共 30 条
[1]  
[Anonymous], 1996, KOREAN J GINSENG SCI
[2]   NOVEL MECHANISM FOR OXIDATIVE CLEAVAGE OF GLYCOSIDIC BONDS - EVIDENCE FOR AN OXYGEN-DEPENDENT REACTION [J].
CUI, JF ;
BYSTROM, S ;
ENEROTH, P ;
BJORKHEM, I .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8251-8255
[3]   The antioxidant activity of a triterpenoid glycoside isolated from the berries of Hedera colchica:: 3-O-(β-D-glucopyranosyl)-hederagenin [J].
Gülçin, I ;
Mshvildadze, V ;
Gepdiremen, A ;
Elias, R .
PHYTOTHERAPY RESEARCH, 2006, 20 (02) :130-134
[4]   OXYGEN-TOXICITY, OXYGEN RADICALS, TRANSITION-METALS AND DISEASE [J].
HALLIWELL, B ;
GUTTERIDGE, JMC .
BIOCHEMICAL JOURNAL, 1984, 219 (01) :1-14
[5]  
HALLIWELL B, 1992, J LAB CLIN MED, V119, P598
[6]   Proof of the mysterious efficacy of ginseng: Basic and clinical trials: Metabolic activation of ginsenoside: Deglycosylation by intestinal bacteria and esterification with fatty acid [J].
Hasegawa, H .
JOURNAL OF PHARMACOLOGICAL SCIENCES, 2004, 95 (02) :153-157
[7]   Free radical scavenging capacity as related to antioxidant activity and ginsenoside composition of Asian and North American ginseng extracts [J].
Hu, C ;
Kitts, DD .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 2001, 78 (03) :249-255
[8]   The chemistry behind antioxidant capacity assays [J].
Huang, DJ ;
Ou, BX ;
Prior, RL .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (06) :1841-1856
[9]  
Jeong SM, 2004, MOL CELLS, V18, P383
[10]   Evidence that the tertiary structure of 20(S)-ginsenoside Rg3 with tight hydrophobic packing near the chiral center is important for Na+ channel regulation [J].
Kang, DI ;
Lee, JY ;
Yang, JY ;
Jeong, SM ;
Lee, JH ;
Nah, SY ;
Kim, Y .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2005, 333 (04) :1194-1201