Hyodeoxycholic acid

Manufactured by Merck Group

Sourced in United States

Hyodeoxycholic acid is a laboratory compound used in various research and analytical applications. It is a bile acid that can be utilized as a chemical building block or reference standard in different experimental setups. The core function of hyodeoxycholic acid is to serve as a research tool without further interpretation of its intended use.

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Hyodeoxycholic (2 citations)

14 protocols using hyodeoxycholic acid

Quantitative Analysis of Senecionine and Bile Acids

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Senecionine was purchased from Shanghai R&D Center for Standardization of Traditional Chinese Medicine (Shanghai, China). Senecionine purity was determined to be 92% through quantitative ¹H nuclear magnetic resonance (NMR) and liquid chromatography−mass spectrometry (LC−MS) (Figures S1 and S2, Supporting Information). Bile acid standards were purchased from Sigma−Aldrich Co. (St. Louis, MO, USA), including CA, deoxycholic acid (DCA), chenodeoxycholic acid (CDCA), ursodeoxycholic acid (UDCA), hyodeoxycholic acid (HDCA), lithocholic acid (LCA), GCA, GDCA, GCDCA, glycoursodeoxycholic acid (GUDCA), glycolithocholic acid (GLCA), TCA, TDCA, taurochenodeoxycholic acid (TCDCA), TUDCA, taurohyodeoxycholic acid (THDCA), and taurolithocholic acid (TLCA). Acetonitrile and methanol were of HPLC grade and purchased from Sigma-Aldrich Co. (St. Louis, MO, USA). Ammonium acetate (99.0%, MS grade) was purchased from Sigma-Aldrich Co. (St. Louis, MO, USA). Formic acid (99.0%, HPLC grade) and ammonia solution (25.0%, HPLC grade) were purchased from Tedia Co. (Fairfield, OH, USA). Water was purified using a Millipore Milli-Q system (Billerica, MA, USA).

Xiong A., Yang F., Fang L., Yang L., He Y., Wan Y.Y., Xu Y., Qi M., Wang X., Yu K., Tsim K.W, & Wang Z. (2014). Metabolomic and Genomic Evidence for Compromised Bile Acid Homeostasis by Senecionine, a Hepatotoxic Pyrrolizidine Alkaloid. Chemical research in toxicology, 27(5), 775-786.

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Quantification of Bile Acids Metabolites

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ANIT, carbamazepine, mycophenolic acid, and reference standards for 18 BAs, including CA, glycocholic acid, TCA, CDCA, glycocheno deoxycholic acid, TCDCA, deoxycholic acid, glycodeoxycholic acid, taurodeoxycholic acid, UDCA, glycoursodeoxycholic acid, TUDCA, LCA, glycolithocholic acid, taurolithocholic acid, hyodeoxycholic acid, glycohyodeoxycholic acid, and taurohyodeoxycholic acid were purchased from Sigma-Aldrich (St. Louis, MO, USA). Chromatography-grade acetonitrile was purchased from Merck (Darmstadt, Germany). Water was purified using a MilliQ water system (Millipore, Bedford, MA, USA). Chromatography-grade acetic acid, formic acid, and methanol were provided by Tedia Company (Fairfield, OH, USA).

Li Y.F., Wu J.S., Li Y.Y., Dai Y., Zheng M., Zeng J.K., Wang G.F., Wang T.M., Li W.K., Zhang X.Y., Gu M., Huang C., Yang L., Wang Z.T, & Ma Y.M. (2017). Chicken bile powder protects against α-naphthylisothiocyanate-induced cholestatic liver injury in mice. Oncotarget, 8(57), 97137-97152.

