Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones

Gładkowski, Witold; Siepka, Monika; Janeczko, Tomasz; Kostrzewa-Susłow, Edyta; Popłoński, Jarosław; Mazur, Marcelina; Żarowska, Barbara; Łaba, Wojciech; Maciejewska, Gabriela; Wawrzeńczyk, Czesław

doi:10.3390/molecules24224151

Cited by 19 publications

(13 citation statements)

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“…2 -Hydroxy-5 -methylchalcone (3) was obtained with a 50.1% yield and was used as the biotransformation substrate, and also as substrate in the second step of the synthesis. 6-Methylflavanone (4) was obtained by cyclization of 2 -hydroxy-5 -methylchalcone (3) in the presence of sodium acetate [54,55] with 62.3% yield.…”

Section: Substratesmentioning

confidence: 99%

Entomopathogenic Filamentous Fungi as Biocatalysts in Glycosylation of Methylflavonoids

et al. 2020

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Flavonoids are known for their numerous biological activities; however, their pharmacological application is limited by poor bioavailability. Glycosides are usually more stable and more soluble in water and in this form, flavonoids are present in nature. Likewise, the presence of the methyl group in the flavonoid skeleton results in facilitated absorption and greater bioavailability. Entomopathogenic filamentous fungi are effective in the biotransformation of flavonoids; they are known especially for efficient glycosylation. In the current study we used strains of Beauveria bassiana KCH J1.5 and Isaria fumosorosea KCH J2 to biotransform flavonoids with a single methyl group. 2′-Hydroxy-5′-methylchalcone was biotransformed by both strains into 2′-hydroxy-5′-methylchalcone 3-O-β-D-(4″-O-methyl)-glucopyranoside. In the culture of B. bassiana KCH J1.5 four products were obtained from 6-methylflavanone: 4′-hydroxy-6-methylflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside; 4′-hydroxyflavanone 6-methylene-O-β-D-(4″-O-methyl)-glucopyranoside; 6-hydroxymethylflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside and 4′-hydroxy-6-hydroxymethylflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside. Biotransformation with I. fumosorosea KCH J2 as a biocatalyst resulted in the formation of 6-methylflavanone 4′-O-β-D-(4″-O-methyl)-glucopyranoside and 2-phenyl-6-methylchromane 4-O-β-D-(4″-O-methyl)-glucopyranoside. All of these flavonoids can be used in biological activity tests and can be useful in studies concerning structure—bioactivity relationships.

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Section: Substratesmentioning

confidence: 99%

Entomopathogenic Filamentous Fungi as Biocatalysts in Glycosylation of Methylflavonoids

et al. 2020

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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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“…Calycosin have significant antiviral activity both in vivo and vitro ( Zhu et al, 2009 ). Most flavonoids have a significant inhibitory effect on the growth of bacteria including Bacillus subtilis , Staphylococcus aureus and Escherichia coli ( Kamrani et al, 2007 ; Gadkowski et al, 2019 ).…”

Section: Introductionmentioning

confidence: 99%

Optimal extraction, purification and antioxidant activity of total flavonoids from endophytic fungi of Conyza blinii H. Lév

Zhao

Wu²,

Duan

et al. 2021

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Background Flavonoids are widely used in the market because of their antibacterial, antiviral, and antioxidant activities. But the production speed of flavonoids is limited by the growth of plants. CBL9 (Chaetomium cruentum) is a flavonoid-producing endophytic fungi from Conyza blinii H. Lév, which has potential to produce flavonoids. Methods In this study, we isolated total flavonoids from endophytic fungus CBL9 of Conyza blinii H. Lév using macroporous resin D101. The process was optimized by response surface and the best extraction process was obtained. The antioxidant activities of total flavonoids were analyzed in vitro. Results It was found that the best parameters were 25 °C pH 2.80, 1.85 h, and the adsorption ratio reached (64.14 ± 0.04)%. A total of 60% ethanol was the best elution solvent. The elution ratio of total flavonoid reached to (81.54 ± 0.03)%, and the purity was 7.13%, which was increased by 14.55 times compared with the original fermentation broth. Moreover its purity could rise to 13.69% after precipitated by ethanol, which is very close to 14.10% prepared by ethyl acetate extraction. In the antioxidant research, the clearance ratio of L9F-M on DPPH, ABTS, •OH, •O2−, (96.44 ± 0.04)% and (75.33 ± 0.03)%, (73.79 ± 0.02)%, (31.14 ± 0.01)% at maximum mass concentration, was higher than L9F. Conclusion The result indicated using macroporous resin in the extraction of total flavonoid from endophytic fungus is better than organic solvents with higher extraction ratio, safety and lower cost. In vitro testing indicated that the flavonoid extracted by macroporous resin have good antioxidant activity, providing more evidence for the production of flavonoid by biological fermentation method.

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Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones

Cited by 19 publications

References 50 publications

Entomopathogenic Filamentous Fungi as Biocatalysts in Glycosylation of Methylflavonoids

Entomopathogenic Filamentous Fungi as Biocatalysts in Glycosylation of Methylflavonoids

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

Optimal extraction, purification and antioxidant activity of total flavonoids from endophytic fungi of Conyza blinii H. Lév

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