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At least 19 recordsLinked to original sources
PubMed1994

Urinary steroids from a newborn human infant. Identification of 2 alpha-hydroxy-4-pregnene-3,20-dione, 3 beta,15 beta-dihydroxy-5-pregnen-20-one and 3 beta,15 alpha-dihydroxy-5-pregnen-20-one.

Urinary steroids from healthy newborn human infants were analyzed by gas-liquid chromatography and gas-liquid chromatography-mass spectrometry. The identification of 2 alpha-hydroxy-4-pregnene-3,20-dione and the characterization of its 2 beta-isomer is recorded here for the first time. Mass spectrometric evidence supporting the identification of 3 beta,15 beta-dihydroxy-5-pregnen-20-one and 3 beta,15 alpha-dihydroxy-5-pregnen-20-one is also presented. Furthermore, the following 15-hydroxylated steroids were also found and identified: 3 beta,15 epsilon,16 epsilon-trihydroxy-5-androsten-17-one, 5-androstene-3 beta,15 alpha,16 alpha,17 beta-tetrol, 3 beta,15 beta,17-trihydroxy-5-pregnen-20-one and 5-pregnene-3 beta,15 epsilon,17,20 epsilon-tetrol. The origin of these 2- and 15-hydroxylated urinary steroids is discussed in relation to current knowledge of 4-pregnene-3,20-dione and 3 beta-hydroxy-5-pregnen-20-one metabolism during the human perinatal period.

17-alpha-Hydroxypregnenolone↗
PubMed1996

15 beta-hydroxysteroids (Part V). Steroids of the human perinatal period: the synthesis of 3 beta, 15 beta, 17 alpha-trihydroxy-5-pregnen-20-one from 15 beta, 17 alpha-dihydroxy-4-pregnen-3,20-dione.

A simple three-step synthetic method is reported on the conversion of delta 4-3-ketosteroids to the corresponding 3 beta-hydroxy-delta 5-steroid analogues. 17 alpha-Hydroxy-4-pregnen-3,20-dione (10a) was used as a model to develop a method for the synthesis of 3 beta, 17 alpha-dihydroxy-5-pregnen-20-one (16). The major problem being the synthesis of 3,17 alpha-diacetoxy-3,5-pregnadien-20-one (14) was solved by acetylating using a mixture of acetic anhydride and perchloric acid. The conversion of 15 beta, 17 alpha-dihydroxy-4-pregnen-3, 20-dione (8), product of Penicillium citrinum fermentation, to the desired 3 beta,15 beta,17 alpha-trihydroxy-5-pregnen-20-one (1), is described using a modification of this method. Reaction of 8 with acetic anhydride and perchloric acid in ethyl acetate gave 3,15 beta,17 alpha-triacetoxy-3,5-pregnadien-20-one (17) which on reduction with sodium borohydride gave 5-pregnen-3 beta,15 beta,17 alpha, 20(S + R)-tetrols (18a and 18b); however, reduction of 17 with a mixture of sodium borohydride and potassium bicarbonate gave after basic hydrolysis with methanolic sodium hydroxide the desired product 3 beta,15 beta,17 alpha-trihydroxy-5-pregnen-20-one (1) in good yield (54%).

17-alpha-Hydroxypregnenolone↗
PubMed1983

Relative in vitro effectiveness of 17 alpha, 20 beta-dihydroxy-4-pregnen-3-one and other pregnene derivatives on germinal vesicle breakdown in oocytes of ayu (Plecoglossus altivelis), amago salmon (Oncorhynchus rhodurus), rainbow trout (Salmo gairdneri), and goldfish (Carassius auratus).

The relative effectiveness of several pregnene derivatives, which had previously been identified in the ovaries of ayu (Plecoglossus altivelis), on germinal vesicle breakdown (GVBD) was investigated in vitro using folliculated oocytes of four species of teleosts, ayu, amago salmon (Oncorhynchus rhodurus), rainbow trout (Salmo gairdneri), and goldfish (Carassius auratus). Although some species differences existed in the relative effectiveness of each steroid on GVBD, 17 alpha, 20 beta-dihydroxy-4-pregnen-3-one (17 alpha, 20 beta-diOHprog) was consistently the most potent inducer of final oocyte maturation. Both progesterone and 17 alpha-hydroxyprogesterone were effective at relatively high concentrations. Of the 5 beta-reduced metabolites, 17 alpha, 20 beta-dihydroxy-5 beta-pregnan-3-one was almost as effective as 17 alpha, 20 beta-diOHprog in oocytes of amago salmon and rainbow trout, while the other 5 beta-reduced compounds (3 alpha-hydroxy-5 beta-pregnan-20-one, 17 alpha-hydroxy-5 beta-pregnane-3,20-dione, 3 alpha, 17 alpha-dihydroxy-5 beta-pregnan-20-one, 5 beta-pregnane-3 alpha, 17 alpha, 20 beta-triol, and 5 beta-pregnane-3 beta, 17 alpha, 20 beta-triol) were almost or totally ineffective at the concentrations tested (1-0.001 micrograms/ml). These bioassay results, together with previous findings on the capacity of the ovary to produce 17 alpha, 20 beta-diOHprog, indicate that 17 alpha, 20 beta-diOHprog is the natural maturation-inducing steroid hormone common to three species of Salmoniformes, ayu, amago salmon, and rainbow trout. These results, however, only suggest that 17 alpha, 20 beta-diOHprog is involved in maturation of goldfish oocytes, since supportive physiological and biochemical data are lacking. Possible regulatory roles of 5 beta-reduced metabolites on steroid-induced oocyte maturation are discussed.

