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Bile acids in tissues: Binding of lithocholic acid to protein

  • Symposium: Bile Acids Presented at the AOCS Annual Meeting St. Louis, Missouri — May 17, 1978
  • Published:
Lipids

Abstract

Human liver contains two forms of lithocholic acid. One form is readily extractable by 95% ethanol/0.1% ammonia (soluble lithocholate, SL), while the other remains firmly bound to the residue (tissue-bound lithocholate, TBL). TBL could be hydrolytically released using clostridial cholanoylamino acid hydrolase, suggesting a peptide link between lithocholate and protein. With bovine serum albumin (BSA), lithocholic acid showed spontaneous amino group-modifying activity. When small molecular weight lysine (α-t-BOC-1-lysyl-β-naphthylamide) and arginine peptides (α-CBZ-di-arginyl-β-naphthylamide) were used in place of BSA, lithocholate bound specifically to the lysine peptide. The unusual affinity for lysine suggested that this amino acid might be involved as a residue in TBL. Synthesis of lithocholyl lysines and comparison with products of acid hydrolysis of TBL established ε-lithocholyl lysine as the predominant form in which lithocholic acid is found in tissue bound form.

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Authors and Affiliations

  1. Biochemistry Research Division, Department of Medicine, Sinai Hospital of Baltimore, Inc., 21215, Baltimore, Maryland

    P. P. Nair, Robert Solomon, Joyce Bankoski & Robert Plapinger

Authors
  1. P. P. Nair
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  2. Robert Solomon
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  3. Joyce Bankoski
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  4. Robert Plapinger
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Additional information

Supported in part by the Gomprecht Hepatitis Fund.

The systematic nomenclature of bile acids referred to in this report by trivial names are as follows: Cholanic acid, 5β-cholan-24-oic acid; lithocholic acid, 3α-hydroxy-5β-cholan-24-oic acid; 3-epilithocholic acid, 3β-hydroxy-5β-cholan-24-oic acid; glycolithocholic acid, 3α-hydroxy-5β-cholan-24-oyl glycine; 3-ketocholanic acid, 3-keto-5β-cholan-24-oic acid; 12α-hydroxycholanic acid, 12α-hydroxy-5β-cholan-24-oic acid; chenodeoxycholic acid, 3α, 7α-dihydroxy-5β-cholan-24-oic acid; glycochenodeoxycholic acid, 3α, 7α-dihydroxy-5β-cholan-24-oyl glycine; deoxycholic acid, 3α, 12α-dihydroxy-5β-cholan-24-oic acid; glycodeoxycholic acid, 3α, 12α-dihydroxy-5β-cholan-24-oyl glycine; cholic acid, 3α, 7α, 12α-trihydroxy-5β-cholan-24-oic acid, glycocholic acid, 3α, 7α, 12α-trihydroxy-5β-cholan-24-oyl glycine; dehydrocholic acid, 3, 7, 12-triketo-5β-cholan-24-oic acid.

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Nair, P.P., Solomon, R., Bankoski, J. et al. Bile acids in tissues: Binding of lithocholic acid to protein. Lipids 13, 966–970 (1978). https://doi.org/10.1007/BF02533857

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  • DOI: https://doi.org/10.1007/BF02533857

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