scholarly journals Pseudomonas μtant strains that accumulate androstane and seco-androstane intermediates from bile acids

1987 ◽  
Vol 243 (1) ◽  
pp. 15-21 ◽  
Author(s):  
R A Leppik ◽  
D J Sinden
Keyword(s):  
Bile Acid ◽  
Bile Acids ◽  
Chenodeoxycholic Acid ◽  
Deoxycholic Acid ◽  
Major Product ◽  
Pseudomonas Spp ◽  
Mutant Strains ◽  
The One ◽  
The Relationship

Transposon mutant strains which were affected in bile acid catabolism were isolated from four Pseudomonas spp. Two of the mutant groups isolated were found to accumulate 12 alpha-hydroxyandrosta-1,4-diene-3,17-dione as the major product from deoxycholic acid. Strains in one of these two groups were able to grow on steroids such as chenodeoxycholic acid, which lacks a 12 alpha-hydroxy function, whereas the one member of the second group could not. With chenodeoxycholic acid, this latter strain accumulated a yellow muconic-like derivative, tentatively identified as 3,7-dihydroxy-5,9,17-trioxo-4(5),9(10)-disecoandrosta-1(10)2 -dien-4-oic acid. Members of two further mutant groups accumulated either 12 beta-hydroxyandrosta-1,4-diene-3,17-dione or 3,12 beta-dihydroxy-9(10)-secoandrosta-1,3,5(10)-triene-9,17-dione as the major product from deoxycholic acid. The relationship between the catabolism of m- and p-cresol, 3-ethylphenol and the bile acids was also examined.

Radioimmunoassay of conjugated cholic acid, chenodeoxycholic acid, and deoxycholic acid from human serum, with use of 125I-labeled ligands.

1979 ◽  
Vol 25 (2) ◽  
pp. 264-268 ◽  
Author(s):  
O Mäentausta ◽  
O Jänne
Keyword(s):  
Bile Acid ◽  
Bile Acids ◽  
Cholic Acid ◽  
Chenodeoxycholic Acid ◽  
Deoxycholic Acid ◽  
Serum Samples ◽  
Analytical Recovery ◽  
Hepatobiliary Diseases ◽  
Polyethylene Glycol Precipitation ◽  
Free Serum

Abstract We describe a method for radioimmunoassay of conjugated cholic acid, chenodeoxycholic acid, and deoxycholic acid in serum. In the method, 125I-labeled bile acid conjugates are used as the tracers along with antibodies raised against individual bile acid-bovine serum albumin conjugates. Antibody-bound and free bile acids were separated by polyethylene glycol precipitation (final concentration, 125 g/L). Before radioimmunoassay, 0.1-mL serum samples were precipitated with nine volumes of ethanol, and portions from the supernate were used in the assays. The lowest measurable amounts of the bile acids, expressed as pmol/tube, were: cholic acid conjugates, 2; chenodeoxycholic acid conjugates, 0.5; and deoxycholic acid conjugates. 2. Analytical recovery of bile acids added to bile acid-free serum ranged from 85 to 110%; intra-assay and inter-assay CVs ranged from 3.2 to 5.3% and from 5.3 to 12.2%, respectively. Concentrations (mean +/- SD) of the bile acid conjugates in serum from apparently healthy women and men (in mumol/L) were: cholic acid conjugates, 0.43 +/- 0.17 (n = 126); chenodeoxycholic acid conjugates, 0.47 +/- 0.23 (n = 111); and deoxycholic acid conjugates, 0.33 +/- 0.11 (n = 96). The values for primary bile acids were greatly increased in patients with various hepatobiliary diseases.

scholarly journals Preparation of the 3-monosulphates of cholic acid, chenodeoxycholic acid and deoxycholic acid

1976 ◽  
Vol 155 (2) ◽  
pp. 401-404 ◽  
Author(s):  
E S. Haslewood ◽  
G A. D. Haslewood
Keyword(s):  
Liver Disease ◽  
Bile Acid ◽  
Bile Acids ◽  
Cholic Acid ◽  
Chenodeoxycholic Acid ◽  
Deoxycholic Acid ◽  
Single Step ◽  
Acid Sulphate

1. The 3-sulphates of cholic, chenodeoxycholic and deoxycholic acids were prepared as crystalline disodium salts. 2. The method described shows that it is possible to prepare specific sulphate esters of polyhydroxy bile acids and to remove protecting acyl groups without removing the sulphate. 3. A study of bile acid sulphate solvolysis showed that none of the usual methods give the original bile acid in major yield in a single step. 4. An understanding of the preparation, properties and methods of solvolysis of bile acid sulphates is basic for investigations of cholestasis and liver disease.

