Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a <i>Streptomyces</i> Isolate
Bacteria of the genus <i>Streptomyces</i> produce various specialized metabolites. Single biosynthetic gene clusters (BGCs) can give rise to different products that can vary in terms of their biological activities. For example, for alnumycin and the shunt product K115, antimicrobial acti...
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MDPI AG
2023-06-01
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| Series: | Antibiotics |
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| author | Leonie Sagurna Sascha Heinrich Lara-Sophie Kaufmann Christian Rückert-Reed Tobias Busche Alexander Wolf Jan Eickhoff Bert Klebl Jörn Kalinowski Julia E. Bandow |
| author_facet | Leonie Sagurna Sascha Heinrich Lara-Sophie Kaufmann Christian Rückert-Reed Tobias Busche Alexander Wolf Jan Eickhoff Bert Klebl Jörn Kalinowski Julia E. Bandow |
| author_sort | Leonie Sagurna |
| collection | DOAJ |
| description | Bacteria of the genus <i>Streptomyces</i> produce various specialized metabolites. Single biosynthetic gene clusters (BGCs) can give rise to different products that can vary in terms of their biological activities. For example, for alnumycin and the shunt product K115, antimicrobial activity was described, while no antimicrobial activity was detected for the shunt product 1,6-dihydro 8-propylanthraquinone. To investigate the antibacterial activity of 1,6-dihydro 8-propylanthraquinone, we produced alnumycin and 1,6-dihydro 8-propylanthraquinone from a <i>Streptomyces</i> isolate containing the alnumycin BGC. The strain was cultivated in liquid glycerol–nitrate–casein medium (GN), and both compounds were isolated using an activity and mass spectrometry-guided purification. The structures were validated via nuclear magnetic resonance (NMR) spectroscopy. A minimal inhibitory concentration (MIC) test revealed that 1,6-dihydro 8-propylanthraquinone exhibits antimicrobial activity against <i>E. coli</i> Δ<i>tolC</i>, <i>B. subtilis</i>, an <i>S. aureus</i> type strain, and a vancomycin intermediate-resistance <i>S. aureus</i> strain (VISA). Activity of 1,6-dihydro 8-propylanthraquinone against <i>E. coli</i> Δ<i>tolC</i> was approximately 10-fold higher than that of alnumycin. We were unable to confirm gyrase inhibition for either compound and believe that the modes of action of both compounds are worth reinvestigating. |
| first_indexed | 2024-03-11T01:22:57Z |
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| institution | Directory Open Access Journal |
| issn | 2079-6382 |
| language | English |
| last_indexed | 2024-03-11T01:22:57Z |
| publishDate | 2023-06-01 |
| publisher | MDPI AG |
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| series | Antibiotics |
| spelling | doaj.art-d75d62b0f362495da387306443d4ba5d2023-11-18T18:02:26ZengMDPI AGAntibiotics2079-63822023-06-01127111610.3390/antibiotics12071116Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a <i>Streptomyces</i> IsolateLeonie Sagurna0Sascha Heinrich1Lara-Sophie Kaufmann2Christian Rückert-Reed3Tobias Busche4Alexander Wolf5Jan Eickhoff6Bert Klebl7Jörn Kalinowski8Julia E. Bandow9Applied Microbiology, Faculty of Biology and Biotechnology, Ruhr University Bochum, 44780 Bochum, GermanyApplied Microbiology, Faculty of Biology and Biotechnology, Ruhr University Bochum, 44780 Bochum, GermanyApplied Microbiology, Faculty of Biology and Biotechnology, Ruhr University Bochum, 44780 Bochum, GermanyTechnology Platform Genomics, Center for Biotechnology, Bielefeld University, 33594 Bielefeld, GermanyTechnology Platform Genomics, Center for Biotechnology, Bielefeld University, 33594 Bielefeld, GermanyLead Discovery Center GmbH, 44227 Dortmund, GermanyLead Discovery Center GmbH, 44227 Dortmund, GermanyLead Discovery Center GmbH, 44227 Dortmund, GermanyTechnology Platform Genomics, Center for Biotechnology, Bielefeld University, 33594 Bielefeld, GermanyApplied Microbiology, Faculty of Biology and Biotechnology, Ruhr University Bochum, 44780 Bochum, GermanyBacteria of the genus <i>Streptomyces</i> produce various specialized metabolites. Single biosynthetic gene clusters (BGCs) can give rise to different products that can vary in terms of their biological activities. For example, for alnumycin and the shunt product K115, antimicrobial activity was described, while no antimicrobial activity was detected for the shunt product 1,6-dihydro 8-propylanthraquinone. To investigate the antibacterial activity of 1,6-dihydro 8-propylanthraquinone, we produced alnumycin and 1,6-dihydro 8-propylanthraquinone from a <i>Streptomyces</i> isolate containing the alnumycin BGC. The strain was cultivated in liquid glycerol–nitrate–casein medium (GN), and both compounds were isolated using an activity and mass spectrometry-guided purification. The structures were validated via nuclear magnetic resonance (NMR) spectroscopy. A minimal inhibitory concentration (MIC) test revealed that 1,6-dihydro 8-propylanthraquinone exhibits antimicrobial activity against <i>E. coli</i> Δ<i>tolC</i>, <i>B. subtilis</i>, an <i>S. aureus</i> type strain, and a vancomycin intermediate-resistance <i>S. aureus</i> strain (VISA). Activity of 1,6-dihydro 8-propylanthraquinone against <i>E. coli</i> Δ<i>tolC</i> was approximately 10-fold higher than that of alnumycin. We were unable to confirm gyrase inhibition for either compound and believe that the modes of action of both compounds are worth reinvestigating.https://www.mdpi.com/2079-6382/12/7/1116secondary metabolitesalnumycinbiosynthetic gene clustersanthraquinones<i>Streptomyces</i> |
| spellingShingle | Leonie Sagurna Sascha Heinrich Lara-Sophie Kaufmann Christian Rückert-Reed Tobias Busche Alexander Wolf Jan Eickhoff Bert Klebl Jörn Kalinowski Julia E. Bandow Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a <i>Streptomyces</i> Isolate Antibiotics secondary metabolites alnumycin biosynthetic gene clusters anthraquinones <i>Streptomyces</i> |
| title | Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a <i>Streptomyces</i> Isolate |
| title_full | Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a <i>Streptomyces</i> Isolate |
| title_fullStr | Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a <i>Streptomyces</i> Isolate |
| title_full_unstemmed | Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a <i>Streptomyces</i> Isolate |
| title_short | Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a <i>Streptomyces</i> Isolate |
| title_sort | characterization of the antibacterial activity of quinone based compounds originating from the alnumycin biosynthetic gene cluster of a i streptomyces i isolate |
| topic | secondary metabolites alnumycin biosynthetic gene clusters anthraquinones <i>Streptomyces</i> |
| url | https://www.mdpi.com/2079-6382/12/7/1116 |
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