| 词条 | Hyocholic acid |
| 释义 |
| ImageFile = gamma-muricholic acid.svg | ImageSize = 200px | IUPACName = | OtherNames = γ-Muricholic acid; Iocholic acid; 3α,6α,7α-Trihydroxy-5β-cholan-24-oic acid | Section1 = {{Chembox Identifiers | CASNo = 547-75-1 | PubChem = 92805 | UNII = 2H5H0Q47FL | EC_number = 208-935-8 | ChEBI = 81244 | ChEMBL = 1908063 | KEGG = C17649 | StdInChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21-,22+,23-,24-/m1/s1 | StdInChIKey = DKPMWHFRUGMUKF-KWXDGCAGSA-N | SMILES = C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H]([C@@H]([C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C | Section2 = {{Chembox Properties | C=24 | H=40 | O=5 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} Hyocholic acid or 3α,6α,7α-trihydroxy-5β-cholan-24-oic acid is a bile acid found as one of the main forms in pig,[1] and at low concentrations in other species including humans.[2][3] Hyocholic acid differs from the primary bile acids found in humans by having a third hydroxyl group in the α-conformation at the 6-position, unlike cholic acid, which has a 12-hydroxyl, and chenodeoxycholic acid which has neither a 6- or 12-hydroxyl. It also differs from the muricholic acids found in rodents, as they are 6β-hydroxylated, and can have the 7-hydroxyl in either the α- or β positions, forming α- or β-muricholic acids. Hyocholic acid is conjugated in the liver before secretion with taurine or with glycine to give taurohyocholate or glycohyocholates. Bacterial 7α-dehydroxylation in the colon produces the secondary bile acid, hyodeoxycholic acid. Epimerization of the 7-hydroxyl to the β-position is found in ω-muricholic acid (also known as β-hyocholic acid).[4] The enzyme responsible for the 6-hydroxylation reaction of chendeoxycholic acid in the pig is the cytochrome P450 CYP4A21.[5] Hyocholic acid can be found in humans with cholestasis[6] and may be increased after sleeve gastrectomy for obesity.[7] References1. ^{{cite journal |last1=Haslewood |first1=GA |title=Bile salts of germ-free domestic fowl and pigs. |journal=The Biochemical Journal |date=June 1971 |volume=123 |issue=1 |pages=15–8 |pmid=5128663|pmc=1176895 }} 2. ^{{cite journal |last1=Bathena |first1=SP |last2=Mukherjee |first2=S |last3=Olivera |first3=M |last4=Alnouti |first4=Y |title=The profile of bile acids and their sulfate metabolites in human urine and serum. |journal=Journal of Chromatography B |date=30 December 2013 |volume=942-943 |pages=53–62 |doi=10.1016/j.jchromb.2013.10.019 |pmid=24212143}} 3. ^{{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 }} 4. ^{{cite journal |last1=Hofmann |first1=AF |last2=Sjövall |first2=J |last3=Kurz |first3=G |last4=Radominska |first4=A |last5=Schteingart |first5=CD |last6=Tint |first6=GS |last7=Vlahcevic |first7=ZR |last8=Setchell |first8=KD |title=A proposed nomenclature for bile acids. |journal=Journal of Lipid Research |date=April 1992 |volume=33 |issue=4 |pages=599–604 |pmid=1527482}} 5. ^{{cite journal |last1=Lundell |first1=K |last2=Hansson |first2=R |last3=Wikvall |first3=K |title=Cloning and expression of a pig liver taurochenodeoxycholic acid 6alpha-hydroxylase (CYP4A21): a novel member of the CYP4A subfamily. |journal=The Journal of Biological Chemistry |date=30 March 2001 |volume=276 |issue=13 |pages=9606–12 |doi=10.1074/jbc.M006584200 |pmid=11113117}} 6. ^{{cite journal |last1=van Berge Henegouwen |first1=GP |last2=Brandt |first2=KH |last3=Eyssen |first3=H |last4=Parmentier |first4=G |title=Sulphated and unsulphated bile acids in serum, bile, and urine of patients with cholestasis. |journal=Gut |date=November 1976 |volume=17 |issue=11 |pages=861–9 |pmid=1001976|pmc=1411206 }} 7. ^{{cite journal |last1=Kindel |first1=TL |last2=Krause |first2=C |last3=Helm |first3=MC |last4=McBride |first4=CL |last5=Oleynikov |first5=D |last6=Thakare |first6=R |last7=Alamoudi |first7=J |last8=Kothari |first8=V |last9=Alnouti |first9=Y |last10=Kohli |first10=R |title=Increased glycine-amidated hyocholic acid correlates to improved early weight loss after sleeve gastrectomy. |journal=Surgical Endoscopy |date=February 2018 |volume=32 |issue=2 |pages=805–812 |doi=10.1007/s00464-017-5747-y |pmid=28779240|pmc=5844265 }} 1 : Bile acids |
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