Liu Zai-Qun, Luo Xu-Yang, Liu Guo-Zong, Chen Yan-Ping, Wang Zhi-Cai, Sun Yun-Xiu
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
J Agric Food Chem. 2003 Apr 23;51(9):2555-8. doi: 10.1021/jf026228i.
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.
人参皂苷是人参中的主要活性成分，已被用于传统中药，它包含一系列由一些糖基连接的三萜达玛烷衍生物。为了阐明人参皂苷的结构与其性质之间的关系，11种单体人参皂苷以及人参皂苷、原人参二醇和原人参三醇的核心结构，被用于2,2'-偶氮二异丁脒盐酸盐（AAPH）诱导的人红细胞溶血实验，这是一个研究自由基诱导的膜损伤以及方便评估各种抗氧化剂的抗氧化或促氧化活性的良好实验模型。研究发现，人参皂苷的核心结构，无论是原人参二醇还是原人参三醇，在AAPH诱导的红细胞溶血中都起促氧化作用。对于单体人参皂苷，如果在三萜达玛烷的20位没有连接糖基，该人参皂苷就作为促氧化剂，即Rg3、Rh2和Rg2。在6位而不是20位连接葡萄糖糖基可使该人参皂苷成为抗氧化剂，即Rh1。人参皂苷中的抗氧化剂遵循两种不同的机制，这两种机制可用玻尔兹曼方程进行数学表达，即Rc和Rb1，以及多项式方程，即Re、Rd、R1、Rg1、Rb3和Rh1。抗氧化能力的顺序分别为Rc > Rb1和Re > Rd > R1 > Rg1 > Rb3 > Rh1。
