School of Pharmacy, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Yantai University, Yantai, 264005, P.R. China.
School of Pharmacy, Binzhou Medical University, Yantai 264003, China.
Mini Rev Med Chem. 2023;23(7):804-820. doi: 10.2174/1389557522666221012095258.
Ginseng, the roots and/or rhizomes of Panax spp.(Araliaceae), has been used as a popular herbal medicine in East Asia for at least two millennia. As a functional food and healthenhancing supplement, ginseng has been shown to have a wide range of pharmacological effects on cognition and blood circulation as well as antioxidant, antitumor, and anti-fatigue effects. The main active properties of ginseng are considered to be the triterpene saponins, often referred to as ginsenosides, which are the basis for their wide-ranging pharmacological effects. Four of these glycosides, including protopanaxadiol, protopanaxatriol, ocotillol, and oleanolic acid, are the most common saponins found in ginseng. Compared to other ginsenosides, the C-20 chimeric ginsenosides, including Rg3, Rh2, Rg2, Rh1, PF11, C-20, and C-24, as well as epimeric ocotillol-type saponins and their derivatives exhibit significant, steric differences in biological activity and metabolism. 20(R)-ginseng saponins, one class of important rare ginsenosides, have antitumor, antioxidative, antifatigue, neuroprotective and osteoclastogenesis inhibitory effects. However, 20(R)- ginsenosides are rare in natural products and are usually prepared from 20(S)-isomers through chemical differential isomerization and microbial transformation. The C20 configuration of 20(R)-ginseng saponins is usually determined by C NMR and X-ray single-crystal diffraction. There are regular differences in the chemical shift values of some of the carbons of the 20(S)- and 20(R)-epimers, including C-17, C-21, and C-22. Owing to their chemical structure and pharmacological and stereoselective properties, 20(R)-ginseng saponins have attracted a great deal of attention in recent years. Herein, the stereoscopic differences in the identification, bioactivity, and metabolism of C-20 and C-24 epimeric ginseng saponins are summarized.
人参是五加科人参属植物的根和/或根茎，作为一种流行的草药，在东亚地区已经使用了至少两千多年。作为一种功能性食品和健康增强补品，人参已被证明具有广泛的药理作用，包括对认知和血液循环的影响，以及抗氧化、抗肿瘤和抗疲劳作用。人参的主要活性成分被认为是三萜皂苷，通常称为人参皂苷，这是其广泛的药理作用的基础。其中四种糖苷，包括原人参二醇、原人参三醇、奥克梯隆醇和齐墩果酸，是人参中最常见的皂苷。与其他人参皂苷相比，C-20 杂合型人参皂苷，包括 Rg3、Rh2、Rg2、Rh1、PF11、C-20 和 C-24，以及差向奥克梯隆醇型皂苷及其衍生物在生物活性和代谢方面表现出显著的立体差异。20(R)-人参皂苷是一类重要的稀有皂苷，具有抗肿瘤、抗氧化、抗疲劳、神经保护和破骨细胞抑制作用。然而，20(R)-人参皂苷在天然产物中很少见，通常通过化学差向异构化和微生物转化从 20(S)-异构体中制备。20(R)-人参皂苷的 C20 构型通常通过 13C NMR 和 X 射线单晶衍射确定。20(S)-和 20(R)-差向异构体的一些碳原子的化学位移值存在规律差异，包括 C-17、C-21 和 C-22。由于其化学结构和药理学及立体选择性，20(R)-人参皂苷近年来引起了广泛关注。本文综述了 C-20 和 C-24 差向异构人参皂苷的鉴定、生物活性和代谢的立体差异。
