Chemical and metabolic transformations of selected bile acids

Eur J Drug Metab Pharmacokinet. 2006 Jul-Sep;31(3):179-235. doi: 10.1007/BF03190713.

Abstract

This article surveys chemical transformations of selected bile acids. Chemical transformations were initially carried out with the aim of determining the structure of bile acids. More recently they have been concerned with bile acid interconversions as well as with the synthesis of steroid hormones, vitamins and therapeutc agents. Studies of similarities and differences in the biosynthesis of bile acids from cholesterol have occupied many researches. However, this article reviews only papers dealing with the synthesis of potential intermediates in the biosynthesis of bile acids. Steroid hormones such as pregnenolone, progesterone and testosterone are synthesized from methyl thiodeoxycholate whereas cortisone is synthesized from methyl deoxycholiate. Numerous papers and patents devoted to the synthesis of ursodeoxycholic acid from cholic or chenodeoxycholic acid testify to its effectiveness in the treatment of cholelithiasis. Chenodeoxycholic acid appears to be an excellent precursor in the synthesis of steroid plant growth regulators, as well as in the synthesis of metabolites and vitamin D analogues. Chirality of bile acids has been exploited in the synthesis of cyclic and acyclic receptors and solvents. Cholic and deoxycholic acids have been used to create new macrocyclic structures which show different capacities to bind and transport other compounds. Another important trend in the chemistry of bile acids is their application in combinatorial chemistry.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Acylation
  • Bile Acids and Salts / chemical synthesis
  • Bile Acids and Salts / chemistry*
  • Bile Acids and Salts / metabolism*
  • Macrocyclic Compounds
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Bile Acids and Salts
  • Macrocyclic Compounds