Abstract: To improve the water solubility without affecting the anti-platelet aggregation activity of quercetin,two acylated derivatives of quercetin,namely quercetin-3-O-acetate and quercetin-3-O-propionate,were synthesized by a four step synthesis route,benzylation-hydrolysis-acylation-hydrogenation,with rutin as raw material.The water solubility of quercetin-3-O-acetate and quercetin-3-O-propionate were 243.27,8.13 μg/mL,respectively,both of which were higher than that of quercetin.These two derivatives inhibited platelet aggregation induced by adenosine diphosphate both in vitro and in vivo. Their half maximal inhibitory concentration in vitro were 94.1,204.9 μmol/L,respectively and both lower than that of quercetin.They also showed higher anti-platelet aggregation activity than quercetin in vivo.The results suggested that the acylation of hydroxyl group at C3 of quercetin with aliphatic acyl donors containing two or three carbons not only provided the suitable water solubility but also improved the anti-platelet aggregation activity of quercetin.

Key words: quercetin, regioselective acylation, water solubility, anti-platelet aggregation