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Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a Streptomyces Isolate

Bacteria of the genus Streptomyces 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,...

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Autores principales: Sagurna, Leonie, Heinrich, Sascha, Kaufmann, Lara-Sophie, Rückert-Reed, Christian, Busche, Tobias, Wolf, Alexander, Eickhoff, Jan, Klebl, Bert, Kalinowski, Jörn, Bandow, Julia E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10376017/
https://www.ncbi.nlm.nih.gov/pubmed/37508212
http://dx.doi.org/10.3390/antibiotics12071116
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author Sagurna, Leonie
Heinrich, Sascha
Kaufmann, Lara-Sophie
Rückert-Reed, Christian
Busche, Tobias
Wolf, Alexander
Eickhoff, Jan
Klebl, Bert
Kalinowski, Jörn
Bandow, Julia E.
author_facet Sagurna, Leonie
Heinrich, Sascha
Kaufmann, Lara-Sophie
Rückert-Reed, Christian
Busche, Tobias
Wolf, Alexander
Eickhoff, Jan
Klebl, Bert
Kalinowski, Jörn
Bandow, Julia E.
author_sort Sagurna, Leonie
collection PubMed
description Bacteria of the genus Streptomyces 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 Streptomyces 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 E. coli ΔtolC, B. subtilis, an S. aureus type strain, and a vancomycin intermediate-resistance S. aureus strain (VISA). Activity of 1,6-dihydro 8-propylanthraquinone against E. coli ΔtolC 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.
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spelling pubmed-103760172023-07-29 Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a Streptomyces Isolate Sagurna, Leonie Heinrich, Sascha Kaufmann, Lara-Sophie Rückert-Reed, Christian Busche, Tobias Wolf, Alexander Eickhoff, Jan Klebl, Bert Kalinowski, Jörn Bandow, Julia E. Antibiotics (Basel) Article Bacteria of the genus Streptomyces 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 Streptomyces 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 E. coli ΔtolC, B. subtilis, an S. aureus type strain, and a vancomycin intermediate-resistance S. aureus strain (VISA). Activity of 1,6-dihydro 8-propylanthraquinone against E. coli ΔtolC 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. MDPI 2023-06-28 /pmc/articles/PMC10376017/ /pubmed/37508212 http://dx.doi.org/10.3390/antibiotics12071116 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Sagurna, Leonie
Heinrich, Sascha
Kaufmann, Lara-Sophie
Rückert-Reed, Christian
Busche, Tobias
Wolf, Alexander
Eickhoff, Jan
Klebl, Bert
Kalinowski, Jörn
Bandow, Julia E.
Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a Streptomyces Isolate
title Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a Streptomyces Isolate
title_full Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a Streptomyces Isolate
title_fullStr Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a Streptomyces Isolate
title_full_unstemmed Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a Streptomyces Isolate
title_short Characterization of the Antibacterial Activity of Quinone-Based Compounds Originating from the Alnumycin Biosynthetic Gene Cluster of a Streptomyces Isolate
title_sort characterization of the antibacterial activity of quinone-based compounds originating from the alnumycin biosynthetic gene cluster of a streptomyces isolate
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10376017/
https://www.ncbi.nlm.nih.gov/pubmed/37508212
http://dx.doi.org/10.3390/antibiotics12071116
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