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Bile acid


DATA No : BBA0396 INFORMANT : Mizuho Une

NAME : 3a,7a,12a-Trihydroxy-5b-cholestan-26-oic acid

COMMON NAME:
SYMBOL:
FORMULA: C27H46O5 MOL.WT (average) : 450.651


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:25D:180-182(Ref. 0433),183-184(Ref. 0412), 25L:195-196(Ref. 0432),195-196(Ref. 0433),199-201(Ref. 0412)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:25D:[a]D=+28,25L:[a]D=+44(Ref. 0412)
25D:[a]D=+27,25L:[a]D=+43(Ref. 0433)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:m/z 680,665,590,500,410,343,303,281,253 (as methyl ester-TMS ether derivative) (Ref. 0392)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Bile from Alligator mississippiensis(Ref. 0316/0400/0436), Caiman crocodilus(Ref. 0436), Crocodilus niloticus(Ref. 0436/0437), Caiman sclerops(Ref. 0438),Caiman latirostris(Ref. 0439).Bile from Varanus monitor(Ref. 0406)Bile from Xenopus mulleri(Ref. 0309), Bufo bufo vulgaris(Ref. 0309), Bufo maculatus(Ref. 0309), Bufo marinus(Ref. 0309), Bufo regularis(Ref. 0309), Aubria subsigillata(Ref. 0309), Dicroglossus occipitalis(Ref. 0309),Xenopus laevis(Ref. 0340),Bombina orientalis(Ref. 0340), Rana brevipoda(Ref. 0340), Rana limnocharis limnocharis(Ref. 0340), Bufo vulgaris formosus(Ref. 0392), Rana plancyi(Ref. 0330), Rana tigrina rugulosa(Ref. 0330), Rana nigromaculata(Ref. 0440), Rana catesbeiana(Ref. 0333/0434/0435)Zellweger syndrome : urine(Ref. 0399/0403/0404/0419/0421/0423/0425), serum(Ref. 0403/0420/0422/0423/0426), bile(Ref. 0403/0420/0423)Infantile Refsum disease:serum(Ref. 0424/0426)Duodenal fluid from intrahepatic bile duct anomalies(Ref. 0417/0418)Gastric contents from patients with intestinal obstraction(Ref. 0413)Human bile(Ref. 0408/0442)Kite bile(Ref. 0429), baboon bile(Ref. 0443)
CHEMICAL SYNTHESIS
(Ref. 0412/0432/0433/0467)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0309]
AUTHOR:Anderson,I.G.,Haslewood,G.A.D,Oldham,R.S.,Amos,B.,and Tokes,L.
TITLE:A more detailed study of bile salt evolution, including techniques for small-scale identification and their application to amphibian biles. PubMed ID:4218097
JOURNAL:Biochem.J.
VOL:141 PAGE : 485 -494 (1974)
[TOP]

[0316]
AUTHOR:Tint,G.S.,Dayal,B.,Batta,A.K.,Sheffer S.,Joanen,T.,McNease,L.,and Salen,G.
TITLE:Biliary bile acids, bile alcohols, and sterols of alligator mississippiensis. PubMed ID:7354247
JOURNAL:J. Lipid Res.
VOL:21 PAGE : 110 -117 (1980)
[TOP]

[0330]
AUTHOR:Une,M.,Matsumoto,N.,Kihira,K.,Yasuhara,M.,Kuramoto,T.,and Hoshita,T.
TITLE:Bile salts of frogs: a new higher bile acid, 3a,7a,12a,26-tetrahydroxy-5b-cholestanoic acid from the bile of Rana plancyi. PubMed ID:7381321
JOURNAL:J.Lipid Res.
VOL:21 PAGE : 269 -276 (1980)
[TOP]

[0333]
AUTHOR:Noma, Y., Une, M., Kihira, K., Yasuda, M., Kuramoto, T., and Hoshita, T.
TITLE:Bile acids and bile alcohols of bullfrog PubMed ID:6966672
JOURNAL:J Lipid Res.
VOL:21 PAGE : 339-346 (1980)
[TOP]

