16α-Hydroxy Steroids

Goodman, Joseph J.; Smith, Leland L.

doi:10.1128/aem.9.5.372-375.1961

Applied Microbiology

1961

DOI: 10.1128/aem.9.5.372-375.1961

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16α-Hydroxy Steroids

Joseph J. Goodman¹,

Leland L. Smith²

Abstract: GOODMAN, JOSEPH J. (American Cyanamid Company Pearl River, N. Y.), AND LELAND L. SMITH. 16a-Hydroxy steroids. XI. 23-and 16a-Hydroxylation of 9a-fluorohydrocortisone by strains of Streptomyces roseochromogenes. Appl. Microbiol. 9:372-375. 1961.-9a-Fluorohydrocortisone is hydroxylated by Streptomyces roseochromogenes in the 16a-, the 213-, and in both the 16a-and 23-positions. 16a-Hydroxylation appears to be the more predominant and rapid pathway of transformation. The degree of 23-hydroxylation is dependent up… Show more

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Cited by 7 publications

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Transformation reactions of progesterone by different species of Streptomyces

Atta

Zohri

1995

J. Basic Microbiol.

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A systematic study of transformation reactions of the genus Streptomyces with respect to the progesterone molecule was undertaken. The types of transformation reactions by different Streptomyces species were evaluated from the point of view of taxonomy. The isolates tested were divided according to the transformation types into six groups: (1) a group of species transform progesterone to 16 alpha-hydroxyprogesterone; (2) a group of species transform progesterone to 6 beta-hydroxyprogesterone; (3) a group of species transform progesterone to 6 beta, 11 alpha-dihydroxyprogesterone; (4) a group of species dehydrogenate progesterone in C1-2 position; (5) a group of species transform progesterone to 3 derivatives namely 6 beta-hydroxyprogesterone, 6 beta, 11 alpha-dihydroxyprogesterone and dehydrogenation in position C1-2; (6) a group of species with no capacity to transform progesterone into another steroid derivative. From the point of view of Streptomyces classification, the transformation reaction of progesterone fulfil all the requirements of taxonomic feature of Streptomyces. These appear to be specific properties and common to all the strains of individual Streptomyces species tested.

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Transformation reactions of progesterone by different species of Streptomyces

Atta

Zohri

1995

J. Basic Microbiol.

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Transformation of prednisolone to a 20β-hydroxy prednisolone compound by Streptomyces roseochromogenes TS79

Zhang

Cui

et al. 2011

Appl Microbiol Biotechnol

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Prednisolone represents an important compound in pharmaceutical preparations. To obtain more bioactive prednisolone derivatives, the microbial transformation of prednisolone was carried out. The steroid products were assigned by an interpretation of their spectral data using mass spectrometry and proton nuclear magnetic resonance ((1)H NMR) analyses. The product was assigned the chemical structure of 11β, 17α, 20β, 21-tetrahydroxypregna-1,4-diene-3-one (named as 20β-hydroxy prednisolone). The conversion of prednisolone to 20β-hydroxy prednisolone by Streptomyces roseochromogenes TS79 was different from a previous study on the microbial transformation of steroid by this organism, which usually generates a 16α-hydroxy steroid product. The different reaction parameters for maximum conversion of prednisolone were optimized. The analysis revealed that the optimum values of the tested variables were 7.5 mg/ml prednisolone dissolved in DMSO and added to the 24-h pre-culture fermentation culture containing 0.05% MgSO(4) and incubated for 24 h. A conversion of 95.1% of prednisolone was observed, which has the potential to be used in industrial production.

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Biotechnological transformation of hydrocortisone to 16α-hydroxy hydrocortisone by Streptomyces roseochromogenes

Restaino

Marseglia

Castro

et al. 2013

Appl Microbiol Biotechnol

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Streptomyces roseochromogenes is able to hydroxylate steroid compounds in different positions of their cycloalkane rings thanks to a cytochrome P-450 multi-enzyme complex. In this paper, the hydroxylation of the hydrocortisone in the 16α position, performed by bacterial whole cells, was investigated in both shake flask and fermentation conditions; the best settings for both cellular growth and transformation reaction were studied by investigating the optimal medium composition, the kinetic of conversion, the most suitable substrate concentration and the preferred addition timing. Using newly formulated malt extract- and yeast extract-based media, a 16α-hydrohydrocortisone concentration of 0.2 ± 0.01 g L(-1) was reached in shake flasks. Batch experiments in a 2-L fermentor established the reproducibility and robustness of the biotransformation, while a pulsed batch fermentation strategy allowed the production to increase up to 0.508 ± 0.01 g L(-1). By-product formation was investigated, and two new derivates of the hydrocortisone obtained during the bacterial transformation reaction and unknown so far, a C-20 hydroxy derivate and a C-21 N-acetamide one, were determined by NMR analyses.

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16α-Hydroxy Steroids

Cited by 7 publications

References 8 publications

Transformation reactions of progesterone by different species of Streptomyces

Transformation reactions of progesterone by different species of Streptomyces

Transformation of prednisolone to a 20β-hydroxy prednisolone compound by Streptomyces roseochromogenes TS79

Biotechnological transformation of hydrocortisone to 16α-hydroxy hydrocortisone by Streptomyces roseochromogenes

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