ChemInform Abstract: Study on the Bile Salts from Sunfish, Mola mola L. Part 1. The Structures of Sodium Cyprinol Sulfates, the Sodium Salt of a New Bile Acid Conjugated with Taurine, and a New Bile Alcohol and Its New Sodium Sulfates.

The transport of taurocholic and glycocholic acids by the small intestine of rats and guinea pigs against a concentration gradient was studied by the everted gutsac technique. Transport of these substances is limited to the distal ileal segment. This transport is inhibited by anoxia, dinitrophenol and sodium azide. The system has a transport maximum. On the basis of these criteria bile acid reabsorption is considered to occur by active transport.

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Unusual Steroid Constituents from the Tropical Starfish Leiaster sp

Natural Product Communications ◽

10.1177/1934578x1601100914 ◽

2016 ◽

Vol 11 (9) ◽

pp. 1934578X1601100

Author(s):

Timofey V. Malyarenko ◽

Alla A. Kicha ◽

Natalia V. Ivanchina ◽

Anatoly I. Kalinovsky ◽

Pavel S. Dmitrenok ◽

...

Keyword(s):

Bile Acid ◽

Sodium Salt ◽

Parallel Evolution ◽

Steroid Glycoside ◽

First Report ◽

Acid Sodium Salt ◽

Steroid Glycosides ◽

First Time ◽

Primary Bile Acid

Two polar steroid compounds, taurochenodeoxycholic acid sodium salt (1) and a rare cyclic steroid glycoside luzonicoside A (2), were isolated from the tropical starfish Leiaster sp. and identified by extensive NMR and ESIMS techniques. The isolation of primary bile acid 1 is the first report from a representative of the class Asteroidea and on the whole in invertebrates. Its presence confirms the hypothesis about the digestive role of some polar steroids in starfish and possibly demonstrates the parallel evolution of fat emulsifying agents in vertebrates and some starfish. Compound 2 was also obtained from starfish belonging to this genus for the first time. This finding indicates that cyclic steroid glycosides are more widely distributed in starfish than the two species of the genus Echinaster from which they were isolated earlier.

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The gallbladder and vermiform appendix influence the assemblage of intestinal microorganisms

Future Microbiology ◽

10.2217/fmb-2019-0325 ◽

2020 ◽

Vol 15 (7) ◽

pp. 541-555

Author(s):

Jiezhong Chen ◽

Avni Sali ◽

Luis Vitetta

Keyword(s):

Bile Acid ◽

Bile Salts ◽

Vermiform Appendix ◽

Epidemiological Studies ◽

Bile Secretion ◽

Proximal Colon ◽

Intestinal Microbiome ◽

Increased Risk ◽

Health And Disease ◽

Risk Of Disease

Surgical procedures for the symptomatic removal of the gallbladder and the vermiform appendix have been posited to adversely shift the assemblage of the intestinal microbiome increasing the risk of disease. The associated mechanisms have been linked with dysbiosis of the gut microbiota. Cholecystectomy causes changes of bile acid compositions and bile secretion patterns as bile acids interact with the intestinal microbiota in a bidirectional capacity. An appendectomy precludes the further recolonization of the proximal colon with a commensal biofilm that could maintain a stable intestinal microbiome. Epidemiological studies indicate that there is an increased risk of disease rather than causality following a cholecystectomy and appendectomy. This narrative review summarizes studies that report on the role that bile salts and the appendix, contribute to the assemblage of the intestinal microbiome in health and disease.

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Comparative studies of bile salts. 5α-Chimaerol, a new bile alcohol from the white sucker Catostomus commersoni Lacépède

Biochemical Journal ◽

10.1042/bj1160581 ◽

1970 ◽

Vol 116 (4) ◽

pp. 581-585 ◽

Cited By ~ 9

Author(s):

I. G. Anderson ◽

G. A. D. Haslewood

Keyword(s):

Bile Acids ◽

Comparative Studies ◽

Bile Salts ◽

Mass Spectra ◽

Parallel Evolution ◽

White Sucker ◽

Minor Constituent ◽

Catostomus Commersoni ◽

Bile Alcohol ◽

A Minor

1. G.l.c. examination of bile alcohols prepared from the sucker Catostomus commersoni Lacépède (family Catostomidae) showed that although 5α-cyprinol (5α-cholestane-3α,7α,12α,26,27-pentol) was a minor constituent, the principal bile alcohol was an undescribed substance, probably present in the bile as the C-26 sulphate ester, whose i.r., n.m.r. and mass spectra agreed with the structure 5α-cholestane-3α,7α,12α,24,26-pentol. 2. MD studies suggest that this 5α-chimaerol is the 24(+), 25S enantiomer and that 5β-chimaerol (chimaerol) from Chimaera monstrosa bile also has the 24(+), 25S configuration. These findings imply that bile alcohol biosynthesis in suckers and chimaeras includes stereospecific oxidation of cholesterol at C-26. 3. C. commersoni bile acids (present in minor amounts) probably consist largely of 3α,7α,12α-trihydroxy-5α-cholan-24-oic acid (allocholic acid). 4. 5α-Chimaerol sulphate and 5α-cyprinol sulphate are probably biochemically equivalent as bile salts, and can be considered as arising by parallel evolution.

