Bile acids

Elliott, William H.; Walsh, Lawrence B.; Mui, Mei Mei; Thorne, Michael A.; Siegfried, Charles M.

doi:10.1016/s0021-9673(01)92569-5

Cited by 62 publications

(4 citation statements)

References 24 publications

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“…Crystallization from benzene/pentane (1 : 1 ) yielded 380 mg of crystalline product; the melting point (74-78" C) was compatible with that reported [7] for synthetic methyl P-muricholate (78 -84" C). The retention times relative to the same derivative of deoxycholic acid of the methyl ester and the methyl ester tris(trimethylsily1) ether corresponded to those reported by Elliott et al [8]. The mass spectrum obtained from the methyl ester tris(trimethylsi1yl) ether was identical to that published [9, o-Muricholic acid was isolated from feces of rats receiving a commercial diet together with penicillin V potassium salt (5 g/1 in the drinking water).…”

Section: Bile Acidssupporting

confidence: 82%

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Effects of Cholesterol Feeding on the Bile Acids of Male and Female Germ-Free Rats

Parmentier¹,

Smets²,

Jannsen³

et al. 1981

Eur J Biochem

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The effect of cholesterol feeding on the intestinal bile acids was studied in male and female germ-free rats. The bile acid pattern of the male animals was not altered considerably by cholesterol supplementation. Bile acids belonging to the chenodeoxycholic acid pathway slightly increased whereas cholic acid decreased. P-Muricholic acid remained the predominant bile acid in male rats. On the other hand, cholesterol feeding to female germ-free rats substantially changed the intestinal bile acid composition. The concentration of cholic acid fell to one third and that of P-muricholic acid decreased by about half. On the contrary, the relative amounts of chenodeoxycholic acid, allochenodeoxycholic acid and a-muricholic acid increased several times. The most striking sex-linked effect of cholesterol feeding was the occurrence in female rats of a bile acid tentatively identified as 3 a,7P-dihydroxy-6-oxo-5 P-cholan-24-oic acid. This bile acid accounted for 16.0 and 26.6 % of the total bile acids in the small intestine and in the cecum plus large intestine, respectively.Cholesterol feeding also influenced the sulfation of bile acids in female germ-free rats. In the small intestine the sulfated fraction increased from 1.1 to 2.8% and in cecum plus large intestine from 23.0'%, to 30.8'1.;,. Allochenodeoxycholic acid was the predominant bile acid in the sulfate fraction. The total amount of bile acids in cecum plus large intestine increased from 72.0 to 225.0 mg/kg body weight in male rats and from 64.8 to 231.3 mg/kg body weight in female animals.Blood cholesterol levels in rats are influenced by the sex of the animal. When fed a basal diet male rats have a lower cholesterol concentration in blood than female animals [l]. Serum cholesterol of male rats is only slightly increased by feeding an excess of cholesterol [2], whereas cholesterol feeding to female rats results in a more pronounced rise [3].In a previous paper we reported marked sex-linked differences in the bile acid composition in germ-free rats fed a basal diet without exogenous cholesterol supplements [4]. Male rats predominantly excreted b-muricholic acid in their bile, whereas in female animals cholic acid was the major compound. The concentration of sulfated bile acids and allo bile acids was more elevated in female rats than in males.Gustafsson and colleagues [5] found that cholesterol feeding to male germ-free rats stimulated 7cc-hydroxylation of cholesterol and 6 P-hydroxylation of lithocholic acid, but decreased 12a-hydroxylation of 7a-hydroxy-4-cholesten-3-one. An increased intake of cholesterol was compensated by an increased excretion of fecal bile acids [6].The present report describes effects of cholesterol feeding on the formation of bile acids in germ-free male and female rats.Symbol und Triviul Nunies. M, molecular ion; lithocholic acid, 3 ahydroxy-5 /kholan-24-oic acid; chenodeoxycholic acid, 3 a,7 a-dihydroxy-5/j'-cholan-24-oic acid; deoxycholic acid, 3 a,l2a-dihydroxy-5 b-cholan-24-oic acid; cholic acid, 3 a,7a,12a-trihydroxy-5P-cholan-24-oi...

