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Volumn 55, Issue 1, 2000, Pages 51-55

Mixed oxo-hydroxy bile acids as actual or potential impurities in ursodeoxycholic acid preparation: A 1H and 13C NMR study

Author keywords

13C NMR; 1H NMR; Bile acids; Nuclear magnetic resonance

Indexed keywords

CHENODEOXYCHOLIC ACID; CHOLIC ACID; DEOXYCHOLIC ACID; URSODEOXYCHOLIC ACID;

EID: 0034018490     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(99)00121-4     Document Type: Article
Times cited : (10)

References (27)
  • 1
    • 0015937537 scopus 로고
    • Efficacy and specificity of chenodeoxycholic acid therapy for dissolving gallstones
    • Thistle J.L., Hofmann A.F. Efficacy and specificity of chenodeoxycholic acid therapy for dissolving gallstones. New Engl. J. Med. 289:1973;655-661.
    • (1973) New Engl. J. Med. , vol.289 , pp. 655-661
    • Thistle, J.L.1    Hofmann, A.F.2
  • 2
    • 0021335877 scopus 로고
    • Ursodeoxycholic acid. A review of its pharmacological properties and therapeutic efficacy
    • Ward A., Brogden R.N., Heel R.C., Speight T.M., Avery G.S. Ursodeoxycholic acid. A review of its pharmacological properties and therapeutic efficacy. Drugs. 27:1984;95-131.
    • (1984) Drugs , vol.27 , pp. 95-131
    • Ward, A.1    Brogden, R.N.2    Heel, R.C.3    Speight, T.M.4    Avery, G.S.5
  • 3
    • 0023816292 scopus 로고
    • HPLC assay of conjugated bile acids in gastric juice during UDCA therapy of bile reflux gastritis
    • Scalia S., Pazzi P., Stabellini G., Guarneri M. HPLC assay of conjugated bile acids in gastric juice during UDCA therapy of bile reflux gastritis. J. Pharm. Biomed. Anal. 6:1988;911-917.
    • (1988) J. Pharm. Biomed. Anal. , vol.6 , pp. 911-917
    • Scalia, S.1    Pazzi, P.2    Stabellini, G.3    Guarneri, M.4
  • 4
    • 0023125182 scopus 로고
    • Is ursodeoxycholic acid an effective treatment for primary biliary cirrhosis?
    • Poupon R., Poupon R.E., Calmus Y., Chretien Y., Ballet F., Darnis F. Is ursodeoxycholic acid an effective treatment for primary biliary cirrhosis? Lancet. 1:1987;834-836.
    • (1987) Lancet , vol.1 , pp. 834-836
    • Poupon, R.1    Poupon, R.E.2    Calmus, Y.3    Chretien, Y.4    Ballet, F.5    Darnis, F.6
  • 6
    • 0024998297 scopus 로고
    • The effects of ursodeoxycholic acid therapy in liver disease associated with cystic fibrosis
    • Colombo C., Setchell K.D.R., Podda M., Curcio L., Ronchi M., Giunta A. The effects of ursodeoxycholic acid therapy in liver disease associated with cystic fibrosis. J. Pediatr. 117:1990;482-489.
    • (1990) J. Pediatr. , vol.117 , pp. 482-489
    • Colombo, C.1    Setchell, K.D.R.2    Podda, M.3    Curcio, L.4    Ronchi, M.5    Giunta, A.6
  • 7
    • 0030769885 scopus 로고    scopus 로고
    • Biotransformations on steroid nucleus of bile acids
    • Bortolini O., Medici A., Poli S. Biotransformations on steroid nucleus of bile acids. Steroids. 62:1997;564-577.
    • (1997) Steroids , vol.62 , pp. 564-577
    • Bortolini, O.1    Medici, A.2    Poli, S.3
  • 8
    • 0030628882 scopus 로고    scopus 로고
    • Key fragmentations for the interpretation of mass spectra of disubstituted bile acids of bovine and porcine origin
    • and references therein
    • Bortolini O., Fantin G., Medici A., Pedrini P. Key fragmentations for the interpretation of mass spectra of disubstituted bile acids of bovine and porcine origin. Rapid Commun. Mass Spectrom. 11:1997;1286-1288. and references therein.
    • (1997) Rapid Commun. Mass Spectrom. , vol.11 , pp. 1286-1288
    • Bortolini, O.1    Fantin, G.2    Medici, A.3    Pedrini, P.4
  • 9
    • 0027551777 scopus 로고
    • Ion spray liquid chromatographic/mass spectrometric characterization of bile acids
    • DiDonato G.C., Warrack B.M. Ion spray liquid chromatographic/mass spectrometric characterization of bile acids. Biol. Mass Spectrom. 22:1993;101-111.
    • (1993) Biol. Mass Spectrom. , vol.22 , pp. 101-111
    • Didonato, G.C.1    Warrack, B.M.2
  • 10
    • 0026731095 scopus 로고
    • Determination of free and amidated bile acids by high-performance liquid chromatography with evaporative light-scattering mass detection
    • Roda A., Cerrè C., Simoni P., Polimeni C., Vaccari C., Pistillo A. Determination of free and amidated bile acids by high-performance liquid chromatography with evaporative light-scattering mass detection. J. Lipid Res. 33:1992;1393-1402.
    • (1992) J. Lipid Res. , vol.33 , pp. 1393-1402
    • Roda, A.1    Cerrè, C.2    Simoni, P.3    Polimeni, C.4    Vaccari, C.5    Pistillo, A.6
  • 15
    • 0343252091 scopus 로고
