cholic acids

Summary

Summary: The 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholanic acid family of bile acids in man, usually conjugated with glycine or taurine. They act as detergents to solubilize fats for intestinal absorption, are reabsorbed by the small intestine, and are used as cholagogues and choleretics.

Top Publications

  1. Pols T, Nomura M, Harach T, Lo Sasso G, Oosterveer M, Thomas C, et al. TGR5 activation inhibits atherosclerosis by reducing macrophage inflammation and lipid loading. Cell Metab. 2011;14:747-57 pubmed publisher
    ..Taken together, these data attribute a significant immune modulating function to TGR5 activation in the prevention of atherosclerosis, an important facet of the metabolic syndrome. ..
  2. Meckley T, Wagner C, Luehring M. Field evaluation of larval odor and mixtures of synthetic pheromone components for attracting migrating sea lampreys in rivers. J Chem Ecol. 2012;38:1062-9 pubmed publisher
  3. Johnson N, Yun S, Buchinger T, Li W. Multiple functions of a multi-component mating pheromone in sea lamprey Petromyzon marinus. J Fish Biol. 2012;80:538-54 pubmed publisher
    ..It is concluded that the sea lamprey male mating pheromone has multiple functions and is composed of multiple components...
  4. Thomas C, Gioiello A, Noriega L, Strehle A, Oury J, Rizzo G, et al. TGR5-mediated bile acid sensing controls glucose homeostasis. Cell Metab. 2009;10:167-77 pubmed publisher
  5. Li W, Scott A, Siefkes M, Yan H, Liu Q, Yun S, et al. Bile Acid secreted by male sea lamprey that acts as a sex pheromone. Science. 2002;296:138-41 pubmed
    ..Hence, the male of this fish species signals both its reproductive status and location to females by secreting a pheromone that can act over long distances. ..
  6. Pellicciari R, Gioiello A, Macchiarulo A, Thomas C, Rosatelli E, Natalini B, et al. Discovery of 6alpha-ethyl-23(S)-methylcholic acid (S-EMCA, INT-777) as a potent and selective agonist for the TGR5 receptor, a novel target for diabesity. J Med Chem. 2009;52:7958-61 pubmed publisher
    ..Herein we report further lead optimization efforts that have led to the discovery of 6alpha-ethyl-23(S)-methylcholic acid (S-EMCA, INT-777) as a novel potent and selective TGR5 agonist with remarkable in vivo activity. ..
  7. Li T, Holmstrom S, Kir S, Umetani M, Schmidt D, Kliewer S, et al. The G protein-coupled bile acid receptor, TGR5, stimulates gallbladder filling. Mol Endocrinol. 2011;25:1066-71 pubmed publisher
    ..They further suggest that TGR5 agonists should be assessed for effects on human gallbladder as they are developed for treating metabolic disease...
  8. Venkatachalam K. Petromyzonol sulfate and its derivatives: the chemoattractants of the sea lamprey. Bioessays. 2005;27:222-8 pubmed
    ..The receptors for the migratory and the reproductive pheromones need to be molecularly cloned and characterized in order to understand the molecular biology of olfaction in the sea lamprey...
  9. Ridlon J, Kang D, Hylemon P. Bile salt biotransformations by human intestinal bacteria. J Lipid Res. 2006;47:241-59 pubmed

More Information

Publications62

  1. Johnson N, Yun S, Thompson H, Brant C, Li W. A synthesized pheromone induces upstream movement in female sea lamprey and summons them into traps. Proc Natl Acad Sci U S A. 2009;106:1021-6 pubmed publisher
    ..4 trillion of damage annually...
  2. Sorensen P, Fine J, Dvornikovs V, Jeffrey C, Shao F, Wang J, et al. Mixture of new sulfated steroids functions as a migratory pheromone in the sea lamprey. Nat Chem Biol. 2005;1:324-8 pubmed
    ..This mixture is the first migratory pheromone identified in a vertebrate and is being investigated for use in lamprey control...
