Transformation of steroids by fungal protoplasts

Sedlaczek, L; Długoński, Jerzy; Jaworski, Adam

doi:10.1007/bf00253725

Cited by 19 publications

(4 citation statements)

References 14 publications

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“…Such an effect of ethanol on the amount of unsaturated fatty acids in the lipid composition was previously reported in R. erythropolis [5], S. cerevisiae [33], Clostridium thermocellum [34], Lactobacillus heterohiochii [35], and Lactobacillus homohiochii [36]. Similar studies have reported on the bioconversion of β-sitosterol to AD by Mycobacterium, where different kinds of permeabilizing agents were used, such as specific kinds of amino acids [7,12], polycations [8], antibiotics [9], CD [10], lecithin [11], and so on. The effect of the nonionic surfactant, Tween 80, on the microbial transformation of AD into its 9α-hydroxy-derivative by resting Rhodococcus sp.…”

Section: Discussionsupporting

confidence: 71%

“…Lecithin influenced the fatty acid profile of the CW, thus resulting in greater AD and ADD formation from β-sitosterol [11]. Glycine was shown to alter the ratio of mycolic acids to other lipids, thus enhancing sterol to AD(D) bioconversion by Mycobacteria [12]. These above findings indicated that steroid biotransformation could be enhanced by the improvement of transport of steroid into the cytosol using various permeabilizing agents.…”

Section: Introductionmentioning

confidence: 88%

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The effect of ethanol on cell properties and steroid 1‐en‐dehydrogenation biotransformation of Arthrobacter simplex

Luo

Ning

Wang

et al. 2014

Biotech and App Biochem

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Resting cells of Arthrobacter simplex with 1-en-dehydrogenation ability were prepared and treated by ethanol at subinhibitory concentrations (4%-15%, v/v), then added into the ethanol-free system containing low concentration of cortisone acetate (1 g L(-1)) to produce prednisone acetate by C1,2 dehydrogenation reaction. Results showed that, within the range of ethanol concentration, the initial conversion rate was varied significantly with the concentration of ethanol and the maximum was obtained at 8% (v/v) ethanol, which was increased by 32.6% compared with the control. A series of cell features closely relevant to biotransformation efficiency were further analyzed. It indicated that ethanol acting on cell wall and membrane could be used as a mediator to enhance cell permeability, which facilitated the penetration of substrate across cell barrier within a short time, resulting in the elevated initial conversation rate. The observation of fatty acids composition suggested that the increased unsaturated fatty acids, especially cis-isomers, in the presence of ethanol led to the disorganization of the native arrangement of lipids and thus increased cell permeability. Our findings demonstrated that another facilitation of ethanol was to promote substrate transport into cells by permeabilization, which would provide the guidance in the practical application of organic solvents in steroid biotransformation.

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Section: Discussionsupporting

confidence: 71%

Section: Introductionmentioning

confidence: 88%

The effect of ethanol on cell properties and steroid 1‐en‐dehydrogenation biotransformation of Arthrobacter simplex

Luo

Ning

Wang

et al. 2014

Biotech and App Biochem

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“…Also, a greater regio-and stereospecificity, induced by the substrate, could be observed with Cunninghamella elegans which hydroxylates Substance S in both 1 la-and 11P-positions, while with 6a-fluoro-l6a,17,2l-trihydroxy-4pregnen-3,20-dione 16,17-acetonide (6a-fluoro-Substance S 16,17-acetonide), only traces of the 1 la-hydroxylated product are formed. 85 Horhold et a1. 86.87 reported recently that Cochfiobofus lunatus is effective in 11 P-hydroxylation of 3-oxo-23,24-dinor-1,4-choladiene-22-0ic acid.…”

