Glycosylation of Methylflavonoids in the Cultures of Entomopathogenic Filamentous Fungi as a Tool for Obtaining New Biologically Active Compounds

Krawczyk-Łebek, Agnieszka; Dymarska, Monika; Janeczko, Tomasz; Kostrzewa-Susłow, Edyta

doi:10.3390/ijms23105558

Cited by 16 publications

(9 citation statements)

References 71 publications

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“…The Isaria fumosorosea KCH J2 strain has already been described in our previous papers as an effective biocatalyst of flavanones and flavones, including quercetin [2,50,[52][53][54]. Based on the results previously described for this strain, we noticed the similarity with Beauveria bassiana strains in the transformation of flavonoid compounds.…”

Section: Resultssupporting

confidence: 61%

“…Based on the previously described results regarding the biotransformations of flavonoid compounds in entomopathogenic strains, especially quercetin biotransformation conducted by those micro-organisms, we decided to use five strains of the Beauveria bassiana species, two of the Beauveria caledonica species and the Isaria farinosa KCh KW1.1 as biocatalysts. Among entomopathogenic filamentous fungi, B. bassiana strains are most commonly used in biotransformation (including flavonoid compounds) [47][48][49][50]. Our previous publications described differences in the biotransformation of methoxyflavones and dehydroepiandrosterone (DHEA) in the cultures of various strains belonging to this species [51,52].…”

Section: Resultsmentioning

confidence: 99%

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Glycosylation of Quercetin by Selected Entomopathogenic Filamentous Fungi and Prediction of Its Products’ Bioactivity

Tronina

Łużny

Dymarska

et al. 2023

IJMS

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Quercetin is the most abundant flavonoid in food products, including berries, apples, cauliflower, tea, cabbage, nuts, onions, red wine and fruit juices. It exhibits various biological activities and is used for medical applications, such as treating allergic, inflammatory and metabolic disorders, ophthalmic and cardiovascular diseases, and arthritis. However, its low water solubility may limit quercetin’s therapeutic potential. One method of increasing the solubility of active compounds is their coupling to polar molecules, such as sugars. The attachment of a glucose unit impacts the stability and solubility of flavonoids and often determines their bioavailability and bioactivity. Entomopathogenic fungi are biocatalysts well known for their ability to attach glucose and its 4-O-methyl derivative to bioactive compounds, including flavonoids. We investigated the ability of cultures of entomopathogenic fungi belonging to Beauveria, Isaria, Metapochonia, Lecanicillium and Metarhizium genera to biotransform quercetin. Three major glycosylation products were detected: (1), 7-O-β-D-(4″-O-methylglucopyranosyl)-quercetin, (2) 3-O-β-D-(4″-O-methylglucopyranosyl)-quercetin and (3) 3-O-β-D-(glucopyranosyl)-quercetin. The results show evident variability of the biotransformation process, both between strains of the tested biocatalysts from different species and between strains of the same species. Pharmacokinetic and pharmacodynamic properties of the obtained compounds were predicted with the use of cheminformatics tools. The study showed that the obtained compounds may have applications as effective modulators of intestinal flora and may be stronger hepato-, cardio- and vasoprotectants and free radical scavengers than quercetin.

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Section: Resultssupporting

confidence: 61%

Section: Resultsmentioning

confidence: 99%

Glycosylation of Quercetin by Selected Entomopathogenic Filamentous Fungi and Prediction of Its Products’ Bioactivity

Tronina

Łużny

Dymarska

et al. 2023

IJMS

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“…Comparing it with the microbial transformation process, it is much simpler and does not require multi-stage reactions and toxic reaction catalysts [17][18][19][20][21]. Filamentous fungi carry out the biotransformation process of polyphenolic compounds very efficiently [18,22,23]. Moreover, the glycosidic molecule improves the solubility and bioavailability of flavonoids and makes them more attractive to use in the pharmacological industry [14,21,24].…”

