335591-72-5Relevant academic research and scientific papers
Synthesis of novel diosgenyl saponin analogs and evaluation effects of rhamnose moeity on their cytotoxic activity
Meng, Xin,Pan, Yiwu,Liu, Tao,Luo, Chen,Man, Shuli,Zhang, Yongmin,Zhang, Yan
, (2021/06/09)
Diosgenyl saponins, as a type of natural products derived from plants, are the main active component of traditional chinese medicine. Inspiringly, a large number of natural diosgensyl saponins have been shown to exert excellent toxicity to hepatocellular cancer (HCC) cells. In order to better understand the relationship between the structures and their biological effects, a group of diosgenyl saponins (1–4 as natural products and 5 and 6 as their analogs) were efficiently synthesized. The cytotoxic activity of these compounds was evaluated on human hepatocellular carcinoma (HepG2) cells. Structure–activity relationship studies showed that the pentasaccharide or hexasaccharide saponin analogs were relatively less active than their corresponding disaccharide analogue or dioscin. The extension of 4-branched rhamnose moiety on these saponin does not exhibit significant effect on their cytotoxic activity, which disclosed that a certain number and the linkage mode of rhamnose moieties could influence the cytotoxicity of steroid saponins on HepG2 cells.
N-Pentenyl-Type Glycosides for Catalytic Glycosylation and Their Application in Single-Catalyst One-Pot Oligosaccharide Assemblies
Zu, Yujia,Cai, Chenglin,Sheng, Jingyuan,Cheng, Lili,Feng, Yingle,Zhang, Shengyong,Zhang, Qi,Chai, Yonghai
supporting information, p. 8270 - 8274 (2019/10/14)
We have developed a new type of n-pentenyl-type glycosides that can be activated by catalytic amounts of promoter, Hg(NTf2)2 or PPh3AuCl/AgNTf2, at room temperature. The mild activation conditions and outstanding stability of common protection/deprotection manipulations enable the enynyl donors to have broad applications in constructing various glycosidic bonds. Furthermore, under the Hg(NTf2)2-catalyzed conditions, the sequential activation of different types of donors was achieved, based on which a gentiotetrasaccharide was synthesized via the newly developed single-catalyst one-pot strategy.
An improved synthesis of methyl protodioscin. II. A direct E-ring opening by BF3-Et2O/Ac2O from dioscin ester
Wang, Bo,Liu, Yang,Liu, Xin,Cheng, Mao-Sheng
, p. 1015 - 1017,3 (2012/12/11)
A direct E-ring opening of dioscin ester by BF3-Et 2O/Ac2O was studied, and methyl protodioscin was synthesized from dioscin ester in three steps with a total yield of 44%. The details of the E-ring opening reaction was di
Fluorophore-appended steroidal saponin (dioscin and polyphyllin D) derivatives
Yang, Zhiqi,Wong, Ella Lai-Ming,Shum, Tina Yuen-Ting,Che, Chi-Ming,Hui, Yongzheng
, p. 669 - 672 (2007/10/03)
(Chemical Equation Presented) The synthesis of three fluorophore-appended derivatives of dioscin and polyphyllin D is reported herein. Starting from trillin, dansyl derivatives A-C were prepared in overall yields of 7-12% over 7-10 steps. A study of their behavior in a variety of polar solvents suggests that dansyl derivatives A-C are capable of micellar self-assembly and can maintain cytotoxicities (IC50 = 15-18 μM) against the HeLa carcinoma cell line evaluated by standard MTT assay.
An improved synthesis of the saponin, polyphyllin D
Li, Bing,Yu, Biao,Hui, Yongzheng,Li, Ming,Han, Xiuwen,Fung, Kwok-Pui
, p. 1 - 7 (2007/10/03)
Polyphyllin D, namely diosgenyl α-L-rhamnopyranosyl-(1→2)-[(α-L-arabinofuranosyl)- (1→4)]-β-D-glucopyranoside, was synthesized from diosgenyl-β-D-glucopyranoside in four steps and in 30% overall yield, taking advantage of regioselective pivaloylation and