Influence of Deoxycholic Acid Feeding on the Elimination of Cholesterol in Normolipaemic Subjects

1974 ◽  
Vol 47 (5) ◽  
pp. 425-433
Author(s):  
K. Einarsson ◽  
K. Hellström ◽  
M. Kallner
Keyword(s):  
Bile Acid ◽  
Total Synthesis ◽  
Bile Acids ◽  
Cholic Acid ◽  
Chenodeoxycholic Acid ◽  
Deoxycholic Acid ◽  
Cholesterol Metabolism ◽  
Pool Size ◽  
Faecal Excretion ◽  
The Mean

1. The turnover of [24−14C]cholic acid and [3H]chenodeoxycholic acid and the faecal excretion of neutral steroids were studied in six normolipaemic subjects before and during the ingestion of 1.3–2.6 mmol (0.5–1.0 g) of deoxycholic acid/day. Before the second study the subjects had been fed deoxycholic acid for 2 weeks. 2. The administration of deoxycholic acid did not appear to influence cholesterol metabolism as judged by the absence of change in the serum concentrations and the overall transformation into primary bile acids and neutral faecal steroids. 3. During the deoxycholic acid feeding period the mean total synthesis of bile acids was reduced by about 30%, corresponding to approximately 0.25 mmol (100 mg)/day. In one subject the pool size and in another the synthesis of cholic acid remained unchanged; otherwise the cholic acid pool size and its rate of formation decreased in all subjects. No consistent effects were observed with regard to the turnover of chenodeoxycholic acid. 4. Assuming that the bile acid turnover is equivalent to bile acid excretion then the total amount of cholesterol eliminated as bile acids and neutral faecal steroids averaged between 1.6 and 1.8 mmol/day before and during the administration of deoxycholic acid.

scholarly journals Human and livestock faecal biomarkers at the prehistorical encampment site of Ullafelsen in the Fotsch Valley, Stubai Alps, Austria – potential and limitations

2021 ◽  
Author(s):  
Marcel Lerch ◽  
Tobias Bromm ◽  
Clemens Geitner ◽  
Jean Nicolas Haas ◽  
Dieter Schäfer ◽  
...  
Keyword(s):  
Bile Acid ◽  
Bile Acids ◽  
Deoxycholic Acid ◽  
Soil Samples ◽  
Hunter Gatherers ◽  
Amazonian Dark Earths ◽  
Biomarker Pattern ◽  
Mesolithic Period ◽  
Exact Timing ◽  
Cattle And Sheep

Abstract. The Ullafelsen at 1869 m a.s.l. in the Tyrolean Stubai Alps next to Innsbruck is an important (geo-)archaeological reference site for the Mesolithic period. Buried fireplaces on the Ullafelsen plateau were dated at 10.9–9.5 cal. kyrs BP and demonstrate together with thousands of flint stone artifacts the presence of hunter-gatherers during the Early Holocene. Most recently, we demonstrated the great potential of n-alkane and black carbon biomarkers for contributing to a better understanding of pedogenesis and landscape evolution. In order to study the importance of human and/or animals for occupation of this relevant geoarchaeological site, we carried out steroid and bile acid analyses on two modern faeces samples from cattle and sheep and on 37 soil samples from seven soil profiles at the Ullafelsen. The modern animal faeces show a dominance of 5β-stigmastanol and deoxycholic acid for ruminants (cattle and sheep), which is in agreement with literature data. The OAh horizons, which have accumulated and developed since the Mesolithic, revealed high contents of steroids and bile acids; the E (LL) horizon coinciding with the Mesolithic living floor is characterized by medium contents of steroids and bile acids. By contrast, the subsoil horizons Bh, Bs and BvCv contain low contents of faecal biomarkers indicating that leaching of steroids and bile acids into the podsolic subsoils is not an important factor. Deoxycholic acid is the most abundant bile acid in all soil samples and gives evidence for strong faeces input of ruminants. The steroid and bile acid patterns and ratios indicate a negligible input of human faeces on the Ullafelsen. β-Sitosterol as plant-derived steroid has also a strong influence on the faecal biomarker pattern in our soils. Root input into the subsoils is likely reflected by β-sitosterol contents. In conclusion, our results reflect a strong faecal input by livestock, rather than by humans as found for other Anthrosols such as Amazonian Dark Earths. Further studies need to focus on the question of the exact timing of faeces deposition.