Section: Introductionmentioning

confidence: 99%

“…Krawczyk-Łebek and coworkers have shown the glycosylation ability of entomopathogenic filamentous fungi. 4 -Methylflavone was transformed via Isaria fumosorosea KCH J2 into four products: 4 -hydroxymethylflavone, flavone 4 -methylene-O-β-D-(4"-O-methyl)-glucopyranoside, flavone 4 -carboxylic acid, and 4 -methylflavone 3-O-β-D-(4"-O-methyl)-glucopyranoside [22]. Moreover, the same strain was able to transform 6-methylfavone into 6-methylflavone 8-O-β-D-(4"-O-methyl)-glucopyranoside and 6-methylflavone 4 -O-β-D-(4"-O-methyl)-glucopyranoside [23].…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of Flavonoids with -NO2, -CH3 Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous Fungi

Perz,

Krawczyk-Łebek,

Dymarska

et al. 2023

IJMS

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Combining chemical and microbiological methods using entomopathogenic filamentous fungi makes obtaining flavonoid glycosides possible. In the presented study, biotransformations were carried out in cultures of Beauveria bassiana KCH J1.5, Isaria fumosorosea KCH J2, and Isaria farinosa KCH J2.6 strains on six flavonoid compounds obtained in chemical synthesis. As a result of the biotransformation of 6-methyl-8-nitroflavanone using the strain I. fumosorosea KCH J2, two products were obtained: 6-methyl-8-nitro-2-phenylchromane 4-O-β-D-(4″-O-methyl)-glucopyranoside and 8-nitroflavan-4-ol 6-methylene-O-β-D-(4″-O-methyl)-glucopyranoside. 8-Bromo-6-chloroflavanone was transformed by this strain to 8-bromo-6-chloroflavan-4-ol 4′-O-β-D-(4″-O-methyl)-glucopyranoside. As a result of microbial transformation by I. farinosa KCH J2.6 effectively biotransformed only 8-bromo-6-chloroflavone into 8-bromo-6-chloroflavone 4′-O-β-D-(4″-O-methyl)-glucopyranoside. B. bassiana KCH J1.5 was able to transform 6-methyl-8-nitroflavone to 6-methyl-8-nitroflavone 4′-O-β-D-(4″-O-methyl)-glucopyranoside, and 3′-bromo-5′-chloro-2′-hydroxychalcone to 8-bromo-6-chloroflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside. None of the filamentous fungi used transformed 2′-hydroxy-5′-methyl-3′-nitrochalcone effectively. Obtained flavonoid derivatives could be used to fight against antibiotic-resistant bacteria. To the best of our knowledge, all the substrates and products presented in this work are new compounds and are described for the first time.

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“…Depending on the substrate structure and the biocatalyst used, chalcones may give products from the reduction of the double bond, cyclisation, hydroxylation, O-demethylation and glycosidation [9][10][11][12][13][14]. The reduction of the carbonyl group present in the dihydrochalcones leading to the formation of the corresponding alcohol is also described [15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Regiospecific Hydrogenation of Bromochalcone by Unconventional Yeast Strains

et al. 2022

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This research aimed to select yeast strains capable of the biotransformation of selected 2′-hydroxybromochalcones. Small-scale biotransformations were carried out using four substrates obtained by chemical synthesis (2′-hydroxy-2″-bromochalcone, 2′-hydroxy-3″-bromochalcone, 2′-hydroxy-4″-bromochalcone and 2′-hydroxy-5′-bromochalcone) and eight strains of non-conventional yeasts. Screening allowed for the determination of the substrate specificity of selected microorganisms and the selection of biocatalysts that carried out the hydrogenation of tested compounds in the most effective way. It was found that the position of the bromine atom has a crucial influence on the degree of substrate conversion by the tested yeast strains. As a result of the biotransformation of the 2′-hydroxybromochalcones, the corresponding 2′-hydroxybromodihydrochalcones were obtained. The products obtained belong to the group of compounds with high potential as precursors of sweet substances.

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Glycosylation of Methylflavonoids in the Cultures of Entomopathogenic Filamentous Fungi as a Tool for Obtaining New Biologically Active Compounds

Cited by 16 publications

References 71 publications

Glycosylation of Quercetin by Selected Entomopathogenic Filamentous Fungi and Prediction of Its Products’ Bioactivity

Glycosylation of Quercetin by Selected Entomopathogenic Filamentous Fungi and Prediction of Its Products’ Bioactivity

Biotransformation of Flavonoids with -NO2, -CH3 Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous Fungi

Regiospecific Hydrogenation of Bromochalcone by Unconventional Yeast Strains

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