  3. Siefkes M, Scott A, Zielinski B, Yun S, Li W. Male sea lampreys, Petromyzon marinus L., excrete a sex pheromone from gill epithelia. Biol Reprod. 2003;69:125-32 pubmed
    ..These results demonstrate that 3ketoPZS is released through the gill epithelia and suggest that this pheromone or its precursor may be produced in the liver. ..
  4. Yun S, Scott A, Li W. Pheromones of the male sea lamprey, Petromyzon marinus L.: structural studies on a new compound, 3-keto allocholic acid, and 3-keto petromyzonol sulfate. Steroids. 2003;68:297-304 pubmed
    ..The possibility that a mixture of 3kACA and 3kPZS might be a more potent pheromonal attractant than either compound alone is discussed. ..
  5. Hamilton J, Xie G, Raufman J, Hogan S, Griffin T, Packard C, et al. Human cecal bile acids: concentration and spectrum. Am J Physiol Gastrointest Liver Physiol. 2007;293:G256-63 pubmed
    ..In the human cecum, deconjugation and dehydroxylation of bile acids are nearly complete, resulting in most bile acids being in unconjugated form at submicellar and subsecretory concentrations. ..
  6. Quinet E, Savio D, Halpern A, Chen L, Miller C, Nambi P. Gene-selective modulation by a synthetic oxysterol ligand of the liver X receptor. J Lipid Res. 2004;45:1929-42 pubmed
    ..DMHCA and related gene-selective ligands of LXR may have application to the study and treatment of atherosclerosis...
  7. Ombelli M, Composto R, Meng Q, Eckmann D. A quantitative and selective chromatography method for determining coverages of multiple proteins on surfaces. J Chromatogr B Analyt Technol Biomed Life Sci. 2005;826:198-205 pubmed
    ..Relative to silicon, the dextranized surfaces were found to strongly inhibit protein adsorption, decreasing BSA and Fg coverages by 76 and 60%, respectively. ..
  8. Fang L, Chan W, He Y, Kwong D, Lee A. Fluorescent anion sensor derived from cholic acid: the use of flexible side chain. J Org Chem. 2005;70:7640-6 pubmed
    ..An unexpected specific fluorescence enhancement of 1 by coordinating bromide ion was observed. ..
  9. Taylor C, Pfeiffer S. Enhanced resolution of glycosylphosphatidylinositol-anchored and transmembrane proteins from the lipid-rich myelin membrane by two-dimensional gel electrophoresis. Proteomics. 2003;3:1303-12 pubmed
    ..We conclude that these detergents are effective tools for the 2-DE analysis of myelin, and that they may be more generally useful for the analysis of membrane-rich biological samples. ..
  10. Luo J, Lin Z. [A new triterpene from the fruiting bodies of Ganoderma lucidum]. Yao Xue Xue Bao. 2001;36:595-8 pubmed
    ..In addition, two known compounds, lucidenic acid A (1) and C (3) were obtained. Compound 2 is a new triterpene compound. ..
  11. Tian H, Sakmar T, Huber T. The Energetics of Chromophore Binding in the Visual Photoreceptor Rhodopsin. Biophys J. 2017;113:60-72 pubmed publisher
    ..Our data provide insights into the ligand-receptor binding reaction for rhodopsin in particular, and for GPCRs more broadly. ..
  12. Ahn J, Wong J, Molday R. The effect of lipid environment and retinoids on the ATPase activity of ABCR, the photoreceptor ABC transporter responsible for Stargardt macular dystrophy. J Biol Chem. 2000;275:20399-405 pubmed
    ..These results support the view that ABCR is an active retinoid transporter, the nucleotidase activity of which is strongly influenced by its lipid environment...
  13. Satomi Y, Hirayama M, Kobayashi H. One-step lipid extraction for plasma lipidomics analysis by liquid chromatography mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2017;1063:93-100 pubmed publisher
    ..In practice, EtOH extraction is thought to be the best approach to cover wide range of lipid species using a simple preparation procedure. ..
  14. Mitamura K, Sogabe M, Sakanashi H, Watanabe S, Sakai T, Yamaguchi Y, et al. Analysis of bile acid glutathione thioesters by liquid chromatography/electrospray ionization-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2007;855:88-97 pubmed
    ..0, and was definitely identified by CID spectra by comparison with those of the authentic sample. The results show that both cholyl-adenylate and cholyl-CoA thioester are able to acylate GSH in vitro. ..
  15. Epand R, Epand R, Savage P. Ceragenins (cationic steroid compounds), a novel class of antimicrobial agents. Drug News Perspect. 2008;21:307-11 pubmed publisher
    ..Factors contributing to the mechanism of action of these agents are discussed. The ceragenins are a class of agents with many properties to make them favorable for application as antiinfective agents. ..
  16. Kim S, Yang H, Shin Y, Kwon H. Hasllibacter halocynthiae gen. nov., sp. nov., a nutriacholic acid-producing bacterium isolated from the marine ascidian Halocynthia roretzi. Int J Syst Evol Microbiol. 2012;62:624-31 pubmed publisher
    ..The name Hasllibacter halocynthiae gen. nov., sp. nov. is proposed for this isolate, and the type strain is KME 002(T) (=JCM 16214(T)=KCCM 90082(T)). ..
  17. Nam T, Park S, Lee S, Park K, Choi K, Song I, et al. Tumor targeting chitosan nanoparticles for dual-modality optical/MR cancer imaging. Bioconjug Chem. 2010;21:578-82 pubmed publisher
    ..These results revealed that the dual-modal imaging probe of Cy5.5-CNP-Gd(III) has the potential to be used as an optical/MR dual imaging agent for cancer treatment. ..
  18. Qin X, Liu M, Zhang X, Yang D. Proton NMR based investigation of the effects of temperature and NaCl on micellar properties of CHAPS. J Phys Chem B. 2011;115:1991-8 pubmed publisher
    ..Our results provide a basis for optimizing CHAPS concentration in the solubilization or stabilization of membrane proteins under nondenaturing conditions and may be helpful to understand its interaction with proteins. ..
  19. Haq S, Khan R. Effect of detergents and hexafluoroisopropanol on the conformation of a non-helical and a helical plant protease inhibitor. Int J Biol Macromol. 2005;36:47-53 pubmed
    ..Fluorescence measurements show slight alterations in the emission intensities. HFIP caused a cooperative increase in alpha-helical secondary structure in the P. aureus inhibitor. ..
  20. Maresso A, Riese M, Barbieri J. Molecular heterogeneity of a type III cytotoxin, Pseudomonas aeruginosa exoenzyme S. Biochemistry. 2003;42:14249-57 pubmed
    ..ExoT, ExoU, and YopE also focus into multiple pI forms, suggesting that this is a common property of type III cytotoxins. ..
  21. Gilat T, Leikin Frenkel A, Goldiner I, Juhel C, Lafont H, Gobbi D, et al. Prevention of diet-induced fatty liver in experimental animals by the oral administration of a fatty acid bile acid conjugate (FABAC). Hepatology. 2003;38:436-42 pubmed
    ..FABAC-fed animals gained weight similarly to the controls. Triglyceride absorption was unaffected by FABAC supplementation. In conclusion, oral FABAC therapy prevents/reduces the development of fatty liver in animals consuming a HFD. ..
  22. Watson V, Barnett J, Schafer R. In vivo cytokine production and resistance to infection after acute exposure to 3,4-dichloropropionaniline. J Toxicol Environ Health A. 2000;60:391-406 pubmed
    ..These results demonstrate that in vivo exposure to propanil during a bacterial infection suppresses the subsequent in vitro production of cytokines but that the endogenous levels are not affected during the initial stages of infection. ..
  23. Hakansson P, Andersson I, Nystrom S, Lofgren L, Amrot L, Li H. Ontogenetic development and spatial distribution of the ileal apical sodium-dependent bile acid transporter and the ileal lipid-binding protein in apoE knockout and C57BL/6 mice. Scand J Gastroenterol. 2002;37:1089-96 pubmed
    ..The bile acid enterohepatic circulation in apoE-/- mice probably does not differ greatly from that in C57BL/6 mice. ..