Section: B I L P -Hydroxylationmentioning

confidence: 97%

Biotransformations of Steroids

Sedlaczek

1988

Critical Reviews in Biotechnology

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115

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Different types of microbiological transformation of steroids are reviewed, with special attention given to bioconversions applied in the manufacturing of steroid hormones, i.e., 11 alpha- 11 beta-, 16 alpha-, 17 alpha-hydroxylations and 1-dehydrogenation. Availability and utilization of raw materials for industrial production of steroids of the estrane, androstane, and pregnane series are discussed. Among the current trends in steroid research of a practical nature, immobilization of enzymes and living cells and the spore process are emphasized as alternative techniques of steroid transformation of possible future importance. Efforts to recognize, in cell-free preparations, the components of steroid-transforming enzyme systems as well as the cellular mechanisms of control of their biosynthesis and activity are described in order to illustrate the main subjects of current basic investigation in steroid bioconversion.

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“…A recent development is the use of fungal protoplasts, instead of mycelium, to effect steroid conversions at a faster rate (than with the mycelium) showing that the cell wall was a ratelimiting factor. This was demonstrated using Cunninghamella elegans in the li-hydroxylation of cortexolone (24) for corticosteroid production (11). Also reported is the use of fungal spores, instead of mycelium, and entrapment of these in the pores of particles of diatomaceous earth (filter aid Celite 560) illustrated by the li-hydroxylation of progesterone (25) (for corticosteroid production) by Aspergillus ochraceus (12).…”

Section: -Glucmentioning

confidence: 99%

Recent Developments in our Knowledge of Steroids¹

Hardman¹

1987

Planta Med

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Annually, the American Chemical Abstracts has some 3000 references to plant steroids or related compounds. This is a review of 34 selected papers mainly from the literature of [1984][1985]. Plant steroids as raw material for the pharmaceutical industry; tissue culture for steroids; horticultural trials of species for sapogenins; the in Vitro use of enzymes to increase the yield of sapogenins from plant material. New furostanol precursors of diosgenin; the cytotoxic activity of these and related compounds; their possible role in plant mineral metabolism. Microorganisms in the biotransformation of steroids; the exploitation of waste material as a source of sterols; the use of fungal spores on diatomaceous particles; the use of fungal protoplasts; hydrophobic resin as a product reservoir in such transformations. Brassinosteroids, their distribution as plant growth hormones; their microquantitative bioassay; physiological studies towards their use for enhancement of crop production; patented analogues obtained by partial synthesis. Ecdysones, their wide distribution in plants; their possible functions: effect on photosynthetic and respiratory rates; root protection against soil nematodes; dietary value in animal nutrition; their use in insect control. 29-Fluorophytosterols as pro-insecticides; fungal pregnanes as insecticides. Cardiac glycosides; ecological significance in plant-insect-bird relationships; new cardenolides, naturally occurring and those obtained by partial synthesis; the use of mesophyll cells in tissue culture; crossbreeding of Digitalis species. Steroidal alkaloids: reference to their annual review and to a steroidal antibiotic; the types of alkaloids now defineable in the Buxaceae and their chemotaxonomic significance for the new ones from the single genus family, Didymelaceae.

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Transformation of steroids by fungal protoplasts

Cited by 19 publications

References 14 publications

The effect of ethanol on cell properties and steroid 1‐en‐dehydrogenation biotransformation of Arthrobacter simplex

The effect of ethanol on cell properties and steroid 1‐en‐dehydrogenation biotransformation of Arthrobacter simplex

Biotransformations of Steroids

Recent Developments in our Knowledge of Steroids¹

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Transformation of steroids by fungal protoplasts

Cited by 19 publications

References 14 publications

The effect of ethanol on cell properties and steroid 1‐en‐dehydrogenation biotransformation of Arthrobacter simplex

The effect of ethanol on cell properties and steroid 1‐en‐dehydrogenation biotransformation of Arthrobacter simplex

Biotransformations of Steroids

Recent Developments in our Knowledge of Steroids1

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Recent Developments in our Knowledge of Steroids¹