6-Hydroxylation, an important route in the metabolism of corticosteroids by the baboon: the fate of administered tetrahydrocortisol.
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Animals↗
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Determination of cortisol, tetrahydrocortisol, tetrahydrocortisone, corticosterone, and aldosterone in human amniotic fluid.
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Aldosterone↗
Studies in the biotransformation of cortisol to the cortoic acids in man. II. The central role of tetrahydrocortisol and tetrahydrocortisone as intermediates.
The possible role of THF and THE as intermediates in the biotransformation of cortisol to the cortoic acids was studied by giving 3H-THF + 14C-cortisol tracers and 3H-THE + 14C cortisol tracers to two subjects each, measuring the 3H/14C isotope ratios of the urinary cortoic acid metabolites and relating these ratios to the dose ratio. Isotope ratios substantially higher than the dose ratio indicate that the tetrahydro compound is a better precursor than cortisol, and isotope ratios that are essentially identical to that of urinary THF or THE, respectively, indicate that the tetrahydro compound may be an obligatory intermediate in the cortisol leads to cortoic acids pathway. The isotope ratio data in these studies clearly establish that THF was a preferential precurosor of the 11 beta-hydroxy cortoic acids (cortolic and beta-cortolic) and THE was a preferential precursor of the 11-ketone cortoic acids (cortolonic and beta-cortolonic). Furthermore, the data strongly suggest that THF and THE may be obligatory intermediates in cortoic acid formation.
Carboxylic Acids↗
Radioimmunoassays of tetrahydrocortisone and tetrahydrocortisol in human urine.
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Adrenocorticotropic Hormone↗
Steroid excretion in anorexia nervosa patients.
Seven anorexia nervosa (A.N.) patients had reduced urinary excretion values of tetrahydrocortisone (THE), androsterone (A) and 5alpha-tetrahydrocortisol (5alpha-THF). THE to tetrahydrocortisol (THF), A to aetiocholanolone (Ae) and 5alpha-THF to THF ratios were all significantly reduced. Six A.N. patients had oral metyrapone tests with quantitatively normal but delayed urinary 3alpha,17alpha,21-trihydroxy-5beta-pregnan-20-one (THS) response. The steroid determinations were done by capillary gaschromatography, which proves to be of value in the study of the above mentioned metabolic abnormalities.
Adolescent↗
[Decomposition of steroids during incubation with beta-glucuronidase and during storage of urine].
Androsterone, etiocholanolone, pregnanetriol, dehydroepiandrosterone, pregnanediol, tetrahydrocortisol, 5-pregnenolone and 11-beta-OH-androsterone were incubated with beta-glucuronidase preparations (Helix pomatia, bovine liver and E. coli) for 96 hrs at 37 degrees C. After extraction and silylation they were gas-chromatographed. The first 3 steroids were left practically intact. The least decomposition of the last 5 steroids occurred with the liver enzyme. Testosterone and 11-ketoandrosterone without the enzymes showed 74 and 35% recoveries. Cortisol and tetrahydrocortisol, incubated with the first two enzymes for 18 hrs at 37 degrees and 48 degrees C, showed nearly 100% recoveries. The recoveries of 17-OHCS in urines (pH 7.8-8.8), stored for 7 days, was 80% at 20 degrees-25 degrees C and 55% at 25 degrees-30 degrees C. The same samples, brought to pH 1.8-2.8 WITH NaHSO4 before the storage, showed a 100% recovery.
17-Hydroxycorticosteroids↗
The pattern of urinary excretion of corticosteroids in Rhesus monkeys (Macaca mulatta).
Urinary total 17-oxogenic steroids (17-OGS), cortisol, cortisone, corticosterone, tetrahydrocortisol (THF), allo-tetrahydrocortisol (all-THF), tetrahydrocortisone (THE), cortols and cortolones, were estimated by established methods in 30 female and 20 male rhesus monkeys. The pattern of the excretion of these steroids in this species was comparable with the human corticosteroids excretion, irrespective of sex difference. The results obtained from this investigation show that they could be used during the study of adrenocortical function and cortisol metabolism in this species.
