Mixed Micelles of Sodium Salts of Bile Acids and Tween 40: Effect of the Steroid Skeleton on the Coefficient of Interaction in Mixed Micelles

2012 ◽  
Vol 51 (45) ◽  
pp. 14722-14728 ◽  
Author(s):  
Mihalj Poša ◽  
Dejan Ćirin
Keyword(s):  
Bile Acids ◽  
Mixed Micelles ◽  
Sodium Salts ◽  
Tween 40 ◽  
Steroid Skeleton

Lysis of Echinococcus granulosus by surface-active agents in bile and the role of this phenomenon in determining host specificity in helminths

1962 ◽  
Vol 156 (965) ◽  
pp. 553-572 ◽  
Keyword(s):  
Bile Acids ◽  
Host Specificity ◽  
Echinococcus Granulosus ◽  
Definitive Host ◽  
Deoxycholic Acid ◽  
Life Cycles ◽  
Sodium Salts ◽  
Lytic Effect ◽  
Surface Active Agents ◽  
Surface Active

An extract of ox bile was found to lyse protoscolices of Echinococcus granulosus and induce abnormal accumulations of cytoplasmic fat. This observation led to a study of the in vitro action of bile and bile salts on this organism. Bile from the following herbivores caused lysis and fat accumulations: hare, rabbit, ox, sheep, man; lysis did not occur with bile from the following carnivores: fox, dog, cat. Sodium salts of cholic, taurocholic and glycocholic had no observable effect. Sodium salts of deoxycholic, glycodeoxycholic and taurodeoxycholic (in order of effectiveness) had a lytic effect. As a rule, herbivore biles producing lysis were those described as being rich in deoxycholic acid, largely conjugated with glycine. Bile from the dog (the natural definitive host) is reported as being relatively poor in deoxycholic acid which in carnivores is largely linked with taurine. It is suggested that the nature, type of conjugation and concentration of bile acids may play (amongst other factors) a major role in determining host specificity for E . granulosus . This hypothesis may prove to be capable of further extension to include intestinal parasites in general and may represent a fundamental controlling factor in many helminth and protozoan life cycles. It follows that the molecular configuration of the exposed surfaces of a successfully established intestinal parasite must be such that it is not susceptible to attack by the lytic agents present in the bile of its definitive host. It is suggested that the mechanism of lysis may be related to the presence of mitochondria in the cestode cuticle since these structures are known to be readily fragmented by deoxycholate and surface active substances. Sodium oleate had a lytic effect similar to, but less rapid than, sodium deoxycholate. There is evidence that the deoxycholic acid content of carnivore bile which is related to the microflora of the gut may be increased by change to a herbivorous diet; if this result is confirmed, it may indicate a nutritional method for controlling E. granulosus in dogs and possibly other helminth infections. It is speculated that a survey of bile acids and bile soaps throughout the animal kingdom may reveal the existence of other surface-active agents with a more pronounced lytic effect on E. granulosus or other helminths, than the limited group of bile compounds examined here.

Synthesis of 5α-Cholestane Type Glycoside Sulfates

1993 ◽  
Vol 58 (5) ◽  
pp. 1180-1190 ◽  
Author(s):  
Libuše Arnoštová ◽  
Ivan Černý ◽  
Vladimír Pouzar ◽  
Pavel Drašar
Keyword(s):  
Steroid Glycoside ◽  
Sodium Salts ◽  
Triethylammonium Salt ◽  
Pregnane Series ◽  
Temporary Protection ◽  
Steroid Skeleton

Synthesis of steroid glycoside sulfates sulfated both on the steroid skeleton and in sugar part are presented. Sodium salts of 5α-cholestane-3β,6α-diol 6-β-D-glucoside 3-sulfate V and 3-β-D-glucoside 6-sulfate XI were prepared from 3β-(2-tetrahydropyranyloxy)-5α-cholestan-6α-ol (I) using acetyl and methoxymethyl groups for temporary protection. Sulfation in the sugar part was at first checked in pregnane series and triethylammonium salts of 3β-(β-D-glucopyranosyloxy)pregn-5-en-20-one 6'-sulfate (XXVI) and 4'-sulfate 2',3'-diacetate XXVII were prepared. Application of the method on cholestane derivatives gave triethylammonium salt of 5α-cholestan-3β-yl β-D-glucopyranoside-6-sulfate (XXXI).

