Microbial synthesis of dihydrochalcones using Rhodococcus and Gordonia species

Stompor, Monika; Potaniec, Bartłomiej; Szumny, Antoni; Zieliński, Paweł; Żołnierczyk, Anna K.; Anioł, Mirosław

doi:10.1016/j.molcatb.2013.09.009

Cited by 25 publications

(15 citation statements)

References 48 publications

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“…In the first stage of conversion naringenin 5 underwent isomerization to chalconaringenin 7 and then, due to hydrogenation of the olefinic bond in the presence of catalytic amounts of NADH-α,β-dihydrochalconaringenin, 6 was formed. Chalconaringenin 7 also undergoes biotransformation to phloretin 6 in the cells of aerobic bacteria, such as Rhodococcus and Gordonia, as we described earlier [33]. The newest study proved the strong antibacterial properties of phloretin 6 and its glycoside derivatives towards Gram-positive (S. aureus ATCC 6538, Listeria monocytogenes ATCC 13932) and Gram-negative (Salmonella typhimurium ATCC 133111) bacteria [34].…”

Section: Discussionmentioning

confidence: 54%

“…The next hop chalcone and a precursor of the prenyl derivatives-chalconaringenin 7 was obtained by alkaline isomerization of racemic (˘)-naringenin 5, with the help of a methanolic KOH solution, according to the modified method of Le Bail et al [37]. Spectral data of 7 were identical with literature values [33].…”

Section: Xanthohumol and Chalconaringeninmentioning

confidence: 74%

“…The purity of the synthesized products (>95%) was established by HPLC chromatography. Analysis were performed according to the procedure described earlier [33]. The NMR spectra ( 1 H-, 13 C-NMR, 13 C-DEPT, and correlation spectra: 1 H-1 H-COSY, 1 H-13 C-HMQC, 1 H-13 C-HMBC) were recorded in a CDCl 3 solution on a Brüker Avance DRX 300 and Brüker Avance II 600 MHz spectrometers (Brüker, Karlsruhe, Germany).…”

Section: Methodsmentioning

confidence: 99%

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Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

Stompor

Żarowska

2016

Molecules

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Abstract:The objective of this study was to evaluate the antimicrobial activity of structural analogues of xanthohumol 1, a flavonoid compound found in hops (Humulus lupulus). The agar-diffusion method using filter paper disks was applied. Biological tests performed for selected strains of Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria, fungi (Alternaria sp.), and yeasts (Rhodotorula rubra, Candida albicans) revealed that compounds with at least one hydroxyl group-all of them have it at the C-4 position-demonstrated good activity. Our research showed that the strain S. aureus was more sensitive to chalcones than to the isomers in which the heterocyclic ring C is closed (flavanones). The strain R. rubra was moderately sensitive to only one compound: 4-hydroxy-4'-methoxychalcone 8. Loss of the hydroxyl group in the B-ring of 4'-methoxychalcones or its replacement by a halogen atom (´Cl,´Br), nitro group (´NO 2 ), ethoxy group (´OCH 2 CH 3 ), or aliphatic substituent (´CH 3 ,´CH 2 CH 3 ) resulted in the loss of antimicrobial activity towards both R. rubra yeast and S. aureus bacteria. Xanthohumol 1, naringenin 5, and chalconaringenin 7 inhibited growth of S. aureus, whereas 4-hydroxy-4 1 -methoxychalcone 8 was active towards two strains: S. aureus and R. rubra.

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Section: Discussionmentioning

confidence: 54%

Section: Xanthohumol and Chalconaringeninmentioning

confidence: 74%

Section: Methodsmentioning

confidence: 99%

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Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

Stompor

Żarowska

2016

Molecules

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“…And transformation of another hydroxylated chalcone, chalconaringenin, in the culture of Rhodococcus sp. led to dihydrochalconaringenin (phloretin) in 84% yield (Stompor et al 2013). …”

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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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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“…Most of the tested cyanobacterial strains converted this compound into its hydrogenated derivative (55) in nearly 100% yield. Chalcones can be also converted to dihydrochalcones using bacterial strains of the genera Rhodococcus, Gordonia, and Lactobacillus (Scheme 12) [79,80]. In turn, Klingel et al [81] modified and applied a recombinant dextransucrase from Lactobacillus reuteri TMW 1.106 to glucosylate various flavonoids and flavonoid glycosides.…”

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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Microbial synthesis of dihydrochalcones using Rhodococcus and Gordonia species

Cited by 25 publications

References 48 publications

Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

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

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

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