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Isaria fumosorosea KCh J2 Entomopathogenic Strain as an Effective Biocatalyst for Steroid Compound Transformations.

ABSTRACT: The catalytic activity of enzymes produced by an entomopathogenic filamentous fungus (Isaria fumosorosea KCh J2) towards selected steroid compounds (androstenedione, adrenosterone, progesterone, 17?-methyltestosterone and dehydroepiandrosterone) was investigated. All tested substrates were efficiently transformed. The structure of the substrate has a crucial impact on regio- and stereoselectivity of hydroxylation since it affects binding to the active site of the enzyme. Androstenedione was hydroxylated in the 7?-position to give a key intermediate in the synthesis of the diuretic-7?-hydroxyandrost-4-ene-3,17-dione with 82% conversion. Adrenosterone and 17?-methyltestosterone were hydroxylated in the 6?-position. Hydroxylated derivatives such as 15?-hydroxy-17?-methyltestosterone and 6?,12?-dihydroxy-17?-methyltestosterone were also observed. In the culture of Isaria fumosorosea KCh J2, DHEA was effectively hydroxylated in the C-7 position and then oxidized to give 7-oxo-DHEA, 3?,7?- and 3?,7?-dihydroxy-17a-oxa-d-homo-androst-5-ene-17-one. We obtained 7?-OH-DHEA lactone with 82% yield during 3 days transformation of highly concentrated (5 g/L) DHEA.

SUBMITTER: Kozlowska E

PROVIDER: S-EPMC6151793 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2.

Project description:Estrone, estradiol, ethynylestradiol and estrone 3-methyl ether underwent a biotransformation process in the submerged culture of Isaria fumosorosea KCh J2. Estrone was transformed into seven metabolites, four of which were glycosylated. Estradiol was selectively glycosylated at C-3 and then transformed to D-ring lactone. Ethynylestradiol was coupled with methylglucoside and 6β-hydroxyderivative was obtained. Estrone 3-methyl ether was not transformed indicating that a free hydroxyl group at C-3 is necessary for glycosylation. Baeyer-Villiger oxidation combined with hydroxylation and glycosylation was observed. All glycosides obtained in this study are 3-O-β-methylglucosides.

| S-EPMC6656742 | biostudies-literature

Glycosylation of 6-methylflavone by the strain Isaria fumosorosea KCH J2.

Project description:Entomopathogenic fungi are known for their ability to carry out glycosylation of flavonoids, which usually results in the improvement of their stability and bioavailability. In this study we used a newly isolated strain of the entomopathogenic filamentous fungus Isaria fumosorosea KCH J2 as a biocatalyst. Our aim was to evaluate its ability to carry out the biotransformation of flavonoids and to obtain new flavonoid derivatives. The fungus was isolated from a spider's carcass and molecularly identified using analysis of the ITS1-ITS2 rDNA sequence. As a result of biotransformation of 6-methylflavone two new products were obtained: 6-methylflavone 8-O-β-D-(4"-O-methyl)-glucopyranoside and 6-methylflavone 4'-O-β-D-(4"-O-methyl)-glucopyranoside. Chemical structures of the products were determined based on spectroscopic methods (1H NMR, 13C NMR, COSY, HMBC, HSQC). Our research allowed us to discover a new species of filamentous fungus capable of carrying out glycosylation reactions and proved that I. fumosorosea KCH J2 is an effective biocatalyst for glycosylation of flavonoid compounds. For the first time we describe biotransformations of 6-methylflavone and the attachment of the sugar unit to the flavonoid substrate having no hydroxyl group. The possibility of using flavonoid aglycones is often limited by their low bioavailability due to poor solubility in water. The incorporation of a sugar unit improves the physical properties of tested compounds and thus increases the chance of using them as pharmaceuticals.

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Glycosylation of Methoxylated Flavonoids in the Cultures of Isaria fumosorosea KCH J2.

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Hydroxylation of Progesterone and Its Derivatives by the Entomopathogenic Strain <i>Isaria farinosa</i> KCh KW1.1.

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Adipokinetic Hormones Enhance the Efficacy of the Entomopathogenic Fungus Isaria fumosorosea in Model and Pest Insects.

Project description:Insect adipokinetic hormones (AKHs) are neuropeptides with a wide range of actions, including the control of insect energy metabolism. These hormones are also known to be involved in the insect defence system against toxins and pathogens. In this study, our aim was to demonstrate whether the application of external AKHs significantly enhances the efficacy of the entomopathogenic fungus Isaria fumosorosea in a model species (firebug Pyrrhocoris apterus) and pest species (Egyptian cotton leafworm Spodoptera littoralis and pea aphid Acyrthosiphon pisum). It was found that the co-application of Isaria with AKHs significantly enhanced insect mortality in comparison to the application of Isaria alone. The mode of action probably involves an increase in metabolism that is caused by AKHs (evidenced by the production of carbon dioxide), which accelerates the turnover of Isaria toxins produced into the infected insects. However, several species-specific differences probably exist. Intoxication by Isaria elicited the stimulation of Akh gene expression and synthesis of AKHs. Therefore, all interactions between Isaria and AKH actions as well as their impact on insect physiology from a theoretical and practical point of view need to be discussed further.

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PTP1B Inhibitors from the Entomogenous Fungi Isaria fumosorosea.