[0340]
AUTHOR:Kuramoto,T.,Kikuchi,H.,and Hoshita,T.
TITLE:Bile salts of anura. PubMed ID:4727363
JOURNAL:Chem.Pharm.Bull.
VOL:21 PAGE : 952 -959 (1973)
[TOP]

[0392]
AUTHOR:Une, M., Kuramoto, T., and Hoshita, T.
TITLE:The minor bile acids of the toad, Bufo vulgaris formosus PubMed ID:6655364
JOURNAL:J Lipid Res.
VOL:24 PAGE : 1468-1474 (1983)
[TOP]

[0399]
AUTHOR:Une, M., Tazawa, Y., Tada, K., and Hoshita, T.
TITLE:Occurrence of both (25R)- and (25S)-3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acids in urine from an infant with Zellweger's syndrome PubMed ID:3448094
JOURNAL:J Biochem (Tokyo).
VOL:102 PAGE : 1525-1530 (1987)
[TOP]

[0400]
AUTHOR:Kihira, K., Okamoto, A., and Hoshita, T.
TITLE:Identification of new C27 and C24 bile acids in the bile of Alligator mississippiensis PubMed ID:3667554
JOURNAL:J Biochem (Tokyo).
VOL:101 PAGE : 1377-1384 (1987)
[TOP]

[0403]
AUTHOR:Parmentier, G. G., Janssen, G. A., Eggermont, E. A., and Eyssen, H. J.
TITLE:C27 bile acids in infants with coprostanic acidemia and occurrence of a 3 alpha,7 alpha,12 alpha-tridhydroxy-5 beta-C29 dicarboxylic bile acid as a major component in their serum PubMed ID:520320
JOURNAL:Eur J Biochem.
VOL:102 PAGE : 173-183 (1979)
[TOP]

[0404]
AUTHOR:Lawson,A.M.,Madigan,M.J.,Shortland,D.,and Clayton,P.T.
TITLE:Rapid diagnosis of Zellweger syndrome and infantile refsum's disease by fast atom bombardment-mass spectrometry of urine bile salts. PubMed ID:2433077
JOURNAL:Clin.Chim.Acta
VOL:161 PAGE : 221 -231 (1986)
[TOP]

[0406]
AUTHOR:Ali,S.S.,Stephenson,E., and Elliott,W.H.
TITLE:The major bile acids of Varanus monitor. PubMed ID:7142816
JOURNAL:J.Lipid Res.
VOL:23 PAGE : 947 -954 (1982)
[TOP]

[0408]
AUTHOR:Matoba, N., Une, M., and Hoshita, T.
TITLE:Identification of unconjugated bile acids in human bile PubMed ID:3559381
JOURNAL:J Lipid Res.
VOL:27 PAGE : 1154-1162 (1986)
[TOP]

[0412]
AUTHOR:Briggs, T.
TITLE:Partial synthesis of 25D- and 25L-cholestanoic acids from some common bile acids PubMed ID:5440333
JOURNAL:J Org Chem.
VOL:35 PAGE : 1431-1434 (1970)
[TOP]

[0413]
AUTHOR:Clayton,P.T.,Muller,D.P.R., and Lawson,A.M.
TITLE:The bile acid composition of gastric contents from neonates with high intestinal obstraction. PubMed ID:7150258
JOURNAL:Biochem.J.
VOL:206 PAGE : 489 -498 (1982)
[TOP]

[0417]
AUTHOR:Eyssen, H., Parmentier, G., Compernolle, F., Boon, J., and Eggermont, E.
TITLE:Trihydroxycoprostanic acid in the duodenal fluid of two children with intrahepatic bile duct anomalies PubMed ID:5064535
JOURNAL:Biochim Biophys Acta.
VOL:273 PAGE : 212-221 (1972)
[TOP]

