Regiospecific Hydrogenation of Bromochalcone by Unconventional Yeast Strains

Abstract

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.

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

“…In the 13 C NMR, there is no characteristic The analysis of NMR spectra confirmed the creation of the product (8a). The 1 H NMR spectrum shows two doublets coming from protons H-7 (δ = 7.54 ppm, J = 2.5 Hz) and H-5 (δ = 7.40 ppm, J = 2.5 Hz), evidencing the substitution at C-8 and C-6 positions, as in the case of the substrate (8). The correlation is visible in the HMBC spectrum (Figure 9 and Supplementary Materials Figure S183).…”

“…As a result of the biotransformation of substrates ( 5), ( 6), ( 7), (8), and (9) in cultures of B. bassiana KCH J1.5, I. fumosorosea KCH J2, and I. farinosa KCH J2.6, glycosidic derivatives of flavonoids were obtained. Only 2 -hydroxy-5 -methyl-3 -nitrochalcone (4) in the cultures of the chosen filamentous fungi was not biotransformed.…”

“…Unconventional yeast strains like Rhodotorula rubra KCH 4 and KCH 82, Rhodotorula marina KCH 77, Rhodotorula glutinis KCH 242, Candida viswanathii KCH 120, Candida parapsilosis KCH 909, Saccharomyces cerevisiae KCH 464, and Yarrowia lipolytica KCH 71 were used to carry out the biotransformation of 2 -hydroxychalcones with bromine atom at C-2, C-3, C-4, C-5 positions. All substrates used were converted to the corresponding dihydrochalcones [8]. Other studies have shown that S. cerevisiae KCH 464 and Y. lipolytica KCH 71 were also able to hydrogenate 3-(2"-furyl)-1-(2 -hydroxyphenyl)-prop-2-en-1-one with >99% yield [9].…”

Microbial-Driven Synthesis and Hydrolysis of Neohesperidin Dihydrochalcone: Biotransformation Process and Feasibility Investigation

“…glutinis had the ability to produce NHDC with good transformation efficiency. Some researchers have reported that the reduction of dihydrochalcone was specific to different biocatalysts, which was attributed to the different biological metabolisms involved in the transformation process of different biocatalysts . Structural variations in substrates can induce the activation of different enzymes within the utilized biocatalysts, resulting in distinct reduction capabilities among various yeasts.…”

“…Some researchers have reported that the reduction of dihydrochalcone was specific to different biocatalysts, which was attributed to the different biological metabolisms involved in the transformation process of different biocatalysts. 18 Structural variations in substrates can induce the activation of different enzymes within the utilized biocatalysts, resulting in distinct reduction capabilities among various yeasts. Janeczko et al pointed out that while some biocatalysts can hydrogenate chalcone to yield dihydrochalcone (1,3-diphenylpropan-1-one), further reduction of the dihydrochalcone resulted in the formation of enantiomerically enriched alcohols ((S)-1,3-diphenylpropan-1-ol).…”