The isolation of 16α-hydroxydehydro<i>epi</i>androsterone (3β:16α-dihydroxyandrost-5-en-17-one) from the urine of normal men

Fotherby, K.; Colás, A.E.; Atherden, Shelia M.; Marrian, G. F.

doi:10.1042/bj0660664

Cited by 48 publications

(18 citation statements)

References 17 publications

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“…ethanol as described above. After distilling the ethanol to a small volume, the extract was partitioned between hexane and methanol as described by Fotherby, Colas, Atherden and Marrian (1957). The aqueous methanol phase was evaporated to a small volume and then made up to 100 ml with water.…”

Section: Methodsmentioning

confidence: 99%

Localization of Ethynyloestradiol in the Reproductive Tract of Women

Reed¹,

Fotherby²,

Steele³

1973

Journal of Endocrinology

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4-14C]Ethynyloestradiol was administered to women at varying times before hysterectomy. At operation, samples of blood, adipose tissue and tissue from the reproductive tract were obtained. All tissues examined took up radioactivity, the concentration at 1 h varying from 0\m=.\22 to 0\m=.\4% of the dose per 100 g of tissue except for stroma and endometrium which showed high levels (0\m=.\68% and 0\m=.\60%,respectively). By 24 h the amount of radioactivity in the tissues had decreased markedly. Mean values for the amount of radioactivity present in total tissues at 1 h were: uterus, 0\m=.\9%; adipose tissue, 28\m=.\2%;blood, 8\m=.\8%.By 24 h these values had declined to 0\m=.\2%,6\m=.\8% and 1\m=.\6%,respectively. In adipose tissue almost all the radioactivity was present in a freely extractable state whereas in myometrium and cervix about 20 % of the radioactivity was in a conjugated form. In plasma, more than 80% of the metabolites were conjugated, mainly as sulphates. The major metabolite detected in the uterus was ethynyloestradiol itself and most of the radioactivity in the myometrium was associated with the nuclear fraction. In one pregnant subject studied, radioactivity crossed the placenta and small amounts of the dose were found in the foetus.

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Section: Methodsmentioning

confidence: 99%

Localization of Ethynyloestradiol in the Reproductive Tract of Women

Reed¹,

Fotherby²,

Steele³

1973

Journal of Endocrinology

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“…Among steroids known to occur in the human urine these requirements are met by 17-deoxycorticosteroids and by the 16:17glycols of the androstane series. Since the latter group of compounds is excreted by man in relatively small amounts (Fotherby, Colas, Atherden & Marrian, 1957) and since they are converted into ferric hydroxamates in very poor yield (see Table 1) it is considered that their contribution to the assay Table 4. 17-Deoxycortico8teroid8 in human urine Compound Reference (i) 21-Hydroxypregn-4-ene-3:20-dione Richardson et al (1955) (1 -Deoxycorticosterone) (ii) 3a:21-Dihydroxy-5,-pregnan-20-one Richardson et al (1955) (iii) 21-Hydroxypregn-4-ene-3:11:20-trione (11-Dehydrocorticosterone, substance A) (iv) 1P:21-Dihydroxypregn-4-ene-3:20-dione Touchstone, Bulaschenko, Richardson & Dohan (1954) (Corticosterone, substance B) (v) 3oc:llp:21-Trihydroxy-5,-pregnan-20-one 1960is negligible.…”

Section: Analyticalmentioning

confidence: 99%

Indirect analysis of corticosteroids. 5. The determination of 17-deoxycorticosteroids

Exley¹,

Ingall²,

Norymberski³

et al. 1961

Biochemical Journal

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Naturally occurring 17-deoxycorticosteroids (the term is used here to denote corticosteroids unsubstituted at position 17) comprise 21-hydroxypregnan-20-ones (I) and pregnane-20:21-diols (II). Oxidation with sodium bismuthate ruptures their 20-21 bond with the resultant formation of formaldehyde from (I) and (II), of aetiocholanic acids I CO2H view of the distinctive chemical properties of aldehydes it was considered that this reaction sequence of proved analytical utility (Appleby, Gibson, Norymberski & Stubbs, 1955) might provide a means for the group determination of 17-deoxycorticosteroids by their conversion into 0-20 aldehydes and the measurement of the latter.

