Microbial Biosynthesis of Chrysazin Derivatives in Recombinant <i>Escherichia coli</i> and Their Biological Activities
Anthraquinone and its derivatives show remarkable biological properties such as anticancer, antibacterial, antifungal, and antiviral activities. Hence, anthraquinones derivatives have been of prime interest in drug development. This study developed a recombinant <i>Escherichia coli </i>s...
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MDPI AG
2022-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/17/5554 |
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| author | Purna Bahadur Poudel Dipesh Dhakal Rubin Thapa Magar Jae Kyung Sohng |
| author_facet | Purna Bahadur Poudel Dipesh Dhakal Rubin Thapa Magar Jae Kyung Sohng |
| author_sort | Purna Bahadur Poudel |
| collection | DOAJ |
| description | Anthraquinone and its derivatives show remarkable biological properties such as anticancer, antibacterial, antifungal, and antiviral activities. Hence, anthraquinones derivatives have been of prime interest in drug development. This study developed a recombinant <i>Escherichia coli </i>strain to modify chrysazin to chrysazin-8-<i>O</i>-<i>α</i>-<span style="font-variant: small-caps;">l</span>-rhamnoside (CR) and chrysazin-8-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-2′-<i>O</i>-methylrhamnoside (CRM) using rhamnosyl transferase and sugar-<i>O</i>-methyltransferase. Biosynthesized CR and CRM were structurally characterized using HPLC, high-resolution mass spectrometry, and various nuclear magnetic resonance analyses. Antimicrobial effects of chrysazin, CR, and CRM against 18 superbugs, including 14 Gram-positive and 4 Gram-negative pathogens, were investigated. CR and CRM exhibited antimicrobial activities against nine pathogens, including methicillin-resistant <i>Staphylococcus aureus</i> (MRSA) and methicillin-sensitive <i>Staphylococcus aureus</i> (MSSA) in a disk diffusion assay at a concentration of 40 µg per disk. There were MIC and MBC values of 7.81–31.25 µg/mL for CR and CRM against methicillin-sensitive <i>S. aureus</i> CCARM 0205 (MSSA) for which the parent chrysazin is more than >1000 µg/mL. Furthermore, the anti-proliferative properties of chrysazin, CR, and CRM were assayed using AGS, Huh7, HL60, and HaCaT cell lines. CR and CRM showed higher antibacterial and anticancer properties than chrysazin. |
| first_indexed | 2024-03-10T01:30:11Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T01:30:11Z |
| publishDate | 2022-08-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-ed3f5944ff5d4d1d9540afc825a4a44b2023-11-23T13:44:00ZengMDPI AGMolecules1420-30492022-08-012717555410.3390/molecules27175554Microbial Biosynthesis of Chrysazin Derivatives in Recombinant <i>Escherichia coli</i> and Their Biological ActivitiesPurna Bahadur Poudel0Dipesh Dhakal1Rubin Thapa Magar2Jae Kyung Sohng3Institute of Biomolecule Reconstruction (iBR), Department of Life Science and Biochemical Engineering, Sun Moon University, 70 Sun Moon-ro 221, Tangjeong-myeon, Asan-si 31460, Chungnam, KoreaInstitute of Biomolecule Reconstruction (iBR), Department of Life Science and Biochemical Engineering, Sun Moon University, 70 Sun Moon-ro 221, Tangjeong-myeon, Asan-si 31460, Chungnam, KoreaInstitute of Biomolecule Reconstruction (iBR), Department of Life Science and Biochemical Engineering, Sun Moon University, 70 Sun Moon-ro 221, Tangjeong-myeon, Asan-si 31460, Chungnam, KoreaInstitute of Biomolecule Reconstruction (iBR), Department of Life Science and Biochemical Engineering, Sun Moon University, 70 Sun Moon-ro 221, Tangjeong-myeon, Asan-si 31460, Chungnam, KoreaAnthraquinone and its derivatives show remarkable biological properties such as anticancer, antibacterial, antifungal, and antiviral activities. Hence, anthraquinones derivatives have been of prime interest in drug development. This study developed a recombinant <i>Escherichia coli </i>strain to modify chrysazin to chrysazin-8-<i>O</i>-<i>α</i>-<span style="font-variant: small-caps;">l</span>-rhamnoside (CR) and chrysazin-8-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-2′-<i>O</i>-methylrhamnoside (CRM) using rhamnosyl transferase and sugar-<i>O</i>-methyltransferase. Biosynthesized CR and CRM were structurally characterized using HPLC, high-resolution mass spectrometry, and various nuclear magnetic resonance analyses. Antimicrobial effects of chrysazin, CR, and CRM against 18 superbugs, including 14 Gram-positive and 4 Gram-negative pathogens, were investigated. CR and CRM exhibited antimicrobial activities against nine pathogens, including methicillin-resistant <i>Staphylococcus aureus</i> (MRSA) and methicillin-sensitive <i>Staphylococcus aureus</i> (MSSA) in a disk diffusion assay at a concentration of 40 µg per disk. There were MIC and MBC values of 7.81–31.25 µg/mL for CR and CRM against methicillin-sensitive <i>S. aureus</i> CCARM 0205 (MSSA) for which the parent chrysazin is more than >1000 µg/mL. Furthermore, the anti-proliferative properties of chrysazin, CR, and CRM were assayed using AGS, Huh7, HL60, and HaCaT cell lines. CR and CRM showed higher antibacterial and anticancer properties than chrysazin.https://www.mdpi.com/1420-3049/27/17/5554rhamnosyltransferase<i>O</i>-methyltransferasechrysazinbiological properties |
| spellingShingle | Purna Bahadur Poudel Dipesh Dhakal Rubin Thapa Magar Jae Kyung Sohng Microbial Biosynthesis of Chrysazin Derivatives in Recombinant <i>Escherichia coli</i> and Their Biological Activities Molecules rhamnosyltransferase <i>O</i>-methyltransferase chrysazin biological properties |
| title | Microbial Biosynthesis of Chrysazin Derivatives in Recombinant <i>Escherichia coli</i> and Their Biological Activities |
| title_full | Microbial Biosynthesis of Chrysazin Derivatives in Recombinant <i>Escherichia coli</i> and Their Biological Activities |
| title_fullStr | Microbial Biosynthesis of Chrysazin Derivatives in Recombinant <i>Escherichia coli</i> and Their Biological Activities |
| title_full_unstemmed | Microbial Biosynthesis of Chrysazin Derivatives in Recombinant <i>Escherichia coli</i> and Their Biological Activities |
| title_short | Microbial Biosynthesis of Chrysazin Derivatives in Recombinant <i>Escherichia coli</i> and Their Biological Activities |
| title_sort | microbial biosynthesis of chrysazin derivatives in recombinant i escherichia coli i and their biological activities |
| topic | rhamnosyltransferase <i>O</i>-methyltransferase chrysazin biological properties |
| url | https://www.mdpi.com/1420-3049/27/17/5554 |
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