Semi-synthesis of Mangiferin-7-O-β-D-glucuronide

YANG Bowei; LIANG Danlin; WEI Xiong; MENG Xiangbao; LI Zhongjun

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Semi-synthesis of Mangiferin-7-O-β-D-glucuronide

YANG Bowei,LIANG Danlin,WEI Xiong,MENG Xiangbao,LI Zhongjun * #

The State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191

*Correspondence author

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Funding: The National Research Foundation for the Doctoral Program of Higher Education of China （No.No.20130001110058）

Opened online: 9 May 2017

Accepted by: none

Citation: YANG Bowei,LIANG Danlin,WEI Xiong.Semi-synthesis of Mangiferin-7-O-β-D-glucuronide[OL]. [ 9 May 2017] http://en.paper.edu.cn/en_releasepaper/content/4729417

Mangiferin is a natural plant polyphenol with a structure of xanthone C-glycoside and it displays a wide spectrum of pharmacological activities. Investigation of the metabolites of mangiferin is valuable in studying on the mechanisms of its various pharmacological properties and developing novel drugs from the mangiferin derivatives. Among the metabolites of mangiferin, mangiferin-7-O-β-D-glucuronide has been reported as the phase II metabolite of mangiferin. Here we describe the first semi-synthesis of mangiferin-7-O-β-D-glucuronide with the natural product mangiferin as the starting material. In this work, we adopted several regioselective protection procedures to distinguish the different hydroxyl groups in the structure of mangiferin. And we accomplished the glycosylation under the phase-transfer catalysis conditions. In this method, we efficiently synthesized the glucuronide derivative of mangiferin in 10 steps with highly regioselective protection.

Keywords:organic chemistry; mangiferin-7-O-β-D-glucuronide; semi-synthesis; regioselective protection; glycosylation

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