title: Semisynthesis and bioactive evaluation of oxidized products from 20(S)-ginsenoside Rg3, Rh2, protopanaxadiol (PPD) and their 20(R)-epimers as cytotoxic agents.
abstract: A series of oxidized products have been systematically semisynthesized from 20(S)-ginsenoside Rg3, Rh2, 20(S)-protopanaxadiol (PPD) and their 20(R)-epimers and the majority of these products were evaluated for their cytotoxic activity against HeLa cells and HepG2 cells by MTT assay for the first time. Twenty-two products were obtained and elucidated based on comprehensive (1)H NMR, (13)C NMR, two-dimensional (2D) NMR, and mass spectral data and the results reported in previous literature. All the four ocotillol type saponins (20S,24R(δ86, δ85); 20S,24S(δ87, δ88); 20R,24R(δ86, δ86); 20R,24S(δ86, δ87) were obtained. In addition, eight compounds (3, 8, 9, 10, 15, 16, 19 and 22) with the cyclized side chain were firstly identified. Most of the tested compounds possessed cytotoxicity to a certain degree against the two types of cells which implied these oxidized products could play a certain role on anti-cancer functions of the raw materials in vivo. Meanwhile, the results proved that the configurations at C-20 or C-24 and the number of glycosyl at C-3 have important influence on the cytotoxicity. The products 1, 2, 11-17, 20 and 22 should possess great activities and deserved further investigation as potential cytotoxic agents.
authors.affiliation: College of Chemistry, Jilin University, Changchun 130021, PR China.
authors.forename: Jie
authors.initials: J
authors.lastname: Yang
authors.affiliation: College of Chemistry, Jilin University, Changchun 130021, PR China.
authors.forename: Xuwen
authors.initials: X
authors.lastname: Li
authors.affiliation: College of Chemistry, Jilin University, Changchun 130021, PR China.
authors.forename: Ting
authors.initials: T
authors.lastname: Sun
authors.affiliation: College of Life Sciences, Jilin University, Changchun 130012, PR China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Gao
authors.affiliation: College of Chemistry, Jilin University, Changchun 130021, PR China.
authors.forename: Yanxin
authors.initials: Y
authors.lastname: Chen
authors.affiliation: College of Chemistry, Jilin University, Changchun 130021, PR China. Electronic address: jinyr@jlu.edu.cn.
authors.forename: Yongri
authors.initials: Y
authors.lastname: Jin
authors.affiliation: College of Life Sciences, Jilin University, Changchun 130012, PR China. Electronic address: liyang915@jlu.edu.cn.
authors.forename: Yang
authors.initials: Y
authors.lastname: Li
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D060326:Chemistry Techniques, Synthetic; D036145:Ginsenosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006367:HeLa Cells; D056945:Hep G2 Cells; D006801:Humans; D010084:Oxidation-Reduction; D012502:Sapogenins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D036145:Ginsenosides; D012502:Sapogenins; D014315:Triterpenes; C097367:ginsenoside Rg3; C055305:ginsenoside Rh2; C062916:protopanaxadiol
keywords: Cytotoxicity; Ginsenoside; Ocotillol; Oxidation; Saponin; Semisynthesis