메뉴 건너뛰기




Volumn 80, Issue , 2014, Pages 80-91

Tandem mass spectrometric characterization of bile acids and steroid conjugates based on low-energy collision-induced dissociation

Author keywords

Bile acid conjugate; Low energy collision induced dissociation; Neutral loss; Product ion; Steroid conjugate

Indexed keywords

AMINO ACID; BILE ACID; GALACTOSIDE; GLUCOSIDE; GLUCURONIDE; GLYCINE; GLYCOCONJUGATE; ION; N ACETYLGLUCOSAMINE; STEROID; SULFATE;

EID: 84890924381     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2013.11.016     Document Type: Article
Times cited : (40)

References (43)
  • 1
    • 0030906963 scopus 로고    scopus 로고
    • High levels of (24S)-24-hydroxycholesterol 3-sulfate, 24-glucuronide in the serum and urine of children with severe cholestatic liver disease
    • L.J. Meng, W.J. Griffiths, H. Nazer, Y. Yang, and J. Sjövall High levels of (24S)-24-hydroxycholesterol 3-sulfate, 24-glucuronide in the serum and urine of children with severe cholestatic liver disease J Lipid Res 38 1997 926 934 (Pubitemid 27255201)
    • (1997) Journal of Lipid Research , vol.38 , Issue.5 , pp. 926-934
    • Meng, L.J.1    Griffiths, W.J.2    Nazer, H.3    Yang, Y.4    Sjovall, J.5
  • 2
    • 0015993413 scopus 로고
    • Measurement of sulfated and nonsulfated bile acids in human serum and urine
    • I. Makino, K. Shinozaki, S. Nakagawa, and K. Mashimo Measurement of sulfated and nonsulfated bile acids in human serum and urine J Lipid Res 15 1974 132 138
    • (1974) J Lipid Res , vol.15 , pp. 132-138
    • Makino, I.1    Shinozaki, K.2    Nakagawa, S.3    Mashimo, K.4
  • 4
    • 84865603445 scopus 로고    scopus 로고
    • Progesterone, pregnanediol-3-glucuronide, relaxin and oestrone sulphate concentrations in saliva, milk and urine of female alpacas (Vicugna pacos) and their application in pregnancy diagnosis
    • J. Volkery, J. Gottschark, A. Sobiraj, T. Wittek, and A. Einspanier Progesterone, pregnanediol-3-glucuronide, relaxin and oestrone sulphate concentrations in saliva, milk and urine of female alpacas (Vicugna pacos) and their application in pregnancy diagnosis Vet Rec 171 2012 195 199
    • (2012) Vet Rec , vol.171 , pp. 195-199
    • Volkery, J.1    Gottschark, J.2    Sobiraj, A.3    Wittek, T.4    Einspanier, A.5
  • 5
    • 0018148486 scopus 로고
    • The biochemical basis for the conjugation of bile acids with either glycine or taurine
    • D.A. Vessey The biochemical basis for the conjugation of bile acids with either glycine or taurine Biochem J 174 1978 621 626 (Pubitemid 8403672)
    • (1978) Biochemical Journal , vol.174 , Issue.2 , pp. 621-626
    • Vessey, D.A.1
  • 6
    • 0014134175 scopus 로고
    • The formation of bile acid sulfates: A new pathway of bile acid metabolism in humans
    • R.H. Palmer The formation of bile acid sulfates: a new pathway of bile acid metabolism in humans Proc Natl Acad Sci USA 58 1967 1047 1050
    • (1967) Proc Natl Acad Sci USA , vol.58 , pp. 1047-1050
    • Palmer, R.H.1
  • 7
    • 0017249218 scopus 로고
    • Bile acid glucuronides, II[1]. Isolation and identification of a chenodeoxycholic acid glucuronide from human plasma in intrahepatic cholestasis
