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7 protocols using glycolithocholic acid

1

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).
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2

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, glycochenodeoxycholic 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).
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3

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.
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4

Quantification of Bile Acids by LC-MS

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Tauroursodeoxycholic acid (TUDCA), taurocholic acid (TCA), glycoursodeoxycholic acid (GUDCA), glycocholic acid (GCA), taurochenodeoxycholic acid (TCDCA), taurodeoxycholic 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), taurocholic acid-d4 (d4-TCA), glycocholic 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)
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5

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).
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6

Bile Acid Profiling Using HPLC-MS/MS

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Ammonium hydroxide (v/v 25%, AR) was purchased from Tianjin Fuyu Fine Chemical Co., Ltd., China. Activated carbon was purchased from Tianjin Damao Chemical Reagent Factory, China. Formic acid, acetonitrile, and methanol were ordered from Merck Company (US). Ammonium formate, 4d-DCA (internal standard), glycoursodeoxycholic acid taurohyodeoxycholic acid (THDCA), and glycolithocholic acid were purchased from Sigma-Aldrich Company (USA). Hyocholic acid (HCA) was ordered from Santa Company (USA). Tauroursodeoxycholic acid (TUDCA), cholic acid (CA), glycocholic acid (GCA), GCDCA, glycodeoxycholic acid hyodeoxycholic acid taurocholic acid TCDCA, taurodeoxycholic acid (T-DCA), ursodeoxycholic acid CDCA, DCA, LCA and TLCA were purchased from Dalian Mellon Biological Technology Co., Ltd.
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7

Plasma Metabolite Extraction and LC-MS Analysis

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LC/MS grade methanol, acetonitrile, isopropanol, ammonium formate, and formic acid were purchased from VWR International (Radnor, PA, USA). Ultra-pure water was purified using a Milli-Q system (Merch Millipore, Darmstadt, Germany). Tauroursodeoxycholic acid (TUDCA), taurocholic acid (TCA), glycoursodeoxycholic acid (GUDCA), glycocholic acid (GCA), taurochenodeoxycholic acid (TCDCA), taurodeoxycholic acid (TDCA), cholic acid (CA), ursodeoxycholic acid (UDCA), glycochenodeoxycholic acid (GCDCA), glycodeoxycholic acid (GDCA), taurolithocholic acid (TLCA), chenodeoxycholic acid (CDCA), glycolithocholic acid (GLCA), deoxycholic acid (DCA), hyodeoxycholic acid (HDCA), taurocholic acid-d4 (d4-TCA), glycocholic 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). Plasma sample preparation was performed as follows. An aliquot of 200 μL of plasma sample was spiked with 780 μL methanol and 20 μL of the internal standard mix in plastic centrifuge tubes. Samples were vortexed for 20 s, centrifuged for 3 min at 25,000× g, and then 200 μL of the supernatant was transferred in a 96-well plate for analysis along with 200 μL of water.
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