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Section: Bile Acidssupporting

confidence: 82%

“…Methyl w-muricholate was obtained as a colourless oil (1 11 mg). The identity was confirmed by gas chromatography [8] and mass spectrometry [9, lo].…”

Section: Bile Acidsmentioning

confidence: 99%

Effects of Cholesterol Feeding on the Bile Acids of Male and Female Germ-Free Rats

Parmentier¹,

Smets²,

Jannsen³

et al. 1981

Eur J Biochem

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“…After GLC on 3% SE-30 the mass spectrum of the underivatized substance (Fig. 3) showed a molecular ion (M) at m/e 452 and a prominent peak at m/e 253, suggesting a 5,8-cholestanepentol with three hydroxyl substituents on the nucleus (12) and two in the side chain. There was a series of fragment ions at m/e 434, 416, 398, 380, and 362 that arose from the consecutive loss of one to five molecules of water, typical of polyhydroxy sterols (13).…”

Section: Resultsmentioning

confidence: 99%

A Biochemical Abnormality in Cerebrotendinous Xanthomatosis IMPAIRMENT OF BILE ACID BIOSYNTHESIS ASSOCIATED WITH INCOMPLETE DEGRADATION OF THE CHOLESTEROL SIDE CHAIN

Setoguchi¹,

Salen²,

Tint³

et al. 1974

J. Clin. Invest.

209

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A B S T R A C T Bile acid production in cerebrotendinous xanthomatosis (CTX) is subnormal, yet the activity of cholesterol 7a-hydroxylase, the rate-determining enzyme of bile acid synthesis, is elevated. To explain this discrepancy, bile acid precursors were sought in bile and feces of three CTX subjects. Over 10% of the total sterols excreted in bile and feces consisted of compounds more polar than cholesterol. Chromatographic analysis of the polar fractions in conjunction with gasliquid chromatography (GLC) -mass spectrometry indicated two major constituents, 5,f-cholestane-3a,7a,12a, 25-tetrol and 5f8-cholestane-3a,7a,12a,24E,25-pentol. After i.v. injection of [4-'C]cholesterol both bile alcohols were radioactive proving that they were derived from cholesterol. The accumulation of alcohols hydroxylated at C-25 and C-24,25 suggests that decreased bile acid synthesis in CTX results from impaired oxidation of the cholesterol side chain. This finding and the virtual absence of intermediates hydroxylated at C-26 indicate that current views of the major pathway of bile acid synthesis may require revision.

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“…In the mass fragmentography, the specific ions at m/e 253, m/e 131, m/e 145, m/e 159 were followed through the gas chromatogram. The ion at m/e 253 is the base peak in the mass spectrum of the trimethylsilyl ether of 5P8-cholestane-3a,7a,12a,26-tetrol (4) and is prominent in mass spectra of trimethylsilyl ethers of all C27-steroids with three hydroxyl groups in the steroid nucleus (4,17). No significant peak with the retention time characteristic of 5,8-cholestane-3a,7a,12a,26-tetrol could be detected in the recording of the ions at m/e 253, whereas peaks could be detected in this recording with retention times characteristic of trimethylsilyl ethers of 5P-cholestane-3a,7a,12a,25-tetrol, 5p-cholestane-3a,7a,-12a,24-tetrol, and 5p-cholestane-3a,7a,12a,23-tetrol (Fig.…”

Section: )mentioning

confidence: 99%

Biosynthesis of bile acids in man. Hydroxylation of the C27-steroid side chain.

Björkhem¹,

Gustafsson

Johansson³

et al. 1975

J. Clin. Invest.

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A B S T R A C T The first step in the degradation of the steroid side chain during biosynthesis of bile acids from cholesterol in man was studied in microsomal and mitochondrial fraction of homogenate of livers from 14 patients.The The mitochondrial fraction was found to catalyze 26-hydroxylation of cholesterol, 5-cholestene-3P,7a-diol, 5P-cholestane-3a,7a-diol, 7a-hydroxy-4-cholesten-3-one, and 5,0-cholestane-3a,7a,12a-triol. Addition of Mg"+ stimulated the 26-hydroxylation of cholesterol but had no effect or an inhibitory effect on 26-hydroxylation of the other substrates, indicating a heterogeneity of the mitochondrial 26-hydroxylating system. The level of 26-hydroxylase activity towards different substrates varied considerably with different mitochondrial preparations.The roles of the microsomal and mitochondrial 26-hydroxylations as well as the microsomal 25-hydroxylation in biosynthesis of bile acids in man are discussed.The results indicate that microsomal 26-hydroxylation is less important than mitochondrial 26-hydroxylation under normal conditions. The possibility that microsomal 25-hydroxylation is important cannot be ruled out.

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Bile acids

Cited by 62 publications

References 24 publications

Effects of Cholesterol Feeding on the Bile Acids of Male and Female Germ-Free Rats

Effects of Cholesterol Feeding on the Bile Acids of Male and Female Germ-Free Rats

A Biochemical Abnormality in Cerebrotendinous Xanthomatosis IMPAIRMENT OF BILE ACID BIOSYNTHESIS ASSOCIATED WITH INCOMPLETE DEGRADATION OF THE CHOLESTEROL SIDE CHAIN

Biosynthesis of bile acids in man. Hydroxylation of the C27-steroid side chain.

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