    • P. Back Bile acid glucuronides, II[1]. Isolation and identification of a chenodeoxycholic acid glucuronide from human plasma in intrahepatic cholestasis Hoppe Seylers Z Physiol Chem 357 1976 213 217
    • (1976) Hoppe Seylers Z Physiol Chem , vol.357 , pp. 213-217
    • Back, P.1
  • 8
    • 0025847114 scopus 로고
    • Urinary excretion of bile acid glucosides and glucuronides in extrahepatic cholestasis
    • H. Wietholtz, H.U. Marschall, R. Reuschenach, H. Matern, and S. Matern Urinary excretion of bile acid glucosides and glucuronides in extrahepatic cholestasis Hepatology 13 1991 656 662
    • (1991) Hepatology , vol.13 , pp. 656-662
    • Wietholtz, H.1    Marschall, H.U.2    Reuschenach, R.3    Matern, H.4    Matern, S.5
  • 9
    • 14844320834 scopus 로고    scopus 로고
    • Identification of a novel conjugate in human urine: Bile acid acyl galactosides
    • DOI 10.1016/j.steroids.2004.12.006
    • T. Goto, A. Shibata, D. Sasaki, N. Suzuki, T. Hishinuma, and G. Kakiyama et al. Identification of a novel conjugate in human urine: bile acid acyl galactosides Steroids 70 2005 185 192 (Pubitemid 40342612)
    • (2005) Steroids , vol.70 , Issue.3 , pp. 185-192
    • Goto, T.1    Shibata, A.2    Sasaki, D.3    Suzuki, N.4    Hishinuma, T.5    Kakiyama, G.6    Iida, T.7    Mano, N.8    Goto, J.9
  • 11
    • 67651171528 scopus 로고    scopus 로고
    • Chemical synthesis of N-acetylcysteine conjugates of bile acids and in vivo formation in cholestatic rats as shown by liquid chromatography/ electrospray ionization-linear ion trap mass spectrometry
    • K. Mitamura, S. Watanabe, T. Sakai, R. Okihara, M. Sogabe, and T. Wakamiya et al. Chemical synthesis of N-acetylcysteine conjugates of bile acids and in vivo formation in cholestatic rats as shown by liquid chromatography/electrospray ionization-linear ion trap mass spectrometry J Chromatogr B 877 2009 2630 2638
    • (2009) J Chromatogr B , vol.877 , pp. 2630-2638
    • Mitamura, K.1    Watanabe, S.2    Sakai, T.3    Okihara, R.4    Sogabe, M.5    Wakamiya, T.6
  • 12
    • 0013103455 scopus 로고    scopus 로고
    • Separation and determination of diastereomeric flurbiprofen acyl glucuronides in human urine by LC/ESI-MS with a simple column-switching technique
    • N. Mano, T. Narui, A. Nikaido, and J. Goto Separation and determination of diastereomeric flurbiprofen acyl glucuronides in human urine by LC/ESI-MS with a simple column-switching technique Drug Metab Pharmacokinet 17 2002 142 149
    • (2002) Drug Metab Pharmacokinet , vol.17 , pp. 142-149
    • Mano, N.1    Narui, T.2    Nikaido, A.3    Goto, J.4
  • 13
    • 56149090837 scopus 로고    scopus 로고
    • Quantification of 19-nortestosterone sulphate and boldenone sulphate in urine from male horses using liquid chromatography/tandem mass spectrometry
    • P.B. Grace, E.C. Drake, P. Teale, and E. Houghton Quantification of 19-nortestosterone sulphate and boldenone sulphate in urine from male horses using liquid chromatography/tandem mass spectrometry Rapid Commun Mass Spectrom 22 2008 2999 3007
    • (2008) Rapid Commun Mass Spectrom , vol.22 , pp. 2999-3007
    • Grace, P.B.1    Drake, E.C.2    Teale, P.3    Houghton, E.4
  • 14
    • 0033792367 scopus 로고    scopus 로고
