Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi

Łużny, Mateusz; Tronina, Tomasz; Kozłowska, Ewa; Dymarska, Monika; Popłoński, Jarosław; Łyczko, Jacek; Kostrzewa-Susłow, Edyta; Janeczko, Tomasz

doi:10.3390/ijms21176121

Cited by 18 publications

(26 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The main aim of our study was to investigate the ability of entomopathogenic filamentous fungi B. bassiana KCH J1.5 and I. fumosorosea KCH J2 to glycosylate two flavonoid compounds, i.e., 2 -methylflavanone and 2 -methylflavone. Both strains of microorganisms had been effective in glycosylation described in our previous studies [19,21,27,28]. The first step of our study was a two-step synthesis of substrates for further biotransformation (Scheme 1) (Section 4.1.…”

Section: Resultsmentioning

confidence: 99%

“…Attempts to biotransform flavones in cultures of entomopathogenic filamentous fungi have been made in many previous studies resulting in 4 -O-methylglucosides attached at almost all possible positions: C-3, C-6, C-7, C-8, C-2 , C-3 , C-4 , and C-5 [16,17,19,20,22,28,31]. In the presented study, in the culture of I. fumosorosea KCH J2, we also obtained glycosylated derivatives of 2 -methylflavone with the 4 -O-methyl-glucosyl moiety at C-3 , C-4 , and C-5 .…”

Section: Discussionmentioning

confidence: 99%

“…Molecular formulas of all products were confirmed by analysis performed on the LC-MS 8045 SHIMADZU Triple Quadrupole Liquid Chromatograph Mass Spectrometer with electrospray ionization (ESI) source (Shimadzu, Kyoto, Japan), as described previously with minor modifications [28]. Analyses were conducted using method "MRM event from precursor ion search".…”

Section: Discussionmentioning

confidence: 99%

See 2 more Smart Citations

Fungal Biotransformation of 2′-Methylflavanone and 2′-Methylflavone as a Method to Obtain Glycosylated Derivatives

Krawczyk-Łebek

Dymarska

Janeczko

et al. 2021

IJMS

Self Cite

View full text Add to dashboard Cite

Methylated flavonoids are promising pharmaceutical agents due to their improved metabolic stability and increased activity compared to unmethylated forms. The biotransformation in cultures of entomopathogenic filamentous fungi is a valuable method to obtain glycosylated flavones and flavanones with increased aqueous solubility and bioavailability. In the present study, we combined chemical synthesis and biotransformation to obtain methylated and glycosylated flavonoid derivatives. In the first step, we synthesized 2′-methylflavanone and 2′-methylflavone. Afterwards, both compounds were biotransformed in the cultures of two strains of entomopathogenic filamentous fungi Beauveria bassiana KCH J1.5 and Isaria fumosorosea KCH J2. We determined the structures of biotransformation products based on NMR spectroscopy. Biotransformations of 2′-methyflavanone in the culture of B. bassiana KCH J1.5 resulted in three glycosylated flavanones: 2′-methylflavanone 6-O-β-d-(4″-O-methyl)-glucopyranoside, 3′-hydroxy-2′-methylflavanone 6-O-β-d-(4″-O-methyl)-glucopyranoside, and 2-(2′-methylphenyl)-chromane 4-O-β-d-(4″-O-methyl)-glucopyranoside, whereas in the culture of I. fumosorosea KCH J2, two other products were obtained: 2′-methylflavanone 3′-O-β-d-(4″-O-methyl)-glucopyranoside and 2-methylbenzoic acid 4-O-β-d-(4′-O-methyl)-glucopyranoside. 2′-Methylflavone was effectively biotransformed only by I. fumosorosea KCH J2 into three derivatives: 2′-methylflavone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, 2′-methylflavone 4′-O-β-d-(4″-O-methyl)-glucopyranoside, and 2′-methylflavone 5′-O-β-d-(4″-O-methyl)-glucopyranoside. All obtained glycosylated flavonoids have not been described in the literature until now and need further research on their biological activity and pharmacological efficacy as potential drugs.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Fungal Biotransformation of 2′-Methylflavanone and 2′-Methylflavone as a Method to Obtain Glycosylated Derivatives