    • Carbon-13 magnetic resonance study of terpenoids. An application of heteronuclear selective decoupling experiments to the spectral assignments of nonproton-bearing carbon-13 resonances of a germacranolide, melampodin
    • Bhacca N.S., Wehrli F.W., Fischer N.H. Carbon-13 magnetic resonance study of terpenoids. An application of heteronuclear selective decoupling experiments to the spectral assignments of nonproton-bearing carbon-13 resonances of a germacranolide, melampodin. J. Org. Chem. 38:1973;3618-3622.
    • (1973) J. Org. Chem. , vol.38 , pp. 3618-3622
    • Bhacca, N.S.1    Wehrli, F.W.2    Fischer, N.H.3
  • 16
    • 0008610732 scopus 로고
    • 2O
    • The stereoview of structure II has been adapted from the crystal structure of cholic acid: AM1 calculations have shown that the structure is slightly distorted in the presence of oxo groups. Functions at C-3, C-7, C-12 and side chain have been omitted for clarity
    • 2O, Cryst. Struct. Comm. 11 (1982) 1787-1792. AM1 calculations have shown that the structure is slightly distorted in the presence of oxo groups. Functions at C-3, C-7, C-12 and side chain have been omitted for clarity.
    • (1982) Cryst. Struct. Comm. , vol.11 , pp. 1787-1792
    • Lessinger, L.1
  • 17
    • 0343252092 scopus 로고    scopus 로고
    • Note that the nomenclature axial-equatorial refers to ring B and the configurational assignment of the proton at C-6 as axial is proposed by analogy with other protons under discussion. The experimental results and the dihedral angle of ca. 90°, however, are consistent with both axial and equatorial configuration for the proton at C-6
    • Note that the nomenclature axial-equatorial refers to ring B and the configurational assignment of the proton at C-6 as axial is proposed by analogy with other protons under discussion. The experimental results and the dihedral angle of ca. 90°, however, are consistent with both axial and equatorial configuration for the proton at C-6.
  • 18
    • 0342817500 scopus 로고    scopus 로고
    • 3 of compound 1 are already reported, see Ref. [22]
    • 3 of compound 1 are already reported, see Ref. [22].
  • 19
    • 84986738357 scopus 로고
    • 13C NMR spectra of steroids. A survey and commentary
    • and references therein
    • 13C NMR spectra of steroids. A survey and commentary. Org. Magn. Reson. 9:1977;439-464. and references therein.
    • (1977) Org. Magn. Reson. , vol.9 , pp. 439-464
    • Blunt, J.W.1    Stothers, J.B.2
  • 20
    • 70350329337 scopus 로고
    • Webb G.A. New York: Academic Press. and references therein
    • Smith W.B. Webb G.A. Annual Reports in NMR Spectroscopy. 8:1978;199 Academic Press, New York. and references therein.
    • (1978) Annual Reports in NMR Spectroscopy , vol.8 , pp. 199
    • Smith, W.B.1
  • 21
    • 0015935719 scopus 로고
    • Nuclear magnetic resonance spectroscopy. Carbon-13 spectra of cholic acids and hydrocarbons included in sodium deoxycholate solutions
    • Leibfritz D., Roberts J.B. Nuclear magnetic resonance spectroscopy. Carbon-13 spectra of cholic acids and hydrocarbons included in sodium deoxycholate solutions. J. Am. Chem. Soc. 95:1973;4996-5003.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 4996-5003
    • Leibfritz, D.1    Roberts, J.B.2
  • 22
    • 84986745997 scopus 로고
    • Carbon-13 NMR spectra of hydroxylated bile acid stereoisomers
    • Iida T., Tamura T., Matsumoto T., Chang F. Carbon-13 NMR spectra of hydroxylated bile acid stereoisomers. Org. Magn. Reson. 21:1983;305-309.
    • (1983) Org. Magn. Reson. , vol.21 , pp. 305-309
    • Iida, T.1    Tamura, T.2    Matsumoto, T.3    Chang, F.4
  • 25
    • 0027360614 scopus 로고
    • Synthesis of 7- And 12-hydroxy and 7,12-dihydroxy-3-keto-5β-cholan-24-oic acids by reduction of 3,7-, 3,12 and 3,7,12-oxo derivatives
    • Fantin G., Fogagnolo M., Medici A., Pedrini P., Cova U. Synthesis of 7- and 12-hydroxy and 7,12-dihydroxy-3-keto-5β-cholan-24-oic acids by reduction of 3,7-, 3,12 and 3,7,12-oxo derivatives. Steroids. 58:1993;524-526.
    • (1993) Steroids , vol.58 , pp. 524-526
    • Fantin, G.1    Fogagnolo, M.2    Medici, A.3    Pedrini, P.4    Cova, U.5
  • 27
    • 0000144507 scopus 로고
    • Preparative-scale regio- And stereospecific oxidoreduction of cholic acid and dehydrocholic acid catalyzed by hydroxysteroid dehydrogenase
    • Riva S., Bovara R., Pasta P., Carrea G. Preparative-scale regio- and stereospecific oxidoreduction of cholic acid and dehydrocholic acid catalyzed by hydroxysteroid dehydrogenase. J. Org. Chem. 51:1986;2902-2906.
    • (1986) J. Org. Chem. , vol.51 , pp. 2902-2906
    • Riva, S.1    Bovara, R.2    Pasta, P.3    Carrea, G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.