7,4'-二甲氧基洋芹素-5-O-葡萄糖苷的高效合成
收稿日期: 2018-07-23
修回日期: 2018-08-25
网络出版日期: 2018-09-10
基金资助
国家自然科学基金（No.81773576）资助项目.
Efficient Synthesis of 7,4'-Dimethylapigenin-5-O-glycoside
Received date: 2018-07-23
Revised date: 2018-08-25
Online published: 2018-09-10
Supported by
Project supported by the National Natural Science Foundation of China (No. 81773576).
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.
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
颜世强 , 李英霞 . 7,4'-二甲氧基洋芹素-5-O-葡萄糖苷的高效合成[J]. 有机化学, 2019 , 39(2) : 561 -565 . DOI: 10.6023/cjoc201807041
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.
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