STUDY ON THE BILE-SALTS FROM SUNFISH, MOLA-MOLA L - I - THE STRUCTURES OF SODIUM CYPRINOL SULFATES, THE SODIUM-SALT OF A NEW BILE-ACID CONJUGATED WITH TAURINE, AND A NEW BILE ALCOHOL AND ITS NEW SODIUM SULFATES

New sodium bile alcohol sulfates (1a and 1b), two sodium cyprinol sulf ates (2a and 2b), and the sodium salt of a new bile acid conjugated wi th taurine (3) were isolated from the bile of sunfish, Mola mola L., b y chromatography on silica gel and octadecylsilane (ODS), together wit h sodium taurocholate (4). On hydrolysis with pyridine and dioxane, th e new sulfates 1a and 1b both afforded a new bile alcohol (5), whose s tructure was determined to be 5 beta-cholestane-3 alpha,7 alpha,11 alp ha,26,27-pentol, based on the physico-chemical data. On the basis of t his result and their physicochemical data, the new sulfates were estab lished as (25S)- and (25R)-(+)-3 alpha,7 alpha,11 alpha,26-tetrahydrox y-5 beta-cholestan-27-yl sodium sulfate. Based on the physicochemical data and chemical transformations, the sodium cyprinol sulfates were i dentified as (25S)- and (25R)-(+)-3 alpha,7 alpha,12 alpha,26-tetrahyd roxy-5 beta-cholestan-27-yl sodium sulfate and compound 3 as sodium 2- [[3 alpha,7 alpha,11 alpha-trihydroxy-24-oxo-5 beta-cholan-24-yl]amino ]ethanesulfonate.