Biomaterial Database

Biotransformation of ursodeoxycholic acid by Pseudomonas sp NCIB 10590. 1988

R W Owen, and R Wait, and R F Bilton

Department of Chemistry and Biochemistry, Liverpool Polytechnic, England.

The metabolism of ursodeoxycholic acid by Pseudomonas sp NCIB 10590 has been studied in phosphate-buffered mineral salts. The organism completely metabolized ursodeoxycholic acid in 24 hr, and time-course experiments revealed that maximum product formation occurred at 14 hr. The major products detected and identified at 14 hr were 7 beta-hydroxychol-4-en-3-one-24-oic acid, 7 beta-hydroxy-3-oxo-pregna-1,4-diene-20-carboxylic acid, and 7 beta-hydroxyandrosta-1,4-diene-3,17-dione. Several minor intermediates were isolated and evidence is given for the following structures: 7 beta-hydroxy-5 beta-cholan-3-oxo-24-oic acid, 7 beta-hydroxyandrost-4-en-3,17-dione, 7 beta,17 beta-dihydroxyandrosta-1,4-diene-3-one, 3-hydroxy-1,3,5(10)-9,10-seco-androstatriene-3,17-dione-7 beta-ol, and 22 alpha-hydroxymethylpregna-1,4-diene-3-one-7 beta-ol.

UI	MeSH Term	Description	Entries
D011549	Pseudomonas	A genus of gram-negative, aerobic, rod-shaped bacteria widely distributed in nature. Some species are pathogenic for humans, animals, and plants.	Chryseomonas,Pseudomona,Flavimonas
D003840	Deoxycholic Acid	A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.	Deoxycholate,Desoxycholic Acid,Kybella,Choleic Acid,Deoxycholic Acid, 12beta-Isomer,Deoxycholic Acid, 3beta-Isomer,Deoxycholic Acid, 5alpha-Isomer,Deoxycholic Acid, Disodium Salt,Deoxycholic Acid, Magnesium (2:1) Salt,Deoxycholic Acid, Monoammonium Salt,Deoxycholic Acid, Monopotassium Salt,Deoxycholic Acid, Monosodium Salt,Deoxycholic Acid, Sodium Salt, 12beta-Isomer,Dihydroxycholanoic Acid,Lagodeoxycholic Acid,Sodium Deoxycholate,12beta-Isomer Deoxycholic Acid,3beta-Isomer Deoxycholic Acid,5alpha-Isomer Deoxycholic Acid,Deoxycholate, Sodium,Deoxycholic Acid, 12beta Isomer,Deoxycholic Acid, 3beta Isomer,Deoxycholic Acid, 5alpha Isomer
D001711	Biotransformation	The chemical alteration of an exogenous substance by or in a biological system. The alteration may inactivate the compound or it may result in the production of an active metabolite of an inactive parent compound. The alterations may be divided into METABOLIC DETOXICATION, PHASE I and METABOLIC DETOXICATION, PHASE II.
D013058	Mass Spectrometry	An analytical method used in determining the identity of a chemical based on its mass using mass analyzers/mass spectrometers.	Mass Spectroscopy,Spectrometry, Mass,Spectroscopy, Mass,Spectrum Analysis, Mass,Analysis, Mass Spectrum,Mass Spectrum Analysis,Analyses, Mass Spectrum,Mass Spectrum Analyses,Spectrum Analyses, Mass
D014580	Ursodeoxycholic Acid	An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.	Deoxyursocholic Acid,3 alpha,7 beta-Dihydroxy-5 beta-cholan-24-oic Acid,Cholit-Ursan,Cholofalk,Delursan,Destolit,Sodium Ursodeoxycholate,Urdox,Ursacholic Acid,Urso,Urso Heumann,Ursobilane,Ursochol,Ursodiol,Ursofalk,Ursogal,Ursolite,Ursolvan,3 alpha,7 beta Dihydroxy 5 beta cholan 24 oic Acid,Acid, Deoxyursocholic,Acid, Ursacholic,Acid, Ursodeoxycholic,Ursodeoxycholate, Sodium