| 5 beta-hydroxylation by the liver. Identification of 3,5,7-trihydroxy nor-bile acids as new major biotransformation products of 3,7-dihydroxy nor-bile acids in rodents. | |
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MedLine Citation:
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PMID: 8496179 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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24-Norursodeoxycholic acid (nor-UDCA), when administered into the anesthetized biliary fistula hamster or injected into the perfusate of an isolated liver, was hydroxylated at C-5 to give 5 beta-hydroxynorursodeoxycholic acid 2 (3 alpha,5,7 beta-trihydroxy-24-nor-5 beta-cholan-23-oic acid), which was secreted into bile mainly as such. Similarly, 24-norchenodeoxycholic acid (nor-CDCA) was 5 beta-hydroxylated to give 5 beta-hydroxynor-chenodeoxycholic acid 4 (3 alpha,5,7 alpha-trihydroxy-24-nor-5 beta-cholan-23-oic acid), which was also secreted into bile without appreciable further biotransformation. The site of hydroxylation was assigned by 13C and 1H NMR and mass spectrometry. 5-Hydroxylation was a major biotransformation pathway at physiological bile acid loads. 5-Hydroxylation of UDCA also occurred in the perfused rat liver but to a lesser extent. 5-Hydroxylation of nor-UDCA was not observed in rabbit, dog, or man, indicating that its formation is species-specific. 5-Hydroxylation of nor-CDCA and nor-UDCA is the first reported example of hydroxylation of a tertiary carbon atom of bile acids. Nor-dihydroxy bile acids appear to be useful for the detection of minor hydroxylation pathways, because their prolonged hepatobiliary retention exposes them repeatedly to hydroxylases present in the hepatobiliary system. |
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Authors:
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C D Schteingart; L R Hagey; K D Setchell; A F Hofmann |
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Publication Detail:
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Type: In Vitro; Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: The Journal of biological chemistry Volume: 268 ISSN: 0021-9258 ISO Abbreviation: J. Biol. Chem. Publication Date: 1993 May |
Date Detail:
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Created Date: 1993-06-24 Completed Date: 1993-06-24 Revised Date: 2007-11-14 |
Medline Journal Info:
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Nlm Unique ID: 2985121R Medline TA: J Biol Chem Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 11239-46 Citation Subset: IM |
Affiliation:
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Department of Medicine, University of California, San Diego, La Jolla 92093. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Bile Acids and Salts / metabolism* Bile Ducts / physiology Biotransformation Carbon Radioisotopes Chenodeoxycholic Acid / analogs & derivatives*, metabolism Cricetinae Dogs Gas Chromatography-Mass Spectrometry Glucose / metabolism Humans Hydroxylation Liver / metabolism* Magnetic Resonance Spectroscopy Rabbits Rats Species Specificity Sulfates / metabolism Sulfur Radioisotopes Taurine / metabolism Ursodeoxycholic Acid / analogs & derivatives*, metabolism |
| Grant Support | |
ID/Acronym/Agency:
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DK21506/DK/NIDDK NIH HHS; DK32130/DK/NIDDK NIH HHS; RR 01614/RR/NCRR NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Bile Acids and Salts; 0/Carbon Radioisotopes; 0/Sulfates; 0/Sulfur Radioisotopes; 107-35-7/Taurine; 128-13-2/Ursodeoxycholic Acid; 474-25-9/Chenodeoxycholic Acid; 50-99-7/Glucose; 86386-61-0/24-norchenodeoxycholic acid; 99697-24-2/24-norursodeoxycholic acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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