Identification of C21O3 and C21O4 Steroids in Human Bile
Open accessAbstract
The steroid glucuronide, and mono- and disulphate fractions were obtained from human bile by chromatography on Sephadex LH-20. The conjugates in the glucuronide fraction were hyderolysed with β-glucuronidase and the mono- and disulphate fractions were solvolysed. The steroids liberated were fractionated on silicic acid and by thin layer chromatography and analysed by gas-liquid chromatography and gas chromatography-mass spectrometry. The following C21O3 and C21O4 steroids were identified: 5α-pregnane-3α,17α,20α-triol, 5β-pregnane-3α,17α,20α-triol, 5-pregnene-3α,17α,20α-triol, 5-pregnene-3β,17α,20α-triol, 5α-pregnane-3α,16α,20α-triol, 3α,21-dihydroxy-5β-pregnan-20-one, 3α,11β,21-trihydroxy-5α-pregnan-20-one, 3α,11β,21-trihydroxy-5β-pregnan-20-one and 3α,21-dihydroxy-5β-pregnane-11,20-dione. Concentrations of these steroids were measured in fistula or gall-bladder bile samples from five subjects.
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
17-deoxysteroids (mineralocorticoids and precursors) have high biliary excretion as opposed to 17-hydroxy C21 steroids like cortisol.
“17-deoxysteroids (mineralocorticoids and precursors) have high biliary excretion as opposed to 17-hydroxy C21 steroids like cortisol [147].”
From Human steroid biosynthesis, metabolism and excretion are differentially reflected by serum and urine steroid metabolomes: a comprehensive review (2019) · cites this paper as [147]
Metabolism by the gut microbiome is relevant for C17-deoxy corticosteroids, e.g. mineralocorticoids and their precursors, which have high biliary excretion.
“Metabolism by the gut microbiome is relevant for C17-deoxy corticosteroids, e.g. mineralocorticoids and their precursors, which have a high biliary excretion [147].”
From Human steroid biosynthesis, metabolism and excretion are differentially reflected by serum and urine steroid metabolomes: a comprehensive review (2019) · cites this paper as [147]
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Cites
METABOLISM OF THE STEROID HORMONES
Fish, W. R., Dorfman, R. I., & Young, W. C. (1942) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)72606-9 · Cited by 407 · see citing works
Steroids in Germfree and Conventional Rats
Gustafsson, J.-Α., & Sjövall, J. (1968) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1968.tb00443.x · Cited by 104 · see citing works
Formation and gas-liquid chromatographic behavior of isometric steroid ketone methoxime derivatives
Horning, M. G., Moss, A. M., & Horning, E. C. (1968) · Analytical Biochemistry · doi:10.1016/0003-2697(68)90318-7 · Cited by 96 · see citing works
Gustafsson, B. E., Gustafsson, J.-Α., & Sjövall, J. (1968) · PubMed · Cited by 93 · see citing works
Sjövall, J., & Vihko, R. (1966) · Steroids · doi:10.1016/0039-128x(66)90072-9 · Cited by 87 · see citing works
Steroids in Germfree and Conventional Rats
Gustafsson, B. E., Gustafsson, J.-Α., & SJÖVALL, J. (1968) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1968.tb00250.x · Cited by 71 · see citing works
Lewbart, M. L., & Schneider, J. J. (1969) · The Journal of Organic Chemistry · doi:10.1021/jo01263a062 · Cited by 66 · see citing works
Steroids in Germfree and Conventional Rats
Gustafsson, J.-Α. (1968) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1968.tb00444.x · Cited by 56 · see citing works
Steroids in Germfree and Conventional Rats
Eriksson, H., Gustafsson, J.-Α., & Sjövall, J. (1969) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1969.tb00644.x · Cited by 53 · see citing works
Steroid Production in “Nonfunctioning” Adrenal Cortical Tumor
Fukushima, D. K., & Gallagher, T. F. (1963) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jcem-23-9-923 · Cited by 45 · see citing works
Identification of C19O2 and C21O2 Steroids in the Glucuronide Fraction of Human Bile
Laatikainen, T. K., & Vihko, R. (2005) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1969.tb00669.x · Cited by 41 · see citing works
Self-citationThe polarographic estimation of steroid hormones
Butt, W. R., Henly, A. A., & Morris, C. J. (1948) · Biochemical Journal · doi:10.1042/bj0420447 · Cited by 40 · see citing works
Identification of 5α-pregnane-3α, 20α, 21-triol in human pregnancy plasma
Sjövall, J., & Sjövall, K. (1968) · Steroids · doi:10.1016/0039-128x(68)90027-5 · Cited by 38 · see citing works
Identification of C19O3 steroids in the mono- and disulfate fractions of human bile
Laatikainen, T. K. (1970) · Steroids · doi:10.1016/s0039-128x(70)80010-1 · Cited by 35 · see citing works
Self-citationApplication of thin-layer chromatography to the separation of saturated 21-deoxy-pregnane steroids
Lisboa, B. P. (1965) · Steroids · doi:10.1016/0039-128x(65)90023-1 · Cited by 34 · see citing works
Steroid sulfates in human bile
