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

Kostrzewa-Susłow, Edyta; Dymarska, Monika; Wojcieszyńska, Danuta; Janeczko, Tomasz

doi:10.3390/molecules22111830

Cited by 14 publications

(18 citation statements)

References 36 publications

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“…In the 1 H spectrum of synthetic compounds 3-9 were observed signals indicate a molecule with no substituent on the B ring; two methylene signals high-field region and two meta-substituted groups on the A ring and corresponding to the basic structure of a dihydrochalcone. In particular, the compound 3 was obtained as an white solid, proved to be identical to 2'-Hydroxy-4'-methoxydihydrochalcone, previously obtained as a biotransformation product of 7-methoxyflavanone by Stenotrophomonas maltophilia [21]. Moreover, compound 7 was obtained as a pale yellow solid in accordance with the data obtained previously for the molecule isolated from Lonchocarpus neuroscapha [24].…”

Section: Chemistrysupporting

confidence: 86%

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Synthesis and Anti-Saprolegnia Activity of New 2’,4’-Dihydroxydihydrochalcone Derivatives

et al. 2020

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In the present study, seven 2’,4’-dihydroxydihydrochalcone derivatives (compounds 3–9) were synthesized and their capacity as anti-Saprolegnia agents were evaluated against Saprolegnia parasitica, S. australis, S. diclina. Derivative 9 showed the best activity against the different strains, with minimum inhibitory concentration (MIC) and minimum oomyceticidal concentration (MOC) values between 100–175 μg/mL and 100–200 μg/mL, respectively, compared with bronopol and fluconazole as positive controls. In addition, compound 9 caused damage and disintegration cell membrane of all Saprolegnia strains over the action of commercial controls.

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Section: Chemistrysupporting

confidence: 86%

“…In addition. this method of synthesis allows to obtain compound 2 with a good yield and in a short period of time; which for us has been excellent, because the reported yields do not exceed 4% both of natural origin or biotransformation product [19][20][21].…”

Section: Chemistrymentioning

confidence: 84%

Synthesis and Anti-Saprolegnia Activity of New 2’,4’-Dihydroxydihydrochalcone Derivatives

et al. 2020

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“…Flavones used in biotransformations were synthesized from those substrates (the reactions are described below). The resulting chalcones were used as substrates for the flavone synthesis and their NMR spectral data are identical to those previously published [ 34 , 35 , 36 ].…”

Section: Methodsmentioning

confidence: 75%

“…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

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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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“…The strains of the species Saccharomyces cerevisiae are widely described as biocatalysts, effectively reducing the double bond in various compounds – derivatives of chalcones [9], containing methyl, methoxy, hydroxy substituents [37], and even bromine or chlorine [33,38], in both A and B-rings. On the basis of the results obtained in this study, it can be concluded that a chalcone derivative, containing a heteroatom in the B-ring, is effectively transformed by this strain.…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2019

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Biotransformations were performed on eight selected yeast strains, all of which were able to selectively hydrogenate the chalcone derivatives 3-(2”-furyl)- (1) and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one (3) into 3-(2”-furyl)- (2) and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-propan-1-one (4) respectively. The highest efficiency of hydrogenation of the double bond in the substrate 1 was observed in the cultures of Saccharomyces cerevisiae KCh 464 and Yarrowia lipolytica KCh 71 strains. The substrate was converted into the product with > 99% conversion just in six hours after biotransformation started. The compound containing the sulfur atom in its structure was most effectively transformed by the Yarrowia lipolytica KCh 71 culture strain (conversion > 99%, obtained after three hours of substrate incubation). Also, we observed that, different strains of tested yeasts are able to carry out the bioreduction of the used substrate with different yields, depending on the presence of induced and constitutive ene reductases in their cells. The biggest advantage of this process is the efficient production of one product, practically without the formation of side products.

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

Cited by 14 publications

References 36 publications

Synthesis and Anti-Saprolegnia Activity of New 2’,4’-Dihydroxydihydrochalcone Derivatives

Synthesis and Anti-Saprolegnia Activity of New 2’,4’-Dihydroxydihydrochalcone Derivatives

Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi

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

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