    • Determination of the site of glucuronidation in an N-(3,5-dichlorophenyl) succinimide metabolite by electrospray ionization tandem mass spectrometry following derivatization to picolinyl esters
    • D. Cui, and P.J. Harvison Determination of the site of glucuronidation in an N-(3,5-dichlorophenyl) succinimide metabolite by electrospray ionization tandem mass spectrometry following derivatization to picolinyl esters Rapid Commun Mass Spectrom 14 2000 1985 1990
    • (2000) Rapid Commun Mass Spectrom , vol.14 , pp. 1985-1990
    • Cui, D.1    Harvison, P.J.2
  • 15
    • 0017397052 scopus 로고
    • Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchanger and computerized gas liquid chromatography mass spectrometry
    • B. Almé, A. Bremmelgaard, J. Sjövall, and P. Thomassen Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchanger and computerized gas-liquid chromatorgaphy-mass spectrometry J Lipid Res 18 1977 339 362 (Pubitemid 8114142)
    • (1977) Journal of Lipid Research , vol.18 , Issue.3 , pp. 339-362
    • Alme, B.1    Bremmelgaard, A.2    Sjovall, J.3    Thomassen, P.4
  • 16
    • 0020037245 scopus 로고
    • Glucuronidation and disposition of drug glucuronides in patients with renal failure
    • R.K. Verbeeck Glucuronidation and disposition of drug glucuronides in patients with renal failure. A review Drug Metab Dispos 10 1982 87 89 (Pubitemid 12177393)
    • (1982) Drug Metabolism and Disposition , vol.10 , Issue.1 , pp. 87-89
    • Verbeeck, R.K.1
  • 18
    • 0027484631 scopus 로고
    • Drug and xenobiotic glucuronidation catalysed by cloned human liver UDP-glucuronosyltransferases stably expressed in tissue culture cell lines
    • R. Wooster, T. Ebner, L. Sutherland, D. Clarke, and B. Burchell Drug and xenobiotic glucuronidation catalysed by cloned human liver UDP- glucuronosyltransferases stably expressed in tissue culture cell lines Toxicology 82 1993 119 129
    • (1993) Toxicology , vol.82 , pp. 119-129
    • Wooster, R.1    Ebner, T.2    Sutherland, L.3    Clarke, D.4    Burchell, B.5
  • 19
    • 0347623265 scopus 로고    scopus 로고
    • The Human UDP-Glucuronosyltransferases: Structural Aspects and Drug Glucuronidation
    • DOI 10.1081/DMR-120026397
    • M. Ouzzine, L. Barré, P. Netter, J. Magdalou, and S. Fournel-Gigleux The human UDP-glucuronosyltransferases: structural aspects and drug glucuronidation Drug Metab Rev 35 2003 287 303 (Pubitemid 38018108)
    • (2003) Drug Metabolism Reviews , vol.35 , Issue.4 , pp. 287-303
    • Ouzzine, M.1    Barre, L.2    Netter, P.3    Magdalou, J.4    Fournel-Gigleux, S.5
  • 21
    • 0032056005 scopus 로고    scopus 로고
    • Separation and characterization of carboxyl-linked glucuronides of bile acids in incubation mixture of rat liver microsomes
    • DOI 10.1016/S0039-128X(98)00002-6, PII S0039128X98000026
    • J. Goto, N. Murao, C. Nakada, T. Motoyama, J. Oohashi, and T. Yanagihara et al. Separation and characterization of carboxyl-linked glucuronides of bile acids in incubation mixture of rat liver microsomes Steroids 63 1998 186 192 (Pubitemid 28198938)
    • (1998) Steroids , vol.63 , Issue.4 , pp. 186-192
    • Goto, J.1    Murao, N.2    Nakada, C.3    Motoyama, T.4    Oohashi, J.5    Yanagihara, T.6    Niwa, T.7    Ikegawa, S.8
  • 25
    • 0029987681 scopus 로고    scopus 로고
    • Metabolism of anabolic androgenic steroids
    • W. Schänzer Metabolism of anabolic androgenic steroids Clin Chem 42 1996 1001 1020 (Pubitemid 26231406)
    • (1996) Clinical Chemistry , vol.42 , Issue.7 , pp. 1001-1020
    • Schanzer, W.1
  • 26
    • 0034759769 scopus 로고    scopus 로고
    • Identification of unusual 7-oxygenated bile acid sulfates in a patient with Niemann-Pick disease, type C
    • G. Alvelius, O. Hjalmarson, W.J. Griffiths, I. Björkhem, and J. Sjövall Identification of unusual 7-oxygenated bile acid sulfates in a patient with Niemann-Pick disease, type C J Lipid Res 42 2001 1571 1577 (Pubitemid 33020089)
    • (2001) Journal of Lipid Research , vol.42 , Issue.10 , pp. 1571-1577
    • Alvelius, G.1    Hjalmarson, O.2    Griffiths, W.J.3    Bjorkhem, I.4    Sjovall, J.5
  • 27
    • 84885000878 scopus 로고    scopus 로고
    • LC/ESI-MS/MS analysis of urinary 3β-sulfooxy-7β-N- acetylglucosaminyl-5-cholen-24-oic acid and its amides: New biomarkers for the detection of Niemann-Pick type C disease
    • M. Maekawa, Y. Misawa, A. Sotoura, H. Yamaguchi, M. Togawa, and K. Ohno et al. LC/ESI-MS/MS analysis of urinary 3β-sulfooxy-7β-N- acetylglucosaminyl-5-cholen-24-oic acid and its amides: new biomarkers for the detection of Niemann-Pick type C disease Steroids 78 2013 967 972
    • (2013) Steroids , vol.78 , pp. 967-972
    • Maekawa, M.1    Misawa, Y.2    Sotoura, A.3    Yamaguchi, H.4    Togawa, M.5    Ohno, K.6
  • 28
    • 0017401311 scopus 로고
    • An improved procedure for the synthesis of glycine and taurine conjugates of bile acids
    • K.Y. Tserng, D.L. Hachey, and P.D. Klein An improved procedure for the synthesis of glycine and taurine conjugates of bile acids J Lipid Res 18 1977 404 407 (Pubitemid 8114149)
    • (1977) Journal of Lipid Research , vol.18 , Issue.3 , pp. 404-407
    • Tserng, K.Y.1    Hachey, D.L.2    Klein, P.D.3
  • 29
    • 0018476938 scopus 로고
    • Synthesis of monosulfates of unconjugated and conjugated bile acids
    • J. Goto, H. Kato, F. Hasegawa, and T. Nambara Synthesis of monosulfates of unconjugated and conjugated bile acids Chem Pharm Bull 27 1979 1402 1411
    • (1979) Chem Pharm Bull , vol.27 , pp. 1402-1411
    • Goto, J.1    Kato, H.2    Hasegawa, F.3    Nambara, T.4
  • 30
    • 0018936780 scopus 로고
    • Synthesis of 3-glucuronides of unconjugated and conjugated bile acids
    • J. Goto, K. Suzaki, and T. Nambara Synthesis of 3-glucuronides of unconjugated and conjugated bile acids Chem Pharm Bull 28 1980 1258 1264 (Pubitemid 10021834)
    • (1980) Chemical and Pharmaceutical Bulletin , vol.28 , Issue.4 , pp. 1258-1264
    • Goto, J.1    Suzaki, K.2    Nambara, T.3
  • 31
    • 0032055625 scopus 로고    scopus 로고
    • Synthesis of bile acid 24-acyl glucuronides
    • DOI 10.1016/S0039-128X(97)00160-8, PII S0039128X97001608
    • J. Goto, N. Murao, J. Oohashi, and S. Ikegawa Synthesis of bile acid 24-acyl glucuronides Steroids 63 1998 180 185 (Pubitemid 28198937)
    • (1998) Steroids , vol.63 , Issue.4 , pp. 180-185
    • Goto, J.1    Murao, N.2    Oohashi, J.3    Ikegawa, S.4
  • 32
    • 0026452165 scopus 로고
    • Synthesis of N-acetylglucosaminides of unconjugated and conjugated bile acids
