First complete NMR data and theoretical study of an antimicrobial formylated dihydrochalcone from <i>Psidium guineense</i> Sw

Lima, Ewerton Matias de; Fernando, Luciana M.; Félix, Leonardo P.; Filho, Abrahão Alves de Oliveira; Neto, Albano N. Carneiro; Moura, Renaldo T.; Teles, Yanna Carolina Ferreira

doi:10.1080/14786419.2020.1771709

Cited by 3 publications

(2 citation statements)

References 24 publications

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“…The latter moderately inhibited the protein tyrosine phosphatase-1B activity, the increased activity of which is related to diseases such as obesity, type 2 diabetes, and carcinoma [ 20 ]. Another dihydrochalcone, 3′-formyl-2′,4′,6′-trihydroxy-5′-methyldihydrochalcone also exhibited antimicrobial and anticancer potential [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

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

Krawczyk-Łebek

Dymarska

Janeczko

et al. 2022

IJMS

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Flavonoid compounds are secondary plant metabolites with numerous biological activities; they naturally occur mainly in the form of glycosides. The glucosyl moiety attached to the flavonoid core makes them more stable and water-soluble. The methyl derivatives of flavonoids also show increased stability and intestinal absorption. Our study showed that such flavonoids can be obtained by combined chemical and biotechnological methods with entomopathogenic filamentous fungi as glycosylation biocatalysts. In the current paper, two flavonoids, i.e., 2′-hydroxy-4-methylchalcone and 4′-methylflavone, have been synthesized and biotransformed in the cultures of two strains of entomopathogenic filamentous fungi Isaria fumosorosea KCH J2 and Beauveria bassiana KCH J1.5. Biotransformation of 2′-hydroxy-4-methylchalcone resulted in the formation of two dihydrochalcone glucopyranoside derivatives in the culture of I. fumosorosea KCH J2 and chalcone glucopyranoside derivative in the case of B. bassiana KCH J1.5. 4′-Methylflavone was transformed in the culture of I. fumosorosea KCH J2 into four products, i.e., 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. 4′-Methylflavone was not efficiently biotransformed in the culture of B. bassiana KCH J1.5. The computer-aided simulations based on the chemical structures of the obtained compounds showed their improved physicochemical properties and antimicrobial, anticarcinogenic, hepatoprotective, and cardioprotective potential.

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Section: Introductionmentioning

confidence: 99%

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

Krawczyk-Łebek

Dymarska

Janeczko

et al. 2022

IJMS

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“…The latter were tested for their in vitro inhibitory activities against protein tyrosine phosphatase-1B, which increased activity is related to obesity, type 2 diabetes and carcinoma [29]. Another compound, 3 -formyl-2 ,4 ,6 -trihydroxy-5 -methyldihydrochalcone, exhibited antimicrobial, and anticancer potential [30].…”

Section: Introductionmentioning

confidence: 99%

New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2′-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi

Krawczyk-Łebek

Dymarska

Janeczko

et al. 2021

IJMS

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Flavonoids, including chalcones, are more stable and bioavailable in the form of glycosylated and methylated derivatives. The combined chemical and biotechnological methods can be applied to obtain such compounds. In the present study, 2′-hydroxy-2-methylchalcone was synthesized and biotransformed in the cultures of entomopathogenic filamentous fungi Beauveria bassiana KCH J1.5, Isaria fumosorosea KCH J2 and Isaria farinosa KCH J2.6, which have been known for their extensive enzymatic system and ability to perform glycosylation of flavonoids. As a result, five new glycosylated dihydrochalcones were obtained. Biotransformation of 2′-hydroxy-2-methylchalcone by B. bassiana KCH J1.5 resulted in four glycosylated dihydrochalcones: 2′-hydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, 2′,3-dihydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, 2′-hydroxy-2-hydroxymethyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, and 2′,4-dihydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside. In the culture of I. fumosorosea KCH J2 only one product was formed—3-hydroxy-2-methyldihydrochalcone 2′-O-β-d-(4″-O-methyl)-glucopyranoside. Biotransformation performed by I. farinosa KCH J2.6 resulted in the formation of two products: 2′-hydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside and 2′,3-dihydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside. The structures of all obtained products were established based on the NMR spectroscopy. All products mentioned above may be used in further studies as potentially bioactive compounds with improved stability and bioavailability. These compounds can be considered as flavor enhancers and potential sweeteners.

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Chemical and biological profile of Psidium bahianum landrum & funch (Myrtaceae)

et al. 2021

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First complete NMR data and theoretical study of an antimicrobial formylated dihydrochalcone from Psidium guineense Sw

Cited by 3 publications

References 24 publications

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

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

New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2′-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi

Chemical and biological profile of Psidium bahianum landrum & funch (Myrtaceae)

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