Abstract
The regular occurrence of a peak due to an unidentified substance (X) in the gas chromatographic traces obtained from phenolic extracts of urine from human pregnant and non-pregnant females has been reported1. The biphasic excretion of X with maxima in the luteal phase of the ovulatory cycle and relatively high levels in the first trimester of pregnancy were noteworthy and suggested that the substance may have a biological significance. Close similarities between the excretory pattern, the chemical and chromatographic properties of X and of those of the known phenolic steroids suggested initially that this compound was steroidal in nature. The same, or a similar, substance seems to be excreted in the vervet monkey (Cercopithecus aethiops pygerythrus)2. We now report the excretory pattern of X in more detail, the isolation of the pure compound from pooled pregnancy urine and the chemical structure. The structure determined by mass spectrometry, IR spectroscopy and NMR spectrometry is: trans-(±)-3,4-bis[(3-hydroxy phenyl)methyl]dihydro-2-(3H)-furanone (HPMF) and was confirmed by synthesis.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
Stitch, S. R., Smith, P.D., Illingworth, D. & Toumba, K. J. Endocr. 85, 23p (1980).
Setchell, K. D. R., Bull, R. & Adlercreutz, H. J. Steroid Biochem. 12, 375–384 (1980).
Smith, P. D. & Stitch, S. R. Clinica chim. Acta 36, 439–451 (1972).
British patent application nos 80. 13. 040, 21. 4. 80.
Kuhn, M. & von Wartburg, A. Helv. chim. Acta 50, 1546–1565 (1967).
Grimshaw, J. in Rodd's Chemistry of Carbon Compounds Vol. IIID, 2nd edn (ed. Coffey, S.)Ch. 16, 258 (Elsevier, Amsterdam, 1976).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Stitch, S., Toumba, J., Groen, M. et al. Excretion, isolation and structure of a new phenolic constituent of female urine. Nature 287, 738–740 (1980). https://doi.org/10.1038/287738a0
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/287738a0
This article is cited by
-
Genetic basis for the cooperative bioactivation of plant lignans by Eggerthella lenta and other human gut bacteria
Nature Microbiology (2019)
-
Production of enterodiol from defatted flaxseeds through biotransformation by human intestinal bacteria
BMC Microbiology (2010)
-
Plasma enterolactone and risk of colon and rectal cancer in a case–cohort study of Danish men and women
Cancer Causes & Control (2010)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.