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词条 Muricholic acid
释义

  1. Chemical structures

  2. References

Muricholic acids are a group of bile acids found as one of the main forms in mice, which gives them their name, and at low concentrations in other species.[1] Muricholic acids differ from the primary bile acids found in humans, cholic acid and chenodeoxycholic acid, by having a hydroxyl group in the β-conformation at the 6-position. The orientation of the hydroxyl group at the 7 position defines α- or β-muricholic acid. Muricholic acids are detectable at low concentrations in human urine.[2]

The three major bile acids in germ-free mice are cholic acid, α-muricholic, and β-muricholic acids.[3] In conventional mice with a normal microbiome, ω-muricholic acid, and various sulfated forms are also found. Conjugation with taurine (to give tauro-murocholic acids which are the major murine forms), or with glycine (to give glyco-murocholic acids) takes place in the liver before secretion.

The enzyme responsible for the 6-hydroxylation reactions forming muricholates in rodents is the cytochrome P450 Cyp2c70. This produces α-muricholic acid from chenodeoxycholic acid, and β-muricholic acid from ursodeoxycholic acid.[4]

Tauro-muricholic acids were shown to be potent antagonists of the bile acid receptor farnesoid X receptor (FXR).[5]

Chemical structures

References

1. ^{{cite journal |author=Russell DW |title=The enzymes, regulation, and genetics of bile acid synthesis |journal=Annu. Rev. Biochem. |volume=72 |issue= |pages=137–74 |year=2003 |pmid=12543708 |doi=10.1146/annurev.biochem.72.121801.161712 }}
2. ^{{cite journal | pmid = 1629271 | year = 1992 | last1 = Goto | first1 = J | last2 = Hasegawa | first2 = K | last3 = Nambara | first3 = T | last4 = Iida | first4 = T | title = Studies on steroids. CCLIV. Gas chromatographic-mass spectrometric determination of 4- and 6-hydroxylated bile acids in human urine with negative ion chemical ionization detection | volume = 574 | issue = 1 | pages = 1–7 | journal = Journal of Chromatography| doi = 10.1016/0378-4347(92)80091-4 }}
3. ^{{cite journal |vauthors=Eyssen HJ, Parmentier GG, Mertens JA |title=Sulfate bile acids in germ-free and conventional mice |journal=Eur. J. Biochem. |volume=66 |issue=3 |pages=507–14 |date=July 1976 |pmid=954753 |doi= 10.1111/j.1432-1033.1976.tb10576.x}}
4. ^{{cite journal |last1=Takahashi |first1=S |last2=Fukami |first2=T |last3=Masuo |first3=Y |last4=Brocker |first4=CN |last5=Xie |first5=C |last6=Krausz |first6=KW |last7=Wolf |first7=CR |last8=Henderson |first8=CJ |last9=Gonzalez |first9=FJ |title=Cyp2c70 is responsible for the species difference in bile acid metabolism between mice and humans. |journal=Journal of Lipid Research |date=December 2016 |volume=57 |issue=12 |pages=2130–2137 |doi=10.1194/jlr.M071183 |pmid=27638959|pmc=5321228 }}
5. ^{{cite journal |vauthors=Sayin SI, Wahlström A, Felin J, etal |title=Gut microbiota regulates bile acid metabolism by reducing the levels of tauro-beta-muricholic acid, a naturally occurring FXR antagonist |journal=Cell Metab. |volume=17 |issue=2 |pages=225–35 |date=February 2013 |pmid=23395169 |doi=10.1016/j.cmet.2013.01.003 |url=http://linkinghub.elsevier.com/retrieve/pii/S1550-4131(13)00011-9}}

2 : Bile acids|Cholanes

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