| Synthesis of (22R and 22S)-3 alpha, 7 alpha, 22-trihydroxy-5 beta-cholan-24-oic acids and structure of haemulcholic acid, a unique bile acid isolated from fish bile. | |
| | |
MedLine Citation:
|
PMID: 7320628 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
(22R and 22S)-3 alpha, 7 alpha, 22-trihydroxy-5 beta-cholan-24-oic acids were synthesized, starting from chenodeoxycholic acid, in order to establish the chemical structure of haemulcholic acid, which has been found in certain fish as the major bile component. Oxidative decarboxylation of diformoxylated chenodeoxycholic acid with lead tetraacetate yielded 24-nor-5 beta-chol-22-ene-3 alpha, 7 alpha-diol, which was hydroxylated to form a mixture of (22R and 22S)-24-nor-5 beta-cholane-3 alpha, 7 alpha, 22,23-tetrols. Lead tetraacetate oxidation of the mixture yielded 3 alpha, 7 alpha-dihydroxy-23,24-dinor-5 beta-cholan-22-a1. A Reformatsky reaction of the dihydroxydinorcholanal with bromoacetate resulted in the formation of a mixture of (22R and 22S)-3 alpha, 7 alpha, 22-trihydroxy-5 beta-cholan-24-oic acids. The bile acids epimeric at C-22 were resolved by silica gel column chromatography, and their configurations of C-22 were assigned by a modification of Horeau's method and 13C-nuclear magnetic resonance spectroscopy. By direct comparison with synthetic bile acids, the naturally occurring haemulcholic acid was shown to be (22S)-3 alpha, 7 alpha, 22-trihydroxy-5 beta-cholan-24-oic acid. |
| | |
Authors:
|
K Kihira; Y Morioka; T Hoshita |
Related Documents
:
|
19117418 - Caffeic acid as antioxidant in fish muscle: mechanism of synergism with endogenous asco... 4982418 - Penicillins and other acylamino compounds synthesized by the cell-bound penicillin acyl... 20153208 - Electrical behavior of stored erythrocytes after exposure to gamma radiation and the ro... 8216688 - Comparative metabolism and structure of bckd-e2 in primary biliary cirrhosis. 15173878 - The case of visceral fat: argument for the defense. 23183718 - Contemporary review of injectable facial fillers. |
Publication Detail:
|
Type: Journal Article |
Journal Detail:
|
Title: Journal of lipid research Volume: 22 ISSN: 0022-2275 ISO Abbreviation: J. Lipid Res. Publication Date: 1981 Nov |
Date Detail:
|
Created Date: 1982-03-13 Completed Date: 1982-03-13 Revised Date: 2006-11-15 |
Medline Journal Info:
|
Nlm Unique ID: 0376606 Medline TA: J Lipid Res Country: UNITED STATES |
Other Details:
|
Languages: eng Pagination: 1181-7 Citation Subset: IM |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Animals Bile / analysis* Bile Acids and Salts / isolation & purification* Cholic Acids / isolation & purification* Chromatography, Gas Chromatography, Thin Layer Fishes Magnetic Resonance Spectroscopy Mass Spectrometry Methods Spectrophotometry, Infrared |
| Chemical | |
Reg. No./Substance:
|
0/Bile Acids and Salts; 0/Cholic Acids; 14959-83-2/hemulcholic acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: On determining the extent of side-pool synthesis in a three-pool model for whole body cholesterol ki...
Next Document: Inhibitors of sterol biosynthesis. Carbon-13 nuclear magnetic resonance studies of 9 alpha-fluoro-5 ...