Chinese Journal of Organic Chemistry >
Design, Synthesis of Pentacyclic Triterpenoid Glucose Conjugate and in vitro Activity against Influenza Virus
Received date: 2021-11-03
Revised date: 2021-12-31
Online published: 2022-01-27
Supported by
National Natural Science Foundation of China(22167018); Foundation of State Key Laboratory of Natural and Biomimetic Drugs(K202003); Yunnan Fundamental Research Projects(2019FB125); Yunnan Fundamental Research Projects(2018FB145)
Previous studies have revealed that oleanolic acid (OA) C28-glucose conjugate displayed potent anti-influenza viral activity in vitro. However, the effect of pentacyclic triterpene scaffold coupled with glucose on anti-influenza virus activity has not been clarified. Herein, as a continuous further study, a series of pentacyclic triterpene-glucose conjugates were prepared via CuAAC reaction, and the anti-influenza activity of these compounds was evaluated in vitro. Among them, compound 4d, an betulinic acid (BA)-glucose conjugate, showed potent anti-influenza virus activity (IC50 value of 9.09 μmol/L), and no obvious cytotoxic effect on MDCK (Madin-Darbey Canine Kidney) cells was observed (CC50>100 μmol/L). Structure-activity relationship studies showed that both triterpene scaffolds and glucose moiety have important effects on the anti-viral activity. Overall, this finding further extends the utility of triterpene derivatives in anti-influenza virus drug design.
Ming Cai , Liang Shao , Fan Yang , Jihong Zhang , Fei Yu . Design, Synthesis of Pentacyclic Triterpenoid Glucose Conjugate and in vitro Activity against Influenza Virus[J]. Chinese Journal of Organic Chemistry, 2022 , 42(5) : 1453 -1462 . DOI: 10.6023/cjoc202111008
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