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“…The present communication describes such a conversion in vitro.Rabbit liver was homogenized and incubated by the procedure described by Davidson & Fotherby (1965) except that: (1) each flask contained in addition 0\m=.\0012 M-NADPH, (2) the incubations proceeded for 16 hr., (3) ethyl acetate was used for extraction instead of benzene and (4) the residue obtained, following evaporation of the ethyl acetate, was submitted to a hexane-methanol partition (Fotherby, Colas, Atherden & Marrian, 1957). For the large-scale incubations, 20 mg. steroid in 0\m=.\2ml.…”

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confidence: 99%

Metabolism of Lynestrenol to Norethisterone by Liver Homogenate

Mazaheri¹,

Fotherby²,

Chapman³

1970

Journal of Endocrinology

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1968) showed that there were similarities between the in-vivo metabolism in man of 14C-labelled norethisterone (17\g=a\-ethynyl -19\x=req-\ nortestosterone) and lynestrenol (3-deoxynorethisterone) and suggested that some of these similarities might be due to the conversion of the latter to the former. The present communication describes such a conversion in vitro.Rabbit liver was homogenized and incubated by the procedure described by Davidson & Fotherby (1965) except that: (1) each flask contained in addition 0\m=.\0012 M-NADPH, (2) the incubations proceeded for 16 hr., (3) ethyl acetate was used for extraction instead of benzene and (4) the residue obtained, following evaporation of the ethyl acetate, was submitted to a hexane-methanol partition (Fotherby, Colas, Atherden & Marrian, 1957). For the large-scale incubations, 20 mg. steroid in 0\m=.\2ml. ethanol were added to an homogenate of 20 g. liver. Thin-layer chromatography was carried out using either silica gel G (Merck and Co.) and the solvent system ethyl acetate: cyclohexane (3:7, v/v), or alumina (Merck and Co.) and the solvent system ethanol in benzene. After development, the plates were sprayed with phosphomolybdic acid solution. Gas-liquid chromatography was carried out on a 5 ft. column containing 3 % SE-30 on Gaschrom Q at 210°or 3 % QF-1 on Chromosorb W at 185°. The flow rate of the carrier gas (nitrogen) was 40 ml./min. Mass spectra were determined using an A.E.I. MS 12 instrument.Thin-layer chromatography on silica gel of extracts of liver homogenate incubated with lynestrenol showed the presence of unchanged lynestrenol (RF value 0-76), another major spot (metabolite B, RF value 0-23) and other compounds with RF values of 0-36, 0-43, 0-48 and 0-71. The RF value of norethisterone in this system was 0-22. By thin-layer chromatography on alumina using 1 % (v/v) ethanol in benzene, metabolite was separated into two spots 1 and 2 with RF values of 0-16 and 0-30, respectively; the latter value was similar to that of norethisterone. On gasliquid chromatography (SE-30) both 2 and norethisterone had similar retention times (17-4 min.) and on chromatography of a mixture of equal amounts of 2 and pure norethisterone only one peak was obtained. Confirmation of the identity of 2 as norethisterone was obtained by showing that the mass spectra of the two compounds were identical.The behaviour of 1 on alumina thin-layer chromatography suggested that it was *

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The isolation of 16α-hydroxydehydroepiandrosterone (3β:16α-dihydroxyandrost-5-en-17-one) from the urine of normal men

Cited by 48 publications

References 17 publications

Localization of Ethynyloestradiol in the Reproductive Tract of Women

Localization of Ethynyloestradiol in the Reproductive Tract of Women

Indirect analysis of corticosteroids. 5. The determination of 17-deoxycorticosteroids

Metabolism of Lynestrenol to Norethisterone by Liver Homogenate

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