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. 2024 Sep 8;25(17):9718.
doi: 10.3390/ijms25179718.

Antimicrobial Activity of Chalcones with a Chlorine Atom and Their Glycosides

Agnieszka Krawczyk-Łebek  1 , Barbara Żarowska  2 , Tomasz Janeczko  1 , Edyta Kostrzewa-Susłow  1
Affiliations

Antimicrobial Activity of Chalcones with a Chlorine Atom and Their Glycosides

Agnieszka Krawczyk-Łebek et al. Int J Mol Sci. .

Abstract

Chalcones, secondary plant metabolites, exhibit various biological properties. The introduction of a chlorine and a glucosyl substituent to the chalcone could enhance its bioactivity and bioavailability. Such compounds can be obtained through a combination of chemical and biotechnological methods. Therefore, 4-chloro-2'-hydroxychalcone and 5'-chloro-2'-hydroxychalcone were obtained by synthesis and then glycosylated in two filamentous fungi strains cultures, i.e., Isaria fumosorosea KCH J2 and Beauveria bassiana KCH J1.5. The main site of the glycosylation of both compounds by I. fumosorosea KCH J2 was C-2' and C-3 when the second strain was utilized. The pharmacokinetics of these compounds were predicted using chemoinformatics tools. Furthermore, antimicrobial activity tests were performed. Compounds significantly inhibited the growth of the bacteria strains Escherichia coli 10536, Staphylococcus aureus DSM 799, and yeast Candida albicans DSM 1386. Nevertheless, the bacterial strain Pseudomonas aeruginosa DSM 939 exhibited significant resistance to their effects. The growth of lactic acid bacteria strain Lactococcus acidophilus KBiMZ 01 bacteria was moderately inhibited, but strains Lactococcus rhamnosus GG and Streptococcus thermophilus KBM-1 were completely inhibited. In summary, chalcones substituted with a chlorine demonstrated greater efficacy in inhibiting the microbial strains under examination compared to 2'-hydroxychalcone, while aglycones and their glycosides exhibited similar effectiveness.

Keywords: Beauveria bassiana; Isaria fumosorosea; antimicrobial activity; biotransformations; chalcones with a chlorine atom; glycosylated dihydrochalcones.

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Conflict of interest statement

The authors declare no conflicts of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript; or in the decision to publish the results.

Figures

Figure 1
Figure 1
Functional modules of glycosyltransferase-methyltransferase (GT-MT) in fungi such as B. bassiana (developed based on Xie and coworkers [15]).
Figure 2
Figure 2
Synthesis of biotransformation substrate 4-chloro-2′-hydroxychalcone (3).
Figure 3
Figure 3
Synthesis of biotransformation substrate 5′-chloro-2′-hydroxychalcone (6).
Figure 4
Figure 4
Biotransformation of 4-chloro-2′-hydroxychalcone (3) in I. fumosorosea KCH J2 culture.
Figure 5
Figure 5
Key COSY (on the left) and HMBC (on the right) correlations of product 3a.
Figure 6
Figure 6
Key COSY (on the left) and HMBC (on the right) correlations of product 3b.
Figure 7
Figure 7
Biotransformation of 4-chloro-2′-hydroxychalcone (3) in B. bassiana KCH J1.5 culture.
Figure 8
Figure 8
Key COSY (on the left) and HMBC (on the right) correlations of product 3c.
Figure 9
Figure 9
Biotransformation of 5′-chloro-2′-hydroxychalcone (6) in I. fumosorosea KCH J2 culture.
Figure 10
Figure 10
Key COSY (on the left) and HMBC (on the right) correlations of product 6a.
Figure 11
Figure 11
Biotransformation of 5′-chloro-2′-hydroxychalcone (6) in B. bassiana KCH J1.5 culture.
Figure 12
Figure 12
Key COSY (on the left) and HMBC (on the right) of product 6b.
Figure 13
Figure 13
The impact of compounds 3, 6, 3a, 6a, 6b, 7 on the growth of E. coli 10536.
Figure 14
Figure 14
The impact of compounds 3, 6, 3a, 6a, 6b, 7 on the growth of P. aeruginosa DSM 939.
Figure 15
Figure 15
The impact of compounds 3, 6, 3a, 6a, 6b, 7 on the growth of S. aureus DSM 799.
Figure 16
Figure 16
The impact of compounds 3, 6, 3a, 6a, 6b, 7 on the growth of C. albicans DSM 1386.
Figure 17
Figure 17
The impact of compounds 3, 6, 3a, 6a, 6b, 7 on the growth of L. acidophilus KBiMZ 01.
Figure 18
Figure 18
The impact of compounds 3, 6, 3a, 6a, 6b, 7 on the growth of L. rhamnosus GG.
Figure 19
Figure 19
The impact of compounds 3, 6, 3a, 6a, 6b, 7 on the growth of S. thermophilus KBM-1.
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References

    1. Zhuang C., Zhang W., Sheng C., Zhang W., Xing C., Miao Z. Chalcone: A Privileged Structure in Medicinal Chemistry. Chem. Rev. 2017;117:7762–7810. doi: 10.1021/acs.chemrev.7b00020. - DOI - PMC - PubMed
    1. Ehrenkranz J.R.L., Lewis N.G., Kahn C.R., Roth J. Phlorizin: A review. Diabetes/Metabolism Res. Rev. 2004;21:31–38. doi: 10.1002/dmrr.532. - DOI - PubMed
    1. Gosch C., Halbwirth H., Stich K. Phloridzin: Biosynthesis, distribution and physiological relevance in plants. Phytochemistry. 2010;71:838–843. doi: 10.1016/j.phytochem.2010.03.003. - DOI - PubMed
    1. Tian L., Cao J., Zhao T., Liu Y., Khan A., Cheng G. The Bioavailability, Extraction, Biosynthesis and Distribution of Natural Dihydrochalcone: Phloridzin. Int. J. Mol. Sci. 2021;22:962. doi: 10.3390/ijms22020962. - DOI - PMC - PubMed
    1. Londzin P., Siudak S., Cegieła U., Pytlik M., Janas A., Waligóra A., Folwarczna J. Phloridzin, an Apple Polyphenol, Exerted Unfavorable Effects on Bone and Muscle in an Experimental Model of Type 2 Diabetes in Rats. Nutrients. 2018;10:1701. doi: 10.3390/nu10111701. - DOI - PMC - PubMed

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