J. Lipid Res.
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A more recent version of this article appeared on September 1, 2003

Papers In Press, published online ahead of print June 16, 2003
J. Lipid Res., doi:10.1194/jlr.M300155-JLR200
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Submitted on April 14, 2003
Revised on June 4, 2003
Accepted on June 10, 2003

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

Takanobu Goto, Fernando Holzinger, Lee R. Hagey, Carolina Cerre, Huong-Thu Ton-Nu, Claudio D. Schteingart, Joseph H. Steinbach, Benjamin L. Shneider, and Alan F. Hofmann

Department of Medicine (Gastroenterology), University of California, San Diego, La Jolla, CA 92093-0813

Corresponding Author: hofmannaf{at}cs.com

5alpha -cyprinol sulfate was isolated from bile of the Asiatic carp, Cyprinus carpio. 5alpha -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 1.5mM; by dye solubilization, its CMC was ~ 4 mM. At concentrations >1mM, 5alpha -cyprinol sulfate solubilized monooleylglycerol efficiently (2.1 moles per mole micellar bile salt). When infused intravenously into the anesthetized rat, 5alpha -cyprinol sulfate was hemolytic, cholestatic, and toxic. In the isolated rat liver, it underwent little biotransformation and was poorly transported (Tmax 0.5 [mu}mol/min-kg) as compared to taurocholate. 5alpha -Cyprinol, its bile alcohol moiety, was oxidized to its corresponding C27 bile acid and to allocholic acid (the latter then conjugated with taurine); these metabolites were efficiently transported. 5alpha -cyprinol sulfate inhibited taurocholate uptake in COS-7 cells transfected with rat asbt, the apical bile salt transporter of the ileal enterocyte. 5alpha -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 5alpha -cyprinol sulfate was present at micellar concentrations, and that it did not undergo hydrolysis during intestinal transit. These studies indicate that 5alpha -cyprinol sulfate is an excellent digestive detergent and suggest that a micellar phase is present during digestion in cyprinid fish.


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