Acidic metabolites. VI. 20 alpha-isosteroids as intermediates in 20 alpha-dihydrosteroid formation

Journal Article · Fri Mar 01 04:00:00 EST 1985 · Steroids; (United States)

DOI:https://doi.org/10.1016/0039-128X(85)90085-6· OSTI ID:5428995

Monder, C; Bradlow, H L; Han, C A; Zumoff, B

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), Journal Name: Steroids; (United States) Vol. 3-4; ISSN STEDA
• Country of Publication: United States
• Language: English

Related Subjects

550501* -- Metabolism-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
ADRENAL HORMONES
CORTICOSTEROIDS
GLUCOCORTICOIDS
HORMONES
HYDROCORTISONE
HYDROXY COMPOUNDS
ISOTOPE APPLICATIONS
KETONES
LABELLED COMPOUNDS
METABOLISM
METABOLITES
ORGANIC COMPOUNDS
PREGNANES
STEREOCHEMISTRY
STEROID HORMONES
STEROIDS
TRACER TECHNIQUES
TRITIUM COMPOUNDS