Adrenal Cortex Hormones↗
Cortisol metabolism in lymphocytes from cancer-bearing patients.
A study was conducted to determine the pattern of cortisol metabolism by lymphocytes obtained from four groups of subjects: 27 male and female patients suffering from various types of malignancy other than malignancy of lymphatic tissues; and 26 healthy male and female controls. Known concentrations of cells were incubated with 1,2-3H-cortisol and the products were isolated by thin-layer and paper chromatography. Three metabolites were found to be produced by lymphocytes from both normal and cancer-bearing patients: 20alpha-hydroxycortisol, 20beta-hydroxycortisol, and tetrahydrocortisol. Cells from the female control group were found to be more active than those from the male controls, while cells from cancer-bearing patients were markedly more active than the normal cells, regardless of sex. It is suggested that this finding of increased metabolism of cortisol by lymphocytes from patients with different types of malignancy other than lymphoma may provide the basis for a new diagnostic aid.
Adult↗
Identification of 7xi-hydroxytetrahydrocortisol and 7xi-hydroxytetrahydrocortisone from urine of newborn baboons (Papio papio).
Two highly polar, unconjugated metabolltes of tetrahydrocortisol and tetrahydrocortisone, which had been shown previously to account for greater than 40% of [14C]cortisol (F) administered to baboon neonates, were isolated from urine of a term newborn animal. Metabolites were extracted with ethyl acetate, purified by sequential paper chromatography and crystallization, and identified by chemical and biochemical procedures. Both metabolites of F are 5beta-pregnanes with a hydroxyl of unknown orientation at C-7, a 3alpha-hydroxyl, and a dihydroxyacetone side chain. The two compounds differ from each other by the presence of either oxo or hydroxyl functions at C-11. The following nomenclature is proposed: unknown 1: 3alpha,7xi,11beta,17,21-pentahydroxy-5beta-pregnan-20-one (7xi-hydroxytetrahydrocortisol); unknown 11: 3alpha,7xi,17,21-tetrahydroxy-5beta-pregnane-11,20-dione (7xi-hydroxytetrahydrocortisone). Production of these compounds compensates quantitatively for the decreased formation of F glucuronoside metabolites by baboon neonates, compared with that in adults. Therefore, we propose that 7-hydroxylation is a major alternative pathway for F metabolism in the perinatal period of the baboon.
Animals↗
3Alpha-hydroxysteroid dehydrogenase from Pseudomonas testosteroni: kinetic properties with NAD and its thionicotinamide analogue.
The kinetics of 3alpha-hydroxysteroid : NAD oxidoreductase (EC 1.1.1.50) from Pseudomonas testosteroni (ATCC 11996) have been investigated. The kinetic analysis based on initial activity measurements and product inhibition studies, indicates that the addition of substrate to the enzyme and the release of products from it, follows an obligatory order (ordered bi bi mechanism). The ability of the enzyme to utilize the thionicotinamide analogue of NAD (sNAD) as cofactor has been investigated using various 3alpha-hydroxysteroids from both the C19, C21, and C24 series. The results show that the reaction velocity with sNAD as the cofactor is generally lower than with NAD. The decrease, however, varies considerably, being negligible with some steroids such as litocholic acid and deoxycholic acid and very pronounced with other such as tetrahydrocortisol and tetrahydrocortisone. The introduction of an 11beta-hydroxy or an 11-oxo group into the steroid molecule significantly reduces the ability of the enzyme to attack the 3alpha-hydroxy group. No such effect could be seen when the 11-hydroxy group was in the alpha-position. The results also indicate that, whereas NAD can serve as cofactor for both the monomeric and the dimeric forms of the enzyme, sNAD only acts as cofactor for the monomeric form. Thus sNAD is a valuable tool for the study of the reversible, concentration-depenedent monomeric-dimeric transition of the 3alpha-hydroxysteroid dehydrogenase.