  24. Hansson C, Frykman S, Farmery M, Tjernberg L, Nilsberth C, Pursglove S, et al. Nicastrin, presenilin, APH-1, and PEN-2 form active gamma-secretase complexes in mitochondria. J Biol Chem. 2004;279:51654-60 pubmed
    ..This novel localization of NCT, PS1, APH-1, and PEN-2 expands the role and importance of gamma-secretase activity to mitochondria. ..
  25. Funasaki N, Fukuba M, Hattori T, Ishikawa S, Okuno T, Hirota S. Micelle formation of bile salts and zwitterionic derivative as studied by two-dimensional NMR spectroscopy. Chem Phys Lipids. 2006;142:43-57 pubmed
    ..The chemical shift changes of several protons of CHAPS and NaTC in the micellar state are close to each other, but are different from those of NaTDC. This finding is consistent with the difference in their micellar structures. ..
  26. Tomlinson A, Jameson S, Naylor S. Strategy for isolating and sequencing biologically derived MHC class I peptides. J Chromatogr A. 1996;744:273-8 pubmed
    ..Ultimately peptides are sequenced using mPC-CE-tandem mass spectrometry (mPC-CE-MS-MS). We describe the strategy for sequencing < 60 femtomoles of a peptide obtained from 3.10(9) Kb-derived EL-4 cells. ..
  27. Frånberg J, Welander H, Aoki M, Winblad B, Tjernberg L, Frykman S. Rat brain gamma-secretase activity is highly influenced by detergents. Biochemistry. 2007;46:7647-54 pubmed
    ..4% CHAPSO. Therefore, using 1% CHAPSO for solubilization and subsequently diluting the sample to 0.4% is an appropriate procedure for obtaining a soluble, highly active gamma-secretase from rat brain. ..
  28. Beck A, Tsamaloukas A, Jurcevic P, Heerklotz H. Additive action of two or more solutes on lipid membranes. Langmuir. 2008;24:8833-40 pubmed publisher
    ..g., toroidal pore formation) but deviate from the model in the case of independent, synergistic, or antagonistic action. ..
  29. Kratzer A, Buchebner M, Pfeifer T, Becker T, Uray G, Miyazaki M, et al. Synthetic LXR agonist attenuates plaque formation in apoE-/- mice without inducing liver steatosis and hypertriglyceridemia. J Lipid Res. 2009;50:312-26 pubmed publisher
    ..Our data provide evidence that DMHCA is a strong candidate as therapeutic agent for the treatment or prevention of atherosclerosis, circumventing the negative side effects of other LXR agonists...
  30. Milkiewicz P, Roma M, Elias E, Coleman R. Hepatoprotection with tauroursodeoxycholate and beta muricholate against taurolithocholate induced cholestasis: involvement of signal transduction pathways. Gut. 2002;51:113-9 pubmed
    ..The hepatoprotective effects of DBcAMP involved Ca(2+) mobilisation, but not PKC or PKA activation. ..
  31. Simons M, Kramer E, Macchi P, Rathke Hartlieb S, Trotter J, Nave K, et al. Overexpression of the myelin proteolipid protein leads to accumulation of cholesterol and proteolipid protein in endosomes/lysosomes: implications for Pelizaeus-Merzbacher disease. J Cell Biol. 2002;157:327-36 pubmed
    ..We propose that these accumulations perturb the process of myelination and impair the viability of oligodendrocytes. ..
  32. Awasthi V, Pandit S, Misra P. Triton X-100 inhibition of yeast plasma membrane associated NADH-dependent redox activities. J Enzyme Inhib Med Chem. 2005;20:205-9 pubmed
    ..0 x 10(-6) M, respectively. The findings are interpreted, in view of the established reports, that the active site architecture of PM bound NADH-dependent oxidoreductase in yeast is likely to be different than in other eukaryotes. ..
