3β-Ursodeoxycholic acid
(Synonyms: 3β-熊去氧胆酸; Isoursodeoxycholic acid) 目录号 : GC61987
3β-Ursodeoxycholic acid是熊去氧胆酸(UDCA)的异构体,属于胆汁酸类。
Cas No.:78919-26-3
Sample solution is provided at 25 µL, 10mM.
3β-Ursodeoxycholic acid is an isomer of ursodeoxycholic acid (UDCA) and belongs to the bile acid class [1]. 3β-Ursodeoxycholic acid reduces hepatocyte damage and liver fibrosis by inhibiting the opening of mitochondrial permeability transition pore, blocking caspase cascade reaction, and regulating PI3K/Akt and other signaling pathways [2-3]. 3β-Ursodeoxycholic acid is commonly used to treat cholestatic liver disease and non-alcoholic fatty liver disease [4].
In HepG2 cells, 3β-Ursodeoxycholic acid (100μM; 24h) has a cytoprotective effect against ethanol-induced cell damage [1].
In bile duct ligation rat cholestasis model, 3β-Ursodeoxycholic acid (2.5g/kg; po; 21d) has cell/tissue protection and bile acid lowering properties [5].
References:
[1]. Marschall HU, Roeb E, Yildiz Y, et al. Study of human isoursodeoxycholic acid metabolism. Journal of hepatology. 1997 Apr 1; 26(4): 863-870.
[2]. Purucker E, Marschall HU, Winograd R, et al. Metabolism and effects on cholestasis of isoursodeoxycholic and ursodeoxycholic acids in bile duct ligated rats. Biochimica et Biophysica Acta (BBA)-General Subjects. 2001 Apr 3; 1526(1): 44-52.
[3]. Zhang Y, Jiang R, Zheng X, et al. Ursodeoxycholic acid accelerates bile acid enterohepatic circulation. British journal of pharmacology. 2019 Aug; 176(16): 2848-2863.
[4]. Li Y, Zhao J. Xiaohua Funing decoction ameliorates non-alcoholic fatty liver disease by modulating the gut microbiota and bile acids. Frontiers in Microbiology. 2025 Feb 10; 16: 1511885.
[5]. Purucker E, Marschall HU, Winograd R, et al. Metabolism and effects on cholestasis of isoursodeoxycholic and ursodeoxycholic acids in bile duct ligated rats. Biochim Biophys Acta. 2001 Apr 3; 1526(1): 44-52.
3β-Ursodeoxycholic acid是熊去氧胆酸(UDCA)的异构体,属于胆汁酸类 [1]。3β-Ursodeoxycholic acid通过抑制线粒体通透性转换孔的开放、阻断caspase级联反应、调控PI3K/Akt等信号通路,减轻肝细胞损伤和肝纤维化 [2-3]。3β-Ursodeoxycholic acid常用于治疗胆汁淤积性肝病和非酒精性脂肪肝 [4]。
在HepG2细胞中,3β-Ursodeoxycholic acid(100μM;24h)对乙醇诱导的细胞损伤具有细胞保护作用 [1]。
在胆管结扎大鼠胆汁淤积模型中,3β-Ursodeoxycholic acid(2.5g/kg;po;21d)具有细胞/组织保护和降低胆汁酸的作用 [5]。
Cell experiment [1]: | |
Cell lines | HepG2 cells |
Preparation Method | Analysis of 3β-Ursodeoxycholic acid in vitro cytoprotection A possible cytoprotective effect of 3β-Ursodeoxycholic acid was studied in vitro in a modified assay using the human hepatoblastoma cell line HepG2. Therefore, liver cell long-term cultures were grown in MEM (minimal essential medium) supplemented with 10% (v/v) fetal calf serum and then changed to serum free medium when treated with ethanol and bile acids. Hepatoblastoma cells were incubated for 24h with and without 80 mM ethanol and various bile acids (3β-Ursodeoxycholic acid, UDCA, cholic (CA), deoxycholic (DCA), or chenodeoxycholic (CDCA) acids), each at 100μM. Ethanol toxicity was tested by trypan blue staining. |
Reaction Conditions | 100μM; 24h |
Applications | 3β-Ursodeoxycholic acid has a cytoprotective effect against ethanol-induced cell damage in HepG2 cells. |
Animal experiment []: | |
Animal models | Bile duct ligation rat cholestasis model |
Preparation Method | 36 male spragu dawley rats, weighing 220-250g, were held in groups of two in macrolon cages and fed ad libitum with free access to water. 18 animals were randomly assigned to bile ductligation and 18 to sham operation. Pentobarbital (40mg/kg) was given intraperitoneally for anesthesia. The common bile duct was exposed through a 1cm long right paramedian incision. In animals randomized to bile duct ligation, the common bile duct was ligated twice, 1cm proximal to duodenum to avoid ligation of parabiliary pancreatic ductuli, and cut through between the ligations. No ligation or dissection was performed in control animals. Groups of six animals with either bile duct ligation or sham operation received standard chow or standard chow supplemented with 2.5g/kg UDCA or 2.5g/kg 3β-Ursodeoxycholic acid. Each subgroup consisted of six animals. The food intake and body weight (b.w.) of the six groups were monitored throughout the 21 days of the experiment. |
Dosage form | 2.5g/kg; po; 21d |
Applications | 3β-Ursodeoxycholic acid has cell/tissue protection and bile acid lowering properties. |
References: |
Cas No. | 78919-26-3 | SDF | |
别名 | 3β-熊去氧胆酸; Isoursodeoxycholic acid | ||
Canonical SMILES | C[C@@]12-;@[C@](-;@C-;@C-;@[C@]-;@2([H])[C@H](C)CCC(O)=O)([H])-;@[C@@]3([H])-;@[C@](-;@[C@@]4(-;@[C@](-;@C-;@[C@@H](O)-;@C-;@C-;@4)([H])-;@C-;@[C@@H]-;@3O)C)([H])-;@C-;@C-;@1 | ||
分子式 | C24H40O4 | 分子量 | 392.57 |
溶解度 | DMSO : 100 mg/mL (254.73 mM) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg |
1 mM | 2.5473 mL | 12.7366 mL | 25.4732 mL |
5 mM | 0.5095 mL | 2.5473 mL | 5.0946 mL |
10 mM | 0.2547 mL | 1.2737 mL | 2.5473 mL |
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