Androstanes↗
Prenatal diagnosis of 11beta-hydroxylase deficiency congenital adrenal hyperplasia.
To predict 11beta-hydroxylase deficiency congenital adrenal hyperplasia antenatally, studies were performed in urines and amniotic fluids from 2 pregnant women who had previously given birth to affected infants and whose present pregnancies also resulted in infants with the disease. Urinary tetrahydro-11-deoxycortisol [pregnane-3alpha, 17alpha, 21-triol-20-one (THS)] was abnormally elevated in the first, second, and third trimesters (maximal values, 3.5 and 0.9 mg/24 h, respectively) but was undetectable after delivery in these mothers, in 15 normal pregnancies (10--40 weeks of gestation), and in 6 heterozygote parents. Amniotic fluid levels of THS, tetrahydrocortisol [pregnane-3alpha, 11beta, 17alpha, 21-tetra-o1-20-one (THF)], tetrahydrocortisone [pregnane-3alpha, 17alpha, 21-triol-11, 20-dione (THE)] measured by RIA at 18 weeks of gestation in the first mother and at 40 weeks in the second revealed 12.5- and 8.4-fold increases in THS, respectively, but normal THF and THE levels compared to mean levels in normal pregnancies. The THS to THF plus THE ratio, which was constant throughout pregnancy in 125 normal women (mean +/- SD, 0.63 +/- 0.34) despite the variable levels of these metabolites, was significantly elevated in both patients (4.4 and 3.8, respectively). These studies indicate that prenatal diagnosis of 11beta-hydroxylase deficiency congenital adrenal hyperplasia based on hormonal measurements is feasible.
Adrenal Hyperplasia, Congenital↗
[Steroid metabolism in primates. XX. Excretion of C21-steroids in urine of women and baboons (Papio hamadryas) during pregnancy].
Urinary excretion of 10 C21 steroids was investigated in women and baboons (Papio hamadryas) in various stages of pregnancy, in comparison to controls. In pregnant women, excretion of total C21 steroids is slightly increased, whereas in pregnant baboons it is slightly decreased. In women, excretion of tetrahydrocortisol and tetrahydrocortisone is diminished, that of 20 beta-OH-F (11-beta,17alpha,20beta,21-tetrahydroxy-4-pregnen-3,20-dione) and of 11-deoxycortisol is increased. In pregnant baboons no significant alterations in corticosteroid metabolism were established.
Adolescent↗
[Adrenal function after long term treatment with beclomethasone dipropionate in childhood asthma (author's transl)].
Evaluating plasma levels of cortisol and corticosterone after ACTH-stimulation, and the urinary metabolites tetrahydrocortisone and tetrahydrocortisol in asthmatic children it could be demonstrated, that in most cases there was no suppression of adrenal function following treatment over 6 to 18 months with a daily dose of 200 to 300 microgram beclomethasone dipropionate. Since in a few patients suppression was found, an ACTH stimulation after a six months treatment is recommended.
Adolescent↗
Cortisol production rate determined by radio gas-chromatography.
We describe a ratio gas-chromatographic method for determination of cortisol production rate by measuring the isotope dilution of urinary cortisol metabolites. The method was calibrated by analyzing [3H]tetrahydrocortisol and [3H]tetrahydrocortisone of known specific activities. Results are reasonably well reproducible, the coefficients of variation ranging from 8-15% of allotetrahydrocortisol/tetrahydrocortisol and from 9-19% for tetrahydrocortisone. Correlation coefficients were 0.966 and 0.998 for tetrahydrocortisone and allotetrahydrocortisol/tetrahydrocortisol, respectively, when the method was compared with a method involving thin-layer chromatography and colorimetry. Only one chromatographic step is needed for both purification and quantitation, thus time and effort are saved.
Chromatography, Gas↗
Metabolism of cortisol by human thrombocytes.