Laatikainen, T. K., PELTOKALLIO, P., & Vihko, R. (1968) · Steroids · doi:10.1016/0039-128x(68)90031-7 · Cited by 32 · see citing works
Self-citationQuantitation of C19O2 and C21O2 steroid mono- and disulfates in human bile
Laatikainen, T. K., & Vihko, R. (1969) · Steroids · doi:10.1016/0039-128x(69)90027-0 · Cited by 23 · see citing works
Self-citationIdentification of C19O2 and C21O2 Steroids in the Mono‐ and Disulphate Fractions of Human Faeces
Laatikainen, T. K., & Vihko, R. (1970) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1970.tb00957.x · Cited by 22 · see citing works
Self-citationBILIARY AND URINARY METABOLITES OF 4-C14-PROGESTERONE IN HUMAN SUBJECTS*
Chang, E., Slaunwhite, W. R., & Sandberg, A. A. (1960) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jcem-20-12-1568 · Cited by 19 · see citing works
Identification of 3α-hydroxyandrost-5-en-17-one in human plasma, urine and bile
Jänne, O. A., Laatikainen, T. K., Vainio, J., et al. (1969) · Steroids · doi:10.1016/s0039-128x(69)80064-4 · Cited by 15 · see citing works
Self-citationHirschmann, H., Hirschmann, F. B., & Corcoran, J. W. (1955) · The Journal of Organic Chemistry · doi:10.1021/jo01123a004 · Cited by 14 · see citing works
Identification of 18-hydroxyandrosterone in human bile
Laatikainen, T. K., & Vihko, R. (1969) · Steroids · doi:10.1016/s0039-128x(69)80015-2 · Cited by 13 · see citing works
Self-citationProduction rate of corticosterone sulfate in normal human adults
Kielmann, N., STACHENKO, J., & Giroud, C. J. P. (1966) · Steroids · doi:10.1016/0039-128x(66)91023-3 · Cited by 13 · see citing works
Gas chromatographic estimation of urinary Δ5-pregnene-3β, 17α, 20β-triol
Kinoshita, K., Isurugi, K., Matsumoto, Y., & Takayasu, H. (1968) · Steroids · doi:10.1016/s0039-128x(68)80047-9 · Cited by 11 · see citing works
Simultaneous Metabolism of3H-corticosterone 21-Sulfate and Corticosterone-14C in Man
Pasqualini, J. R. (1967) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jcem-27-6-885 · Cited by 10 · see citing works
BILIARY AND URINARY METABOLITES OF 4-C14-17α-HYDROXYPROGESTERONE IN HUMAN SUBJECTS*
Vermeulen, A. C. J., Slaunwhite, W. R., & SAXDBERG, A. (1961) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jcem-21-12-1534 · Cited by 9 · see citing works
Kraiem, Z., Lunenfeld, B., & Skalka, J. (1969) · European Journal of Endocrinology · doi:10.1530/acta.0.0610001 · Cited by 7 · see citing works
Urinary Excretion of Glucuronides and Sulfates of Acetaldehydogenic Steroids
RILEY, W. J. (1968) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jcem-28-1-83 · Cited by 5 · see citing works
Romanoff, L. P., MALHOTRA, K. K., BAXTER, M. N., et al. (1968) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jcem-28-6-836 · Cited by 4 · see citing works
Menzel, P., WENDLBERGER, F., & Oertel, G. W. (1969) · Hoppe-Seyler´s Zeitschrift für physiologische Chemie · doi:10.1515/bchm2.1969.350.1.269 · Cited by 2 · see citing works
Flagged first, then by citations
Research works printed but not linked: 3
- Rdlercreutz, H., Laiho, S., and Luukkainen, T., I n Gas Chromatographic Determination of Hormonal Steroids (edited by F. Polvani, M. Surace, and M. Luisi), Aca- demic Press, New York 1967, p. 69.
- I , (1970) 534. ' crinol. 23 (1963) 923. Endocrinol., in press.
- T. Laatikainen Laaketieteellisen Kemian Laitos, Helsingin Yliopisto Siltavuorenpenger 10, Helsinki 17, Finland 14321033, 1970, 2, Downloaded from https://febs.onlinelibrary.wiley.com/doi/10.1111/j.1432-1033.1970.tb00299.x by Test, Wiley Online Library on [07/06/2023]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License · DOI
Cited by
Sorted by citations
Schiffer, L., Barnard, L., Baranowski, E. S., Gilligan, L. C., Taylor, A. E., Arlt, W., Shackleton, C. H. L., & Storbeck, K.-H. (2019) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2019.105439 · Cited by 450 · see citing works
- Authors
- Laatikainen, T.
- Affiliations
- University of Helsinki (FI)
- Corresponding author
- Laatikainen, Timo
- Venue
- European Journal of Biochemistry
- Publisher
- Wiley
- Published
- 1970-06
- Volume
- 14
- Issue
- 2
- Pages
- 372-378
- ISSN
- 0014-2956 (ISSN-L)
- 1432-1033
- OpenAlex
- W2039631419
- Cited by
- 17
- References
- 30
- Citations by year
- 2024: 2 · 2020: 1 · 2019: 1
- FWCI
- 1.13
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- European Journal of Biochemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Health Sciences › Medicine › Surgery › Cholesterol and Lipid Metabolism
- Health Sciences › Medicine › Endocrinology, Diabetes and Metabolism › Adrenal Hormones and Disorders
- Keywords
- C21 steroids, steroid glucuronides, steroid sulfates
- MeSH terms
- Adult, Alcohols, Bile, Chromatography, Gas, Chromatography, Gel, Chromatography, Thin Layer, Female, Glucuronates, Glucuronidase, Humans, Male, Middle Aged, Pregnanes, Spectrum Analysis, Sulfuric Acids
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