    • T. Niwa, T. Koshiyama, J. Goto, and T. Nambara Synthesis of N-acetylglucosaminides of unconjugated and conjugated bile acids Steroids 57 1992 522 529
    • (1992) Steroids , vol.57 , pp. 522-529
    • Niwa, T.1    Koshiyama, T.2    Goto, J.3    Nambara, T.4
  • 33
    • 0028939754 scopus 로고
    • Potential bile acid metabolites. 23. Syntheses of 3-glucosides of nonamidated and glycine- and taurine-amidated bile acids
    • T. Iida, S. Nishida, Y. Yamaguchi, M. Kodake, F.C. Chang, and T. Niwa et al. Potential bile acid metabolites. 23. Syntheses of 3-glucosides of nonamidated and glycine- and taurine-amidated bile acids J Lipid Res 36 1995 628 638
    • (1995) J Lipid Res , vol.36 , pp. 628-638
    • Iida, T.1    Nishida, S.2    Yamaguchi, Y.3    Kodake, M.4    Chang, F.C.5    Niwa, T.6
  • 34
    • 14844316418 scopus 로고    scopus 로고
    • Chemical synthesis of 24-β-d-galactopyranosides of bile acids: A new type of bile acid conjugates in human urine
    • DOI 10.1016/j.chemphyslip.2005.01.002
    • G. Kakiyama, S. Sadakiyo, T. Iida, K. Mushiake, T. Goto, and N. Mano et al. Chemical synthesis of 24-β-d-galactopyranosides of bile acids: a new type of bile acid conjugates in human urine Chem Phys Lipids 134 2005 141 150 (Pubitemid 40387393)
    • (2005) Chemistry and Physics of Lipids , vol.134 , Issue.2 , pp. 141-150
    • Kakiyama, G.1    Sadakiyo, S.2    Iida, T.3    Mushiake, K.4    Goto, T.5    Mano, N.6    Goto, J.7    Nambara, T.8
  • 35
    • 28544435981 scopus 로고    scopus 로고
    • Chemical synthesis of the 3-sulfooxy-7-N-acetylglucosaminyl-24-amidated conjugates of 3β,7β-dihydroxy-5-cholen-24-oic acid, and related compounds: Unusual, major metabolites of bile acid in a patient with Niemann-Pick disease type C1
    • DOI 10.1016/j.steroids.2005.07.008, PII S0039128X05001923
    • T. Iida, G. Kakiyama, Y. Hibiya, S. Miyata, T. Inoue, and K. Ohno et al. Chemical synthesis of the 3-sulfooxy-7-N-acetylglucosaminyl-24-amidated conjugates of 3β,7β-dihydroxy-5-cholen-24-oic acid, and related compounds: Unusual, major metabolites of bile acid in a patient with Niemann-Pick disease type C1 Steroids 71 2006 18 29 (Pubitemid 41743824)
    • (2006) Steroids , vol.71 , Issue.1 , pp. 18-29
    • Iida, T.1    Kakiyama, G.2    Hibiya, Y.3    Miyata, S.4    Inoue, T.5    Ohno, K.6    Goto, T.7    Mano, N.8    Goto, J.9    Nambara, T.10    Hofmann, A.F.11
  • 36
    • 0034754966 scopus 로고    scopus 로고
    • Methylcellulose-immobilized reversed-phase precolumn for direct analysis of drugs in plasma by HPLC
    • DOI 10.2116/analsci.17.1155
    • E. Yamamoto, K. Murata, Y. Ishihama, and N. Asakawa Methylcellulose- immobilized reversed-phase precolumn for direct analysis of drugs in plasma by HPLC Anal Sci 17 2001 1155 1159 (Pubitemid 33042977)
    • (2001) Analytical Sciences , vol.17 , Issue.10 , pp. 1155-1159
    • Yamamoto, E.1    Murata, K.2    Ishihama, Y.3    Asakawa, N.4
  • 37
    • 32644462215 scopus 로고    scopus 로고
    • Ionization of unconjugated, glycine- and taurine-conjugated bile acids by electrospray ionization mass spectrometry
    • DOI 10.1016/j.jpba.2005.09.012, PII S0731708505006217
