An efficient, scalable approach to hydrolyze flavonoid glucuronides via activation of glycoside bond

被引:7
|
作者
Jiang, Xue-Yang [1 ]
Li, Xin-Chen [4 ]
Liu, Wen-Yuan [2 ]
Xu, Yun-Hui [1 ,5 ]
Feng, Feng [1 ,3 ]
Qu, Wei [1 ,3 ]
机构
[1] China Pharmaceut Univ, Dept Nat Med Chem, Nanjing 210009, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, Dept Pharmaceut Anal, Nanjing 210009, Jiangsu, Peoples R China
[3] China Pharmaceut Univ, Key Lab Biomed Funct Mat, Nanjing 211198, Jiangsu, Peoples R China
[4] Anhui Normal Univ, Dept Coll Life Sci, Wuhu 241000, Peoples R China
[5] Marshall Univ, Marshall Inst Interdisciplinary Res, Huntington, WV 25755 USA
基金
中国国家自然科学基金;
关键词
Flavonoid glucuronide; Acid-catalyzed hydrolysis; Optimizations; Large-scale; SCUTELLAREIN; METABOLITE; CHEMISTRY; MECHANISM; BAICALEIN;
D O I
10.1016/j.tet.2017.02.039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hydrolyzing flavonoid glucuronides into corresponding aglycones posed some significant challenges. To improve acid-catalyzed hydrolysis process of flavonoid glucuronide, structures of glucuronide, hydrolysis parameters and post-processing were optimized. The optimized condition was performed by hydrolysis flavonoid glycoside methyl ester in a mixed solvent consisting of 2 mol/L H2SO4/EtOH/H2O (1/8/1, v/v/v) at 95 degrees C for 7 h and resulted in up to 90% aglycone yields, minimal byproduct formations and milder hydrolysis conditions. Furthermore, the optimized method avoids tedious purification steps and is easily conducted on a relatively large-scale using economical and commercially available reagents. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1895 / 1903
页数:9
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