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Synthesis of tigogenin MeON-Neoglycosides and their antitumor activity.
Fitoterapia 2018 March
To discover new potent cytotoxic steroidal saponins, a series of tigogenin neoglycosides were synthesized via oxyamine neoglycosylation for the first time. The preliminary bioassays for their in vitro antitumor activities against five human cancer cell lines (A375, A-549, HCT-116, HepG2 and MCF-7) were conducted. The results revealed a sugar-dependent activity profile of their cytotoxicity, the glycoconjugation converted the non-active tigogenin to the most potential product Tg29 ((3R)-N-methoxyamino-tigogenin-β-2-deoxy-d-galactoside) with IC50 value of 2.7μM and 4.6μM against HepG2 and MCF-7 cells respectively. And the 3R-tigogenin neoglycosides exhibited enhanced antitumor activity while the 3S-tigogenin almost showed no activity. Among the five cell lines, HepG2 and MCF-7 cells showed more sensitive cytotoxic responses to the products. Therefore, the neoglycosylation could be a promising strategy for the synthesis of antitumor steroidal saponins and it also proved the essential role of carbohydrate moiety of steroidal saponins in the biological activity.
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