Enhancement of microbial hydroxylation of 13-ethyl-gon-4-ene-3,17-dione by <i>Metarhizium anisopliae</i> using nano-liposome technique

Feng, Meiqing; Liao, Ziwei; Lei, Han; Li, Jiyang; Li, Ye

doi:10.1007/s10295-014-1414-7

Cited by 5 publications

(3 citation statements)

References 28 publications

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“…The main reaction product 11a-hydroxy-13ethyl-gon-4-ene-3,17-dione (HGD) was also produced at high concentration of GD as 6 g L -1 with no reduction of transformation efficiency. The main byproduct of the reaction 6b,11a-dihydroxy derivative was found to benefit the purification of HGD (Feng et al 2014).…”

Section: Steroid Biotransformationmentioning

confidence: 99%

Entomopathogenic fungi: unconventional applications

Litwin

Nowak

Różalska

2020

Rev Environ Sci Biotechnol

159

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Entomopathogenic fungi (EPF) are microorganisms that cause fatal diseases of arthropods. The infection process involves several stages that consist of direct contact of the fungus with the surface of the cuticle of the attacked insect. The factors that determine the effectiveness of the infection process include lytic enzymes, secondary metabolites, and adhesins produced by EPF. Because of their high insecticidal effectiveness, these fungi are commonly used as biopesticides in organic farming. As the environment and farmlands are contaminated with many compounds of anthropogenic origin (e.g., pesticides), the effects of these toxic compounds on EPF and the mechanisms that affect their survival in such a toxic environment have been studied in recent years. This review presents information on the capacity of EPF to remove toxic contaminants, including alkylphenols, organotin compounds, synthetic estrogens, pesticides and hydrocarbons. Moreover, these fungi produce numerous secondary metabolites that can be potentially used in medicine or as antimicrobial agents. Despite their huge potential in biocontrol processes, the use of EPF has been underestimated due to a lack of knowledge on their abilities. In our work, we have presented the available data on the possibilities of the additional and unconventional use of these microorganisms.

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Section: Steroid Biotransformationmentioning

confidence: 99%

Entomopathogenic fungi: unconventional applications

Litwin

Nowak

Różalska

2020

Rev Environ Sci Biotechnol

159

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“…Hydroxylations at the C-7α and C-11α position and Baeyer–Villiger oxidation to d -homo lactones are described in the literature [ 18 – 24 ]. Also Metarhizium anisopliae have ability of hydroxylation at 6β and 11α position [ 25 ]. The catalytic activity of Isaria fumosorosea towards selected steroid compounds with high substrate specificity was described [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of steroids by entomopathogenic strains of Isaria farinosa

et al. 2018

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BackgroundSteroid 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.ResultsTwelve 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.ConclusionsIsaria 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.

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“…We also decided to use the Beauveria bassiana KCh J1.5 strain, which is a representative of the species of entomopathogenic filamentous fungi most often used for the biotransformation of steroid compounds [ 36 , 37 , 38 , 39 ] and the Beauveria caledonica KCh J3.3 strain belonging to the same genus [ 36 ]. Two strains of species with relatively little known catalytic abilities were also used as biocatalysts: Metarhizium anisopliae , capable of hydroxylating 13-ethyl-gon-4-ene-3,17-dione [ 40 ], and Isaria tenuipes , known as the zearalenone biocatalyst [ 41 ].…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of Δ1-Progesterone Using Selected Entomopathogenic Filamentous Fungi and Prediction of Its Products’ Bioactivity

Panek,

Wójcik,

Świzdor

et al. 2023

IJMS

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This research aimed at obtaining new derivatives of pregn-1,4-diene-3,20-dione (Δ1-progesterone) (2) through microbiological transformation. For the role of catalysts, we used six strains of entomopathogenic filamentous fungi (Beauveria bassiana KCh J1.5, Beauveria caledonica KCh J3.3, Isaria fumosorosea KCh J2, Isaria farinosa KCh KW1.1, Isaria tenuipes MU35, and Metarhizium robertsii MU4). The substrate (2) was obtained by carrying out an enzymatic 1,2-dehydrogenation on an increased scale (3.5 g/L) using a recombinant cholest-4-en-3-one Δ1-dehydrogenase (AcmB) from Sterolibacterium denitrificans. All selected strains were characterized by the high biotransformation capacity for the used substrate. As a result of the biotransformation, six steroid derivatives were obtained: 11α-hydroxypregn-1,4-diene-3,20-dione (3), 6β,11α-dihydroxypregn-1,4-diene-3,20-dione (4), 6β-hydroxypregn-1,4-diene-3,11,20-trione (5), 6β,17α-dihydroxypregn-1,4-diene-3,20-dione (6), 6β,17β-dihydroxyandrost-1,4-diene-3-one (7), and 12β,17α-dihydroxypregn-1,4-diene-3,20-dione (8). The results show evident variability of the biotransformation process between strains of the tested biocatalysts from different species described as entomopathogenic filamentous fungi. The obtained products were tested in silico using cheminformatics tools for their pharmacokinetic and pharmacodynamic properties, proving their potentially high biological activities. This study showed that the obtained compounds may have applications as effective inhibitors of testosterone 17β-dehydrogenase. Most of the obtained products should, also with a high probability, find potential uses as androgen antagonists, a prostate as well as menopausal disorders treatment. They should also demonstrate immunosuppressive, erythropoiesis-stimulating, and anti-inflammatory properties.

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Enhancement of microbial hydroxylation of 13-ethyl-gon-4-ene-3,17-dione by Metarhizium anisopliae using nano-liposome technique

Cited by 5 publications

References 28 publications

Entomopathogenic fungi: unconventional applications

Entomopathogenic fungi: unconventional applications

Biotransformation of steroids by entomopathogenic strains of Isaria farinosa

Biotransformation of Δ1-Progesterone Using Selected Entomopathogenic Filamentous Fungi and Prediction of Its Products’ Bioactivity

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