Biotransformation of steroids by entomopathogenic strains of Isaria farinosa
Abstract Background Steroid compounds are very interesting substrates for biotransformation due to their high biological activity and a high number of inactivated carbons which make chemical modification difficult. Microbial transformation can involve reactions which are complicated and uneconomical...
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BioMed Central
2018-05-01
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| Series: | Microbial Cell Factories |
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| Online Access: | http://link.springer.com/article/10.1186/s12934-018-0920-0 |
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doaj-art-fbb3cf205768412ea5cf7b84f53bd09f2018-08-20T08:42:08ZengBioMed CentralMicrobial Cell Factories1475-28592018-05-0117111110.1186/s12934-018-0920-0Biotransformation of steroids by entomopathogenic strains of Isaria farinosaEwa Kozłowska0Natalia Hoc1Jordan Sycz2Monika Urbaniak3Monika Dymarska4Jakub Grzeszczuk5Edyta Kostrzewa-Susłow6Łukasz Stępień7Elżbieta Pląskowska8Tomasz Janeczko9Department of Chemistry, Wrocław University of Environmental and Life SciencesDepartment of Chemistry, Wrocław University of Environmental and Life SciencesDepartment of Chemistry, Wrocław University of Environmental and Life SciencesDepartment of Pathogen Genetics and Plant Resistance, Institute of Plant Genetics, Polish Academy of SciencesDepartment of Chemistry, Wrocław University of Environmental and Life SciencesDepartment of Plant Protection, Plant Pathology and Mycology Division, Wrocław University of Environmental and Life SciencesDepartment of Chemistry, Wrocław University of Environmental and Life SciencesDepartment of Pathogen Genetics and Plant Resistance, Institute of Plant Genetics, Polish Academy of SciencesDepartment of Plant Protection, Plant Pathology and Mycology Division, Wrocław University of Environmental and Life SciencesDepartment of Chemistry, Wrocław University of Environmental and Life SciencesAbstract Background Steroid compounds are very interesting substrates for biotransformation due to their high biological activity and a high number of inactivated carbons which make chemical modification difficult. Microbial transformation can involve reactions which are complicated and uneconomical in chemical synthesis, and searching for a new effective biocatalyst is necessary. The best known entomopathogenic species used in steroid modification is Beauveria bassiana. In this study we tested the ability of Isaria farinosa, another entomopathogenic species, to transform several steroids. Results Twelve strains of the entomopathogenic filamentous fungus Isaria farinosa, collected in abandoned mines located in the area of the Lower Silesian Voivodeship, Poland, from insects’ bodies covered by fungus, were used as a biocatalyst. All the tested strains effectively transformed dehydroepiandrosterone (DHEA). We observed 7α- and 7β-hydroxy derivatives as well as changes in the percentage composition of the emerging products. Due to the similar metabolism of DHEA in all tested strains, one of them was selected for further investigation. In the culture of the selected strain, Isaria farinosa KCh KW1.1, transformations of androstenediol, androstenedione, adrenosterone, 17α-methyltestosterone, 17β-hydroxyandrost-1,4,6-triene-3-one and progesterone were performed. All the substrates were hydroxylated with high yield and stereoselectivity. We obtained 6β-hydroxyandrost-4-ene-3,11,17-trione, 15α,17β-dihydroxy-6β,7β-epoxyandrost-1,4-diene-3-one and 6β,11α-dihydroxyprogesterone. There is no evidence of either earlier microbial transformation of 17β-hydroxyandrost-1,4,6-triene-3-one or new epoxy derivatives. Conclusions Isaria farinosa has a broad spectrum of highly effective steroid hydroxylases. The obtained 7-hydroxydehydroepiandrosterone has proven high biological activity and can be used in Alzheimer’s disease and as a key intermediate in the synthesis of aldosterone antagonists. Transformation of progesterone leads to high yield of 6β,11α-dihydroxyprogesterone and it is worth further study.http://link.springer.com/article/10.1186/s12934-018-0920-0Isaria farinosaBiotransformationDHEAProgesteroneHydroxylation |
