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Free access | 10.1172/JCI109158

Biosynthesis of Chenodeoxycholic Acid in Man: STEREOSPECIFIC SIDE-CHAIN HYDROXYLATIONS OF 5β-CHOLESTANE-3α, 7α-DIOL

S. Shefer, F. W. Cheng, A. K. Batta, B. Dayal, G. S. Tint, and G. Salen

The Public Health Research Institute of The City of New York, Inc., New York 10016

College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, New Jersey 07103

Veterans Administration Hospital, East Orange, New Jersey 07019

Cabrini Health Care Center, New York 10003

Find articles by Shefer, S. in: PubMed | Google Scholar

The Public Health Research Institute of The City of New York, Inc., New York 10016

College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, New Jersey 07103

Veterans Administration Hospital, East Orange, New Jersey 07019

Cabrini Health Care Center, New York 10003

Find articles by Cheng, F. in: PubMed | Google Scholar

The Public Health Research Institute of The City of New York, Inc., New York 10016

College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, New Jersey 07103

Veterans Administration Hospital, East Orange, New Jersey 07019

Cabrini Health Care Center, New York 10003

Find articles by Batta, A. in: PubMed | Google Scholar

The Public Health Research Institute of The City of New York, Inc., New York 10016

College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, New Jersey 07103

Veterans Administration Hospital, East Orange, New Jersey 07019

Cabrini Health Care Center, New York 10003

Find articles by Dayal, B. in: PubMed | Google Scholar

The Public Health Research Institute of The City of New York, Inc., New York 10016

College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, New Jersey 07103

Veterans Administration Hospital, East Orange, New Jersey 07019

Cabrini Health Care Center, New York 10003

Find articles by Tint, G. in: PubMed | Google Scholar

The Public Health Research Institute of The City of New York, Inc., New York 10016

College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, New Jersey 07103

Veterans Administration Hospital, East Orange, New Jersey 07019

Cabrini Health Care Center, New York 10003

Find articles by Salen, G. in: PubMed | Google Scholar

Published September 1, 1978 - More info

Published in Volume 62, Issue 3 on September 1, 1978
J Clin Invest. 1978;62(3):539–545. https://doi.org/10.1172/JCI109158.
© 1978 The American Society for Clinical Investigation
Published September 1, 1978 - Version history
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Abstract

Stereospecific side-chain hydroxylations of 5β-cholestane-3α, 7α-diol were studied in mitochondrial and microsomal fractions of human liver. Incubation of 5β-cholestane-3α, 7α-diol resulted in hydroxylations at C-12, C-24, C-25, and C-26. Hydroxylations at C-24 and C-26 were accompanied by the introduction of additional asymmetric carbon atoms at C-24 and C-25 respectively, that led to the formation of two distinct pairs of diastereoisomers, namely 5β-cholestane-3α, 7α,24-triols (24R and 24S) and 5β-cholestane-3α, 7α,26-triols (25R and 25S). A sensitive and reproducible radioactive assay to measure the formation of the different biosynthetic 5β-cholestanetriols was developed. Optimal assay conditions for human mitochondrial and microsomal systems were tentatively established.

The mitochondrial fraction was found to predominantly catalyze the 26-hydroxylation of 5β-cholestane-3α, 7α-diol with the formation of the 25R-diastereoisomer of 5β-cholestane-3α, 7α,26-triol as the major product. In the microsomal fraction, on the other hand, 25-hydroxylation was more efficient than 26-hydroxylation and accounted for 6.4% of the total hydroxylations. The microsomes catalyzed the formation of both diastereoisomers of 5β-cholestane-3α, 7α,26-triol (25R and 25S, 4.2 and 1.6% respectively).

These experiments suggest that the initial step in the degradation of the steroid side chain during the biosynthesis of chenodeoxycholic acid in man is mediated by the mitochondria, and involves the formation of the 25R-diastereoisomer of 5β-cholestane-3α, 7α,26-triol. The role of the microsomal 25- and 26-hydroxylated intermediates requires further exploration.

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