A study was made in order to see whether human thrombocytes are capable to metabolize cortisol. Known concentrations of thrombocytes were incubated with 1.23H-cortisol and the products isolated and identified by t.l.c., paper chromatography, and derivations. Two metabolites were found to be produced by thrombocytes: 20beta-hydroxycortisol and tetrahydrocortisol. The enzymatic nature of the reactions was proved by (1) heat treatment (2) finding out NADPH to be a specific cofactor and (3) the dependence of the activity on the number of thrombocytes in suspensions.
Blood Platelets↗
Licorice raises urinary cortisol in man.
The finding that urine cortisol excretion was increased in patients with hypokalaemic hypertension induced by licorice addiction led to this study on the effect of licorice in normal subjects. Thirteen normal volunteers ate either 100 or 200 g licorice for 1-4 weeks and assessment of pituitary-adrenal function was made before, during, and 1 week after cessation of licorice ingestion. Urine cortisol excretion more than doubled in 10 of 13 subjects (mean, 33.8 +/- 15.6 SD before and 83.3 +/- 56 SD micrograms/24 h at 1 week after commencing licorice) and excretion rates similar to those observed in Cushing's syndrome were seen in 7 subjects (range, 91-226, compared to normal range of 11-82 micrograms/24 h). Urine cortisol excretion remained significantly elevated (P less than 0.01) above control levels for at least 1 week after licorice was withdrawn. Despite these increases, urinary steroid metabolite (tetrahydrocortisol, tetrahydrocortisone, tetrahydro-11-deoxycortisol, 17-ketogenicsteroids, and 17-ketosteroids) excretion was not affected, plasma cortisol and ACTH values were unchanged, and normal 0800-1600-h diurnal variation of plasma cortisol was maintained. The direct intraadrenal infusion of the active mineralocorticoid component of licorice, glycyrrhetinic acid, in two sheep with autotransplanted adrenal glands failed to stimulate cortisol secretion acutely. It is concluded from these studies that the licorice-induced changes in cortisol excretion are not a result of adrenocoritcal stimulation but more likely represent a change in the renal handling of cortisol.
Adenoma↗
Urinary steroid excretion by the squirrel monkey (Saimuri sciureus).
Urinary steroids and steroid conjugates were measured in the squirrel monkey (Saimuri sciureus). The principal steroids excreted were cortisol, 11beta,17alpha,20beta,21-tetrahydroxy-4-pregnen-3-one (20beta-dihydrocortisol), alpha- and beta-cortol and alpha- and beta-cortolone. The majority of the steroids were excreted unconjugated and a conspicuous feature of the pattern was the large amount of urinary free cortisol. Unlike man there was an insignificant excretion of 3alpha,17alpha,21-trihydroxy-5beta-pregnane-11,20-dione (tetrahydrocortisone) and 3alpha,11beta,17alpha,21-tetrahydroxy-5beta-pregnan-20-one (tetrahydrocortisol). A steroid not previously identified in urine from any species was one of the major glucuronide conjugates; it was characterized as having the structure 3beta,17alpha,20xi,21-tetrahydroxy-5beta-pregnan-11-one. Administration of dexamethosone resulted in complete suppression of steroid output, whilst the response to adrenocorticotrophic hormone was inconstant.
Adrenocorticotropic Hormone↗
[Effect of ethyl ether of p-chlorphenoxyisobutyric acid on the glucocorticoid function of the adrenal cortex of guinea pigs].
In administration to quinea pigs of ethyl-p-chlorophenoxyisobutyrate daily in a dose of 0.2 g/kg per os for 15-26 days decreased the 17-OHCS concentration in the peripheral blood plasma. A fall of the urinary excretion of individual 17-OHCS occurred chiefly at the expense of free unchanged cortisol, tetrahydrocortisol and tetrahydro-11-desoxycortisol. The zona fasciculate displays the abundance of the sudanophilic material. A test with ACTH demonstrated that the present functional reserves of the adrenal cortex failed to change under the effect of the preparation. The content of NEFA decreased in the blood serum; as to cholesterol level - it reamined unchanged. Possible mechanisms of the action of the preparation and prospects of its use for the treatment of hypercorticism are discussed.
17-Hydroxycorticosteroids↗