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Journal of Lipid Research, Vol. 44, 1643-1651, September 2003
Copyright © 2003 by American Society for Biochemistry and Molecular Biology

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

T. Goto^1,*, F. Holzinger^2,*, L. R. Hagey^*, C. Cerrè^3,*, H-T. Ton-Nu^4,*, C. D. Schteingart^5,*, J. H. Steinbach^*, B. L. Shneider and A. F. Hofmann^6,*

^* Division of Gastroenterology, Department of Medicine, University of California, San Diego, CA 92093-0813
Department of Pediatrics, Mount Sinai School of Medicine, New York, NY 10029-0313

⁶ To whom correspondence should be addressed. e-mail: ahofmann{at}ucsd.edu

5-Cyprinol sulfate was isolated from bile of the Asiatic carp, Cyprinus carpio. 5-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, 5-cyprinol sulfate solubilized monooleylglycerol efficiently (2.1 molecules per mol micellar bile salt). When infused intravenously into the anesthetized rat, 5-cyprinol sulfate was hemolytic, cholestatic, and toxic. In the isolated rat liver, it underwent little biotransformation and was poorly transported (T_max 0.5 µmol/min/kg) as compared with taurocholate. 5-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. 5-Cyprinol sulfate inhibited taurocholate uptake in COS-7 cells transfected with rat asbt, the apical bile salt transporter of the ileal enterocyte. 5-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 5-cyprinol sulfate was present at micellar concentrations, and that it did not undergo hydrolysis during intestinal transit.

These studies indicate that 5-cyprinol sulfate is an excellent digestive detergent and suggest that a micellar phase is present during digestion in cyprinid fish.

Supplementary key words Cyprinus carpio • bile acids • micelles • bacterial deconjugation • fat digestion • fat absorption • hepatic transport • cholestasis • intestinal absorption • solubilization

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