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

ORCID
0009-0000-0660-791X
Affiliation
Applied Microbiology, Faculty of Biology and Biotechnology, Ruhr University Bochum, 44780 Bochum, Germany;(L.S.);(S.H.);(L.-S.K.)
Sagurna, Leonie;
ORCID
0000-0003-2193-5422
Affiliation
Applied Microbiology, Faculty of Biology and Biotechnology, Ruhr University Bochum, 44780 Bochum, Germany;(L.S.);(S.H.);(L.-S.K.)
Heinrich, Sascha;
Affiliation
Applied Microbiology, Faculty of Biology and Biotechnology, Ruhr University Bochum, 44780 Bochum, Germany;(L.S.);(S.H.);(L.-S.K.)
Kaufmann, Lara-Sophie;
ORCID
0000-0002-9722-4435
Affiliation
Technology Platform Genomics, Center for Biotechnology, Bielefeld University, 33594 Bielefeld, Germany;(C.R.-R.);(T.B.);(J.K.)
Rückert-Reed, Christian;
Affiliation
Technology Platform Genomics, Center for Biotechnology, Bielefeld University, 33594 Bielefeld, Germany;(C.R.-R.);(T.B.);(J.K.)
Busche, Tobias;
Affiliation
Lead Discovery Center GmbH, 44227 Dortmund, Germany;(A.W.);(J.E.);(B.K.)
Wolf, Alexander;
ORCID
0000-0002-5537-438X
Affiliation
Lead Discovery Center GmbH, 44227 Dortmund, Germany;(A.W.);(J.E.);(B.K.)
Eickhoff, Jan;
Affiliation
Lead Discovery Center GmbH, 44227 Dortmund, Germany;(A.W.);(J.E.);(B.K.)
Klebl, Bert;
ORCID
0000-0002-9052-1998
Affiliation
Technology Platform Genomics, Center for Biotechnology, Bielefeld University, 33594 Bielefeld, Germany;(C.R.-R.);(T.B.);(J.K.)
Kalinowski, Jörn;
Affiliation
Applied Microbiology, Faculty of Biology and Biotechnology, Ruhr University Bochum, 44780 Bochum, Germany;(L.S.);(S.H.);(L.-S.K.)
Bandow, Julia E.

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 Δ tolC , 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 Δ tolC 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.

Category

Editor:
Franco, Carlos M.
Published in:
Antibiotics  
Vol. 12, No. 7 (28.06.2023)
Volume:
12
No.:
7
Date Issued:
28.06.2023
DOI:
10.3390/antibiotics12071116
Language:
English
Type of Resource:
Text
Keywords:
secondary metabolites; alnumycin; biosynthetic gene clusters; anthraquinones; Streptomyces
Subject of DNB:
610 Medical sciences Medicine

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