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Discovery of Betulinic Acid Derivatives as Potent Intestinal Farnesoid X Receptor Antagonists to Ameliorate Nonalcoholic Steatohepatitis

Chenlu Zhang, Yameng Liu, Ying Wang, Xiu Run Ge, Tingying Jiao, Jianpeng Yin, Kanglong Wang, Cuina Li, Shimeng Guo, Xin Xie, Cen Xie, Fajun Nan

2022Journal of Medicinal Chemistry36 citationsDOIOpen Access PDF

Abstract

Farnesoid X receptor (FXR) has emerged as a promising therapeutic target for nonalcoholic steatohepatitis (NASH) because of its tightly interwoven relationship with bile acid homeostasis, inflammation, fibrosis, and glucose and lipid metabolism. Evidence showed that intestinal FXR antagonism exhibited remarkable metabolic improvements in mice. Herein, we developed a series of betulinic acid derivatives as potent intestinal FXR antagonists, and F6 was identified as the most potent one with an IC50 at 2.1 μM. F6 selectively inhibited intestinal FXR signaling and ameliorated the hepatic steatosis, inflammation, and fibrosis in Gubra-amylin NASH (GAN) and high-fat with methionine and choline deficiency (HFMCD) diet-induced NASH models. The beneficial effects were achieved by direct antagonism of intestinal FXR and feedback activation of hepatic FXR, thereby decreasing ceramides and repressing inflammasome activation in the liver. Collectively, our work substantially supports F6 as a promising drug candidate against NASH and demonstrates that antagonism of intestinal FXR signaling is a practical strategy for treating metabolic diseases.

Topics & Concepts

Farnesoid X receptorObeticholic acidSteatohepatitisBetulinic acidChemistryG protein-coupled bile acid receptorSteatosisPharmacologyNonalcoholic fatty liver diseaseBile acidInternal medicineEndocrinologyFatty liverNuclear receptorBiochemistryReceptorMedicineBiologyAgonistTranscription factorGeneticsGeneDiseaseDrug Transport and Resistance MechanismsLiver Disease Diagnosis and TreatmentLiver Diseases and Immunity