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β-Muricholic Acid

(Synonyms: Β-鼠胆酸,5β-Cholanic Acid-3α,6β,7β-triol, β-MCA) 目录号 : GC40719

β-胆酸β-muricholic acid是一种天然存在的三羟基亲水性胆汁酸,作为胆道胆固醇去饱和剂,促进胆固醇胆结石的溶解。

β-Muricholic Acid Chemical Structure

Cas No.:2393-59-1

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1mg
¥900.00
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10mM (in 1mL DMSO)
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5mg
¥2,070.00
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10mg
¥3,510.00
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Sample solution is provided at 25 µL, 10mM.

Description

β-Muricholic acid is a naturally occurring trihydroxy hydrophilic bile acid, as a biliary cholesterol-desaturating agent and facilitates the dissolution of cholesterol gallstones. It found in mice and differs from human primary bile acids by featuring a hydroxyl group in the β- configuration at the 6-position[1-3].

β-muricholic acid(100 µM;48h) inhibited lipid accumulation in primary-cultured mouse hepatocytes after exposure to palmitic acid (PA)/oleic acid (OA), it may be useful in the treatment of nonalcohol fatty liver disease (NAFLD) [4].

β-muricholic acid(0.5% β-muricholic acid in food; p.o; 8 weeks) is more effective than UDCA in enhancing the dissolution rates of cholesterol gallstones via increasing a liquid crystals-containing phase. Addition of beta-muricholic acid decreased gallstone prevalence to 20% through significantly reducing biliary secretion rate, saturation index, and intestinal absorption of cholesterol that prevented the transition of cholesterol from its liquid crystalline phase to solid crystals and stones [5].

[1]. Denk GU, Kleiss CP, et,al. Tauro-β-muricholic acid restricts bile acid-induced hepatocellular apoptosis by preserving the mitochondrial membrane potential. Biochem Biophys Res Commun. 2012 Aug 10;424(4):758-64. doi: 10.1016/j.bbrc.2012.07.029. Epub 2012 Jul 15. PMID: 22809502.
[2]. Montet JC, Parquet M, et,al. beta-Muricholic acid; potentiometric and cholesterol-dissolving properties. Biochim Biophys Acta. 1987 Mar 13;918(1):1-10. doi: 10.1016/0005-2760(87)90002-6. PMID: 3828364.
[3]. Sacquet E, Parquet M, et,al. Metabolism of beta-muricholic acid in man. Steroids. 1985 May;45(5):411-26. doi: 10.1016/0039-128x(85)90006-6. PMID: 3834660.
[4]. Takada S, Matsubara T, et,al. Stress can attenuate hepatic lipid accumulation via elevation of hepatic β-muricholic acid levels in mice with nonalcoholic steatohepatitis. Lab Invest. 2021 Feb;101(2):193-203. doi: 10.1038/s41374-020-00509-x. Epub 2020 Dec 10. PMID: 33303970.
[5]. Wang DQ, Tazuma S. Effect of beta-muricholic acid on the prevention and dissolution of cholesterol gallstones in C57L/J mice. J Lipid Res. 2002 Nov;43(11):1960-8. doi: 10.1194/jlr.m200297-jlr200. PMID: 12401895.

β-胆酸β-muricholic acid是一种天然存在的三羟基亲水性胆汁酸,作为胆道胆固醇去饱和剂,促进胆固醇胆结石的溶解。它在小鼠中发现,不同于人类的原胆汁酸,它在6位的β-结构中具有羟基[1-3]

β-muricholic acid(100 µM;48h)可抑制暴露于棕榈酸(PA)/油酸(OA)后的原代培养小鼠肝细胞的脂质积累, 可能对治疗非酒精性脂肪肝(NAFLD)有用[4]

β-muricholic acid(0.5% β-muricholic acid in food; p.o; 8 weeks)通过增加含液晶相,比UDCA更有效地提高胆固醇胆结石的溶解速率, 添加β-muricholic acid可显著降低胆汁分泌率、饱和指数和肠道对胆固醇的吸收,从而阻止胆固醇从液晶状态转变为固体晶体和结石,从而使胆结石患病率降至20%[5]

实验参考方法

Cell experiment [1]:

Cell lines

Primary hepatocytes

Preparation Method

Hepatocytes were exposed to 100 µM β-muricholic acid after treatment with palmitic acid (PA)/oleic acid (OA).

Reaction Conditions

100 µM;48h

Applications

β-muricholic acid inhibited lipid accumulation in primary-cultured mouse hepatocytes after exposure to palmitic acid (PA)/oleic acid (OA).

Animal experiment [2]:

Animal models

Male C57L/J mice

Preparation Method

For gallstone dissolution study, mice that have formed cholesterol gallstones were fed chow (control) with or without 0.5% ursodeoxycholic acid (UDCA) or 0.5% β-muricholic acid for 8 weeks.

Dosage form

0.5% β-muricholic acid in food; p.o; 8 weeks

Applications

β-muricholic acid is more effective than UDCA in enhancing the dissolution rates of cholesterol gallstones via increasing a liquid crystals-containing phase.

References:
[1]:Takada S, Matsubara T, et,al. Stress can attenuate hepatic lipid accumulation via elevation of hepatic β-muricholic acid levels in mice with nonalcoholic steatohepatitis. Lab Invest. 2021 Feb;101(2):193-203. doi: 10.1038/s41374-020-00509-x. Epub 2020 Dec 10. PMID: 33303970.
[2]:Wang DQ, Tazuma S. Effect of beta-muricholic acid on the prevention and dissolution of cholesterol gallstones in C57L/J mice. J Lipid Res. 2002 Nov;43(11):1960-8. doi: 10.1194/jlr.m200297-jlr200. PMID: 12401895.

化学性质

Cas No. 2393-59-1 SDF
别名 Β-鼠胆酸,5β-Cholanic Acid-3α,6β,7β-triol, β-MCA
化学名 (5β)-3α,6β,7β-trihydroxy-cholan-24-oic acid
Canonical SMILES OC(CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@@H](O)[C@@H](O)[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C)=O
分子式 C24H40O5 分子量 408.6
溶解度 20mg/ml in ethanol & DMSO, 30mg/ml in DMF 储存条件 Store at -20°C
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1 mM 2.4474 mL 12.2369 mL 24.4738 mL
5 mM 0.4895 mL 2.4474 mL 4.8948 mL
10 mM 0.2447 mL 1.2237 mL 2.4474 mL
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