- Synthesis of novel diosgenyl saponin analogs and evaluation effects of rhamnose moeity on their cytotoxic activity
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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.
- Meng, Xin,Pan, Yiwu,Liu, Tao,Luo, Chen,Man, Shuli,Zhang, Yongmin,Zhang, Yan
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- Fluorophore-appended steroidal saponin (dioscin and polyphyllin D) derivatives
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(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.
- Yang, Zhiqi,Wong, Ella Lai-Ming,Shum, Tina Yuen-Ting,Che, Chi-Ming,Hui, Yongzheng
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p. 669 - 672
(2007/10/03)
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- An improved synthesis of the saponin, polyphyllin D
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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
- Li, Bing,Yu, Biao,Hui, Yongzheng,Li, Ming,Han, Xiuwen,Fung, Kwok-Pui
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- Synthesis of three diosgenyl saponins: Dioscin, polyphyllin D, and balanitin 7
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Dioscin, polyphyllin D, and balanitin 7, which belong to a group of structurally similar diosgenyl saponins with promising bioactivities, were synthesized by stepwise glycosylation. Copyright (C) 1999 Elsevier Science Ltd.
- Deng, Shaojiang,Yu, Biao,Hui, Yongzheng,Yu, Hai,Han, Xiuwen
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- A facile synthetic approach to a group of structurally typical diosgenyl saponins
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A facile approach was developed for synthesizing an important group of plant diosgenyl saponins, three members (dioscin, polyphyllin D, and balanitin 7) with promising bioactivities were prepared.
- Deng, Shaojiang,Yu, Biao,Hui, Yongzheng
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p. 6511 - 6514
(2007/10/03)
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