2. Academic Validation
  3. In vitro absorption and lipid-lowering activity of baicalin esters synthesized by whole-cell catalyzed esterification

In vitro absorption and lipid-lowering activity of baicalin esters synthesized by whole-cell catalyzed esterification

  • Bioorg Chem. 2022 Mar;120:105628. doi: 10.1016/j.bioorg.2022.105628.
Mengmeng Zhang 1,  Xuan Xin 2,  Guanglei Zhao 3,  Yucong Zou 1,  Xiao-Feng Li 4
Affiliations

Affiliations

  • 1 College of Food Science and Engineering, South China University of Technology, Wushan Road 381, Guangzhou, Guangdong 510640, China.
  • 2 College of Light Industry and Food Technology, Zhongkai University of Agriculture and Engineering, Dongsha Street 24, Guangzhou, Guangdong 510225, China. Electronic address: [email protected].
  • 3 State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Wushan Road 381, Guangzhou, Guangdong 510640, China.
  • 4 College of Food Science and Engineering, South China University of Technology, Wushan Road 381, Guangzhou, Guangdong 510640, China. Electronic address: [email protected].
PMID: 35066316 DOI: 10.1016/j.bioorg.2022.105628
Abstract

Baicalin, a phenolic glycoside with good lipid-lowering activity, has poor intestinal absorption due to low lipophilicity. In this study, six ester derivatives of baicalin, named BECn (n = 2, 3, 4, 6, 8, and 10) based on their fatty chain lengths, were synthesized by whole-cell catalyzed esterification to improve lipophilicity, and the intestinal absorption and lipid-lowering activity of the synthesized esters were investigated using cell models in vitro. BEC2, BEC3, and BEC4 exhibited higher Papp values than baicalin in Caco-2 cell monolayers. The lipid-lowering activity of the three esters was stronger than baicalin in the cell models of hepatic steatosis, adipocytes and foam macrophages, and was attributed to their higher intracellular accumulation and stronger direct activation of the carnitine palmitoyltransferase 1A. Moreover, these esters were easily hydrolyzed by carboxylesterase and were unstable at pH 7.4, which significantly weakened their absorption and lipid-lowering activity. This study laid the foundation for industrial production and practical application of BAI esters.

Keywords

Carboxylesterase; Carnitine palmitoyltransferase 1A; Derivatives; Fatty chains; Hydrolysis; Lipophilicity.

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