IDENTIFICATION OF (24E)-3-ALPHA,7-ALPHA-DIHYDROXY-5-BETA-CHOLEST-24-ENOIC ACID AND (24R,25S)-3-ALPHA,7-ALPHA,24-TRIHYDROXY-5-BETA-CHOLESTANOIC ACID AS INTERMEDIATES IN THE CONVERSION OF 3-ALPHA,7-ALPHA-DIHYDROXY-5-BETA-CHOLESTANOIC ACID TO CHENODEOXYCHOLIC ACID IN RAT-LIVER HOMOGENATES

Studies of chemical structure of the intermediates in the biosynthetic sequence between 3 alpha,7 alpha-dihydroxy-5 beta-cholestanoic acid (DHCA) and chenodeoxycholic acid have been undertaken. Radiolabeled DHCA was incubated with a rat liver preparation. The reaction products were converted to the...

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Published inJournal of lipid research Vol. 35; no. 4; pp. 620 - 624
Main Authors UNE, M, INOUE, A, KUROSAWA, T, TOHMA, T, HOSHITA, T
Format Journal Article
LanguageEnglish
Published BETHESDA LIPID RESEARCH INC 01.04.1994
Elsevier
Subjects
Animals
Biochemistry & Molecular Biology
Carbon Radioisotopes
Chenodeoxycholic Acid - biosynthesis
Cholestanols - chemistry
Cholestanols - metabolism
Cholesterol - analogs & derivatives
Cholesterol - chemistry
Cholesterol - metabolism
In Vitro Techniques
Life Sciences & Biomedicine
Liver - metabolism
Rats
Rats, Wistar
Science & Technology
CHOLIC-ACID
ALCOHOLS
ALPHA,BETA-UNSATURATED BILE ACID
PEROXISOMES
MECHANISM
3-ALPHA,7-ALPHA,12-ALPHA-TRIHYDROXY-5-BETA-CHOLESTANOIC ACID
24-HYDROXYLATION
BIOSYNTHESIS
BETA-HYDROXY BILE ACID
BILE-ACIDS
BILE ACID BIOSYNTHESIS
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Summary:Studies of chemical structure of the intermediates in the biosynthetic sequence between 3 alpha,7 alpha-dihydroxy-5 beta-cholestanoic acid (DHCA) and chenodeoxycholic acid have been undertaken. Radiolabeled DHCA was incubated with a rat liver preparation. The reaction products were converted to the p-bromophenacyl esters, and analyzed by reversed-phase high performance liquid chromatography. Under the conditions used, the radioactivity was found in (24E)-3 alpha, 7 alpha-dihydroxy-5 beta-cholest-24-enoic acid (31%) and (24R, 25S)-3 alpha,(7 alpha,(24-trihydroxy-5 beta-cholestanoic acid (7%) along with the starting material (62%). Neither the 24Z isomer of the alpha,beta-unsaturated bile acid nor the other three isomers of the beta-hydroxy bile acid were detected. The findings support the proposed pathway for the side chain cleavage in chenodeoxycholic acid biosynthesis, which is thought to be identical to that of cholic acid biosynthesis.
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ISSN:0022-2275
DOI:10.1016/s0022-2275(20)41175-7