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Bile acid


DATA No : BBA0063 INFORMANT : Takashi Iida

NAME : 1b,3a,12a-Trihydroxy-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:262-264degC, (Me ester-12-acetate; mp, 203-205degC)(Ref. 0016)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-22: +64.4deg (C=0.378, CHCl3) (Me ester-12-acetate)(Ref. 0016)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 3400, 3300, 1705(Ref. 0016)

NMR SPECTRA:1H-NMR (Pyridine-d5) d: 18-Me 0.75(s), 19-Me 1.34(s), 1a- and 12b-H 4.10-4.36(m), 3b-H 4.58-4.96(m)(Ref. 0016)
Me ester 1H-NMR (CDCl3; 100MHz ) d: 18-Me 0.68(s), 19-Me 1.04(s), COOMe 3.65(s), 12b-H 3.87(m), 1a-H 3.94(m), 3b-H 4.08(brm)(Ref. 0004/0136)

MASS SPECTRA:Me-TMS ether (70eV) m/z: 623(M-15), 548(M-TMSOH, 12%), 368(M-3TMSOH, 18%), 253(M-3TMSOH-SC, 6%), 217 (100%)(Ref. 0016/0136)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
A hepatic hydroxylation product of deoxycholic acid in sheep.(Ref. 0102)
A microbial transformation product of deoxycholic acid by Penicillium species ATCC 12556.(Ref. 0136)
Identified in serum, faeces, liver tissues and urine from healthy adults and patients with liver cirrhosis.(Ref. 0145/0149/0176/0189/0200)
A hydroxyation metabolite of deoxycholic acid in urine of a patient with intrahepatic cholestasis.(Ref. 0153)
Bile acid of the human fetus in early gestation.(Ref. 0156)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191/0198)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Excreted in urine of healthy newborn.(Ref. 0194)
Identified in human umbilical cord blood and amniotic fluid from newborns and in sera and urine from adult patients with cholestatic liver diseases.(Ref. 0199)
Identified in urine, bile, portal and peripheral venous sera, and liver specimens from subjects with liver diseases (cholestasis, liver cirrhosis, chronic hepatitis, acute hepatitis).(Ref. 0201)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0004]
AUTHOR:Barnes, S., and Kirk, D. N. (1988) Nuclear Magnetic Resonance Spectroscopy of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchell, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp65-136, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0016]
AUTHOR:Tohma, M., Mahara, R., Takeshita, H., Kurosawa, T., and Ikegawa, S.
TITLE:Synthesis of the 1 beta-hydroxylated bile acids, unusual bile acids in human biological fluids PubMed ID:3769090
JOURNAL:Chem Pharm Bull (Tokyo).
VOL:34 PAGE : 2890-2899 (1986)
[TOP]

[0102]
AUTHOR:Hofmann, A. F., Schteingart, C. D., and Hagey, L. R. (1995) Species Differences in Bile Acid Metabolism, in Bile Acids in Liver Diseases (Paumgartner, G., and Beuers, U. eds), pp 3-30, Kluwer Academic Publishers, Dordrecht.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0136]
AUTHOR:Carlstrom, K., Kirk, D. N., and Sjovall, J.
TITLE:Microbial synthesis of 1 beta- and 15 beta-hydroxylated bile acids PubMed ID:7320633
JOURNAL:J Lipid Res.
VOL:22 PAGE : 1225-1234 (1981)
[TOP]

[0145]
AUTHOR:Amuro, Y., Hayashi, E., Endo, T., Higashino, K., and Kishimoto, S.
TITLE:Unusual trihydroxylated bile acids in urine of patients with liver cirrhosis PubMed ID:6825311
JOURNAL:Clin Chim Acta.
VOL:127 PAGE : 61-67 (1983)
[TOP]

[0149]
AUTHOR:Batta, A. K., Arora, R., Salen, G., Tint, G. S., Eskreis, D., and Katz, S.
TITLE:Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment PubMed ID:2621422
JOURNAL:J Lipid Res.
VOL:30 PAGE : 1953-1962 (1989)
[TOP]

[0153]
AUTHOR:Bremmelgaard, A., and Sjovall, J.
TITLE:Hydroxylation of cholic, chenodeoxycholic, and deoxycholic acids in patients with intrahepatic cholestasis PubMed ID:7462803
JOURNAL:J Lipid Res.
VOL:21 PAGE : 1072-1081 (1980)
[TOP]

