title: Physicochemical and physiological properties of 5alpha-cyprinol sulfate, the toxic bile salt of cyprinid fish.
abstract: 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 1.5 mM; by dye solubilization, its CMC was approximately 4 mM. At concentrations >1 mM, 5alpha-cyprinol sulfate solubilized monooleylglycerol efficiently (2.1 molecules per mol 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 congruent with 0.5 micromol/min/kg) as compared with taurocholate. 5alpha-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. 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.
authors.affiliation: Division of Gastroenterology, Department of Medicine, University of California, San Diego, CA 92093-0813, USA.
authors.forename: T
authors.initials: T
authors.lastname: Goto
authors.forename: F
authors.initials: F
authors.lastname: Holzinger
authors.forename: L R
authors.initials: LR
authors.lastname: Hagey
authors.forename: C
authors.initials: C
authors.lastname: Cerrè
authors.forename: H-T
authors.initials: HT
authors.lastname: Ton-Nu
authors.forename: C D
authors.initials: CD
authors.lastname: Schteingart
authors.forename: J H
authors.initials: JH
authors.lastname: Steinbach
authors.forename: B L
authors.initials: BL
authors.lastname: Shneider
authors.forename: A F
authors.initials: AF
authors.lastname: Hofmann
mesh_terms: D000818:Animals; D001646:Bile / Q000737:chemistry; D001647:Bile Acids and Salts / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism* / Q000633:toxicity; D001692:Biological Transport; D001711:Biotransformation; D002347:Carps / Q000378:metabolism; D002460:Cell Line; D002777:Cholestanols / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism* / Q000633:toxicity; D066298:In Vitro Techniques; D007413:Intestinal Mucosa / Q000378:metabolism; D008099:Liver / Q000378:metabolism; D015394:Molecular Structure; D010477:Perfusion; D051381:Rats; D021241:Spectrometry, Mass, Electrospray Ionization; D013500:Surface Tension
chemical_list: D001647:Bile Acids and Salts; D002777:Cholestanols; C023378:anhydrocyprinol