Interaction between bile acids and staphylococcal polysaccharide: inhibition of capsule formation in encapsulated mutant strains (taurine+, taurine−) of Staphylococcus aureus

1983 ◽  
Vol 29 (12) ◽  
pp. 1653-1660 ◽  
Author(s):  
Toshichika Ohtomo
Keyword(s):  
Staphylococcus Aureus ◽  
Bile Acid ◽  
Bile Acids ◽  
Cholic Acid ◽  
Taurocholic Acid ◽  
Polysaccharide Antigen ◽  
Capsule Formation ◽  
Mutant Strains ◽  
Bile Acid Derivatives ◽  
Capsular Material

In a previous paper, we showed that bile acid derivatives inhibit capsule formation as well as taurine biosynthesis in a taurine+ (Tau+) encapsulated strain of Staphylococcus aureus. In the present study, binding of [14C]cholic acid ([14C]CA) and [14C]taurocholic acid ([14C]TA) to the staphylococcal polysaccharide antigen (SPA) of the capsular fraction was examined. The bile acids were found to bind with SPA via taurine of the Tau+ cells. [14C]CA bound with the SPA fraction of the Tau+ strain within 10–30 min, whereas 60–120 min was required in the binding of [14C]TA. Various bile acids competed with cholic acid binding to Tau+ cells which was shown by the inhibition of binding with cholic acid or taurocholic acid but not with glycholic acid. Binding of bile acid derivatives to a Tau− encapsulated mutant or to capsular material from this mutant was not observed.

scholarly journals Metabolism of Oxo-Bile Acids and Characterization of Recombinant 12α-Hydroxysteroid Dehydrogenases from Bile Acid 7α-Dehydroxylating Human Gut Bacteria

2018 ◽  
Vol 84 (10) ◽  
Author(s):  
Heidi Doden ◽  
Lina A. Sallam ◽  
Saravanan Devendran ◽  
Lindsey Ly ◽  
Greta Doden ◽  
...  
Keyword(s):  
Phylogenetic Analysis ◽  
Bile Acid ◽  
Bile Acids ◽  
Cholic Acid ◽  
Deoxycholic Acid ◽  
Gut Bacteria ◽  
Dietary Lipids ◽  
Human Gut ◽  
Content Type ◽  
Low Activity

ABSTRACTBile acids are important cholesterol-derived nutrient signaling hormones, synthesized in the liver, that act as detergents to solubilize dietary lipids. Bile acid 7α-dehydroxylating gut bacteria generate the toxic bile acids deoxycholic acid and lithocholic acid from host bile acids. The ability of these bacteria to remove the 7-hydroxyl group is partially dependent on 7α-hydroxysteroid dehydrogenase (HSDH) activity, which reduces 7-oxo-bile acids generated by other gut bacteria. 3α-HSDH has an important enzymatic activity in the bile acid 7α-dehydroxylation pathway. 12α-HSDH activity has been reported for the low-activity bile acid 7α-dehydroxylating bacteriumClostridium leptum; however, this activity has not been reported for high-activity bile acid 7α-dehydroxylating bacteria, such asClostridium scindens,Clostridium hylemonae, andClostridium hiranonis. Here, we demonstrate that these strains express bile acid 12α-HSDH. The recombinant enzymes were characterized from each species and shown to preferentially reduce 12-oxolithocholic acid to deoxycholic acid, with low activity against 12-oxochenodeoxycholic acid and reduced activity when bile acids were conjugated to taurine or glycine. Phylogenetic analysis suggests that 12α-HSDH is widespread amongFirmicutes,Actinobacteriain theCoriobacteriaceaefamily, and human gutArchaea.IMPORTANCE12α-HSDH activity has been established in the medically important bile acid 7α-dehydroxylating bacteriaC. scindens,C. hiranonis, andC. hylemonae. Experiments with recombinant 12α-HSDHs from these strains are consistent with culture-based experiments that show a robust preference for 12-oxolithocholic acid over 12-oxochenodeoxycholic acid. Phylogenetic analysis identified novel members of the gut microbiome encoding 12α-HSDH. Future reengineering of 12α-HSDH enzymes to preferentially oxidize cholic acid may provide a means to industrially produce the therapeutic bile acid ursodeoxycholic acid. In addition, a cholic acid-specific 12α-HSDH expressed in the gut may be useful for the reduction in deoxycholic acid concentration, a bile acid implicated in cancers of the gastrointestinal (GI) tract.

