In vitro study of the relationship between the structure of ginsenoside and its antioxidative or prooxidative activity in free radical induced hemolysis of human erythrocytes.
Ginsenoside, the major active component in Panax ginseng, which has been used in traditional Chinese medicine, contains a series of derivatives of the triterpene dammarane being attached by some sugar moieties. To clarify the relationship between the structure of ginsenoside and its properties, 11 individual ginsenosides, along with the central structures of ginsenoside, protopanaxadiol and protopanaxatriol, are used in 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH) induced hemolysis of human erythrocytes, a good experimental model to research free radical induced membrane damage and to evaluate the antioxidative or prooxidative activities of various antioxidants conveniently. It is found that the central structures of ginsenosides, either protopanaxadiol or protopanaxatriol, play a prooxidative role in AAPH-induced hemolysis of erythrocytes. As to the individual ginsenoside, if there are no sugar moieties attached to the 20-position of the triterpene dammarane, the ginsenoside acts as a prooxidant, that is, Rg3, Rh2, and Rg2. A glucose attached to the 6-position instead of the 20-position sugar moieties can make the ginsenoside an antioxidant, that is, Rh1. The antioxidants among ginsenosides follow two different mechanisms that can be expressed mathematically by the Boltzmann equation, that is, Rc and Rb1, and a polynomial equation, that is, Re, Rd, R1, Rg1, Rb3, and Rh1. The orders of antioxidative ability are Rc > Rb1 and Re > Rd > R1 > Rg1 > Rb3 > Rh1, respectively.
Liu
Zai-Qun
ZQ
Department of Organic Chemistry and Center for Teaching, College of Chemistry, Jilin University, No. 119 Jiefang Road, Changchun 130023, China. zaiqun-liu@mail,jlu.edu.cn
Luo
Xu-Yang
XY
Liu
Guo-Zong
GZ
Chen
Yan-Ping
YP
Wang
Zhi-Cai
ZC
Sun
Yun-Xiu
YX
D000578:Amidines / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004912:Erythrocytes / Q000187:drug effects*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D036145:Ginsenosides / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D006461:Hemolysis / Q000187:drug effects; D016877:Oxidants / Q000494:pharmacology; D005894:Panax / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000578:Amidines; D000975:Antioxidants; D016166:Free Radical Scavengers; D036145:Ginsenosides; D016877:Oxidants; C046728:2,2'-azobis(2-amidinopropane)