Diglucuronide: a novel bile acid metabolite
Bile acids can be glucuronidated on steroidal hydroxyl groups. Recent results from the laboratory also documented the formation of carboxyl-linked glucuronides as the major type of conjugation for short-chain bile acids. Now they report the identification of a short-chain bile acid glucuronidated on both the carboxyl and hydroxyl group. (3-/sup 3/H)Norlithocholate was administered to rats prepared with a biliary fistula and its metabolites were identified. 75% of the metabolites found in bile were glucuronides, the ratio of hydroxyl-linked to carboxyl-linked being 2:1. The assignment of a compound to one of these two classes of conjugate can be made based on their NMR spectra, which differ characteristically in the chemical shifts of several hydrogens. One metabolite, homogeneous by chromatographic and spectral criteria and accounting for 11% of the biliary radioactivity, exhibited NMR signals of both types of glucuronide in a ratio of 1:1. This, and TLC comparison with a chemically synthesized standard, allowed the assignment of the diglucuronide structure to this compound. Further confirmation was obtained from in vitro experiments. Norlithocholate glucuronide, when incubated with UDP-(/sup 14/C)-glucuronic acid and rat liver microsomes, is converted to a radioactive product, presumably the diglucuronide. Under identical conditions, lithocholate glucuronide does not give rise to a radiolabeled product.
- Research Organization:
- Univ. of Texas Medical School, Houston
- OSTI ID:
- 6991212
- Report Number(s):
- CONF-8606151-
- Journal Information:
- Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States), Vol. 45:6; Conference: 76. annual meeting of the Federation of American Society for Experimental Biology, Washington, DC, USA, 8 Jun 1986
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
62 RADIOLOGY AND NUCLEAR MEDICINE
BILE ACIDS
METABOLISM
METABOLITES
NMR SPECTRA
CARBON 14 COMPOUNDS
CHEMICAL SHIFT
LIVER
NUCLEAR MAGNETIC RESONANCE
RATS
THIN-LAYER CHROMATOGRAPHY
TRACER TECHNIQUES
TRITIUM COMPOUNDS
ANIMALS
BODY
CARBOXYLIC ACIDS
CHROMATOGRAPHY
DIGESTIVE SYSTEM
GLANDS
HYDROXY COMPOUNDS
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
MAGNETIC RESONANCE
MAMMALS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANS
RESONANCE
RODENTS
SEPARATION PROCESSES
SPECTRA
STEROIDS
STEROLS
VERTEBRATES
550501* - Metabolism- Tracer Techniques
550600 - Medicine