  33. Ogawa S, Adachi Y, Kakiyama G, Shimada M, Mano N, Goto J, et al. Chemical synthesis of (22E)-3alpha,6alpha,7alpha,12alpha-Tetrahydroxy-5beta-chol-22-en-24-oic acid and its N-acylamidated conjugates with glycine or taurine: precursors of the [22,23-(3)H] labelled tracers. Chem Pharm Bull (Tokyo). 2010;58:1103-6 pubmed
  34. Padilla Morales L, Colón Sáez J, González Nieves J, Quesada González O, Lasalde Dominicci J. Assessment of the functionality and stability of detergent purified nAChR from Torpedo using lipidic matrixes and macroscopic electrophysiology. Biochim Biophys Acta. 2016;1858:47-56 pubmed publisher
  35. Trottier J, El Husseini D, Perreault M, Paquet S, Caron P, Bourassa S, et al. The human UGT1A3 enzyme conjugates norursodeoxycholic acid into a C23-ester glucuronide in the liver. J Biol Chem. 2010;285:1113-21 pubmed publisher
  36. Heinecke K, Seher A, Schmitz W, Mueller T, Sebald W, Nickel J. Receptor oligomerization and beyond: a case study in bone morphogenetic proteins. BMC Biol. 2009;7:59 pubmed publisher
    ..This indicates that despite prominent ligand receptor promiscuity a manifold of diverse signals might be generated in this receptor limited system. ..
  37. Gall A, Ruff M, Moras D. The dual role of CHAPS in the crystallization of stromelysin-3 catalytic domain. Acta Crystallogr D Biol Crystallogr. 2003;59:603-6 pubmed
    ..This detergent molecule is also involved in packing interactions. The other detergent molecule is located in a pocket formed by the N- and C-terminal parts of the ST3 and stabilizes a loop that normally binds a Ca atom. ..
  38. Baghdasaryan A, Claudel T, Gumhold J, Silbert D, Adorini L, Roda A, et al. Dual farnesoid X receptor/TGR5 agonist INT-767 reduces liver injury in the Mdr2-/- (Abcb4-/-) mouse cholangiopathy model by promoting biliary HCO?? output. Hepatology. 2011;54:1303-12 pubmed publisher
    ..This study shows that FXR activation improves liver injury in a mouse model of chronic cholangiopathy by reduction of biliary BA output and promotion of HCO?3--rich bile secretion. ..
  39. Francis M, Allen C, Sorg J. Muricholic acids inhibit Clostridium difficile spore germination and growth. PLoS ONE. 2013;8:e73653 pubmed publisher
    ..These results highlight an important difference between humans and mice and may have an impact on C. difficile virulence in the mouse-model of C. difficile infection. ..
  40. Chen W, Sheu J, Fang L, Hu W, Sung P. 3Alpha,7alpha,12alpha-triacetoxy-5beta-cholanic acid, a steroid from the Formosan soft coral Alcyonium sp. (Alcyoniidae). Nat Prod Res. 2006;20:748-53 pubmed
    ..The structure of steroid 1 was assigned on the basis of spectroscopic evidence, particularly in 1D and 2D NMR experiments. The configuration of steroid 1 was further supported by molecular mechanics calculations. ..
  41. Curnow P, Booth P. Combined kinetic and thermodynamic analysis of alpha-helical membrane protein unfolding. Proc Natl Acad Sci U S A. 2007;104:18970-5 pubmed
    ..1, indicating that the transition state is close to the unfolded state. We thus present a basis for mapping the structural and energetic properties of membrane protein folding by mutagenesis and classical kinetics. ..
  42. Batta A, Salen G, Tint G. Hydrophilic 7 beta-hydroxy bile acids, lovastatin, and cholestyramine are ineffective in the treatment of cerebrotendinous xanthomatosis. Metabolism. 2004;53:556-62 pubmed
    ..The role of chenodeoxycholic acid in downregulating abnormal bile acid synthesis in CTX is emphasized. ..
  43. Cho K, Sakong J, Kim Y. Inhibition of microsomal ATPases by high concentration of Mg2+ in tracheal epithelial cells. Life Sci. 2001;69:2875-86 pubmed
    ..In conclusion, Mg2+ has two types of modulatory effects on these enzymes, a catalytic effect at low concentration and an inhibitory effect at high concentration. ..
