7,4’-二甲氧基洋芹素-5-O-葡萄糖苷的高效合成  

Efficient Synthesis of 7,4’-Dimethylapigenin-5-O-glycoside

作　　者：颜世强[1] 李英霞[1] Yan Shiqiang;Li Yingxia(School of Pharmacy, Fudan University, Shanghai 201203)

机构地区：[1]复旦大学药学院

出　　处：《有机化学》2019年第2期561-565,共5页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.81773576)资助项目~~

摘　　要：7,4'-二甲氧基洋芹素-5-O-葡萄糖苷作为珍贵中药白木香的有效成分具有抑制LPS诱导巨噬细胞生成NO活性.由于5-位羟基具有较强的分子内氢键,5-位氧苷的黄酮类化合物在传统的糖苷化条件不能高效合成.以价廉易得的柚皮素和D-葡萄糖为原料,经选择性羟基保护、硼氢化钠还原、相转移催化下的糖苷化、2,3-二氯-5,6-二氰基对苯醌(DDQ)氧化等6步反应,以36.0%的总收率完成了7,4'-二甲氧基洋芹素-5-O-葡萄糖苷的化学合成,为该化合物进一步的生物活性研究奠定了物质基础.As the active component of precious Chinese medicine Aquilaria sinensis, 7,4'-dimethylapigenin-5-O-glycoside showed inhibitory activity for nitric oxide (NO) production by activated RAW 264.7 cells. Because of the strong intramolecular H-bond, the 5-O-glucosidic linkage in flavonoids could not be efficiently constructed via conventional glycosylation method. In this paper, the efficient chemical synthesis of 7,4'-dimethylapigenin-5-O-glycoside has been achieved for the first time starting from commercially available naringenin and D-glucose via a linear reaction sequence of 6 steps with the overall yield of 36.0%, wherein selective hydroxy protecting, reduction with sodium borohydride, glycosylation under phase transfer catalytic condition, oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and other reactions were used. This work definitely laid the foundation for the further pharmacological study of this natural compound.

关 键 词：白木香 7 4’-二甲氧基洋芹素-5-O-葡萄糖苷 黄酮 化学合成 

分 类 号：TQ28[化学工程—有机化工]