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PubMed1991

Isolation and identification of bile salts conjugated with cysteinolic acid from bile of the red seabream, Pagrosomus major.

Bile salts present in gallbladder of wild and cultured red seabream, Pagrosomus major, a marine teleost were analyzed. The bile from wild red seabream was found to contain two previously unknown bile salts along with two known bile salts, taurocholate and taurochenodeoxycholate. Isolation of each bile salt was performed by column chromatography. Fast atom bombardment mass spectra of the unknown bile salts showed the molecular ions (M-H)- of m/z 544 and 528 which are shifted 30 mass units upfield compared to those (m/z 514 and 498) of taurocholate and taurochendeoxycholate, respectively; this is consistent with the presence of cysteinolic acid (mol wt 155) instead of taurine (mol wt 125). Enzymatic hydrolysis of the bile salts released cholic acid and chenodeoxycholic acid, respectively, and an amino acid that was identified as D-cysteinolic acid by direct comparison with an authentic sample. From these results, the bile salts in the bile of wild red seabream were identified as the conjugates of cholic acid and chenodeoxycholic acid with cysteinolic acid. 1H- and 13C-magnetic resonance spectra of the bile salts were also consistent with the proposed structure. The cysteinolic acid conjugates were found only in wild and not in cultured red seabream; this distinction seems to result from differences in dietary cysteinolic acid.

Animals↗
PubMed1986

Bile salt related secretion of acid phosphatase in rat bile.

The biliary excretion of bile salts, lysosomal acid phosphatase, and total proteins were studied in rats under different experimental conditions: during bile salt loss through a bile fistula and after loading with exogenous sodium taurocholate. The experimental models were suitable to demonstrate that variations in the excretion of bile salts were associated with those of acid phosphatase output. During bile salt depletion, acid phosphatase output showed a decrease parallel to that of bile salts. Following a single i.v. injection of sodium taurocholate and during its i.v. infusion, a rapid increase of acid phosphatase excretion in bile was seen. The patterns of enzyme outputs observed after administration of sodium taurocholate suggested a bulk discharge in bile of lysosomal contents. The profiles of protein output were similar to those of acid phosphatase suggesting an association between the secretory mechanism of these bile constituents. In contrast to sodium taurocholate, 4-methylumbelliferone, which also increases canalicular bile flow, did not produce changes in the excretory patterns of the bile components studied. Therefore, the results suggested a bile salt related secretion of acid phosphatase in the rat, which may involve protein secretion in bile.

Acid Phosphatase↗
PubMed1984

Sodium absorption with bacterial fatty acids and bile salts in the proximal and distal colon as a guide to colonic resection.

Rates of sodium absorption in the presence of bacterial fatty acids and bile salts are unknown along the length of the colon. Such information may guide resection of colon with a view to leaving colon most optimal for ion absorption. Absorption of sodium and permeability of the colonic mucosa to 51Cr EDTA was measured in the proximal (PC) and distal colon (DC) instilled with NaCl (120 mM), n-butyrate (40 mM) and chenodeoxycholic acid (1 or 2 mM) in varying combinations. Sodium absorption in the PC was 123.6 +/- 19 (nmoles/min/cm2)(n = 7) with saline alone and was doubled (P less than .001) when 40 mM n-butyrate replaced chloride anions. Sodium absorption in the DC with saline alone was 106.9 +/- 18 without significant alteration by addition of n-butyrate. CDC (1 mM) diminished sodium absorption in the PC and DC. Diminished sodium absorption induced by bile salts was significantly reversed by n-butyrate in the PC but not DC. Permeability of 51Cr EDTA was greatest with 2 mM CDC in the distal colon. Mucosal function--sodium absorption with SCFAs, permeability changes, and protection by bacterial fatty acids from sodium losses due to bile salts--was superior in the PC compared with DC. Our results suggest that it may be preferable to preserve the proximal rather than distal colon in operations of the colon to secure optimal absorption of sodium.

Animals↗
PubMed2003

Separation of homologues and isomers of linear alkylbenzenesulfonates by capillary electrophoresis with sodium dodecyl sulfate, carboxylic acids and bile salts.

The ability of several anionic compounds, including carboxylic and dicarboxylic acids, sodium dodecyl sulfate (SDS), and sodium deoxycholate (SDC) and other bile salts, to separate the C(10)-C(13) homologues and the corresponding 20 positional isomers of linear alkylbenzenesulfonates (LAS) by capillary electrophoresis was studied. Up to 19 peaks and a shoulder were observed with a background electrolyte (BGE) containing 10 mM phosphate (pH 6.8), 30% acetonitrile and 40 mM SDS, and 18 peaks were obtained with a BGE containing 10 mM borate (pH 9), 40% ethanol and 40 mM palmitic acid (PA). Resolution increased with the alkyl chain length of the carboxylic acid. Dicarboxylic acids with a short alkyl chain, as azelaic acid, were useful to separate the homologues without distinguishing between the isomers. Up to 16 peaks and a shoulder were distinguished with SDC. Resolution decreased with the other bile salts. The 6-C(11)/5-C(11) isomer pair was better resolved with SDC than with SDS, and the 2-C(12) isomer was isolated using both PA and SDC, but not with SDS. Only the 7-C(13)/6-C(13) pair could not be resolved with any of the discriminating agents used.

