"17-Ketosteroid II" Isolated from Urine; its Reaction with Hydrochloric Acid

Dingemanse, E.; Veld, L. G. Huis in 't; Hartogh-Katz, S. Lore

doi:10.1038/162492a0

Cited by 16 publications

(8 citation statements)

References 3 publications

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“…(b) Pattern obtained from the urinary ketosteroid extract of a normal female (age, 26 years). Hydrolysis and extraction carried out according to the method of Dingemanse et al (1952).…”

Section: Pure Steroid8mentioning

confidence: 99%

“…-~, one; ----, andrositerone. (b) Chromatographic pattern obtained after the pyridinium salt androst-5-en-3#-ol-17one sulphate had been subjected to the neutral benzene extraction conditions of Dingemanse et al (1952). sulphate of androst-5-en-3,-ol-17-one by the action of boiling benzene.…”

Section: I953mentioning

confidence: 99%

“…We have refluxed the pyridinium salt of androst-5-en-3,-ol-17-one sulphate in a neutral benzene/ water system similar to that employed for the neutral extraction of urine (Dingemanse et al 1952). Chromatography of the extract gave rise to a peak in the position corresponding to 3:5-cycloandrostan-6-ol-17-one ( Fig.…”

Section: I953mentioning

confidence: 99%

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The separation of ketosteroids by partition chromatography using nitromethane as stationary phase

Jones

Stitch

1953

Biochemical Journal

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“…(b) Pattern obtained from the urinary ketosteroid extract of a normal female (age, 26 years). Hydrolysis and extraction carried out according to the method of Dingemanse et al (1952).…”

Section: Pure Steroid8mentioning

confidence: 99%

Section: I953mentioning

confidence: 99%

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The separation of ketosteroids by partition chromatography using nitromethane as stationary phase

Jones

Stitch

1953

Biochemical Journal

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“…Brooksbank & Haslewood (95) described an improved method for the isolation and purifi cation of the "pregnanediof'-like-glucuronide" complex. Dingemanse et al (96) described the isolation of i-androsten-6-01-17-one, which, these investi gators believe, is excreted in an unconjugated form.…”

Section: Partial Synthesis Of Steroidsmentioning

confidence: 99%

Biochemistry of Steroids

Lieberman¹,

Dobriner²

1951

Annu. Rev. Biochem.

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The unique role of the steroid hormones in nearly all phases of life has been established. With the discovery of the sex hormones in the early thirties, it seemed that the physiological action of steroids was primarily concerned with the phenomena of sex. With ' the discovery of the steroid hormones of the adrenal gland in the late thirties it was soon found that these compounds had a profound influence on metabolism and that this was also true of the so-called sex hormones. Progress in a steadily expanding area of investiga tion in biology, biochemistry, and medicine was handicapped by the lack of sufficient quantities of the adrenal hormones. These hormones were for all practical purposes not available because the chemical introduction of the biologically essentially C-ll oxygen function into the steroid nucleus had not been accomplished. As a result of the brilliant work of Reichstein, Kendall, Gallagher, and Wintersteiner in the middle forties, this objective was achieved and together with the further contributions· of these investiga tors, as well as the very significant achievements of Sarett, Miescher, Wallis, and Julian, the large scale preparation of the most important cortical hor mones became practicable. Fin ally, large amounts were made available for extensive investigations. At about the same time the adrenfll-stimulating hormone of the pituitary (ACTH) became available in sufficient amounts and in a usable stage of purity so that both hormones were at hand for the study of the essential physiological processes controlled by the internal secre tions of the adrenal. Within an extremely short time the epoch-making dis covery of Hench and Kendall of the effect of these hormones in arthritis was reported. These observations opened a new era in medicine, physiology and biochemistry, and it was recognized as such by the award of the Nobel prize to Reichstein, Kendall, and Hench in 1950. The number of investigations has increased rapidly during the last 1 The following abbreviations have been used in this review. It should be noted that, unless otherwise mentioned, reference has been made to the acetoxy derivatives of the adrenal hormones

