Effective Hydrogenation of 3-(2”-furyl)- and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures

Łużny, Mateusz; Krzywda, Martyna; Kozłowska, Ewa; Kostrzewa-Susłow, Edyta; Janeczko, Tomasz

doi:10.3390/molecules24173185

Cited by 9 publications

(19 citation statements)

References 35 publications

(53 reference statements)

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“…All used substrates were synthesized in the laboratory by carrying out two kinds of reactions. Firstly five different methoxychalcones were synthesized in the Claisen-Schmidt reaction of 2-hydroxyacetophenone with suitable methoxybenzaldehyde in reaction, described earlier and shown in Scheme 2 [ 34 , 35 , 36 , 37 , 38 ]. The resulting flavones ( 1 – 5 ) were used as substrates for the biotransformation and their NMR spectral data are identical to those previously published [ 32 , 39 ].…”

Section: Methodsmentioning

confidence: 99%

Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi

Łużny

Tronina

Kozłowska

et al. 2020

IJMS

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The synthesis and biotransformation of five flavones containing methoxy substituents in the B ring: 2′-, 3′-, 4′-methoxyflavones, 2′,5′-dimethoxyflavone and 3′,4′,5′-trimethoxyflavone are described. Strains of entomopathogenic filamentous fungi were used as biocatalysts. Five strains of the species Beauveria bassiana (KCh J1.5, J2.1, J3.2, J1, BBT), two of the species Beauveria caledonica (KCh J3.3, J3.4), one of Isaria fumosorosea (KCh J2) and one of Isaria farinosa (KCh KW 1.1) were investigated. Both the number and the place of attachment of the methoxy groups in the flavonoid structure influenced the biotransformation rate and the amount of nascent products. Based on the structures of products and semi-products, it can be concluded that their formation is the result of a cascading process. As a result of enzymes produced in the cells of the tested strains, the test compounds undergo progressive demethylation and/or hydroxylation and 4-O-methylglucosylation. Thirteen novel flavonoid 4-O-methylglucosides and five hydroxy flavones were isolated and identified.

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Section: Methodsmentioning

confidence: 99%

Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi

Łużny

Tronina

Kozłowska

et al. 2020

IJMS

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“…Chalcones (1-(2′-hydroxyphenyl)-3-phenylprop-2-en-1-ones) and their derivatives are often obtained from natural sources or as a result of chemical synthesis [ 6 , 7 ]. The most commonly used chemical synthesis method is the Claisen–Schmidt condensation of the corresponding aromatic aldehyde and 2′-hydroxyacetophenones in alkaline or acid catalysis [ 8 , 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Chalcone Methoxy Derivatives Exhibit Antiproliferative and Proapoptotic Activity on Canine Lymphoma and Leukemia Cells

et al. 2020

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Chalcones are interesting candidates for anti-cancer drugs due to the ease of their synthesis and their extensive biological activity. The study presents antitumor activity of newly synthesized chalcone analogues with a methoxy group on a panel of canine lymphoma and leukemia cell lines. The antiproliferative effect of the 2′-hydroxychalcone and its methoxylated derivatives was evaluated in MTT assay after 48 h of treatment in different concentrations. The proapoptotic activity was studied by cytometric analysis of cells stained with Annexin V/FITC and propidium iodide and by measure caspases 3/7 and 8 activation. The DNA damage was evaluated by Western blot analysis of phosphorylated histone H2AX. The new compounds had selective antiproliferative activity against the studied cell lines, the most effective were the 2′-hydroxy-2″,5″-dimethoxychalcone and 2′-hydroxy-4′,6′-dimethoxychalcone. 2′-Hydroxychalcone and the two most active derivatives induced apoptosis and caspases participation, but some percentage of necrotic cells was also observed. Comparing phosphatidylserine externalization after treatment with the different compounds it was noted that the addition of two methoxy groups increased the proapoptotic potential. The most active compounds triggered DNA damage even in the cell lines resistant to chalcone-induced apoptosis. The results confirmed that the analogues could have anticancer potential in the treatment of canine lymphoma or leukemia.

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“…The strain Rhodotorula rubra AM 82 biotransformed chalcones into dihydrochalcones and respective secondary alcohols. In addition, some other species of yeast like Saccharomyces and Yarrowia posses a high ability to reduce the double bond in chalcones and their derivatives, which was described recently [77]. The substrates in these reactions included predominantly hydroxy-and methoxyderivatives of chalcones and compounds containing furan and thiophene substituents.…”

Section: Microbiological and Enzymatic Hydrogenation Of Chalconesmentioning

confidence: 99%

Dihydrochalcones: Methods of Acquisition and Pharmacological Properties—A First Systematic Review

2019

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Dihydrochalcones are a class of secondary metabolites, for which demand in biological and pharmacological applications is still growing. They posses several health-endorsing properties and, therefore, are promising candidates for further research and development. However, low content of dihydrochalcones in plants along with their low solubility and bioavailability restrict the development of these compounds as clinical therapeutics. Therefore, chemomicrobial and enzymatic modifications are required to expand their application. This review aims at analyzing and summarizing the methods of obtaining dihydrochalcones and of presenting their pharmacological actions that have been described in the literature to support potential future development of this group of compounds as novel therapeutic drugs. We have also performed an evaluation of the available literature on beneficial effects of dihydrochalcones with potent antioxidant activity and multifactorial pharmacological effects, including antidiabetic, antitumor, lipometabolism regulating, antioxidant, anti-inflammatory, antibacterial, antiviral, and immunomodulatory ones. In addition, we provide useful information on their properties, sources, and usefulness in medicinal chemistry.

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Effective Hydrogenation of 3-(2”-furyl)- and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures

Cited by 9 publications

References 35 publications

Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi

Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi

Chalcone Methoxy Derivatives Exhibit Antiproliferative and Proapoptotic Activity on Canine Lymphoma and Leukemia Cells

Dihydrochalcones: Methods of Acquisition and Pharmacological Properties—A First Systematic Review

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