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

doi:10.5246/jcps.2017.08.062

Journal of Chinese Pharmaceutical Sciences ›› 2017, Vol. 26 ›› Issue (8): 556-565.DOI: 10.5246/jcps.2017.08.062

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

Bowei Yang¹, Danlin Liang¹, Xiong Wei¹, Xiangbao Meng¹, Zhongjun Li^1,2*

1. State Key Laboratory of Natural and Biomimetic Drugs; Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China
2. National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China

Received:2017-05-22 Revised:2017-07-15 Online:2017-08-31 Published:2017-07-28
Contact: Tel.: +86-010-82805496, E-mail: zjli@bjmu.edu.cn
Supported by:
The National Research Foundation for the Doctoral Program of Higher Education of China (Grant No. 20130001110058).

Abstract

Abstract:

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 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. Herein we described 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.

Key words: Mangiferin-7-O-β-D-glucuronide, Semi-synthesis, Regioselective protection, Glycosylation

CLC Number:

R916

Supporting:

Bowei Yang, Danlin Liang, Xiong Wei, Xiangbao Meng, Zhongjun Li. Semi-synthesis of mangiferin-7-O-β-D-glucuronide[J]. Journal of Chinese Pharmaceutical Sciences, 2017, 26(8): 556-565.

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

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