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Bovine adrenal cytochrome P-450(11 beta)-mediated conversion of 11-deoxycortisol to 18- and 19-hydroxy derivatives; structural analysis by 1H-NMR.
- Source :
-
The Journal of steroid biochemistry and molecular biology [J Steroid Biochem Mol Biol] 1991 Dec; Vol. 39 (6), pp. 911-20. - Publication Year :
- 1991
-
Abstract
- Incubation of 11-deoxycortisol with a cytochrome P-450(11 beta)-reconstituted system yielded, in addition to cortisol, several new steroid products. In this study, structures of the three steroid products were elucidated. Retention time of the first product (Peak 2 substance) coincided with that of authentic 18-hydroxycortisol on reverse phase HPLC. To further confirm the chemical identity of this product, the purified sample was subjected to 1H-NMR analysis. The spectrum was essentially identical to that of 18-hydroxycortisol. The retention time of the second product (Peak 3 substance) did not coincide with those of commonly occurring steroids. The one- and two-dimension 1H-NMR spectra provided strong evidence for its structure of 19-hydroxy-11-deoxycortisol. The retention time of the third product (Peak 4 substance) did not coincide with those of commonly occurring steroids. The 1H-NMR spectrum showed the presence of signals of 19-CH3 and 18-CH2 protons. There was also evidence that this product is not hydroxylated at the 11-position. Further analysis of the COSY spectra identified its structure as 18-hydroxy-11-deoxycortisol. From these results, we conclude that bovine P-450(11 beta) can catalyze the hydroxylation of 11-deoxycortisol at 11 beta-, 18- and 19-positions and produce cortisol, 18-hydroxy-11-deoxycortisol, 18-hydroxycortisol and 19-hydroxy-11-deoxycortisol.
- Subjects :
- Adrenal Cortex chemistry
Animals
Catalysis
Cattle
Chromatography, High Pressure Liquid
Cortodoxone analysis
Hydrocortisone analysis
Hydrocortisone metabolism
Hydroxylation
Magnetic Resonance Spectroscopy
Adrenal Cortex enzymology
Cortodoxone metabolism
Cytochrome P-450 Enzyme System physiology
Hydrocortisone analogs & derivatives
Subjects
Details
- Language :
- English
- ISSN :
- 0960-0760
- Volume :
- 39
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- The Journal of steroid biochemistry and molecular biology
- Publication Type :
- Academic Journal
- Accession number :
- 1751390
- Full Text :
- https://doi.org/10.1016/0960-0760(91)90349-a