  44. Allen S, Kim J, Khorana H, Lu H, Booth P. Structure and function in bacteriorhodopsin: the effect of the interhelical loops on the protein folding kinetics. J Mol Biol. 2001;308:423-35 pubmed
    ..Thus the CD and EF loops may contribute to the transition state for the rate-limiting apoprotein folding step and the FG loop to that for final folding and covalent binding of retinal. ..
  45. Luo J, Xiao K, Li Y, Lee J, Shi L, Tan Y, et al. Well-defined, size-tunable, multifunctional micelles for efficient paclitaxel delivery for cancer treatment. Bioconjug Chem. 2010;21:1216-24 pubmed publisher
    ..The toxicity and antitumor efficacy profiles of these paclitaxel-loaded micelles in xenograft models were found to be superior to those of Taxol and Abraxane. ..
  46. Balmer M, Siegrist K, Zimmermann A, Dufour J. Effects of ursodeoxycholic acid in combination with vitamin E on adipokines and apoptosis in patients with nonalcoholic steatohepatitis. Liver Int. 2009;29:1184-8 pubmed publisher
    ..These results suggest that the UDCA+VitE combination has metabolic effects in addition to its beneficial cytoprotective properties. ..
  47. Andersson A, Mäler L. Magnetic resonance investigations of lipid motion in isotropic bicelles. Langmuir. 2005;21:7702-9 pubmed
    ..An analytical expression for the size dependence of the bicelles, relating the radius of the bilayer region with physical properties of the detergent and the lipid, is also presented. ..
  48. Carter T, Verdile G, Groth D, Bogush A, Thomas S, Shen P, et al. Alzheimer amyloid precursor aspartyl proteinase activity in CHAPSO homogenates of Spodoptera frugiperda cells. Alzheimer Dis Assoc Disord. 2004;18:261-3 pubmed
    ..Immunoprecipitation-mass spectrometry of AICD-L revealed its identity as the minor of the two known AICDs. ..
  49. Mortiboys H, Aasly J, Bandmann O. Ursocholanic acid rescues mitochondrial function in common forms of familial Parkinson's disease. Brain. 2013;136:3038-50 pubmed publisher
    ..We therefore propose both ursolic acid as a naturally occurring compound, and ursodeoxycholic acid as an already licensed drug as promising compounds for future neuroprotective trials in Parkinson's disease. ..
  50. Poša M, Sebenji A. Chemometric and conformational approach to the analysis of the aggregation capabilities in a set of bile salts of the allo and normal series. J Pharm Biomed Anal. 2016;121:316-324 pubmed publisher
    ..It is assumed that for the analyzed allo derivatives, the A ring of the steroid skeleton is in the twisted boat conformation, which explains the spatial sheltering of their C3-OH group in micelles. ..
  51. Nozawa K, Kurumiya Y, Yamamoto A, Isobe Y, Suzuki M, Yoshida S. Up-regulation of telomerase in primary cultured rat hepatocytes. J Biochem. 1999;126:361-7 pubmed
    ..In this case, however, the levels of TR, TERT, and TEP1 mRNA did not show any detectable changes. ..
  52. Yao S, Westphal D, Babon J, Thompson G, Robin A, Adams J, et al. NMR studies of interactions between Bax and BH3 domain-containing peptides in the absence and presence of CHAPS. Arch Biochem Biophys. 2014;545:33-43 pubmed publisher
    ..However, Bax?C remained monomeric upon binding either CHAPS or a BH3 peptide alone, but the presence of both provoked it to form a dimer. ..
  53. Roque M, Castagnet P, Giusto N. Effect of surfactants and natural detergents on phosphatidylcholine synthesis in photoreceptor membranes. Membr Cell Biol. 2001;14:587-604 pubmed
    ..These results suggest that PC synthesis in ROS membranes is modified by bioregulators and surfactants altering the physico-chemical state of the membrane. ..