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

Biochemical Journal ◽

10.1042/bj1710409 ◽

1978 ◽

Vol 171 (2) ◽

pp. 409-412 ◽

Cited By ~ 8

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.

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Facilitation of hepatic uptake of phenol 3,6-dibromphthalein disulfonate by taurocholate.

AJP Endocrinology and Metabolism ◽

10.1152/ajpendo.1977.232.6.e560 ◽

1977 ◽

Vol 232 (6) ◽

pp. E560

Author(s):

Y Marinovic ◽

J C Glasinovic ◽

B Semelle ◽

J F Boivieux ◽

S Erlinger

Keyword(s):

Bile Acid ◽

Initial Velocity ◽

Bile Salts ◽

Sodium Taurocholate ◽

Hepatic Uptake ◽

Disappearance Rate ◽

Plasma Disappearance Rate ◽

Common Site ◽

Half Saturation Constant ◽

Uptake Process

The influence of sodium taurocholate (TC) on the hepatic uptake of phenol 3,6-dibromphthalein disulfonate (dibromosulphophthalein, DBSP) was examined in the dog. Single injections of DBSP (7.5-83.3 mg-kg-1) were given intravenously and the initial velocity of uptake (V) of the dye was calculated from the plasma disappearance rate measured during the 1st 5 min. It was observed that: a) the initial velocity of uptake of DBSP increased with the dose (D) in a nonlinear way, a finding consistent with Michaelis-Menten kinetics; the maximal initial velocity of uptake (Vmax) was 7.5+/-1.0 (SD) mg-min-1-kg body wt-1, and the half-saturation constant (Kd) was 27.7+/-7.0 (SD) mg-kg-1; b) when a TC infusion was given prior to the DBSP injection, the initial disappearance of the dye was more rapid than in the absence of the bile acid; Vmax increased to 12.3+/-2.0 (SD) mg-min-1-kg-1 (P less than 0.001) and Kd increased to 50.3+/-12.8 (SD) mg-kg-1 (P less than 0.001). These results indicate that: 1) the uptake of DBSP by the liver cell is a saturable process; 2) TC increases both the Vmax, suggesting a facilitation of the uptake process, and the Kd, suggesting competition for a common site. This effect of TC on DBSP uptake is similar to the previously described effect of this bile salt on BSP excretion into bile and suggests an interaction of bile salts with the uptake process of dyes.

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Abstract 282: Murine Abcb1 Functions as an Efflux Transporter for Bile Salts After Chronic Administration of a Western Diet

Arteriosclerosis Thrombosis and Vascular Biology ◽

10.1161/atvb.32.suppl_1.a282 ◽

2012 ◽

Vol 32 (suppl_1) ◽

Author(s):

Stephen D Lee ◽

Sheila J Thornton ◽

Kishor M Wasan

Keyword(s):

Bile Acid ◽

Bile Salt ◽

Bile Acids ◽

Knockout Mice ◽

Health Research ◽

Bile Salts ◽

Molar Ratio ◽

Wild Type ◽

Transport Pathway ◽

Efflux Mechanism

Rationale: Removal of bile salts from the liver is the final step of the reverse cholesterol transport pathway. We studied the contribution of Abcb1 (P-glycoprotein), in bile acid efflux. Although a number of endogenous substrates have been postulated for Abcb1 based on in vitro evidence, studies using animal models have not supported these claims. Recent studies in mice demonstrated that in the absence of the Bile Salt Efflux Pump (Bsep), Abcb1 is required for removal of bile salts, especially when challenged with a cholic acid containing diet. To date, no study using atherogenic diets has demonstrated the role of Abcb1 in the removal of bile salts in the presence of functional Bsep. Methods: We fed male mice lacking both isoforms of Abcb1 (Abcb1a -/- /1b -/- ) and wild-type controls a diet providing either 25% or 45% of the kcal from fat, supplemented with either normal chow or high levels of cholesterol (0.02% w/w or 0.2% w/w respectively) for nine weeks; n=5 per group. On the tenth week, we assessed the efflux of cholesterol, phospholipid and bile acids to the gallbladder. Enzymatic assays were used to measure cholesterol and phospholipid, the pool of bile acids was quantified by HPLC to determine the concentrations of the six most prevalent murine bile acids. Results: Abcb1 knockout mice have a >30% reduction in the moles of bile salt normalized to phospholipid relative to wild type mice after administration of diets containing either elevated fat or cholesterol (p<0.05). Neither the efflux of phospholipid, nor the molar composition of the six bile acids was affected by deletion of Abcb1. Conclusions: We conclude that Abcb1 is a secondary efflux mechanism required for the removal of bile acids after consumption of diets rich in fat and/or cholesterol. Although Abcb1 knockout mice have reduced total bile acids in the gallbladder, the molar ratio of the specific bile acids is the same as in the wild type mice. These data suggest that Abcb1 effluxes the six bile acids in a non-specific manner, unlike Bsep which preferentially effluxes hydrophobic bile acids. The lack of specificity demonstrated by Abcb1 is desirable for a low- affinity secondary efflux mechanism, which supplements Bsep activity in bile acid output. Acknowledgments: Canadian Institutes of Health Research, Michael Smith Foundation for Health Research

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