scholarly journals Bile salts of the green turtle Chelonia mydas (L.)

1978 ◽  
Vol 171 (2) ◽  
pp. 409-412 ◽  
Author(s):  
G A D Haslewood ◽  
S Ikawa ◽  
L Tökés ◽  
D Wong
Keyword(s):  
Bile Acid ◽  
Bile Acids ◽  
Cholic Acid ◽  
Green Turtle ◽  
Bile Salts ◽  
Deoxycholic Acid ◽  
Enterohepatic Circulation ◽  
Chelonia Mydas ◽  
Independent Evolution ◽  
Alpha 7

1. Bile salts of the green turtle Chelonia mydas (L.) were analysed as completely as possible. 2. They consist of taurine conjugates of 3 alpha, 7 alpha, 12 alpha, 22 xi-tetrahydroxy-5 beta-cholestan-26-oic acid (tetrahydroxysterocholanic acid) and 3 alpha 12 alpha, 22 xi-trihydroxy-5 beta-cholestan-26-oic acid, with minor amounts of 3 alpha, 7 alpha, 12 alpha-trihydroxy-5beta-cholan-24-oic acid (cholic acid), 3alpha, 12 alpha-dihydroxy-5beta-cholan-24-oic acid (deoxycholic acid) and possibly other bile acids. 3. Cholic acid and deoxycholic acid represent the first known examples of bile acids common to chelonians and other animal forms: they may indicate independent evolution in chelonians to C24 bile acids. 4. The discovery of a 7-deoxy C27 bile acid is the first evidence that C27 bile acids or their conjugates have an enterohepatic circulation.

scholarly journals Deoxycholic Acid Could Induce Apoptosis and Trigger Gastric Carcinogenesis on Gastric Epithelial Cells by Quantitative Proteomic Analysis

2016 ◽  
Vol 2016 ◽  
pp. 1-10 ◽  
Author(s):  
Yanyan Shi ◽  
Ying Wei ◽  
Ting Zhang ◽  
Jing Zhang ◽  
Ye Wang ◽  
...  
Keyword(s):  
Bile Acid ◽  
Gastric Mucosa ◽  
Bile Acids ◽  
Molecular Mechanisms ◽  
Deoxycholic Acid ◽  
Bile Reflux ◽  
Epithelial Cell Line ◽  
Gastric Mucosal Lesions ◽  
Tandem Mass Spectrometric ◽  
String Programs

Background.Pathologic duodenogastric reflux can induce or aggravate gastritis because of the presence of bile acids. Bile reflux has been generally considered to be associated with intestinal metaplasia and gastric cancer. However, the pathogenic mechanisms of the effects of bile acids on gastric mucosa are still unknown.Methods.To explore the mechanisms by which bile acids induce gastric mucosal lesions, we examined cell apoptosis in the gastric epithelial cell line GES-1 and investigated the changes in protein profiles of GES-1 cells in response to a bile acid deoxycholic acid using a proteomics approach. Changes in the profiles of the differently expressed proteins were analyzed using the DAVID and STRING programs.Results.We found apoptosis was significantly induced in GES-1 cells by deoxycholic acid. Using liquid chromatographic/tandem mass spectrometric (LC-MS/MS) methods, 134 upregulated proteins and 214 downregulated proteins were identified in the bile acid treated GES-1 cells. Bioinformatics analysis revealed the interactions and signaling networks of these differentially expressed proteins.Conclusion.These findings may improve the understanding of the molecular mechanisms underlying the pathogenicity of bile acids on gastric mucosa.

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