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

Janeczko, Tomasz; Dymarska, Monika; Siepka, Monika; Gniłka, Radosław; Leśniak, Agnieszka; Popłoński, Jarosław; Kostrzewa-Susłow, Edyta

doi:10.1016/j.molcatb.2014.08.006

Cited by 25 publications

(31 citation statements)

References 42 publications

(62 reference statements)

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“…The chalcone analogues used in the study are numbered from 1 to 8. All were obtained via a Claisen–Schmidt condensation of an appropriate 2-hydroxyacetophenone and a substituted benzaldehyde dissolved in methanol in an alkaline environment at high temperature according to the procedure described previously [ 37 , 38 , 39 ]. The structures of the tested chalcones are shown in Figure 6 .…”

Section: Methodsmentioning

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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Section: Methodsmentioning

confidence: 99%

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

et al. 2020

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“…The compounds 2′-methoxyflavanone ( 1 ), 3′-methoxyflavanone ( 2 ), and 4′-methoxyflavanone ( 3 ) were prepared according to the method we described earlier [ 26 ]. A total of 10 g of the 2′-hydroxychalcone with a metoxy substituent (obtained from 2′-hydroxyacetophenone and methoxy-substituted benzaldehyde) was dissolved in ethanol (75 mL) with the addition of sodium acetate (8 g), and the reaction mixture was refluxed for 48 h. Crystallization from ethanol afforded pure methoxyflavanone.…”

Section: Methodsmentioning

confidence: 99%

Glycosylation of Methoxylated Flavonoids in the Cultures of Isaria fumosorosea KCH J2

2018

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Flavonoids are widely described plant secondary metabolites with high and diverse pro-health properties. In nature, they occur mostly in the form of glycosides. Our research showed that an excellent way to obtain the sugar derivatives of flavonoids is through biotransformations with the use of entomopathogenic filamentous fungi as biocatalysts. In the current paper, we described the biotransformations of five methoxylated flavonoid compounds (2′-methoxyflavanone, 3′-methoxyflavanone, 4′-methoxyflavanone, 6-methoxyflavanone, and 6-methoxyflavone) in cultures of Isaria fumosorosea KCH J2. As a result, we obtained twelve new flavonoid 4-O-methylglucopyranosides. The products were purified with methods that enabled the reduction of the consumption of organic solvents (preparative TLC and flash chromatography). The structures of the products were confirmed with spectroscopic methods (NMR: 1H, 13C, HSQC, HMBC, COSY). The compounds obtained by us expand the library of available flavonoid derivatives and can be used in biological research.

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“…For transformations of flavonoid compounds, enzymatic systems of filamentous fungi [ 1 , 2 , 3 , 4 ], yeasts [ 5 , 6 ], bacteria [ 7 , 8 , 9 ], higher plants [ 10 ], and isolated enzymes are used [ 11 ]. The main aim of these transformations is to improve the biological properties of flavonoids [ 12 , 13 , 14 ], increase their antioxidant properties [ 15 , 16 ], and obtain derivatives with high optical purity [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Stenotrophomonas maltophilia: A Gram-Negative Bacterium Useful for Transformations of Flavanone and Chalcone

et al. 2017

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A group of flavones, isoflavones, flavanones, and chalcones was subjected to small-scale biotransformation studies with the Gram-negative Stenotrophomonas maltophilia KB2 strain in order to evaluate the capability of this strain to transform flavonoid compounds and to investigate the relationship between compound structure and transformation type. The tested strain transformed flavanones and chalcones. The main type of transformation of compounds with a flavanone moiety was central heterocyclic C ring cleavage, leading to chalcone and dihydrochalcone structures, whereas chalcones underwent reduction to dihydrochalcones and cyclisation to a benzo-γ-pyrone moiety. Substrates with a C-2–C-3 double bond (flavones and isoflavones) were not transformed by Stenotrophomonas maltophilia KB2.

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

Cited by 25 publications

References 42 publications

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

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

Glycosylation of Methoxylated Flavonoids in the Cultures of Isaria fumosorosea KCH J2

Stenotrophomonas maltophilia: A Gram-Negative Bacterium Useful for Transformations of Flavanone and Chalcone

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