Bioconversion of steroids by Cochliobolus lunatus—II. 11β-hydroxylation of 17α,21-dihydroxypregna-1,4-diene-3,20-dione 17-acetate in dependence of the inducer structure
| Autor: | Cläre Hörhold-Schubert, Heinz Stopsack, Helmuth Groh, Katrin Undisz |
|---|---|
| Rok vydání: | 1992 |
| Předmět: |
Stereochemistry
Prednisolone Endocrinology Diabetes and Metabolism Clinical Biochemistry Biology Hydroxylation Biochemistry Structure-Activity Relationship chemistry.chemical_compound Endocrinology Ascomycota Biotransformation Inducer Molecular Biology Pregnane Substrate (chemistry) Cell Biology Metabolism Pregnanes Cochliobolus lunatus biology.organism_classification Sterol chemistry Enzyme Induction Steroid 11-beta-Hydroxylase Molecular Medicine |
| Zdroj: | The Journal of Steroid Biochemistry and Molecular Biology. 43:543-547 |
| ISSN: | 0960-0760 |
| DOI: | 10.1016/0960-0760(92)90242-b |
| Popis: | The 11 beta-hydroxylase of the filamentous fungus Cochliobolus lunatus m 118 was induced with the substrate 17 alpha, 21-dihydroxypregna-1,4-diene-3,20-dione 17-acetate (11 beta-deoxyprednisolone 17-acetate) itself, substrate analogues, different pregnane compounds, sterols, intermediates of microbial sterol side-chain degradation or bile acids, together with 24 different steroids in a standardized test system. The resulting 11 beta-hydroxylation rate, leading to prednisolone 17-acetate and prednisolone, respectively, was determined and compared with the hydroxylation rate of non-induced cultures. The transformation yield strongly depended on the inducer structure. The microbial sterol side-chain degradation intermediates (20S)-20-hydroxymethylpregn-4-en-3-one and the corresponding pregna-1,4-diene compound caused the highest induction effects (induction factors 5.1 and 4.9, respectively). The metabolism of (20S)-20-hydroxymethylpregna-1,4-dien-3-one during the cultivation was elucidated. The induction effect decreased with the rising oxidation of the inducer. The significant increase of the 11 beta-hydroxylation rate of 1-dehydro-pregnane substrates by specific induction allows alternative pathways to glucocorticoid partial syntheses. |
| Databáze: | OpenAIRE |
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