[0418]
AUTHOR:Hanson, R. F., Isenberg, J. N., Williams, G. C., Hachey, D., Szczepanik, P., Klein, P. D., and Sharp, H. L.
TITLE:The metabolism of 3alpha, 7alpha, 12alpha-trihydorxy-5beta-cholestan-26-oic acid in two siblings with cholestasis due to intrahepatic bile duct anomalies. An apparent inborn error of cholic acid synthesis PubMed ID:1159074
JOURNAL:J Clin Invest.
VOL:56 PAGE : 577-587 (1975)
[TOP]

[0419]
AUTHOR:Hanson,R.F.,Szczepanik-Van Leeuween,P.,Williams,G.C.,Grabowski,G., and Sharp,H.L.
TITLE:Defects of bile acid synthesis in Zellweger's syndrome. PubMed ID:424737
JOURNAL:Science
VOL:203 PAGE : 1107 -1108 (1979)
[TOP]

[0420]
AUTHOR:Monnens, L., Bakkeren, J., Parmentier, G., Janssen, G., van Haelst, U., Trijbels, F., and Eyssen, H.
TITLE:Disturbances in bile acid metabolism of infants with the Zellweger (cerebro-hepato-renal) syndrome PubMed ID:7353569
JOURNAL:Eur J Pediatr.
VOL:133 PAGE : 31-35 (1980)
[TOP]

[0421]
AUTHOR:Mathis, R. K., Watkins, J. B., Szczepanik-Van Leeuwen, P., and Lott, I. T.
TITLE:Liver in the cerebro-hepato-renal syndrome: defective bile acid synthesis and abnormal mitochondria PubMed ID:7439636
JOURNAL:Gastroenterology.
VOL:79 PAGE : 1311-1317 (1980)
[TOP]

[0422]
AUTHOR:Kase, B. F., Bjorkhem, I., Haga, P., and Pedersen, J. I.
TITLE:Defective peroxisomal cleavage of the C27-steroid side chain in the cerebro-hepato-renal syndrome of Zellweger PubMed ID:3973012
JOURNAL:J Clin Invest.
VOL:75 PAGE : 427-435 (1985)
[TOP]

[0423]
AUTHOR:Kase, B. F., Pedersen, J. I., Strandvik, B., and Bjorkhem, I.
TITLE:In vivo and vitro studies on formation of bile acids in patients with Zellweger syndrome. Evidence that peroxisomes are of importance in the normal biosynthesis of both cholic and chenodeoxycholic acid PubMed ID:4077985
JOURNAL:J Clin Invest.
VOL:76 PAGE : 2393-2402 (1985)
[TOP]

[0424]
AUTHOR:Poulos, A., and Whiting, M. J.
TITLE:Identification of 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestan-26-oic acid, an intermediate in cholic acid synthesis, in the plasma of patients with infantile Refsum's disease PubMed ID:2581062
JOURNAL:J Inherit Metab Dis.
VOL:8 PAGE : 13-17 (1985)
[TOP]

[0425]
AUTHOR:Deleze, G., Bjorkhem, I., and Karlaganis, G.
TITLE:Bile acids and bile alcohols in two patients with Zellweger (cerebro-hepato-renal) syndrome PubMed ID:3761102
JOURNAL:J Pediatr Gastroenterol Nutr.
VOL:5 PAGE : 701-710 (1986)
[TOP]

[0426]
AUTHOR:Clayton, P. T., Lake, B. D., Hall, N. A., Shortland, D. B., Carruthers, R. A., and Lawson, A. M.
TITLE:Plasma bile acids in patients with peroxisomal dysfunction syndromes: analysis by capillary gas chromatography-mass spectrometry PubMed ID:2436918
JOURNAL:Eur J Pediatr.
VOL:146 PAGE : 166-173 (1987)
[TOP]

