Entomopathogenic Filamentous Fungi as Biocatalysts in Glycosylation of Methylflavonoids

Abstract

Flavonoids are known for their numerous biological activities; however, their pharmacological application is limited by poor bioavailability. Glycosides are usually more stable and more soluble in water and in this form, flavonoids are present in nature. Likewise, the presence of the methyl group in the flavonoid skeleton results in facilitated absorption and greater bioavailability. Entomopathogenic filamentous fungi are effective in the biotransformation of flavonoids; they are known especially for efficient glycosylation. In the current study we used strains of Beauveria bassiana KCH J1.5 and Isaria fumosorosea KCH J2 to biotransform flavonoids with a single methyl group. 2′-Hydroxy-5′-methylchalcone was biotransformed by both strains into 2′-hydroxy-5′-methylchalcone 3-O-β-D-(4″-O-methyl)-glucopyranoside. In the culture of B. bassiana KCH J1.5 four products were obtained from 6-methylflavanone: 4′-hydroxy-6-methylflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside; 4′-hydroxyflavanone 6-methylene-O-β-D-(4″-O-methyl)-glucopyranoside; 6-hydroxymethylflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside and 4′-hydroxy-6-hydroxymethylflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside. Biotransformation with I. fumosorosea KCH J2 as a biocatalyst resulted in the formation of 6-methylflavanone 4′-O-β-D-(4″-O-methyl)-glucopyranoside and 2-phenyl-6-methylchromane 4-O-β-D-(4″-O-methyl)-glucopyranoside. All of these flavonoids can be used in biological activity tests and can be useful in studies concerning structure—bioactivity relationships.

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

“…The presented results continue our previous research on C-methylated flavonoids [19,21]. In this study, we synthesized 2 -methylflavanone and 2 -methylflavone, and then biotransformed them in the cultures of entomopathogenic filamentous fungi strains of B. bassiana KCH J1.5 and I. fumosorosea KCH J2.…”

“…Chemical glycosylation of flavonoids leads to low isolated yields caused by the need for drastic reaction conditions resulting in the decomposition of reaction substrate and laborious procedures required to achieve regio-and stereoselectivity [3,16,17]. However, biotransformation with entomopathogenic filamentous fungi as biocatalysts can be applied to efficient production of flavonoid's glycosides [16][17][18][19][20][21][22][23][24][25].…”

Interaction of 4′-methylflavonoids with biological membranes, liposomes, and human albumin

“…The first step was Claisen-Schmidt condensation between 2 ′ -hydroxyacetophenone ( 1 ) and 4-methylbenzaldehyde ( 2 ). The chemical reagents were dissolved in methanol, and the reaction was carried out under alkaline conditions at high temperature 16 – 18 . 2 ′ -Hydroxy-4-methylchalcone ( 3 ) was obtained with 65.5% yield.…”

“…The flow rate was 1 mL/min, the injection volume was 5 µL, and detection wavelength 280 nm. Details have been described in our earlier work 18 .…”

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

“…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.…”