Animals↗
PubMed1995

Biosynthesis of 17,20 alpha-dihydroxy-4-pregnen-3-one, 17,20 beta-dihydroxy-4-pregnen-3-one, and 11-ketotestosterone by testicular fragments and sperm of the roach, Rutilus rutilus.

The effect of incubation time and substrate concentration on the in vitro metabolism of 17-hydroxyprogesterone by testes of the roach has been examined. There was a shift from synthesis of the 11-oxygenated androgens, 11-ketotestosterone, and androstenetrione at low substrate concentration to 17,20 alpha-dihydroxy-4-pregnen-3-one (17,20 alpha P) at high substrate. Glucuronides and sulfates were of significant importance only at low substrate and long incubation times. There was a shift from 17,20 beta-dihydroxy-4-pregnen-3-one to 17,20 alpha P with increased substrate. The results confirm that substrate affects the steroidogenic profile and that 3 hr is optimal time for such studies. Incubations of sperm with 17-hydroxyprogesterone gave predominantly 11-ketotestosterone at low substrate concentrations and 17,20 alpha P at high substrate. The synthesis of 11-ketotestosterone is demonstrated for the first time in teleost sperm.

Animals↗
PubMed1985

18-Substituted steroids: synthesis of 18-hydroxycortisol (11 beta,17 alpha,18,21-tetrahydroxy-4-pregnene-3,20-dione) and 18-hydroxycortisone (17 alpha,18,21-trihydroxy-4-pregnene-3,11,20-trione).

The isolation of 18-hydroxycortisol from the urine of patients with primary aldosteronism was recently described and no synthetic procedure was available for its preparation. The C-13 angular methyl group of prednisolone-17 alpha,21-acetonide-11 beta-nitrite was functionalized by photolysis in the presence of oxygen to give the product 18-hydroxy-prednisolone-17 alpha,21-acetonide-18-nitrate. The 18-nitrate was reduced with zinc and ammonium acetate to the corresponding 18-hydroxy compound, 18-hydroxy-prednisolone-17 alpha,21-acetonide. Homogeneous hydrogenation with Tris(triphenyl-phosphine)rhodium (I) chloride as catalyst resulted in the formation of 18-hydroxy-cortisol-17 alpha,21-acetonide. Acid hydrolysis of the latter compound gave 18-hydroxycortisol. Oxidation of 18-hydroxycortisol-17 alpha,21-acetonide with pyridinium dichromate followed by acid hydrolysis gave 18-hydroxycortisone. The 18-hydroxylated steroids exist as the 18,21-hemiacetals. Catalytic reduction with tritium gas with Tris(triphenyl-phosphine)rhodium (I) chloride of 18-hydroxyprednisolone-17 alpha,21-acetonide and acid hydrolysis gave [1,2(3)H]18-hydroxycortisol.

Chemical Phenomena↗
PubMed1972

The intermediary role of 5-pregnene-3 ,20 -diol in the biosynthesis of 16-unsaturated C 19 steroids in boar testis.

1. The possible involvement of 5-pregnene-3beta,20beta-diol in 16-unsaturated C(19) steroid biosynthesis has been investigated. 2. 5,16-Androstadien-3beta-ol (andien-beta) formation from [4-(14)C]pregnenolone (3beta-hydroxy-5-pregnen-20-one), 5-pregnene-3beta,20alpha-diol and 5-pregnene-3beta,20beta-diol was studied in homogenates of boar testis and the mean yields obtained were 25.6, 2.7 and 16.0% respectively. 3. Short-term kinetic studies with pregnenolone and 5-pregnene-3beta,20beta-diol separately and together suggested that the latter compound might be an intermediate in the biosynthesis of andien-beta. 4. In agreement with this interpretation, radioactive 5-pregnene-3beta,20beta-diol has been isolated during andien-beta biosynthesis from [4-(14)C]pregnenolone in the presence of NADPH, more radioactivity being trapped under limiting conditions of andien-beta formation with NADH present as cofactor. 5. Further, 5-pregnene-3beta,20beta-diol and andien-beta have been shown to inhibit the formation of the 16-unsaturated C(19) steroid from [4-(14)C]pregnenolone, the yield of radioactive 5-pregnene-3beta,20beta-diol increasing in the presence of added unlabelled andien-beta. 6. It is concluded that there may be two pathways leading to 16-unsaturated C(19) steroid formation from pregnenolone, one of these involving 5-pregnene-3beta,20beta-diol as an intermediate. Possible mechanisms are presented and discussed.