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Metabolic Effects on Human Retinal Cells

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O-phosphorylethanolamine (Sigma, USA, #P0503-1G), hyodeoxycholic acid (Sigma, USA, H3878-5G), L-tryptophanamide (Selleck, USA, #S6155), cyclamic acid (Yuanye Biology, China, #S70017-5G), sodium cyclamate (Sigma, USA, #47827), curcumin [65 (link)] (Selleck, USA, #S1848), bevacizumab (Selleck, USA, #A2006). Blank control group (culture medium), negative control (0.1% DMSO group), curcumin (positive control group when studying the effect of differential metabolites on HRPECs), bevacizumab group (positive control group when studying the effect of differential metabolites on HRECs) were set.

Deng Y., Shuai P., Wang H., Zhang S., Li J., Du M., Huang P., Qu C, & Huang L. (2021). Untargeted metabolomics for uncovering plasma biological markers of wet age-related macular degeneration. Aging (Albany NY), 13(10), 13968-14000.

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HPLC-based Bile Acid and Metabolite Analysis

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Methanol (MeOH), acetonitrile and formic acid were of HPLC grade. Analytical grade of NaOH, propan-1-ol, pyridine, hexane and propylchloroformate (PCF) were purchased as well from Sigma-Aldrich (Saint Quentin Fallavier, France). Deionized water comes from a Milli-Q Elix system fitted with a LC-PaK and a MilliPak filter at 0.22 μm (Merck Millipore, Guyancourt, France). The following bile acid standards: cholic acid (CA), chenodeoxycholic acid (CDCA), deoxycholic acid (DCA), lithocholic acid (LCA), ursodeoxycholic acid (UDCA), hyodeoxycholic acid (HDCA), lycocholic acid (GCA), glycochenodeoxycholic acid (GCDCA), glycodeoxycholic acid (GDCA), glycolithocholic acid (GLCA), taurocholic acid (TCA), taurochenodeoxycholic acid (TCDCA), taurodeoxycholic acid (TDCA), tauroursodeoxycholic acid (TUDCA), and taurolithocholic acid (TLCA) and ammonium acetate were purchased from Sigma Chemical (St. Louis, MO, USA). All tryptophan reference, isotope labeled metabolites and SCFAs (acetate, propionate, butyrate, isobutyrate, valerate, isovalerate, acetate-D3, butyrate-13C2 and valerate-D9) were purchased from Sigma-Aldrich (Saint Quentin Fallavier, France). The stock solutions of bile acids, tryptophan metabolite and SCFAs were prepared separately in methanol at the concentration of 10 mmol/l.

Sencio V., Benech N., Robil C., Deruyter L., Heumel S., Machelart A., Sulpice T., Lamazière A., Grangette C., Briand F., Sokol H, & Trottein F. (2022). Alteration of the gut microbiota’s composition and metabolic output correlates with COVID-19-like severity in obese NASH hamsters. Gut Microbes, 14(1), 2100200.

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Synthesis and Purification of Bile Acids and Steroids

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Chenodeoxycholic acid (1), ursodeoxycholic acid (5), hyodeoxycholic acid (8), hyocholic acid (9), coprostan-3-ol (12), trans-dehydroandrosterone (15), progesterone (17), 11α-hydroprogesterone (18), α-estradiol (19), and diosgenin (22) were purchased from Sigma-Aldrich. Cholic acid (2), lithocholic acid (3), deoxycholic acid (4), cholesterol (11), testosterone (13), and oestron (20) were purchased from Fluka. Dehydrocholic acid (10) and hydrocortisone (21) were purchased from Janssen Chimica and BDH Chemicals, respectively. Glyco (6) and tauroursodeoxycholic acid (7) were prepared as previously reported¹⁴ (link)^,¹⁵ (link). Purity of tested compounds 1–22 was >95%.

Nocentini A., Bonardi A., Gratteri P., Cerra B., Gioiello A, & Supuran C.T. (2018). Steroids interfere with human carbonic anhydrase activity by using alternative binding mechanisms. Journal of Enzyme Inhibition and Medicinal Chemistry, 33(1), 1453-1459.