Bile Acids and Salts↗
PubMed2000

A comparison of the permeation enhancement potential of simple bile salt and mixed bile salt:fatty acid micellar systems using the CaCo-2 cell culture model.

The aim of this study was to compare the permeation enhancing potential and toxicity of simple bile salt and bile salt:fatty acid mixed micellar systems using the CaCo-2 cell culture model. The effects of micellar systems of sodium cholate, (NaC), and sodium taurocholate, (NaTC), on the permeability of the hydrophilic markers, mannitol (182) and polyethylene glycols (PEGS) 900 and 4000, were assessed. Simple micelle systems of the unconjugated bile salt, NaC, caused greater enhancement of the hydrophilic markers than the conjugated bile salt, NaTC. In the case of NaC systems the enhancement was coincident with excess membrane disruption and toxicity as indicated by altered TEERs, TEMs, MTT values, and, the lack of recovery following removal of the enhancer. In contrast, the NaTC systems were less toxic, and, in the simple micelle form the likely mechanism of enhancement of the hydrophilic markers is via a transient effect on the tight junctions. Formation of mixed micellar systems with linoleic acid (LA) accentuated the toxic effects of NaC. In comparison, NaTC:LA mixed micelles showed superior permeability enhancement versus simple micelles without increasing membrane toxicity. The mechanism of enhancement of NaTC:LA appears more complex and involves a possible combination effect on both the paracellular and transcellular routes.

Bile Acids and Salts↗
PubMed1976

Lecithin inhibits fatty acid and bile salt absorption from rat small intestine in vivo.

During digestion of a fatty meal, long chain free fatty acids (FFA) and lecithin are among the lipids solubilized in intestinal contents as mixed micelles with bile salts. We hypothesized that if lecithin were not hydrolyzed, the mixed micelles would be abnormal, and absorption of FFA and bile salts would be depressed. To test this hypothesis, isolated segments of rat small intestine were infused in vivo with micellar solutions of 2 mMolar linoleic acid and 10 mMolar taurocholate to which was added 3 mMolar 1-palmitoyl, 2-oleoyl lecithin (a common lecithin in bile and food), or 1-palmitoyl lysolecithin (the hydrolytic product of lecithin). Absorption of FFA and bile salt was measured under steady state conditions using a single-pass technique. Lecithin depressed the rate of FFA absorption by 40% (p less than 0.025) in jejunal and ileal segments whereas lysolecithin was associated with normal rates of FFA absorption. Lecithin also reduced taurocholate absorption from the ileum by 30% (p less than 0.05). These data support the idea that lecithin may depress FFA and bile salt absorption from the small intestine in pancreatic insufficiency.

Animals↗
PubMed2006

Free radical production in the esophago-gastro-duodenal mucosa in response to acid and bile.

Several studies have demonstrated the role of free radicals in causing esophagus-gastro-duodenal mucosal injury. The present study has been designed to investigate: whether acid, bile salts and a combination of bile + acid could determine the production of O2-derived free radicals by oesophageal, gastric and duodenal mucosa; which agent is capable of producing more free radicals and if O2-derived free radicals production depends on the duration of contact with acid, bile salts and their combination. Wistar rats' gastro-intestinal mucosa were perfused with bile, acid and a combination of bile + acid at pH4 and pH2 for 1 hour and 2 hours. Free radical production (FRP) was assessed by chemoluminescence. After 1 hour, the increase in FRP in comparison with control reached statistical significance (P < 0.05) at all tested pH levels in the duodenum, at pH1, 2 and 3 in the esophagus, and at pH1 in the stomach. Comparing different segments, both the esophagus and duodenum behaved similarly, producing more free radicals than the stomach at all pH values. However, this difference reached statistical significance at pH1 and 2 only. In comparison to control, FRP was increased by bile (pH7) infusion after 1 and 2 hours. There was increased FRP in all segments after the infusion of bile at pH2 and 4 in comparison to control. Infusion of bile at pH2 stimulates more FRP than infusion of bile at pH4 in all segments. This increased FRP reaches statistical significance in the esophagus after 2 hours of infusion, in the stomach after 1 and 2 hours of infusion, but in the duodenum it does not reach statistical significance. Acid, bile and bile + acid at pH2 and 4 can cause free radical production in esophageal, gastric and duodenal mucosa. Their role in producing free radicals is different according to the segment and the chemical composition of the solution.

Animals↗
PubMed1968

Effect of sodium taurolithocholate on bile flow and bile acid exeretion.