    • N. Mano, M. Mori, M. Ando, T. Goto, and J. Goto Ionization of unconjugated, glycine- and taurine-conjugated bile acids by electrospray ionization mass spectrometry J Pharm Biomed Anal 40 2006 1231 1234 (Pubitemid 43247463)
    • (2006) Journal of Pharmaceutical and Biomedical Analysis , vol.40 , Issue.5 , pp. 1231-1234
    • Mano, N.1    Mori, M.2    Ando, M.3    Goto, T.4    Goto, J.5
  • 38
    • 84855875118 scopus 로고    scopus 로고
    • A tandem mass spectrometric study of bile acids: Interpretation of fragmentation pathways and differentiation of steroid isomers
    • X. Qiao, M. Ye, C.F. Liu, W.Z. Yang, W.J. Miao, and J. Dong et al. A tandem mass spectrometric study of bile acids: Interpretation of fragmentation pathways and differentiation of steroid isomers Steroids 77 2012 204 211
    • (2012) Steroids , vol.77 , pp. 204-211
    • Qiao, X.1    Ye, M.2    Liu, C.F.3    Yang, W.Z.4    Miao, W.J.5    Dong, J.6
  • 40
    • 0030933887 scopus 로고    scopus 로고
    • Separatory determination of bile acid 3-sulfates by liquid chromatography/electrospray ionization mass spectrometry
    • DOI 10.1002/(SICI)1096-9888(199704)32:4<401::AID-JMS488>3.0.CO;2-E
    • S. Ikegawa, T. Yanagihara, N. Murao, H. Watanabe, J. Goto, and T. Niwa Separatory determination of bile acid 3-sulfates by liquid chromatography/ electrospray ionization mass spectrometry J Mass Spectrom 32 1997 401 407 (Pubitemid 27171156)
    • (1997) Journal of Mass Spectrometry , vol.32 , Issue.4 , pp. 401-407
    • Ikegawa, S.1    Yanagihara, T.2    Murao, N.3    Watanabe, H.4    Goto, J.5    Niwa, T.6
  • 41
    • 0000954344 scopus 로고
    • Identification and quantification of lipid sulfate esters by electrospray ionization MS/MS techniques: Cholesterol sulfate
    • K. Metzger, P.A. Rehberger, W.D. Erben, and W.D. Lehmann Identification and quantification of lipid sulfate esters by electrospray ionization MS/MS techniques: cholesterol sulfate Anal Chem 67 1995 4178 4183
    • (1995) Anal Chem , vol.67 , pp. 4178-4183
    • Metzger, K.1    Rehberger, P.A.2    Erben, W.D.3    Lehmann, W.D.4
  • 42
    • 84878734303 scopus 로고    scopus 로고
    • Profiling intact steroid sulfates and unconjugated steroids in biological fluids by liquid chromatography-tandem mass spectrometry (LC-MS-MS)
    • C.E. Galuska, M.F. Hartmann, A. Sánchez-Guijo, K. Bakhaus, J. Geyer, and G. Schuler et al. Profiling intact steroid sulfates and unconjugated steroids in biological fluids by liquid chromatography-tandem mass spectrometry (LC-MS-MS) Analyst 138 2013 3792 3801
    • (2013) Analyst , vol.138 , pp. 3792-3801
    • Galuska, C.E.1    Hartmann, M.F.2    Sánchez-Guijo, A.3    Bakhaus, K.4    Geyer, J.5    Schuler, G.6
  • 43
    • 0033389587 scopus 로고    scopus 로고
    • Separation and detection of bile acid 24-glucuronides in human urine by liquid chromatography combined with electrospray ionization mass spectrometry
    • S. Ikegawa, H. Okuyama, J. Oohashi, N. Murao, and J. Goto Separation and detection of bile acid 24-glucuronides in human urine by liquid chromatography combined with electrospray ionization mass spectrometry Anal Sci 15 1999 625 631
    • (1999) Anal Sci , vol.15 , pp. 625-631
    • Ikegawa, S.1    Okuyama, H.2    Oohashi, J.3    Murao, N.4    Goto, J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.