Acidic metabolites. VI. 20 alpha-isosteroids as intermediates in 20 alpha-dihydrosteroid formation
We have previously shown that human subjects metabolize the 20 beta-epimer of isocortisol (11 beta, 17,20 beta-trihydroxy-3-oxo-pregn-4-en-21-al) to both 20 alpha- and 20 beta-hydroxy steroid end products. In this paper we describe the synthesis of tritium labeled 20 alpha-epimers of isocortisol and isoTHF (3 alpha, 11 beta, 17,20 alpha-tetrahydroxy-5 beta-pregnan-21-al) and their metabolic fate in humans. Both steroids yielded 20 alpha-hydroxy urinary neutral end-products (cortols and cortolones) and no 20 beta-hydroxy epimers. Regeneration of 17-ketols from aldols occurred to a small extent with isoTHF, but not with isocortisol. Isocortisol and isoTHF yielded less cortoic acids than did the corresponding ketols. The results provide further evidence that in man the stereochemistry at C-20 of the end-products of corticosteroid metabolism is determined by the configuration of the aldol at C-20 prior to subsequent metabolic events.
- Research Organization:
- Population Council, New York, NY
- OSTI ID:
- 5428995
- Journal Information:
- Steroids; (United States), Vol. 3-4
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
STEROIDS
METABOLISM
HYDROCORTISONE
METABOLITES
STEREOCHEMISTRY
TRACER TECHNIQUES
TRITIUM COMPOUNDS
ADRENAL HORMONES
CORTICOSTEROIDS
GLUCOCORTICOIDS
HORMONES
HYDROXY COMPOUNDS
ISOTOPE APPLICATIONS
KETONES
LABELLED COMPOUNDS
ORGANIC COMPOUNDS
PREGNANES
STEROID HORMONES
550501* - Metabolism- Tracer Techniques