The isolation of 3β-hydroxy-Δ5-steroids from the urine of normal men

Fotherby, K.

doi:10.1042/bj0690596

Cited by 45 publications

(8 citation statements)

References 21 publications

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“…The procedures used in the extraction of the urine and purification of the extract have already been described in detail (Fotherby, 1958). Briefly they consisted in boiling urine without adjustment of the pH, a procedure which appears to be specific for the hydrolysis of the 3,B-sulphates of 3,Bhydroxy-A5-steroids and separation and isolation of the 3#-hydroxy-A5-steroids present in the extract by countercurrent distribution and chromatography.…”

Section: Resultsmentioning

confidence: 99%

“…The melting point indicated that this compound might bepregn-5-ene-3/:l16ac:20a.triol, and this was proved 14 to be so by comparing the acetate of the isolated material with authentic 3B: 16oc:20Oc-triacetoxypregn-5-ene. EXPERIMENTAL Details of the extraction of the urine, purification of the urine extract and the methods used have been published (Fotherby, 1958). lsolation of pregn-5-ene-3/3:16=:20o-triol.…”

Section: Resultsmentioning

confidence: 99%

“…In addition to this 3/3hydroxy-A5-steroid, Hirschmann & Hirschmann (1950b) have isolated six other steroids containing this grouping from the urine of a boy with an adrenal tumour. Before 1956 only two steroids of this type, namely dehydroepiandrosterone (Butenandt & Dannenbaum, 1934) and androst-5-ene-3p:16oc:17fl-triol (Marrian & Butler, 1944), had been isolated from the urine of normal people, but recently 16oc-hydroxydehydroepiandrosterone (Fotherby, Colas, Atherden & Marrian, 1957) and androst-5-ene-3,B: 17/3-diol, androst-5-ene-3/3: 16#: 17,B-triol and pregn-5-ene-3,B: 17ac:20cxtriol (Fotherby, 1958) have been isolated from this source. The present paper describes the isolation of another 3/3-hydroxy-_A5-steroid, pregn-5-ene-3f:-16a:20oc-triol, from the urine of normal males.…”

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The isolation of pregn-5-ene-3β:16α:20α-triol from the urine of normal males

Fotherby

1959

Biochemical Journal

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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The isolation of pregn-5-ene-3β:16α:20α-triol from the urine of normal males

Fotherby

1959

Biochemical Journal

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“…More general methods of detection were used for both steroid sulfates and free steroids in the present study and, as a consequence, our findings suggest that androstenediol sulfate is the major component of the sulfate fraction. No specific attempts were made to isolate either andrsstenediol disulfate or testosterone sulfate, but it was concluded from chromatographic evidence after hydrolysis (13) and solvolysis (14) that no more than trace amounts, if any, could have been present.…”

Section: Fig 3 Column Partition Chromatography On Celite As Ammonimentioning

confidence: 99%

The Isolation and Identification of Androstenediol Sulfate from Spermatic Vein Blood and Testes of the Boar

Raeside¹,

Howells²

1971

Can. J. Biochem.