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Article |
| author |
Ewa Kozłowska Natalia Hoc Jordan Sycz Monika Urbaniak Monika Dymarska Jakub Grzeszczuk Edyta Kostrzewa-Susłow Łukasz Stępień Elżbieta Pląskowska Tomasz Janeczko |
| spellingShingle |
Ewa Kozłowska Natalia Hoc Jordan Sycz Monika Urbaniak Monika Dymarska Jakub Grzeszczuk Edyta Kostrzewa-Susłow Łukasz Stępień Elżbieta Pląskowska Tomasz Janeczko Biotransformation of steroids by entomopathogenic strains of Isaria farinosa Microbial Cell Factories Isaria farinosa Biotransformation DHEA Progesterone Hydroxylation |
| author_facet |
Ewa Kozłowska Natalia Hoc Jordan Sycz Monika Urbaniak Monika Dymarska Jakub Grzeszczuk Edyta Kostrzewa-Susłow Łukasz Stępień Elżbieta Pląskowska Tomasz Janeczko |
| author_sort |
Ewa Kozłowska |
| title |
Biotransformation of steroids by entomopathogenic strains of Isaria farinosa |
| title_short |
Biotransformation of steroids by entomopathogenic strains of Isaria farinosa |
| title_full |
Biotransformation of steroids by entomopathogenic strains of Isaria farinosa |
| title_fullStr |
Biotransformation of steroids by entomopathogenic strains of Isaria farinosa |
| title_full_unstemmed |
Biotransformation of steroids by entomopathogenic strains of Isaria farinosa |
| title_sort |
biotransformation of steroids by entomopathogenic strains of isaria farinosa |
| publisher |
BioMed Central |
| series |
Microbial Cell Factories |
| issn |
1475-2859 |
| publishDate |
2018-05-01 |
| description |
Abstract Background Steroid compounds are very interesting substrates for biotransformation due to their high biological activity and a high number of inactivated carbons which make chemical modification difficult. Microbial transformation can involve reactions which are complicated and uneconomical in chemical synthesis, and searching for a new effective biocatalyst is necessary. The best known entomopathogenic species used in steroid modification is Beauveria bassiana. In this study we tested the ability of Isaria farinosa, another entomopathogenic species, to transform several steroids. Results Twelve strains of the entomopathogenic filamentous fungus Isaria farinosa, collected in abandoned mines located in the area of the Lower Silesian Voivodeship, Poland, from insects’ bodies covered by fungus, were used as a biocatalyst. All the tested strains effectively transformed dehydroepiandrosterone (DHEA). We observed 7α- and 7β-hydroxy derivatives as well as changes in the percentage composition of the emerging products. Due to the similar metabolism of DHEA in all tested strains, one of them was selected for further investigation. In the culture of the selected strain, Isaria farinosa KCh KW1.1, transformations of androstenediol, androstenedione, adrenosterone, 17α-methyltestosterone, 17β-hydroxyandrost-1,4,6-triene-3-one and progesterone were performed. All the substrates were hydroxylated with high yield and stereoselectivity. We obtained 6β-hydroxyandrost-4-ene-3,11,17-trione, 15α,17β-dihydroxy-6β,7β-epoxyandrost-1,4-diene-3-one and 6β,11α-dihydroxyprogesterone. There is no evidence of either earlier microbial transformation of 17β-hydroxyandrost-1,4,6-triene-3-one or new epoxy derivatives. Conclusions Isaria farinosa has a broad spectrum of highly effective steroid hydroxylases. The obtained 7-hydroxydehydroepiandrosterone has proven high biological activity and can be used in Alzheimer’s disease and as a key intermediate in the synthesis of aldosterone antagonists. Transformation of progesterone leads to high yield of 6β,11α-dihydroxyprogesterone and it is worth further study. |
| topic |
Isaria farinosa Biotransformation DHEA Progesterone Hydroxylation |
| url |
http://link.springer.com/article/10.1186/s12934-018-0920-0 |
| _version_ |
1612690593179238400 |