Potentiometric study on critical micellization concentrations (CMC) of sodium salts of bile acids and their amino acid derivatives

2002 ◽  
Vol 24 (2) ◽  
pp. 103-110 ◽  
Author(s):  
Toshio Nakashima ◽  
Tomoyuki Anno ◽  
Hiroshi Kanda ◽  
Yuka Sato ◽  
Tatsuaki Kuroi ◽  
...  
Keyword(s):  
Amino Acid ◽  
Bile Acids ◽  
Amino Acid Derivatives ◽  
Sodium Salts ◽  
Potentiometric Study

scholarly journals Small-Angle Scattering of X-Rays in Aqueous Solutions of Sodium Salts of Conjugated and Unconjugated Bile Acids.

1957 ◽  
Vol 11 ◽  
pp. 190-192 ◽  
Author(s):  
Per Ekwall ◽  
Krister Fontell ◽  
Arne Norman ◽  
J. Schliack ◽  
L. Reio
Keyword(s):  
Aqueous Solutions ◽  
Bile Acids ◽  
Small Angle ◽  
Small Angle Scattering ◽  
X Rays ◽  
Sodium Salts ◽  
Angle Scattering

scholarly journals Effect of sodium salts of 3α,12α-dihydroxy-7-oxo-5β-cholanoic and 3,7,12-trioxo-5β-cholanoic acids on verapamil hydrochloride in biophysical-chemical model experiments

2011 ◽  
Vol 76 (2) ◽  
pp. 189-199 ◽  
Author(s):  
Mihalj Posa ◽  
Valéria Guzsvány ◽  
Momir Mikov ◽  
Janos Canadi
Keyword(s):  
Bile Acid ◽  
Cell Membrane ◽  
Bile Acids ◽  
Spin Lattice Relaxation ◽  
Lipid Phase ◽  
Verapamil Hydrochloride ◽  
Bile Acid Concentration ◽  
Sodium Salts ◽  
Oh Groups ◽  
Cholanoic Acid

It is known that certain bile acids have a promotive effect on the action of some drugs. Special attention is paid to bile acids having oxo groups instead of OH groups in the steroid skeleton of their molecule, since these derivatives have a lower hemolytic potential (membrane toxicity). This study examined the effects of sodium salts of 3?,12?-dihydroxy-7-oxo-5?-cholanoic acid (7-oC) and 3,7,12-trioxo-5?- cholanoic acid (3,7,12-toC) on the adsorption of verapamil hydrochloride on activated carbon (model of the cell membrane). The interaction was followed by measuring the effect of verapamil on the functional dependence between the spin-lattice relaxation time T1 (protons of the C18 angular group of the bile acid molecule) and the bile acid concentration in deuterated chloroform (model of the cell membrane lipid phase). Whether a depot effect of verapamil exists when 7-oC and 3,7,12-toC (in the form of methyl esters) are present in chloroform was also investigated. It was found that 7-oC exhibited a significant effect in the experiments with verapamil, whereas 3,7,12-toC showed no difference of the measured parameters with respect to the control. This indicates that bile acid molecules should have OH groups bound to the steroid nucleus, in order to exhibit an effect on the monitored physico-chemical parameters of verapamil.

scholarly journals Degradation of Bile Acids by Soil and Water Bacteria

2021 ◽  
Vol 9 (8) ◽  
pp. 1759
Author(s):  
Franziska Maria Feller ◽  
Johannes Holert ◽  
Onur Yücel ◽  
Bodo Philipp
Keyword(s):  
Bile Acids ◽  
Heterotrophic Bacteria ◽  
Resistance Mechanisms ◽  
Side Chain ◽  
Steroid Nucleus ◽  
Metabolic Intermediates ◽  
Surface Active ◽  
Antimicrobial Barrier ◽  
Steroid Skeleton ◽  
Soil And Water

Bile acids are surface-active steroid compounds with a C5 carboxylic side chain at the steroid nucleus. They are produced by vertebrates, mainly functioning as emulsifiers for lipophilic nutrients, as signaling compounds, and as an antimicrobial barrier in the duodenum. Upon excretion into soil and water, bile acids serve as carbon- and energy-rich growth substrates for diverse heterotrophic bacteria. Metabolic pathways for the degradation of bile acids are predominantly studied in individual strains of the genera Pseudomonas, Comamonas, Sphingobium, Azoarcus, and Rhodococcus. Bile acid degradation is initiated by oxidative reactions of the steroid skeleton at ring A and degradation of the carboxylic side chain before the steroid nucleus is broken down into central metabolic intermediates for biomass and energy production. This review summarizes the current biochemical and genetic knowledge on aerobic and anaerobic degradation of bile acids by soil and water bacteria. In addition, ecological and applied aspects are addressed, including resistance mechanisms against the toxic effects of bile acids.

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