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

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.

1982 ◽  
Vol 62 (6) ◽  
pp. 627-642 ◽  
Author(s):  
Kaoru Tanaka ◽  
Kenzo Takeshita ◽  
Minoru Takita

1. Serum bile acids in seven patients with adult type myotonic dystrophy and 22 normal persons were quantitatively analysed by gas—liquid chromatography and gas chromatography—mass spectrometry for cholesterol, γ-glutamyltransferase and bilirubin. There was no bile obstruction in any patient. 2. Deoxycholic acid values in all mothers of patients with congenital type myotonic dystrophy were three times (2.1 μmol/l) that of the control (0.7 μmol/l). 3. Uncommon bile acids were detected in the patients' sera. One of them appeared to be dihydroxymono-oxocholanic acid, having a longer side chain. Another one appeared to be dihydroxycholanic acid, with a steroid-nucleus structure similar to chenodeoxycholic acid and with a longer side chain. 4. Biliary bile acids from three patients and one normal person were also analysed, and this revealed a remarkable decrease in ursodeoxycholic acid in the patients. 5. The presence of bile acid abnormality in patients with myotonic muscular dystrophy is proposed.


1965 ◽  
Vol 33 (1) ◽  
pp. 67-73
Author(s):  
D. A. SHAW

SUMMARY Specific activities were determined for cortisol and its metabolites isolated from several successive urine samples collected from patients who had each received a single injection of a tracer dose of [4-14C]cortisol. Some theoretical aspects of the curves relating specific activity to time after injection are considered. Evidence is presented and discussed for an alternative route to the 11-oxygenated 17-oxosteroid metabolites of cortisol probably involving not an initial reduction of the ring A of cortisol but a simultaneous cleavage of the side-chain at C-17 of the steroid nucleus and reduction of ring A.


1962 ◽  
Vol 40 (2) ◽  
pp. 188-202 ◽  
Author(s):  
Shlomo Burstein ◽  
Ralph I. Dorfman

ABSTRACT 3H and 14C specific activities of dehydroepiandrosterone, androsterone, 3α-hydroxy-5β-androstan-17-one and 3α-hydroxy-5α-androst-16-ene (without dilution) have been determined following a single intravenous injection of 4-14C-cholesterol and 7α-3H-pregnenolone to a virilized woman with an adrenal adenoma and massive dehydroepiandrosterone excretion. Assuming a one compartment model, or a two compartment model in which the injected radioactivity enters the compartment in which the precursor is secreted exclusively, a new pathway by which dehydroepiandrosterone is formed from cholesterol not through pregnenolone and possibly by cleavage of the side chain C-17 and C-20 is indicated. Analysis of the data by a model in which pregnenolone is secreted into two separate compartments in which progesterone and dehydroepiandrosterone are made, respectively, would explain the findings without necessitating the assumption of a new pathway. 3α-Hydroxy-5α-androst-16-ene was isolated from urine following incubation with β-glucuronidase and partition chromatography on celite suggesting that this steroid is a genuine natural product as surmised by Prelog & Ruzicka (1944) and Brooksbank & Haslewood (1950). 2-14C-Mevalonate was shown to give rise to C19 steroids which is the first in vivo demonstration that mevalonic acid is a precursor of the steroid nucleus in man.


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.


1976 ◽  
Vol 154 (3) ◽  
pp. 577-587 ◽  
Author(s):  
S Hayakawa ◽  
Y Kanematsu ◽  
T Fujiwara ◽  
H Kako

1. To identify the intermediates involved in the degradation of cholic acid, the further degradation of (4R)-4-[4a-(2-carboxyethyl)-3aa-hexahydro-7ab-methyl-5-oxoindan-1β-yl]valeric acid (IVa) by Arthrobacter simplex was attempted. The organism could not utilize this acid but some hypothetical intermediate metabolities of compound (IVa) were prepared for later use as reference compounds. 2. The nor homologue (IIIa) and the dinor homologue (IIIb) of compound (IVa) were prepared by exposure of 3-oxo-24-nor-5β-cholan-23-oic acid (I) and (20S)-3b-hydroxy-5-pregnene-20-carboxylic acid (II) to A. simplex respectively. These compounds correspond to the respective metabolites produced by the shortening of the valeric acid side chain of compound (IVa) in a manner analogous to the conventional fatty acid a- and b-oxidation mechanisms. Their structures were confirmed by partial synthesis. 3. The following authentic samples of reduction products of the oxodicarboxylic acids (IIIa), (IIIb) and (IVa) were also synthesized as hypothetical metabolities: (4R)-4-[3aa-hexahydro-5a-hydroxy-4a-(3-hydroxypropyl)-7ab-methylindan-1b-yl]valeric acid (Vb) and its nor homologue (VIIa) and dinor homologue (IXa);(4R)-4-[3Aaa-hexahydro-5a-hydroxy-4a-(3-hydroxypropyl)-7ab-methylindan-1b-yl]-pentan-1-ol (Vc); and their respective 5β epimers (Ve), (VIIc), (IXc) and (Vf). 4. In connexion with the non-utilization of compound (IVa) by A. simplex, the possibility that not all the metabolites formed from cholic acid by a certain micro-organism can be utilized by the same organism is considered.


1988 ◽  
Vol 255 (3) ◽  
pp. 769-774 ◽  
Author(s):  
S B Mahato ◽  
S Banerjee ◽  
S Podder

Metabolic processes involving side-chain and ring cleavage of progesterone, 17-hydroxyprogesterone, 11-deoxycortisol and 16-dehydropregnenolone by Arthrobacter simplex were studied. The formation of the metabolites from progesterone indicates a pathway somewhat different from normal in the enzymic reaction sequence, and the 17-hydroxyprogesterone metabolites reveal a non-enzymic rearrangement step. The presence of a hydroxy group at C-21, as in 11-deoxycortisol, induces reduction of the C-20 carbonyl group. The microbial preparation of a novel androstane analogue, 17 beta-hydroxy-16 alpha-methoxyandrosta-1,4-dien-3-one, by incubation of 16-dehydropregnenolone with the bacterial strain was achieved. The formation of this metabolite is a multistep process involving a novel microbial generation of a methoxy group from a double-bond transformation in a steroid skeleton.


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