Hepatic metabolism of 3-oxoandrost-4-ene-17-carboxylic acid
3-oxoandrost-4-ene-17..beta..-carboxylic acid (etienic acid), a likely catabolite of deoxycorticosterone, was synthesized in the radioactive form and injected intravenously into rats prepared with a biliary fistula. The biliary metabolites (77% of the dose) were isolated, separated into individual compounds, and identified by high-field /sup 1/H-NMR and by gas chromatographic comparison with standards. After deconjugation, aglycones were characterized by GC-MS. The administered etienic acid underwent full reduction, yielding three of the four possible distereomers: 3..cap alpha..- and 3..beta..-hydroxy-5..cap alpha..-etianic acids and 3..cap alpha..-hydroxy-5..beta..-etianic acid, accounting together for at least one third of the biliary radioactivity. In addition to the reduction, a sizeable fraction (> 25% of the recovered dose) underwent additional hydroxylation to at least two di- and one trihydroxy acid. Most (approx. 75%) of the recovered metabolites were present in conjugated form. Ester glucuronidation (conjugation on the steroidal carboxyl group) predominated, followed by ether glucuronidation (on a steroidal hydroxyl group). By the criteria of structure and biliary, rather than urinary, excretion, the saturated steroidal acids derived from etienic acid can be classified as short-chain bile acids. They conclude that degradation to short-chain bile acids followed by glucuronidation is likely to be an important catabolic pathway for certain steroid hormones.
- Research Organization:
- Univ. of Texas Medical School, Houston
- OSTI ID:
- 6935784
- Report Number(s):
- CONF-8606151-
- Journal Information:
- Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States), Vol. 45:6; Conference: 76. annual meeting of the Federation of American Society for Experimental Biology, Washington, DC, USA, 8 Jun 1986
- Country of Publication:
- United States
- Language:
- English
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62 RADIOLOGY AND NUCLEAR MEDICINE
CARBOXYLIC ACIDS
METABOLISM
METABOLITES
NMR SPECTRA
BILIARY TRACT
BIOLOGICAL PATHWAYS
GAS CHROMATOGRAPHY
GLUCURONIDE CONJUGATES
LIVER
MASS SPECTROSCOPY
RATS
STEROIDS
ANIMALS
BODY
CHROMATOGRAPHY
DIGESTIVE SYSTEM
GLANDS
MAMMALS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANS
RODENTS
SEPARATION PROCESSES
SPECTRA
SPECTROSCOPY
VERTEBRATES
550501* - Metabolism- Tracer Techniques
550600 - Medicine