Krawczyk-Łebek

Dymarska

Janeczko

et al. 2021

IJMS

Self Cite

View full text Add to dashboard Cite

show abstract

“…The application of microorganisms and enzymes as biocatalysts allows to obtain these compounds in sufficient amounts for research such as the Structure-Activity Relationship (SAR). Transformation of flavonoids by microorganisms is often connected with the second phase of metabolism, i.e., conjugation, with polar compounds such as sugars or sulfates [29][30][31][32][33][34][35][36][37][38][39][40]. The resulting glycosides exhibit significantly higher water solubility, stability and bioavailability.…”

Section: Biotransformationmentioning

confidence: 99%

Simple and Rapid Method for Wogonin Preparation and Its Biotransformation

Tronina

Mrozowska

Bartmańska

et al. 2021

IJMS

Self Cite

View full text Add to dashboard Cite

Wogonin is one of the most active flavonoids from Scutellaria baicalensis Georgi (baikal skullcap), widely used in traditional Chinese medicine. It exhibits a broad spectrum of health-promoting and therapeutic activities. Together with baicalein, it is considered to be the one of main active ingredients of Chinese medicines for the management of COVID-19. However, therapeutic use of wogonin may be limited due to low market availability connected with its low content in baikal skullcap and lack of efficient preparative methods for obtaining this compound. Although the amount of wogonin in skullcap root often does not exceed 0.5%, this material is rich in wogonin glucuronide, which may be used as a substrate for wogonin production. In the present study, a rapid, simple, cheap and effective method of wogonin and baicalein preparation, which provides gram quantities of both flavonoids, is proposed. The obtained wogonin was used as a substrate for biotransformation. Thirty-six microorganisms were tested in screening studies. The most efficient were used in enlarged scale transformations to determine metabolism of this xenobiotic. The major phase I metabolism product was 4′-hydroxywogonin—a rare flavonoid which exhibits anticancer activity—whereas phase II metabolism products were glucosides of wogonin. The present studies complement and extend the knowledge on the effect of substitution of A- and B-ring on the regioselective glycosylation of flavonoids catalyzed by microorganisms.

show abstract

“…There are many reports in the literature on microbial transformations of flavonoid compounds. For several years, our team has been utilizing entomopathogenic filamentous fungi as biocatalysts [18][19][20][21][22][23]. Using these microorganisms, we mainly observe the attachment of the 4-O-methylglucopyranose molecule to the flavonoid aglycon.…”

Section: Introductionmentioning

confidence: 99%

The Callus of Phaseolus coccineus and Glycine max Biotransform Flavanones into the Corresponding Flavones

2020

Self Cite

View full text Add to dashboard Cite

In vitro plant cultures are gaining in industrial importance, especially as biocatalysts and as sources of secondary metabolites used in pharmacy. The idea that guided us in our research was to evaluate the biocatalytic potential of newly obtained callus tissue towards flavonoid compounds. In this publication, we describe new ways of using callus cultures in the biotransformations. In the first method, the callus cultures grown on a solid medium are transferred to the water, the reaction medium into which the substrate is introduced. In the second method, biotransformation is carried out on a solid medium by growing callus cultures. In the course of the research, we have shown that the callus obtained from Phaseolus coccineus and Glycine max is capable of converting flavanone, 5-methoxyflavanone and 6-methoxyflavanone into the corresponding flavones.

show abstract

Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi

Cited by 18 publications

References 40 publications

Fungal Biotransformation of 2′-Methylflavanone and 2′-Methylflavone as a Method to Obtain Glycosylated Derivatives

Fungal Biotransformation of 2′-Methylflavanone and 2′-Methylflavone as a Method to Obtain Glycosylated Derivatives

Simple and Rapid Method for Wogonin Preparation and Its Biotransformation

The Callus of Phaseolus coccineus and Glycine max Biotransform Flavanones into the Corresponding Flavones

Contact Info

Product

Resources

About