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RAESIDE, J. I., AND HOWELES, G . A. The isogation and identification of androstenedioi sulfate from spermatic vein blood and testes of the boar. Can. J. Biochern. 49, 80-84 (1971).A method is described for the extraction and purification of steroid sulfates from testicdar tissues and blood of the boar. Androsteraediol sulfate (3b91'9S-dihydroxy-5-andPo9tene 3-sulfate) was isolated from extracts of both spermatic vein blood and boar testis. Final identification was achieved by infrared spectroscopy, as the ammsnium salt of androstenediol 3-sulfate 17-acetate. Additional evidence of identity was obtained with the 3-monosulfate of androstenediol-7a-"H as an internal standard in several chromatographic systems for steroid sulfates, and for free steroids after hydrolysis. Androstenediol sulfate was not detected in peripheral or spermatic arterial blood, and it was concluded that andrsstenediol sulfate is a major secretory product of the boar testis. RAESIDE, J. I., ET MOWELIS, G. A. m e isolation and identification of androstenediol sulfate from spermatic vein blood and testes of the boar. Can. 3. Biochem. 49, 80-84 (19'71).Ce travail decrit une mdthode d'extraetion et de purification des sulfates de stkroldes B partir de tissus testiculaires et de sang de samglier. Ee sulfate d9androstenediol (3D,1918-dihydroxy-5-androst6ne 3-sulfate) a Ct C isole a partir d9extraits de sang de veine spermatique et de testicule de sanglier. E9identification finale a Ctk effectuke par spectroscopic infrarouge; il s'agit de l'androstdndiol 3-sulfate 17-acktate sous forme de sel d9arnmonium. Cette identit6 a 6tk vkrifike en outre par un standard de rkfkrence, B e 3-monosulfate d'androst&nediol-701-~H, utiIis6 dans plusieurs systemes chromatographiques pour les sulfates de st6rofdes et pour les stkoides Iibres apres hydrolyse, be sulfate d9androstenedioI n'ayant pas Ct C dkele au niveau du sang pCripherique ou de 19artkre spermatique il est conch que Ie sulfate d9androstenediol est un produit de s6crktion majeur du testicule de sanglier. Inbodnetionsulfate from the testes and spermatic vein blood Testosterone has been isolated from the boar testis (1) and spermatic vein blood (21, in which dehydroepiandrosterone s u l f a t e b a s detected also (31, Subsequently, dehydroepisandrosterone and dehydroepiandrosterone sulfate were isolated from the testes and the spermatic vein plasma of a boar receiving human chorica;nZc gonadotrophin $4). Testosterone and dehydroepiandrosterone sulfate appeared to be the most important steroids in both testes and spermatic vein plasma.A preliminary report from our laboratory suggested that androstenediol sulfate was quantitatively a more important csmpsund in the spermatic vein blood of the boar (5). Since androstenediol sulfate may serve as a precursor of testosterone (6) and androstenediol has androgenic activity of its own (' 71, we wish to report the isolation and identification of andrsstenedisl 'This research was supported by the Ontario Department of Agriculture and Food.following trivial names have...

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“…It is produced in the adrenal glands. DHEA was the first steroid of its type to be isolated from the urine of a normal man, and identified as the most abundant steroid in human body 4 . DHEA and its metabolites have been found to strengthen the immune system in animals [5][6][7][8] .…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of dehydroepiandrosterone with Macrophomina phaseolina and β-glucuronidase inhibitory activity of transformed products

Choudhary

Zafar

Khan

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

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The biotransformation of dehydroepiandrosterone (1) with Macrophomina phaseolina was investigated. A total of eight metabolites were obtained which were characterized as androstane-3,17-dione (2), androst-4-ene-3,17-dione (3), androst-4-ene-17β-ol-3-one (4), androst-4,6-diene-17β-ol-3-one (5), androst-5-ene-3β,17β-diol (6), androst-4-ene-3β-ol-6,17-dione (7), androst-4-ene-3β,7β,17β-triol (8), and androst-5-ene-3β,7α,17β-triol (9). All the transformed products were screened for enzyme inhibition, among which four were found to inhibit the β-glucuronidase enzyme, while none inhibited the α-chymotrypsin enzyme.

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The isolation of 3β-hydroxy-Δ5-steroids from the urine of normal men

Cited by 45 publications

References 21 publications

The isolation of pregn-5-ene-3β:16α:20α-triol from the urine of normal males

The isolation of pregn-5-ene-3β:16α:20α-triol from the urine of normal males

The Isolation and Identification of Androstenediol Sulfate from Spermatic Vein Blood and Testes of the Boar

Biotransformation of dehydroepiandrosterone with Macrophomina phaseolina and β-glucuronidase inhibitory activity of transformed products

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