Alcohols↗
PubMed1990

Plasma levels of ovarian steroids, including 17 alpha,21-dihydroxy-4-pregnene-3,20-dione and 3 alpha,17 alpha,21-trihydroxy-5 beta-pregnan-20-one, in female plaice (Pleuronectes platessa) induced to mature with human chorionic gonadotrophin.

In one previous paper we reported on the identification of 11-deoxycortisol and 3 alpha,17 alpha,21-trihydroxy-5 beta-pregnan-20-one in the ovaries and plasma of mature female plaice and also described the development of radioimmunoassays for these two steroids. The present paper describes temporal changes in plasma levels of the free and conjugated forms of these and of some other steroids (17 alpha,20 beta-dihydroxy-4-pregnen-3-one, 17 alpha,20 beta,21-trihydroxy-4-pregnen-3-one, 17 alpha,20 alpha-dihydroxy-4-pregnen-3-one, 17 alpha-hydroxy-4-pregnen-3-one, testosterone, and 17 beta-oestradiol) in female plaice injected with and without human chorionic gonadotrophin (HCG). Oocyte final maturation, but not ovulation, was induced by HCG injections. Levels of most of the steroids were also elevated by the HCG injections and were significantly higher than in control fish throughout the experiment (112 hr). The two most abundant steroids were 11-deoxycortisol and 3 alpha,17 alpha,21-trihydroxy-5 beta-pregnan-20-one (up to 600 ng ml-1). Only relatively small amounts of 17 alpha-hydroxy-4-pregnen-3,20-dione (less than 15 ng ml-1), 17 alpha,20 beta-dihydroxy-4-pregnen-3-one, and 17 alpha,20 alpha-dihydroxy-4-pregnen-3-one (less than 5 ng ml-1) were found. 17 alpha,20 beta,21-Trihydroxy-4-pregnen-3-one was not present. Testosterone and 17 beta-oestradiol levels rose briefly, in response to the first of the two HCG injections, and then fell significantly. The ratio of conjugated to free steroids (except for 17 alpha-hydroxy-4-pregnene-3,20-dione and 17 beta-oestradiol) was almost always greater than 1. In the HCG-injected fish, there was a significant negative correlation between the response of 17 beta-oestradiol levels and the response of 11-deoxycortisol and 3 alpha,17 alpha,21-trihydroxy-5 beta-pregnan-20-one levels. This further confirms that, as teleosts approach the time of full maturity, there is switch-over in the ovaries from predominantly C19 and C18 steroid production to predominantly C21 steroid production.

17-Hydroxycorticosteroids↗
PubMed1996

15 beta-hydroxysteroids (Part III). Steroids of the human perinatal period: the synthesis of 3 beta, 15 beta, 17 alpha-trihydroxy-5-pregnen-20-one. Application of n-butyl boronic acid protection of a 17,20-glycol.

We report the synthesis of 3 beta,15 beta,17 alpha-trihydroxy-5-pregnen-20- one (1) from 3 beta,15 beta-dihydroxy-5,16-pregnadien-20-one (11) in 7 steps using boronate derivatives as a means of protecting the 17,20-glycol side-chain of steroid intermediates. 16 alpha,17 alpha-Epoxy-3 beta,15 beta-dihydroxy-5- pregnen-20-one (12), an intermediate in the synthesis was prepared by epoxidation of 11 using a mixture of sodium hydroxide and hydrogen peroxide. Reduction of 12 with lithium aluminium hydride gave the two isomers of 5-pregnene-3 beta, 15 beta,17 alpha,20 (S+R)-tetrol (13a and 13b) which on subsequent reaction with n-butyl boronic acid gave 5-pregnene-3 beta,15 beta,17 alpha, 20(S+R)-tetrol 17 alpha,20-butyl boronate (15a and 15b). Acetylation with acetic anhydride and pyridine yielded 3 beta,15 beta-diacetoxy-5-pregnene-17 alpha,20(S+R)-diol 17 alpha,20(S+R)-butyl boronate (15c and 15d). Oxidative cleavage of the boronic ester using sodium hydroxide and hydrogen peroxide gave 3 beta,15 beta-diacetoxy-5-pregnene-17 alpha,20(S+R)-diol (13c and 13d). After isolation of these latter two products, dibromide protection of the C-5,6 olefin of 13d and oxidation with N-bromosuccinimide gave 3 beta,15 beta-diacetoxy-17 alpha-hydroxy-5-pregnen-20-one (16) which on deacetylation gave in good yield (35%) the desired product 3 beta,15 beta,17 alpha-trihydroxy-5-pregnen-20-one (1) in an overall yield of 24% from 11.

17-alpha-Hydroxypregnenolone↗