The bile acids in mammals are all derivatives of 5β-cholan-26-oic acid. They represent the major quantitative pathway by which cholesterol is metabolized in the body. This article covers the microbial and enzymatic transformations of free, saturated bile acids, that kept unaltered the C-24 cyclopentane-perhydrophenantrene nucleus. The bile acids that have been considered include the primary cholic and chenodeoxycholic acids, the secondary deoxycholic and lithocholic acids as well as the relevant dehydrocholic, ursocholic and ursodeoxycholic acids. Among the bile acid biotransformations, attention is paid to reactions that lead to pharmaceutically significant compounds. This is the case of 7α-hydroxy epimerization of chenodeoxycholic acid to ursodeoxycholic acid, currently used for cholesterol gallstone dissolution therapy and in the treatment of cholestatic liver diseases. Emphasis has placed on reporting reactions that may be of general interest and on the practical aspects of work in the field of biotransformations.
Biotransformations on steroid nucleus of bile acids
BORTOLINI, Olga;MEDICI, Alessandro;
1997
Abstract
The bile acids in mammals are all derivatives of 5β-cholan-26-oic acid. They represent the major quantitative pathway by which cholesterol is metabolized in the body. This article covers the microbial and enzymatic transformations of free, saturated bile acids, that kept unaltered the C-24 cyclopentane-perhydrophenantrene nucleus. The bile acids that have been considered include the primary cholic and chenodeoxycholic acids, the secondary deoxycholic and lithocholic acids as well as the relevant dehydrocholic, ursocholic and ursodeoxycholic acids. Among the bile acid biotransformations, attention is paid to reactions that lead to pharmaceutically significant compounds. This is the case of 7α-hydroxy epimerization of chenodeoxycholic acid to ursodeoxycholic acid, currently used for cholesterol gallstone dissolution therapy and in the treatment of cholestatic liver diseases. Emphasis has placed on reporting reactions that may be of general interest and on the practical aspects of work in the field of biotransformations.I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.