Resveratrol-Related Polymethoxystilbene Glycosides: Synthesis, Antiproliferative Activity, and Glycosidase Inhibition

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• 作者：Nunzio Cardullo ; Carmela Spatafora ; Nicol貌 Musso ; Vincenza Barresi ; Daniele Condorelli ; Corrado Tringali
• 刊名：Journal of Natural Products
• 出版年：2015
• 出版时间：November 25, 2015
• 年：2015
• 卷：78
• 期：11
• 页码：2675-2683
• 全文大小：416K
• ISSN：1520-6025

文摘

A small library of polymethoxystilbene glycosides (20鈥?b>25) related to the natural polyphenol resveratrol have been synthesized and subjected, together with their aglycones 17鈥?b>19, to an antiproliferative activity bioassay toward Caco-2 and SH-SY5Y cancer cells. Six of the compounds exhibit antiproliferative activity against at least one cell line. In particular, compounds 17 and 18 proved highly active on at least one of the two cell cultures. Compound 18 showed a GI₅₀ value of 3 渭M against Caco-2 cells, a value comparable to that of the anticancer drug 5-fluorouracil. The closely related compound 19 proved inactive, and its conjugates 22 and 25 showed weak cell growth inhibition. The results indicate that minimal differences in the structure of both polymethoxystilbenes and their glycosides can substantially affect the antiproliferative activity. The possible hydrolytic release of the aglycones 17鈥?b>19 by 尾-glucosidase or 尾-galactosidase was also evaluated. Compounds 20鈥?b>25 were also tested as potential 尾-glucosidase, 尾-galactosidase, and 伪-glucosidase inhibitors. A promising inhibitory activity toward 伪-glucosidase was observed for 21 (IC₅₀ = 78 渭M) and 25 (IC₅₀ = 70 渭M), which might be indicative of their potential as lead compounds for development of antidiabetic or antiobesity agents.