Sodium taurolithocholate and sodium taurocholenate were infused intravenously into rats and hamsters. Each bile acid salt was given alone or in combination with varying amounts of a primary bile salt, either sodium taurocholate or sodium taurochenodeoxycholate. Bile flow, total bile acid salt excretion, and the excretion of sodium taurolithocholate were quantitatively determined. In addition, mannitol excretion in bile was determined at various flow rates. Sodium taurolithocholate was found to be rapidly excreted in bile in concentrations greater than its aqueous solubility. When the endogenous excretion rate of bile salt or the infusion of primary bile salt was less than the molar amount of administered sodium taurolithocholate, cholestasis always occurred. Increasing molar amounts of primary bile salt prevented cholestasis and enhanced the excretion rate of sodium taurolithocholate. Infusion of sodium taurocholenate, a nonhemolytic bile salt, caused an effect on bile flow and bile acid salt excretion qualitatively similar to sodium taurolithocholate. The induction of cholestasis can be attributed to the physical properties of these poorly water soluble bile salts. The reduction in bile flow could not be shown to be related to water reabsorption from the biliary tree since there was no increase in mannitol concentration in bile during cholestasis. Reduction in bile flow may be related to obstruction of segments of the biliary tree by precipitates of sodium taurolithocholate and possibly to a decrease in water entry into the biliary tree during infusion of this bile acid salt.

Animals↗
PubMedDate not supplied

Bile acids and bile salts: ionization and solubility properties.

The number, position and orientation of nuclear OH substituents profoundly influence the equilibrium solubilities of undissociated bile acids in water. Estimates from several studies range from 5 X 10(-8) for lithocholic acid to 1.6 X 10(-3) M for ursocholic acid at 37 degrees C. Fully dissociated sodium bile salts are extremely soluble in water, attaining values as high as 1 to 2 M. However, ionized unconjugated bile salts are appreciably less soluble than their glycine and taurine conjugates. In contrast to aqueous solutions of typical soaps and detergents, aqueous bile salt systems in concentrations beyond the micellar phase limit exhibit no liquid-crystalline phases. The critical micellar temperatures of the common di- and trihydroxy bile salts lie below 0 degree C, hence most bile salts form micelles at all ambient temperatures. With many monohydroxy and certain uncommon dihydroxy bile salts, the critical micellar temperatures lie above body temperature, and a micellar phase is observed only at temperatures in excess of 50 degrees C. The pKa' values of aqueous micellar concentrations of bile salts are influenced by the nuclear substituents, the state of conjugation and bile salt concentration. In contrast, the intrinsic thermodynamic pK'a values of all monocarboxylated bile salts in monomeric solution are similar, are not influenced by nuclear substituents and are equivalent to that expected for propionic acid (pKa' approximately 4.8 to 5.0). These values can be deduced by extrapolation from acidimetric titrations of bile salts in aqueous methanol mixtures or from acidometric aqueous titration of the carboxylate groups of pansulfated bile salts which remain water soluble when the ionic group of the side chain is protonated.(ABSTRACT TRUNCATED AT 250 WORDS)

Bile Acids and Salts↗
PubMed2005

Bile salt and acid tolerance of Lactobacillus rhamnosus strains isolated from Parmigiano Reggiano cheese.

This study aimed to compare phenotypic and genetic characteristics of Lactobacillus rhamnosus strains isolated at the end of the ripening of Parmigiano Reggiano cheese and to investigate an important prerequisite of probiotic interest, such as the capability to survive at low pH and in presence of bile salts. The use of API 50 CH, RAPD-PCR analysis and species-specific PCR allowed to ascertain the identity of 63 L. rhamnosus strains. Three L. rhamnosus strains isolated from Parmigiano Reggiano cheese, L. rhamnosus ATCC 7469T and the commercial strain L. GG were assayed to estimate the resistance to various stress factors reproducing in vitro some conditions of the gastro-intestinal environment such as low pH and different amounts of bile salts and acids. The behaviour of almost all the tested strains isolated from Parmigiano Reggiano cheese resulted analogous to that showed by L. GG.

Base Sequence↗
PubMed2002

Oral absorption of insulin encapsulated in artificial chyles of bile salts, palmitic acid and alpha-tocopherol dispersions.

The hypoglycemic effect of orally given insulin was studied on rabbits, using different bile salts as absorption promoters, in two different carriers to form an artificial chyloform system ready to be absorbed by intestinal mucosa. The rank order of enhancement by bile salts in the presence of 1% ethanol was deoxycholate>cholate>glycocholate>glycodeoxycholate>taurodeoxycholate>no bile salts. The dose response studies with increased insulin loaded in the chyle showed a greater corresponding hypoglycemic effect with the system of cholate-palmitic-alpha-tocopherol dispersions than the cholate-palmitic acid dispersions. A more effective hypoglycemic effect was achieved using lower doses of the deoxycholate-palmitate-tocopherol-chyle dispersions.

Administration, Oral↗