Synthesis and Anticancer Activity of 3-O-Acyl Quercetin
CAO Rui-mei1, LI Ke1, FENG Ya-li1, ZHU Wei2, ZHAI Guang-yu1*
1. School of Pharmacy and Chemical Engineering, Zhengzhou University of Industrial Technology, Zhengzhou 451100, China; 2. School of Pharmacy, Zhengzhou University, Zhengzhou 450001, China
Abstract：OBJECTIVE To synthesize quercetin-3-O-acyl ester and explore the antitumor activity.METHODS Using cheap rutin as the raw material, twelve kinds of quercetin-3-O-acyl esters were obtained by benzylation protection, acid hydrolysis, esterification reaction, and then catalytic hydrogenation and debenzylation by Pd/C. Then, infrared(IR), hydrogen spectrum(1H-NMR), carbon spectrum(13C-NMR), and liquid chromatography-mass spectrometry(ESI-MS) were used to determine the structure. Meanwhile, the antioxidant activities of the twelve target compounds were investigated by o-phenanthroline method and 1,1-diphenyl-2-picrylhydrazyl( DPPH ) method, and the antitumor activities were determined by 3-(4,5-dimethylthiazol-2) -2,5 - diphenyltetrazolium bromide(MTT) method.RESULTS The structure of the target compounds was determined by spectroscopic analysis, and the results of antioxidant activity showed that the SC50 of the most target compounds was less than or equal to quercetin, which suggested that 3-OH is not an essential group for the antioxidant activity of quercetin, and the proliferation inhibition of the target compounds on human esophageal cancer cell EC109, human esophageal squamous cell carcinoma EC9706, human gastric cancer cell MGC-803 and human prostate cancer cell PC-3 in vitro was enhanced.CONCLUSION Twelve target compounds are synthesized and their inhibitory effects on tumor cell proliferation are significantly enhanced compared with quercetin.
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2022, Vol. 57 