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Quantification of Bile Acids by HPLC

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SBA standards of lithocholic acid 3-sulfate (LCA-3S), glycolithocholic acid 3-sulfate (GLCA-3S) and taurolithocholic acid 3-sulfate (TLCA-3S) were purchased from Sigma–Aldrich (St. Louis, MO, USA). The authentic compounds of five kinds of unconjugated BAs, including cholic acid (CA), chenodeoxycholic acid (CDCA), deoxycholic acid (DCA), ursodeoxycholic acid (UDCA), and hyodeoxycholic acid (HDCA), and four kinds of glycine conjugated BAs including GCA, GCDCA, GDCA and GUDCA, and four kinds of taurine conjugated BAs including TCA, TCDCA, TDCA, and TUDCA were all obtained from Sigma–Aldrich (St. Louis, MO, USA). 5β-cholanicacid-3α, 6β, 7α-triol, as internal standard (IS), was purchased from Steraloids Chemical (Newport, Rhode Island, USA). Water was prepared by a MilliQ™ System (Millipore, Milford, MA, USA). HPLC-grade methanol (MeOH) and acetonitrile (ACN) were obtained from Merck KGaA (Merck KGaA, Darmstadt, Germany).

Li Y., Zhang X., Chen J., Feng C., He Y., Shao Y, & Ding M. (2018). Targeted metabolomics of sulfated bile acids in urine for the diagnosis and grading of intrahepatic cholestasis of pregnancy. Genes & Diseases, 5(4), 358-366.

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Bile Acid Standards for Analytical Methods

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Cholic acid, chenodeoxyCholic acid, hyodeoxyCholic acid, sodium glycochenodeoxycholate, sodium taurochenodeoxycholate glycoCholic acid hydrate, sodium taurolithoCholic acid, sodium taurodeoxycholate hydrate, sodium taurohyodeoxycholate hydrate, and tauroCholic acid sodium salt hydrate were purchased from Sigma-Aldrich (Saint Louis, MI, USA). GlycodeoxyCholic acid sodium salt (EMD, Millipore Corp., Burlington, MA, USA), ursodeoxyCholic acid, deoxyCholic acid (Chem-Cruz, Santa Cruz Biotechnology Inc., Dallas TX, USA), lithoCholic acid (Cayman Chemical Company, Ann Arbor, MI, USA), and glycodeoxyCholic acid, glycolithoCholic acid, glycodeoxyCholic acid, 7-ketodeoxycholate and 7-ketolithoCholic acid were purchased from Toronto Research Chemicals (North York, ON, Canada). Formic acid (99+%) was purchased in 1 mL ampoules from Thermo Scientific (Rockford, IL). Ammonium formate and 2-propanol (both Optima® LC/MS grade), acetonitrile and water (both Optima® grade) were purchased from Fisher Chemical (Fair Lawn, NJ, USA).

Charkoftaki G., Tan W.Y., Berrios-Carcamo P., Orlicky D.J., Golla J.P., Garcia-Milian R., Aalizadeh R., Thomaidis N.S., Thompson D.C, & Vasiliou V. (2022). Liver metabolomics identifies bile acid profile changes at early stages of alcoholic liver disease in mice. Chemico-biological interactions, 360, 109931.

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Quantification of Bile Acids by LC-MS

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Tauroursodeoxy cholic acid (TUDCA), tauro cholic acid (TCA), glycoursodeoxy cholic acid (GUDCA), glyco cholic acid (GCA), taurochenodeoxy cholic acid (TCDCA), taurodeoxy cholic acid (TDCA), cholic acid (CA), ursodeoxycholic acid (UDCA), glycochenodeoxycholic acid (GCDCA), hyodeoxycholic acid (HDCA), glycodeoxycholic acid (GDCA), taurolithocholic acid (TLCA), chenodeoxycholic acid (CDCA), glycolithocholic acid (GLCA), deoxycholic acid (DCA), tauro cholic acid-d4 (d4-TCA), glyco cholic acid-d4 (d4-GCA), cholic acid-d4 (d4-CA), ursodeoxycholic acid-d4 (d4-UDCA), chenodeoxycholic acid-d4 (d4-CDCA), and deoxycholic acid-d4 (d4-DCA) were purchased from Sigma–Aldrich (St. Louis, MO, USA) or Cayman Chemical (Ann Arbor, MI, USA). LC/MS grade methanol, acetonitrile, isopropanol, ammonium formate, and formic acid were purchased from VWR International (Radnor, PA, USA)

