7-羟基-4′-(β-D-吡喃葡萄糖苷基)葛根素的合成

Synthesis and Characterization of 7-Hydroxyl-4’-(β-D-glucopyranosyloxy)puerarin Derivatives

摘要:

先将葡萄糖经酰化和溴化反应制备α-溴代四乙酰葡萄糖，再与葛根素在丙酮溶液中碳酸钾作用下醚化得到7-羟基-4′-(2,3,4,6-四乙酰基-β-D-吡喃葡萄糖苷基)葛根素，收率61.4%（以葛根素计）。最后进一步在甲醇溶液中与碳酸钠作用得到目标产物7-羟基-4′-(β-D-吡喃葡萄糖苷基)葛根素，收率90.5%。中间体和产物结构经1H NMR、MS确证。7-羟基-4′-(β-D-吡喃葡萄糖苷基)葛根素的水溶性与葛根素相比，提高了15.3倍。

Abstract:

Glucose via acylation and bromization pathway gave acetobromo-α-D-glucose. The etherification of puerarin to 7-Hydroxyl-4′-(2,3,4,6-tetraacetyl- β-D-glucopyranosyloxy) puerarin with acetobromo-α-D-glucose was carried out in acetone in the presence of potassium carbonate. The isolated yield was 61.4% (based on puerarin). Finally, 7-hydroxyl-4′-(β-D- glucopyranosyloxy)puerarin was obtained via deacetylation in anhydrous methanol in the presence of potassium carbonate with isolated yield of 90.5%. Structures of intermediates and final product were characterized by 1H NMR spectra and MS. Compared to puerarin, the water-soluble of 7-hydroxyl-4′-(β-D-glucopyranosyloxy) puerarin was increased by 15.3 times.