Misplaced Pages

Hyocholic acid

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Type of bile acid
Hyocholic acid
Names
IUPAC name 3α,6α,7α-Trihydroxy-5β-cholan-24-oic acid
Systematic IUPAC name (4R)-4-phenanthren-1-yl]pentanoic acid
Other names γ-Muricholic acid; Iocholic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ECHA InfoCard 100.008.124 Edit this at Wikidata
EC Number
  • 208-935-8
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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/s1Key: DKPMWHFRUGMUKF-KWXDGCAGSA-N
SMILES
  • C(CCC(=O)O)1CC21(CC32((43(CC(C4)O)C)O)O)C
Properties
Chemical formula C24H40O5
Molar mass 408.579 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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, and at low concentrations in other species including humans. 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).

The enzyme responsible for the 6-hydroxylation reaction of chenodeoxycholic acid in the pig is the cytochrome P450 CYP4A21.

Hyocholic acid can be found in humans with cholestasis and may be increased after sleeve gastrectomy for obesity.

References

  1. Haslewood, GA (June 1971). "Bile salts of germ-free domestic fowl and pigs". The Biochemical Journal. 123 (1): 15–8. doi:10.1042/bj1230015. PMC 1176895. PMID 5128663.
  2. Bathena, SP; Mukherjee, S; Olivera, M; Alnouti, Y (30 December 2013). "The profile of bile acids and their sulfate metabolites in human urine and serum". Journal of Chromatography B. 942–943: 53–62. doi:10.1016/j.jchromb.2013.10.019. PMID 24212143.
  3. Russell DW (2003). "The enzymes, regulation, and genetics of bile acid synthesis". Annu. Rev. Biochem. 72: 137–74. doi:10.1146/annurev.biochem.72.121801.161712. PMID 12543708.
  4. Hofmann, AF; Sjövall, J; Kurz, G; Radominska, A; Schteingart, CD; Tint, GS; Vlahcevic, ZR; Setchell, KD (April 1992). "A proposed nomenclature for bile acids". Journal of Lipid Research. 33 (4): 599–604. doi:10.1016/S0022-2275(20)41624-4. PMID 1527482.
  5. Lundell, K; Hansson, R; Wikvall, K (30 March 2001). "Cloning and expression of a pig liver taurochenodeoxycholic acid 6alpha-hydroxylase (CYP4A21): a novel member of the CYP4A subfamily". The Journal of Biological Chemistry. 276 (13): 9606–12. doi:10.1074/jbc.M006584200. PMID 11113117.
  6. van Berge Henegouwen, GP; Brandt, KH; Eyssen, H; Parmentier, G (November 1976). "Sulphated and unsulphated bile acids in serum, bile, and urine of patients with cholestasis". Gut. 17 (11): 861–9. doi:10.1136/gut.17.11.861. PMC 1411206. PMID 1001976.
  7. Kindel, TL; Krause, C; Helm, MC; McBride, CL; Oleynikov, D; Thakare, R; Alamoudi, J; Kothari, V; Alnouti, Y; Kohli, R (February 2018). "Increased glycine-amidated hyocholic acid correlates to improved early weight loss after sleeve gastrectomy". Surgical Endoscopy. 32 (2): 805–812. doi:10.1007/s00464-017-5747-y. PMC 5844265. PMID 28779240.
Categories: