Physicochemical and physiological properties of 5α-cyprinol sulfate, the toxic bile salt of cyprinid fish

T. Goto, F. Holzinger, L. R. Hagey, C. Cerrè, H. T. Ton-Nu, C. D. Schteingart, J. H. Steinbach, B. L. Shneider, A. F. Hofmann

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44 Citations (Scopus)

Abstract

5α-Cyprinol sulfate was isolated form bile of the Asiatic carp, Cyprinus carpio. 5α-Cyprinol sulfate was surface active and formed micelles; its critical micellization concentration (CMC) in 0.15 M Na + using the maximum bubble pressure device was 1.5 mM; by dye solubilization, its CMC was ∼4 mM. At concentrations > 1 mM, 5α-cyprinol sulfate solubilized monooleylglycerol efficiently (2.1 molecules per mol micellar bile salt). When infused intravenously into the anesthetized rat, 5α-cyprinol sulfate was hemolytic, cholestatic, and toxic. In the isolated rat liver, it underwent little biotransformation and was poorly transporled (Tmax ≅ 0.5 μmol/min/kg) as compared with taurocholate. 5α-Cyprinol, its bile alcohol moiety, was oxidized to its corresponding C27 bile acid and to allocholic acid (the latter was then conjugated with taurine); these metabolites were efficiently transported. 5α-Cyprinol sulfate inhibited taurocholate uptake in COS-7 cells transfected with rat asbt, the apical bile salt transporter of the ileal enterocyte. 5α-Cyprinol had limited aqueous solubility (0.3 mM) and was poorly absorbed from the perfused rat jejunum or ileum. Sampling of carp intestinal content indicated that 5α-cyprinol sulfate was present at micellar concentrations, and that it did not undergo hydrolysis during intestinal transit. These studies indicate that 5α-cyprinol sulfate is an excellent digestive detergent and suggest that a micellar phase is present during digestion in cyprinid fish.-Goto, T., F. Holzinger, L. R. Hagey, C. Cerrè, H-T. Ton-Nu, C. D. Schteingart, J. H. Steinbach, B. L. Shneider, and A. F Hofmann. Physicochemical and physiological properties of 5α-cyprinol sulfate, the toxic bile salt of cyprinid fish.

Original languageEnglish
Pages (from-to)1643-1651
Number of pages9
JournalJournal of lipid research
Volume44
Issue number9
DOIs
Publication statusPublished - 2003 Sep 1

Keywords

  • Bacterial deconjugation
  • Bile acids
  • Colestasis
  • Cyprinus carpio
  • Fat absorption
  • Fat digestion
  • Hepatic transport
  • Intestinal absorption
  • Micelles
  • Solubilization

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Cell Biology

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