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

5α-Cyprinol sulfate was isolated from 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...

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Bibliographic Details
Published in:Journal of lipid research 2003-09, Vol.44 (9), p.1643-1651
Main Authors: Goto, T., Holzinger, F., Hagey, L.R., Cerrè, C., Ton-Nu, H-T., Schteingart, C.D., Steinbach, J.H., Shneider, B.L., Hofmann, A.F.
Format: Article
Language:English
Subjects:
bacterial deconjugation
bile acids
cholestasis
Cyprinus carpio
fat absorption
fat digestion
hepatic transport
intestinal absorption
micelles
solubilization
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Summary:5α-Cyprinol sulfate was isolated from 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 transported (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.
ISSN:0022-2275
1539-7262
DOI:10.1194/jlr.M300155-JLR200