Danese E., Negrini D., Pucci M., De Nitto S., Ambrogi D., Donzelli S., Lievens P.M., Salvagno G.L, & Lippi G. (2020). Bile Acids Quantification by Liquid Chromatography–Tandem Mass Spectrometry: Method Validation, Reference Range, and Interference Study. Diagnostics, 10(7), 462.

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Bile Acid Profiling by LC-MS/MS

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ANIT, carbamazepine, mycophenolic acid, cholic acid (CA), glycocholic acid (GCA), taurocholic acid (TCA), chenodeoxycholic acid (CDCA), glycochenodeoxycholic acid (GCDCA), taurochenodeoxycholic acid (TCDCA), deoxycholic acid (DCA), glycodeoxycholic acid (GDCA), taurodeoxycholic acid (TDCA), ursodeoxycholic acid (UDCA), glycoursodeoxycholic acid (GUDCA), tauroursodeoxycholic acid (TUDCA), lithocholic acid (LCA), glycolithocholic acid (GLCA), taurolithocholic acid (TLCA), hyodeoxycholic acid (HDCA), glycohyodeoxycholic acid (GHDCA), and taurohyodeoxycholic acid (THDCA) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Chromatography grade acetonitrile was purchased from Merck (Darmstadt, Germany). Water was purified using a MilliQ water system (Millipore, Bedford, MA, USA). Chromatography grade acetic acid, formic acid, and methanol were provided by Tedia Company (Fairfield, OH, USA).

Wu J.S., Li Y.F., Li Y.Y., Dai Y., Li W.K., Zheng M., Shi Z.C., Shi R., Wang T.M., Ma B.L., Liu P, & Ma Y.M. (2017). Huangqi Decoction Alleviates Alpha-Naphthylisothiocyanate Induced Intrahepatic Cholestasis by Reversing Disordered Bile Acid and Glutathione Homeostasis in Mice. Frontiers in Pharmacology, 8, 938.

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Bile Acids Quantification by HPLC-MS/MS

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Bile acids were analyzed using high-performance liquid chromatography coupled to tandem mass spectrometry (HPLC-MS/MS), in the serum from fasted patients and in the liver and plasma from unfasted mice, as previously described,²⁰ (link)^,³⁴ using a Q-Trap 5500. All chemicals and solvents were of the highest purity available. Cholic acid, deoxyCholic acid, chenodeoxyCholic acid, UDCA, lithoCholic acid, hyoCholic acid, hyodeoxyCholic acid and their glyco- and tauro-derivatives were obtained from Sigma-Aldrich (Saint Quentin Fallavier, France); 3-sulfate derivatives were a generous gift from J Goto (Niigita University of Pharmacy and Applied Life Science, Niigata, Japan); 23-Nor-5β-cholanoic acid-3α,12β diol, all muriCholic acids, and their glyco and tauro derivatives were purchased from Steraloids Inc (Newport, USA). Acetic acid, ammonium carbonate, ammonium acetate and methanol, all of HPLC grade, were purchased from Sigma-Aldrich. The hydrophobicity index was determined based on the concentration and retention time of the different bile acids along a methanol gradient on a C18 column, lithoCholic acid and tauroursodeoxyCholic acid-3 S, displaying the highest and lowest retention time, respectively.

Cazzagon N., Gonzalez-Sanchez E., El-Mourabit H., Wendum D., Rainteau D., Humbert L., Corpechot C., Chazouillères O., Arrivé L., Housset C, & Lemoinne S. (2022). Protective potential of the gallbladder in primary sclerosing cholangitis. JHEP Reports, 5(4), 100649.

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