[0156]
AUTHOR:Colombo, C., Zuliani, G., Ronchi, M., Breidenstein, J., and Setchell, K. D.
TITLE:Biliary bile acid composition of the human fetus in early gestation PubMed ID:3822601
JOURNAL:Pediatr Res.
VOL:21 PAGE : 197-200 (1987)
[TOP]

[0176]
AUTHOR:Jonsson, G., Hedenborg, G., Wisen, O., and Norman, A.
TITLE:Presence of bile acid metabolites in serum, urine, and faeces in cirrhosis PubMed ID:1411266
JOURNAL:Scand J Clin Lab Invest.
VOL:52 PAGE : 555-564 (1992)
[TOP]

[0188]
AUTHOR:Meng, L. J., Reyes, H., Palma, J., Hernandez, I., Ribalta, J., and Sjovall, J.
TITLE:Effects of ursodeoxycholic acid on conjugated bile acids and progesterone metabolites in serum and urine of patients with intrahepatic cholestasis of pregnancy PubMed ID:9453429
JOURNAL:J Hepatol.
VOL:27 PAGE : 1029-1040 (1997)
[TOP]

[0189]
AUTHOR:Miyara, T., Shindo, N., Tohma, M., and Murayama, K.
TITLE:Capillary gas chromatography/negative ion chemical ionization mass spectrometry for the quantification of bile acids including 1 beta-hydroxylated and unsaturated bile acids in serum and urine PubMed ID:2350598
JOURNAL:Biomed Chromatogr.
VOL:4 PAGE : 56-60 (1990)
[TOP]

[0191]
AUTHOR:Nakagawa, M., Colombo, C., and Setchell, K. D.
TITLE:Comprehensive study of the biliary bile acid composition of patients with cystic fibrosis and associated liver disease before and after UDCA administration PubMed ID:2391071
JOURNAL:Hepatology.
VOL:12 PAGE : 322-334 (1990)
[TOP]

[0192]
AUTHOR:Nakagawa, M., and Setchell, K. D.
TITLE:Bile acid metabolism in early life: studies of amniotic fluid PubMed ID:2373959
JOURNAL:J Lipid Res.
VOL:31 PAGE : 1089-1098 (1990)
[TOP]

[0194]
AUTHOR:Obinata, K., Nittono, H., Yabuta, K., Mahara, R., and Tohma, M.
TITLE:1 beta-hydroxylated bile acids in the urine of healthy neonates PubMed ID:1403443
JOURNAL:J Pediatr Gastroenterol Nutr.
VOL:15 PAGE : 1-5 (1992)
[TOP]

[0198]
AUTHOR:Setchell, K. D., Dumaswala, R., Colombo, C., and Ronchi, M.
TITLE:Hepatic bile acid metabolism during early development revealed from the analysis of human fetal gallbladder bile PubMed ID:3182806
JOURNAL:J Biol Chem.
VOL:263 PAGE : 16637-16644 (1988)
[TOP]

[0199]
AUTHOR:Shoda, J., Mahara, R., Osuga, T., Tohma, M., Ohnishi, S., Miyazaki, H., Tanaka, N., and Matsuzaki, Y.
TITLE:Similarity of unusual bile acids in human umbilical cord blood and amniotic fluid from newborns and in sera and urine from adult patients with cholestatic liver diseases PubMed ID:3411245
JOURNAL:J Lipid Res.
VOL:29 PAGE : 847-858 (1988)
[TOP]

[0200]
AUTHOR:Shoda, J., Osuga, T., Mahara, R., Tohma, M., Matsuura, K., Tanaka, N., Matsuzaki, Y., and Miyazaki, H.
TITLE:Altered metabolism of bile acids in cholestasis: determination of 1 beta- and 6 alpha-hydroxylated metabolites PubMed ID:2745625
JOURNAL:J Chromatogr.
VOL:488 PAGE : 315-328 (1989)
[TOP]

[0201]
AUTHOR:Shoda, J., Tanaka, N., Osuga, T., Matsuura, K., and Miyazaki, H.
TITLE:Altered bile acid metabolism in liver disease: concurrent occurrence of C-1 and C-6 hydroxylated bile acid metabolites and their preferential excretion into urine PubMed ID:2324645
JOURNAL:J Lipid Res.
VOL:31 PAGE : 249-259 (1990)
[TOP]

[0202]
AUTHOR:Strandvik, B., Wahlen, E., and Wikstrom, S. A.
TITLE:The urinary bile acid excretion in healthy premature and full-term infants during the neonatal period PubMed ID:8171265
JOURNAL:Scand J Clin Lab Invest.
VOL:54 PAGE : 1-10 (1994)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.