ISOLATION OF 15α-Hydroxy-Oestriol FROM PREGNANCY URINE AND FROM THE URINE OF NEWBORN INFANTS

Zucconi, G; Lisboa, B. P.; E, Simonitsch; Roth, L; Hagen, A. Ainsworth; Diczfalusy, E.

doi:10.1530/acta.0.0560413

Cited by 51 publications

(14 citation statements)

References 13 publications

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“…This mass spectrum was identical with that of 15a-hydroxyoestriol silyl ether [13]. Table 3 shows the excreted amounts of steroids in urine from the pregnant women.…”

Section: Compound 26supporting

confidence: 52%

“…The steroid monosulphate fraction contained two 15j3-hydroxylated pregnanolones; this is the first report of 15P-hydroxylated C,, steroids in the human. 1561-Hydroxylated neutral steroids [31,32] and oestrogens [13,33,34] as well as 15j3-hydroxylated oestrogens [35] have previously been isolated from human pregnancy urine but l5p-hydroxylated C,, steroids have not been described in mammalia. Schneider reported 15p-hydroxylation of 21-hydroxy-4-pregnene-3,2O-dione and regarded this as a biochemically "primitive" hydroxylation [36].…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Excretion of Steroid Hormones in Adults

Eriksson

Gustafsson

1970

European Journal of Biochemistry

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The steroids in urine from a pregnant woman have been studied by gas chromatographymass spectrometry. The major part, 64O/,, of the steroids identified occurred in the glucuronide fraction, whereas the free, monosulphate and disulphate fractions contained 24 Ole, 5 and 7 Ole, respectively. The compounds had the following general structures : 3-hydroxy-178-pregnan-20-one, 3a-hydroxy-5/?,17a-pregnan-20-one, 3a-hydroxy-5a-androstan-17-one, pregnane-3,20-diol, 3a,21-dihydroxy-58-pregnan-20-one, 3a,l6a-dihydroxy-5t3-pregnan-20-one, 3,15@-dihydroxypregnan-20-one, pregnane-3,16a,2O-triol, 5,4-pregnane-3a,l7a,2Oa-triol, 38,16a-dihydroxy-5-androsten-l7-one, 5-pregnene-38,20u-dol, 5a-pregnane-3,20a,21-triol, 5-androstene-3@,16,17-triol, oestriol, 15-hydroxyoestriol and pregnane-3,16,20,21-tetrol. I n the free and glucuronide fractions the C,,O, steroids mainly had a 58 configuration whereas about 9001, of the mono-and disulphurylated C,,O, steroids had a 5a structure. The results are discussed in relation to what is known about faecal excretion of steroids during pregnancy.I n a previous investigation we reported the identifications of a number of C,, and CZ1 steroids in faeces from pregnant women [l]. It was shown that the faecal pattern of steroid hormone metabolites is greatly influenced by the steroid metabolizing intestinal micro0ora. Since reabsorption of steroids from the intestinal tract is an important process [2] it was of interest to study the existence of possible microbial steroid metabolites in urine from pregnant women. Many previous studies have been carried out on total steroids after hydrolysis of urine from pregnant women, but until recently no adequate methods were available for separating and studying the major conjugate groups. New purification methods (for references see [l]) in conjunction with gas chromatographic-mass spectrometric techniques for separating and identifying even minor constituents in a small sample of urine have now made it possible to draw a much more detailed picture than could be done with older techniques. Trivial and Systematic Names and Unuawl Abbreviations.Progesterone, 4-pregnene-3,20-dione; oestriol, oestra-l,3,5-(lO)-triene-3,16a,17,9-triol; silyl, trimethylsilyl. Retention times t~ are calculated relative to 6a-cholestane. Pregnane or l7p-pregnane refers to a pregnane with a 17/? side chain. When a compound has the less common 17a side chain the term l7a-pregnane is used. The terms pregnanolone and pregnanediol are used as collective names for isomers of 3-hydroxy-l7,9(0r 17a)-pregnan-20-one and pregnane-3,20-diol, respectively. The term pregnanetriol is used for pregnane derivatives with three hydroxyl groups and no keto groups. Enzymes. 20a(and 20p)-Hydroxysteroid MATERIALS AND METHODS SterolidsSeveral of the reference compounds used in this investigation were obtained from sources given in a previous paper [l]. 3a,21-Dihydroxy-5/?-pregnan-20-one and 3~,16a,21-trihydroxy-5-pregnen-20-one triacetate were gifts from Dr. C. H. L. Shackleton.15a-Hydroxy-4-pregnene-3,20-di...

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“…This mass spectrum was identical with that of 15a-hydroxyoestriol silyl ether [13]. Table 3 shows the excreted amounts of steroids in urine from the pregnant women.…”

Section: Compound 26supporting

confidence: 52%

Section: Discussionmentioning

confidence: 99%

Excretion of Steroid Hormones in Adults

Eriksson

Gustafsson

1970

European Journal of Biochemistry

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“…This natural hormone was discovered in urine of pregnant women by Diczfalusy and coworkers in 1965 [1]. Based on its physical and chemical characteristics it was concluded that E 4 is identical with 15α-hydroxyestriol (15α-OHE3) or estra-1, 3, 5(10)-triene-3,15α-, 16α-, 17β-tetrol [2]. Estetrol has the structure of an estrogenic steroid with four hydroxyl groups which explains the acronym E 4 .…”

Section: Introductionmentioning

confidence: 99%

Clinical applications for estetrol

Visser

Bennink

2009

The Journal of Steroid Biochemistry and Molecular Biology

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In this paper the potential clinical applications for the human fetal estrogen estetrol (E 4 ) are presented based on recently obtained data in preclinical and clinical studies. In the past E 4 has been classified as a weak estrogen due to its rather low estrogen receptor affinity. However, recent research has demonstrated that due to its favorable pharmacokinetic properties, especially the slow elimination and long half-life, E 4 is an effective orally bioavailable estrogen agonist with estrogen antagonistic effects on the breast in the presence of estradiol. Based on the pharmacokinetic properties, the pharmacological profile and the safety and efficacy results in human studies, E 4 seems potentially suitable as a drug for human use in applications such as hormone replacement therapy (vaginal atrophy and vasomotor

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“…During the same period, Diczfalusy and co-workers [5] succeeded in isolating and identifying the novel estrogen by extracting 200 L of late pregnancy urine. On the basis of physical and chemical characteristics they concluded that the compound was identical with 15␣-hydroxyestriol (15␣-OHE 3 ) or estra-1,3,5(10)-triene-3,15␣-,16␣-,17␤-tetrol.…”

Section: The Discovery Of Estetrolmentioning

confidence: 99%