[0429]
AUTHOR:Kuramoto, T., and Hoshita, T.
TITLE:The identification of C 27 -bile acids in kite bile PubMed ID:5069745
JOURNAL:J Biochem (Tokyo).
VOL:72 PAGE : 199-201 (1972)
[TOP]

[0432]
AUTHOR:Komatsubara,T.
TITLE:The synthesis of 3a,7a,12a-trihydroxycoprostanic acids.
JOURNAL:Proc.Japan Acad.
VOL:30 PAGE : 618 -621 (1954)
[TOP]

[0433]
AUTHOR:Bridgwater, R. J.
TITLE:Partial synthesis of the two 3alpha:7alpha:12alpha-trihydroxycoprostanic acids and of similar bile acids with extended chains PubMed ID:13382806
JOURNAL:Biochem J.
VOL:64 PAGE : 593-599 (1956)
[TOP]

[0434]
AUTHOR:Kurauti,Y., and Kazuno,T.
TITLE:Tetraoxycholan, trioxycholen, und trioxy-bisnorsterocholansaure aus der galle von Rana catesbina shaw.
JOURNAL:Z.Physiol.Chem.
VOL:262 PAGE : 53 -60 (1939)
[TOP]

[0435]
AUTHOR:Mabuti,H.
TITLE:Uber trioxy-bisnorsterocholansaure C26H44O5 aus der galle von Rana catesbina shaw.
JOURNAL:J.Biochem.
VOL:33 PAGE : 117 -130 (1941)
[TOP]

[0436]
AUTHOR:Haslewood, G. A.
TITLE:Comparative studies of bile salts. V. Bile salts of Crocodylidae PubMed ID:13018282
JOURNAL:Biochem J.
VOL:52 PAGE : 583-587 (1952)
[TOP]

[0437]
AUTHOR:Mendelsohn, D., and Mendelsohn, L.
TITLE:The catabolism of cholesterol in vitro. Formation of 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanoic acid from cholesterol by rat liver PubMed ID:5810058
JOURNAL:Biochem J.
VOL:114 PAGE : 1-3 (1969)
[TOP]

[0438]
AUTHOR:Shah, P. P., Staple, E., and Rabinowitz, J. L.
TITLE:Trihydroxycoprostanic acid from crocodilians PubMed ID:4296053
JOURNAL:Arch Biochem Biophys.
VOL:123 PAGE : 427-428 (1968)
[TOP]

[0439]
AUTHOR:Komatsubara,T.
TITLE:On the bile acid of Rana nigromaculata nigromaculata.
JOURNAL:Proc.Japan Acad.
VOL:30 PAGE : 614 -617 (1954)
[TOP]

[0440]
AUTHOR:Kazuno,T.,Betsuki,S.,Tanaka,Y., and Hoshita,T.
TITLE:Studies on bile of Rana nigromaculata. PubMed ID:5861329
JOURNAL:J.Biochem.
VOL:58 PAGE : 243 -247 (1965)
[TOP]

[0442]
AUTHOR:Carey, J. B., Jr, and Haslewood, G. A.
TITLE:Crystallization of trihydroxycoprostani acid from human bile PubMed ID:14040575
JOURNAL:J Biol Chem.
VOL:238 PAGE : 855-856 (1963)
[TOP]

[0443]
AUTHOR:Shah, P. P., Staple, E., Shapiro, I. L., and Kritichevsky, D.
TITLE:Isolation of 3 alpha, 7 alpha, 12 alpha-trihydroxycoprostanic acid from baboon bile PubMed ID:4974941
JOURNAL:Lipids.
VOL:4 PAGE : 82-83 (1969)
[TOP]

[0467]
AUTHOR:Gengenbacher, T., Gerok, W., Giese, U., and Kurz, G.
TITLE:Synthesis and applicability of photolabile 7,7-azo analogues of natural bile salt precursors PubMed ID:2324650
JOURNAL:J Lipid Res.
VOL:31 PAGE : 315-327 (1990)
[TOP]

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