Microbial transformations of chalcones to produce food sweetener derivatives

Janeczko, Tomasz; Gładkowski, Witold; Kostrzewa-Susłow, Edyta

doi:10.1016/j.molcatb.2013.09.021

Cited by 43 publications

(54 citation statements)

References 46 publications

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“…The retention time, the high agreement with the pattern of specific fragmentation and the compatibility with spectroscopic data published in the literature confirmed that 2′-hydroxydihydrochalcone was obtained as the product of cyanobacterial biotransformation of 2′-hydroxychalcone (Janeczko et al 2013). This conclusion is supported by the exemplary LC-MS profiles of two samples in Fig.…”

Section: Resultssupporting

confidence: 71%

“…This biotechnological approach does not require chemical catalysts, which may be highly specific and therefore expensive (Luan et al 2014). For comparison, biotransformation of 2′-hydroxychalcone by yeast strains and filamentous fungi cultures afford the corresponding dihydrochalcone with 2–98% substrate conversion (Janeczko et al 2013). And transformation of another hydroxylated chalcone, chalconaringenin, in the culture of Rhodococcus sp.…”

Section: Discussionmentioning

confidence: 99%

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Biocatalytic hydrogenation of the C=C bond in the enone unit of hydroxylated chalcones—process arising from cyanobacterial adaptations

Żyszka-Haberecht

Poliwoda

Lipok

2018

Appl Microbiol Biotechnol

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To verify the hypothesis that cyanobacteria naturally biosynthesising polyphenolic compounds possess an active enzymatic system that enables them to transform these substances, such an ability of the biocatalytic systems of whole cells of these biota was assessed for the first time. One halophilic strain and seven freshwater strains of cyanobacteria representing four of the five taxonomic orders of Cyanophyta were examined to determine the following: (i) whether they contain polyphenols, including flavonoids; (ii) the resistance of their cultures when suppressed by the presence of exogenous hydroxychalcones—precursors of flavonoid biosynthesis and (iii) whether these photoautotrophs can transform hydroxylated chalcones. All examined strains were found to contain polyphenols and flavonoids, and the growth of their cultures was inhibited in the presence of 2′-hydroxychalcone, 2″-hydroxychalcone and 4″-hydroxychalcone. We also confirmed that the examined cyanobacteria transformed hydroxychalcones via hydrogenative bio-reduction and formed the corresponding hydroxydihydro derivatives with yields above 90% whenever the substrates were bioavailable for such a conversion. Moreover, we observed that the routes and efficiency of biohydrogenation (and hydroxylation) of chalcones were dependent on the location of the hydroxyl substituent. The final products obtained as the results of biotransformations were extracted from the media and identified by mass spectrometry (LC-MS/MS) and nuclear magnetic resonance (1H NMR, 13C NMR, COSY, HSQC). Based on those results, we believe that the very efficient biohydrogenation of hydroxychalcones, which may easy be scaled up for biotechnological purposes, reflects the natural activity of the cyanobacterial defence system, because hydroxydihydrochalcones were less active inhibitors of the growth of cyanobacterial cultures than the corresponding substrates.

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Section: Resultssupporting

confidence: 71%

Section: Discussionmentioning

confidence: 99%

Biocatalytic hydrogenation of the C=C bond in the enone unit of hydroxylated chalcones—process arising from cyanobacterial adaptations

Żyszka-Haberecht

Poliwoda

Lipok

2018

Appl Microbiol Biotechnol

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“…The best biocatalyst in the studied group of microorganisms was D. igniaria KCh6670. The ability of this strain for the hydroxylation of unactivated C‐atom and reduction in C=O group is described in the literature but the dehalogenation of halocompound is first reported.…”

Section: Resultsmentioning

confidence: 99%

Dehalogenation Activity of Selected Fungi Toward δ‐Iodo‐γ‐Lactone Derived from trans,trans‐Farnesol

Gliszczyńska

Gładkowski

Świtalska

et al. 2016

Chemistry & Biodiversity

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Time‐course of biotransformation of racemic trans‐4‐((E)‐4′,8′‐dimethylnona‐3′,7′‐dien‐1‐yl)‐5‐iodomethyl‐4‐methyldihydrofuran‐2‐one (1) in fungal and yeast cultures was investigated. In these conditions, the substrate 1 was enantioselectively dehalogenated yielding 4‐((E)‐4′,8′‐dimethylnona‐3′,7′‐dien‐1‐yl)‐4‐methyl‐5‐methylenedihydrofuran‐2‐one (2) and its structure was established based on the spectroscopic data. The most effective biocatalyst used was Didymosphaeria igniaria, which catalyzed the process with highest rate and enantioselectivity (ee of product = 76%). The antiproliferative activity of δ‐iodo‐γ‐lactone 1, product of its biotransformation 2, and starting substrate (farnesol) were evaluated toward two cancer cell lines: A549 (human lung adenocarcinoma) and HL‐60 (human promyelocytic leukemia).

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“…The selected microorganism comprised: yeast of the genus Rhodotorula: R. rubra KCh 4, R. rubra KCh 82, and R. glutinis KCh 242; of the genus Candida: C. wiswanathi KCh 120, C. parapsilosis KCh 909, C. sake KCh 908, and C. pelliculosa ZP22; of the genus Saccharomyces: S. cerevisiae KCh 464, S. brasiliensis KCh 905, and S. pastorianus KCh 906 and two other yeast strains: Y. lipolytica KCh 71 and Z. bailii KCh 907. The biocatalysts were selected based on their biocatalytic properties, such as fast growth rate, capability for effective enantioselective reduction of aliphaticaromatic ketones and oxidation of the respective alcohols [30][31][32][33]. Moreover, unlike in the case of filamentous fungi, in the cultures of yeasts competitive reactions such as hydroxylation, dehydratation and degradation rarely occur [34,35].…”

Section: Resultsmentioning

confidence: 99%

Enantioselective reduction of flavanone and oxidation of cis- and trans-flavan-4-ol by selected yeast cultures

Janeczko

Dymarska

Siepka

et al. 2014

Journal of Molecular Catalysis B: Enzymatic

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Microbial transformations of chalcones to produce food sweetener derivatives

Cited by 43 publications

References 46 publications

Biocatalytic hydrogenation of the C=C bond in the enone unit of hydroxylated chalcones—process arising from cyanobacterial adaptations

Biocatalytic hydrogenation of the C=C bond in the enone unit of hydroxylated chalcones—process arising from cyanobacterial adaptations

Dehalogenation Activity of Selected Fungi Toward δ‐Iodo‐γ‐Lactone Derived from trans,trans‐Farnesol

Enantioselective reduction of flavanone and oxidation of cis- and trans-flavan-4-ol by selected yeast cultures

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