Project description:Protein tyrosine phosphatase 1B (PTP1B) is implicated as a negative regulator of insulin receptor (IR) signaling and a potential drug target for the treatment of type II diabetes and other associated metabolic syndromes. Thus, small molecule inhibitors of PTP1B can be considered as an attractive approach for the design of new therapeutic agents of type II diabetes and cancer diseases. In a continuing search for new PTP1B inhibitors, a new tetramic acid possessing a rare pyrrolidinedione skeleton named fumosorinone A (1), together with five known ones 2-6 were isolated from the entomogenous fungus Isaria fumosorosea. The structures of 2-6 were elucidated by extensive spectroscopic analysis. Fumosorinone A (1) and beauvericin (6) showed significant PTP1B inhibitory activity with IC50 value of 3.24 ?M and 0.59 ?M.

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Microbial Transformation of Flavonoids by Isaria fumosorosea ACCC 37814.

Project description:Glycosylation is an efficient strategy to modulate the solubility, stability, bioavailability and bioactivity of drug-like natural products. Biological methods, such as whole-cell biocatalyst, promise a simple but highly effective approach to glycosylate biologically active small molecules with remarkable regio- and stereo-selectivity. Herein, we use the entomopathogenic filamentous fungus Isaria fumosorosea ACCC 37814 to biotransform a panel of phenolic natural products, including flavonoids and anthraquinone, into their glycosides. Six new flavonoid (4-O-methyl)glucopyranosides are obtained and structurally characterized using high resolution mass and nuclear magnetic resonance spectroscopic techniques. These compounds further expand the structural diversity of flavonoid glycosides and may be used in biological study.

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The Entomopathogenic Fungi Isaria fumosorosea Plays a Vital Role in Suppressing the Immune System of Plutella xylostella: RNA-Seq and DGE Analysis of Immunity-Related Genes.

Project description:Most, if not all, entomopathogenic fungi have been used as alternative control agents to decrease the insect resistance and harmful effects of the insecticides on the environment. Among them, Isaria fumosorosea has also shown great potential to control different insect pests. In the present study, we explored the immune response of P. xylostella to the infection of I. fumosorosea at different time points by using RNA-Sequencing and differential gene expression technology at the genomic level. To gain insight into the host-pathogen interaction at the genomic level, five libraries of P. xylostella larvae at 12, 18, 24, and 36 h post-infection and a control were constructed. In total, 161 immunity-related genes were identified and grouped into four categories; immune recognition families, toll and Imd pathway, melanization, and antimicrobial peptides (AMPs). The results of differentially expressed immunity-related genes depicted that 15, 13, 53, and 14 up-regulated and 38, 51, 56, and 49 were down-regulated in P. xylostella at 12, 18, 24, and 36 h post-treatment, respectively. RNA-Seq results of immunity-related genes revealed that the expression of AMPs was reduced after treatment with I. fumosorosea. To validate RNA-Seq results by RT-qPCR, 22 immunity-related genes were randomly selected. In conclusion, our results demonstrate that I. fumosorosea has the potential to suppress the immune response of P. xylostella and can become a potential biopesticide for controlling P. xylostella.

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Cloning and expression analysis of the chitinase gene Ifu-chit2 from Isaria fumosorosea.

Project description:Entomopathogenic fungi can produce a series of chitinases, some of which function synergistically with proteases and other hydrolytic enzymes to degrade the insect cuticle. In the present study, the chitinase gene Ifu-chit2 from Isaria fumosorosea was investigated. The Ifu-chit2 gene is 1,435-bp long, interrupted by three short introns, and encodes a predicted protein of 423 amino acids with a 22 residue signal peptide. The predicted Ifu-Chit2 protein is highly homologous to Beauveria bassiana chitinase Bbchit2 and belongs to the glycohydrolase family 18. Ifu-Chit2 was expressed in Escherichia coli to verify chitinase activity, and the recombinant enzyme exhibited activity with a colloidal chitin substrate. Furthermore, the expression profiles of Ifu-chit2 were analyzed at different induction times under in vivo conditions. Quantitative real-time PCR analysis revealed that Ifu-chit2 expression peaked at two days post-induction. The expression of chitinase Ifu-chit2 in vivo suggests that the chitinase may play a role in the early stage of pathogenesis.

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Lack of resistance development in Bemisia tabaci to Isaria fumosorosea after multiple generations of selection.

Project description:The emergence of insecticide resistant insect pests is of significant concern worldwide. The whitefly, Bemisia tabaci, is an important agricultural pest and has shown incredible resilience developing resistance to a number of chemical pesticides. Entomopathogenic fungi such as Isaria fumosorosea offer an attractive alternative to chemical pesticides for insect control, and this fungus has been shown to be an effective pathogen of B. tabaci. Little is known concerning the potential for the development of resistance to I. fumosorosea by B. tabaci. Five generations of successive survivors of B. tabaci infected by I. fumosorosea were assayed with I. fumosorosea. No significant differences in susceptibility to I. fumosorosea, number of ovarioles, or ovipostioning were seen between any of the generations tested. Effects of I. fumosorosea and cell-free ethyl acetate fractions derived from the fungus on the B. tabaci fat body, ovary, and vitellogenin were also investigated. These data revealed significant deformation and degradation of ovary tissues and associated vitellogenin by the fungal mycelium as well as by cell-free ethyl acetate fungal extracts. These data indicate the lack of the emergence of resistance to I. fumosorosea under the conditions tested and demonstrate invasion of the insect reproductive tissues during fungal infection.

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