Syntheses and Anti-cancer Activities of Glycosylated Derivatives of Diosgenin

doi:10.1007/s40242-016-6296-y

Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (1): 80-86.doi: 10.1007/s40242-016-6296-y

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Syntheses and Anti-cancer Activities of Glycosylated Derivatives of Diosgenin

TAN Yonghua¹, XIAO Xiao^1,2, YAO Jianing¹, HAN Fei¹, LOU Huayong^1,2, LUO Heng^1,2, LIANG Guangyi¹, BEN-DAVID Yaacov^1,2, PAN Weidong^1,2

1. Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550002, P. R. China;
2. Key Laboratory of Chemistry for Natural Products of Guizhou Medical University, Guiyang 550001, P. R. China

Received:2016-07-11 Revised:2016-10-18 Online:2017-02-01 Published:2016-11-07
Contact: BEN-DAVID Yaacov,E-mail:yaacovbendavid@hotmail.com;PAN Weidong,E-mail:wdpan@163.com E-mail:yaacovbendavid@hotmail.com;wdpan@163.com
Supported by:
Supported by the National Natural Science Foundation of China(Nos.81360479, 81472609) and the Project of the Science and Technology Department of Guizhou Province, China(Nos.QKHRC[2016]4037,QKHRCTD[2015]4026, QKHJZ[2014]2099).

Abstract

Abstract:

In order to obtain better anti-cancer compounds, nine glycosylated derivatives were designed and synthesized using diosgenin as starting material. Their structures were confirmed by ¹H NMR, ¹³C NMR and MS spectra. The anti-cancer activities of intermediate compounds 5a-5i and the target compounds 6a-6i were investigated against human leukemia HEL, K562, HL60 and melanoma WM9 cell lines via MTT method. The bioassay results show that these derivatives possess good inhibitory activities against the four cancer cell lines. Furthermore, these derivatives show better inhibitory activities against K562 than against other cell lines, and most derivatives show better inhibitory activities than the parental material. Moreover, compounds 6a-6i are more active than their intermediates 5a-5i when against these cells. The above results demonstrate the effects of glycosylation on 3-OH of diosgenin and acetylation of the sugar moiety on their antitumor activities.

Key words: Diosgenin, Glycosylation, Anti-cancer activity

TAN Yonghua, XIAO Xiao, YAO Jianing, HAN Fei, LOU Huayong, LUO Heng, LIANG Guangyi, BEN-DAVID Yaacov, PAN Weidong. Syntheses and Anti-cancer Activities of Glycosylated Derivatives of Diosgenin[J]. Chemical Research in Chinese Universities, 2017, 33(1): 80-86.

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Syntheses and Anti-cancer Activities of Glycosylated Derivatives of Diosgenin

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