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“…Moreover, it seems not unreasonable to assume that, in a number of endocrinological disorders, the determination of individual 17-oxosteroids may contribute to a better understanding of the underlying pathobiochemical processes. The first method for the fractionation of 17-oxosteroids was published by Dingemanse and her colleagues (2,3) and later improved by Kellie & Wade (4); the indiviual 17-oxosteroids were separated from each other by chromatography on alumina. These time-consuming methods were succeeded by procedures involving gas chromatography (5,6,7).…”

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confidence: 99%

An Improved Method for the Simultaneous Determination of Individual 17-Oxosteroids and of Pregnanediol in Urine by Gas-Liquid Chromatography

Külpmann¹,

Breuer²

1977

Clinical Chemistry and Laboratory Medicine

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Summary: An improved method for the simultaneous gas-chromatographic determination of individual 17-oxosteroids and of pregnanediol in the same sample of urine is described. The method involves the following steps. The urinary sample is chromatographed on Amberlite XAD-2. The fraction containing the steroid conjugates is evaporated; the residue is dissolved in -heptane and the organic phase extracted with water. The steroid glucuronides are hydrolysed by a bacterial ß-glucuronidase; subsequently, the steroid sulphates are solvolysed in ethyl acetate. Free 17-oxosteroids and pregnanediol are separated by two-dimensional thin-layer chromatography. The zone containing the steroids to be investigated is eluted; after evaporation, the residue is treated with N-methyl N-trimethyl silyl trifluoroacetamide. The reaction mixture is injected into a gas Chromatograph; the trimethyl silyl ethers of the individual 17-oxosteroids and of pregnanediol are quantitated by measuring the peak heights.The losses occurring during the working-up procedure are corrected for by measuring the recovery of radioactive dehydroepiandrosterone which is added as glucuronide and as sulphate to the urinary sample. The specificity of the method was established by mass fragmentography. Eine verbesserte Methode zur gleichzeitigen Bestimmung verschiedener 17-Oxosteroide und von Pregnandiol im Urin mit Hilfe der GaschromatographieZusammenfassung: Es wird eine verbesserte Methode zur gleichzeitigen Bestimmung verschiedener 17-Oxosteroide und von Pregnandiol in derselben Urinprobe mit Hilfe der Gaschromatographie angegeben. Das Verfahren umfaßt folgende Analysen-und Reaktionsschritte. Die Urinprobe wird an Amberlite XAD-2 chromatographiert. Die Fraktion, welche die Steroidkonjugate enthält, wird eingedampft und der Rückstand in rc-Heptan aufgenommen. Die Steroidkonjugate werden mit Wässer aus der organischen Phase extrahiert. Anschließend werden die Steroidglucuronide mit einer bakteriellen ß-Glucurdnidase hydrolysiert und die Steroidsulfate in Essigsäureethylester solvolysiert. Die freien 17-Oxosteroide und Pregnandiol werden durch Dünnschichtchromatographie von begleitenden Verunreinigungen befreit. Die steroidhaltende Zone des Dünnschichtchromatogramms wird eluiert und der Rückstand des Eluats mit N-Methyl-N-trimethylsilyl-trifluoracetamid behandelt. Ein aliquoter Teil der Reaktionsmischung wird in den Gaschromatographen injiziert; die quantitative Bestimmung der Trimethylsilyläther der verschiedenen 17-Oxosteroide und von Pregnandiol erfolgt durch Ausmessung der aufgezeichneten Peakhöhen. Die Korrektur von Aufarbeitungsverlusten erfolgt durch Ermittlung der Wiederfindung von radioaktivem Dehydroepiandrosteron, das als Glucuronid und Sulfat der Urinprobe zugesetzt wird. Die Spezifität der hier beschriebenen Methode wurde mit Hilfe der Massenfragmentographie überprüft und bestätigt.Introduction the procedure as modified by Norymberski et al. (1) in 1953 has been the most popular one. However, in certain The determination of 17-oxosteroids in urine ha...

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"17-Ketosteroid II" Isolated from Urine; its Reaction with Hydrochloric Acid

Cited by 16 publications

References 3 publications

The separation of ketosteroids by partition chromatography using nitromethane as stationary phase

The separation of ketosteroids by partition chromatography using nitromethane as stationary phase

Biochemistry of Steroids

An Improved Method for the Simultaneous Determination of Individual 17-Oxosteroids and of Pregnanediol in Urine by Gas-Liquid Chromatography

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