Skip to main content
NCBI home page
Biochemical Journal logoLink to Biochemical Journal
. 1968 Jun;108(2):185–193. doi: 10.1042/bj1080185

The partial characterization of 1-oxygenated steroids from urine of a hypertensive newborn child

R W H Edwards 1, D J H Trafford 1
PMCID: PMC1198792  PMID: 5665883

Abstract

1. Four substances from the urine of a hypertensive newborn girl were partially characterized and shown to be 17α-hydroxy-5β-pregnane-1,3,20-trione, 3α,17α-dihydroxy-5β-pregnane-1,20-dione, 3α,17α,20α-trihydroxy-5β-pregnan-1-one and 5β-pregnane-1β,3α,17α,20α-tetrol. 2. The characterization rested mainly on RM analysis of the substances and their derivatives by glycol fission, providing evidence for position and degree of substitution and for steroidal character. Supporting evidence was provided by chemically specific location reactions. 3. Certain problems in the manipulation of these β-disubstituted steroids are discussed.

Full text

PDF
185

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. APPLEBY J. I., GIBSON G., NORYMBERSKI J. K., STUBBS R. D. Indirect analysis of corticosteroids. I. The determination of 17-hydroxycorticosteroids. Biochem J. 1955 Jul;60(3):453–460. doi: 10.1042/bj0600453. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. BROOKS C. J., NORYMBERSKI J. K. The oxidation of corticosteroids with sodium bismuthate. Biochem J. 1953 Oct;55(3):371–378. doi: 10.1042/bj0550371. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. BUSH I. E., MAHESH V. B. Metabolism of 11-oxygenated steroids. 2. 2-Methyl steroids. Biochem J. 1959 Apr;71(4):718–742. doi: 10.1042/bj0710718. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. BUSH I. E. Methods of paper chromatography of steroids applicable to the study of steroids in mammalian blood and tissues. Biochem J. 1952 Jan;50(3):370–378. doi: 10.1042/bj0500370. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. BUSH I. E. The detection of steroid 17: 20-diols on chromatograms. Biochem J. 1954 Dec 17;59(335TH):xiv–xv. [PubMed] [Google Scholar]
  6. Bush I. E., Mahesh V. B. Metabolism of 11-oxygenated steroids. 3. Some 1-dehydro and 9 alpha-fluoro steroids. Biochem J. 1964 Nov;93(2):236–255. doi: 10.1042/bj0930236. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. EDWARDS R. W., MAKIN H. L., BARRATT T. M. THE STEROID 11-OXYGENATION INDEX; A RAPID METHOD FOR USE IN THE DIAGNOSIS OF CONGENITAL ADRENAL HYPERPLASIA. J Endocrinol. 1964 Sep;30:181–194. doi: 10.1677/joe.0.0300181. [DOI] [PubMed] [Google Scholar]
  8. GRAY C. H., GREEN M. A., HOLNESS N. J., LUNNON J. B. Urinary metabolic products of prednisone and prednisolone. J Endocrinol. 1956 Oct;14(2):146–154. doi: 10.1677/joe.0.0140146. [DOI] [PubMed] [Google Scholar]
  9. GUAL C., MORATO T., HAYANO M., GUT M., DORFMAN R. I. Biosynthesis of estrogens. Endocrinology. 1962 Dec;71:920–925. doi: 10.1210/endo-71-6-920. [DOI] [PubMed] [Google Scholar]
  10. Idler D. R., Truscott B. 1-alpha-hydroxycorticosterone: synthesis in vitro and properties of an interrenal steroid in the blood of cartilaginous fish (genus Raja). Steroids. 1967 May;9(5):457–477. doi: 10.1016/0039-128x(67)90100-6. [DOI] [PubMed] [Google Scholar]
  11. Monder C. A new approach to the characterization of steroids containing the 17-alpha-ketol side chain. Biochem J. 1964 Mar;90(3):522–527. doi: 10.1042/bj0900522. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Noguchi S., Fukushima D. K. Microbiological hydroxylation of saturated 17-keto steroids. J Org Chem. 1965 Oct;30(10):3552–3555. doi: 10.1021/jo01021a063. [DOI] [PubMed] [Google Scholar]
  13. ROBERTSON J. G., BUTLER G. W. THE DETECTION OF AMIDES ON PAPER CHROMATOGRAMS. J Chromatogr. 1964 Jan;13:262–262. doi: 10.1016/s0021-9673(01)95110-6. [DOI] [PubMed] [Google Scholar]
  14. Schneider J. J., Bhacca N. S. 1-beta-Hydroxylation of 3-alpha,20-beta,21-tetrahydroxy 5-beta-pregnan-11-one and of other 5-beta-steroids in a man and by surviving liver slices of the guinea pig. J Biol Chem. 1966 Nov 25;241(22):5313–5324. [PubMed] [Google Scholar]
  15. Smith L. L., Foell T. J., Teller D. M. Retropinacol rearrangement of 1-alpha-hydroxy steroids. A new route to 1-beta-methyl 19-norsteroids. J Org Chem. 1965 Nov;30(11):3781–3786. doi: 10.1021/jo01022a044. [DOI] [PubMed] [Google Scholar]
  16. WILSON H., FAIRBANKS R. A micromethod for the detection and assay of steroid C21 17-hydroxy-alpha-glycols. Arch Biochem Biophys. 1955 Feb;54(2):457–466. doi: 10.1016/0003-9861(55)90058-8. [DOI] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES