The Preparation of Chenodeoxycholic Acid and Its Glycine and Taurine Conjugates.

Hofmann, Alan F.; Lundgren, Georg; Theander, Olof; Brimacombe, J. S.; Cook, Matthew

doi:10.3891/acta.chem.scand.17-0173

Cited by 208 publications

(54 citation statements)

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“…a) Bile salts. For Subjects 2, 4, and 5, synthetic taurocholate (7,8) and taurodeoxycholate 1 were used; both conjugated bile salts were pure by thin layer chromatography (9) except for traces of free bile acid, which by potentiometric determination (10), was less than 4%o of the total bile acid present. In Subjects 1 and 3, a mixture of conjugated bile salts was isolated from a commercially available preparation of iron bile salts 2 conjugates and contained neither free bile acids, appreciable pigments, iron, nor phospholipid.…”

Section: B) Experimental Subjectsmentioning

confidence: 99%

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Absorption of Cholesterol from a Micellar Solution: Intestinal Perfusion Studies in Man*

Simmonds¹,

Hofmann²,

Theodor³

1967

J. Clin. Invest.

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181

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Summary. The absorption of cholesterol has been studied in man by perfusing the upper jejunum with a micellar solution of bile salt, 1-monoglyceride, and cholesterol-14C, with a triple lumen tube with collection sites 50 cm apart. The absorption of micellar components between the collection sites was calculated from their concentration changes relative to those of the watersoluble marker, polyethylene glycol. Control experiments were performed with cholesterol-free perfusions of saline or bile salt-monoglyceride solutions. Steady state conditions were obtained.Each of the components of the micelle was absorbed to a different extent during passage through the test segment of jejunum. Bile salt was not absorbed (mean, -3%), but micellar monoglyceride was rapidly hydrolyzed and absorbed almost completely (mean, 98%). Cholesterol radioactivity was absorbed to an intermediate extent (mean, 73%), and the absorption of chemically determined cholesterol (mean, 46%) indicated that much of the disappearance of radioactivity represented true absorption and not simple exchange.The specific activity of the perfused cholesterol fell during passage through the loop. This fall was interpreted as signifying the continuous addition of nonradioactive endogenous cholesterol by the test segment. However, the decrease in specific activity may also be considered to signify exchange, in that nonradioactive molecules entered the lumen as radioactive molecules were absorbed. Plant sterols appeared in the intestinal contents during the perfusion and must have been contributed by the perfused segment.The perfusate and samples taken from the upper and lower collection sites were examined by ultracentrifugation to define the physical state of cholesterol. It was found that cholesterol in the perfusate or upper collection site samples did not sediment, but that 23% of the cholesterol in the lower collection site samples was sedimentable (mean of three experiments); bile salt, as control, was not sedimentable. Solubility experiments in model systems showed that cholesterol possessed low solubility in bile salt solution; its solubility increased markedly and in linear proportion to the amount of

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Section: B) Experimental Subjectsmentioning

confidence: 99%

“…Cholic acid-24-4"C8 was purified by ion exchange chromatography (11) and thin layer chromatography (9) before use. Sodium taurocholate-24-'4C was prepared as described above (7,8).…”

Section: B) Experimental Subjectsmentioning

confidence: 99%

Absorption of Cholesterol from a Micellar Solution: Intestinal Perfusion Studies in Man*

Simmonds¹,

Hofmann²,

Theodor³

1967

J. Clin. Invest.

Self Cite

181

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“…J.) as described by Hofmann (7). The products migrated as single spots on thin-layer chromatography.…”

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confidence: 99%

Interactions between Intraluminal Bile Acids and Digestive Products on Pancreatic and Gallbladder Function

Malagelada¹,

Go²,

DiMagno³

et al. 1973

J. Clin. Invest.

103

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A B S T R A C T Interactions between bile acids (tauro ( CCK-PZ). Perfusion of TC alone had no effect, but addition of 10 mM of either TC, TCDC, or TDC to perfusates containing EAA, or 10 nm-M TC to MO, or both significantly reduced pancreatic enzyme output and prevented gallbladder contraction. A lower concentration of TC (5 mM) added to EAA also produced a significant inhibitory effect. Inhibition of the stimulatory action of digestive products occurred in the jejunum as well as in the duodentum. The inhibitory action of bile acid was considered to be intralutlminal since (a) bile acid did not modify the effects of ( CK-PZ given intravenously; and (b) the stimulatory effect of digestive products perfused in the duodenum on pancreatic and gallbladder function was not influenced by-simultaneous perfusion of bile acid in the jejunumn.It is proposed that this inhibitory-effect of bile acid is mediated through inhibition of CCK-PZ secretion by high intraluminal concentrations of bile acid. Inlhibition of CCK-PZ secretion by bile acid mav contribute to the regulation of pancreatic and gallbladder functioin during

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“…The NaTC (Koch Light Laboratories) moved as one spot on TLC when 1 mg was applied and was used as supplied. The NaTDC was synthesized from taurine (Eastman Organic Chemicals) and deoxjchoiic acid (Nutritional Biochemical Corporation) by the method of Norman as modified by Hofmann (1963). The final product migrated as a single spot on TLC.…”

Section: Methodsmentioning

confidence: 99%

The Effect of Micellar Solubilization on Mucosal Metabolism of Absorbed Glyceryl‐1‐monoether

Simmonds

1972

Aust J Exp Biol Med

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Summary. A lipid Jiiixture containing labelled oleic acid and labelled glyccrol-1-monoethcr was infused intraduodenally at a steady rate for 6 hours in unanaesthetized rats with l)iliary and thoracic dnct lymph fi.stulae. There were three groups, each of which received the same lipid mixture and dose but in dillerent physical states: miccllar in bile salts 10 mM, micellar in non-ionic detergent (Pluronic F68) and as a fine emulsion in bile salts 1 mM with no micellar phase. When a steady state of absorption had been reached the absorjition rate relati\e to area of small intestine utilized was greatest for micellar bile salt infusate and least for ni)n-niicellar enmlsion, with intermediate values for non-ionic micellar solution. There were differences in distdbiition of alxsorbed monoether label in the mucosa which suggested that metabolism of this model compound was affected by the rate of absorption. The percentage of monoether label which was saponifiable, i.e. which had been hydrolyzed and oxidized to fatty acid, was greater the more slowly the lipid was alxsorbed. On the other hand, the proportion of unsplit nionoethcr label which was estcrified wa.s smaller the more slowly the lipid was absorbed. .Since the results for non-ionic micellar infusate. containing no bilf salts, fell between those for high and low concentrations of bile salts, it seemed that metabolism of monoetber was uHected more by the absorptive Hnx rate than by a metabolic eftect of bile salts, per se.

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The Preparation of Chenodeoxycholic Acid and Its Glycine and Taurine Conjugates.

Cited by 208 publications

References 0 publications

Absorption of Cholesterol from a Micellar Solution: Intestinal Perfusion Studies in Man*

Absorption of Cholesterol from a Micellar Solution: Intestinal Perfusion Studies in Man*

Interactions between Intraluminal Bile Acids and Digestive Products on Pancreatic and Gallbladder Function

The Effect of Micellar Solubilization on Mucosal Metabolism of Absorbed Glyceryl‐1‐monoether

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