Planta Med 2018; 84(18): 1363-1371
DOI: 10.1055/a-0653-7451
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Antimicrobial Dialkylresorcins from Marine-Derived Microorganisms: Insights into Their Mode of Action and Putative Ecological Relevance

Henrik Harms
1   Institute for Pharmaceutical Biology, University of Bonn, Germany
2   German Center for Infection Research (DZIF) Partner Site Cologne/Bonn, Germany
,
Anna Klöckner
2   German Center for Infection Research (DZIF) Partner Site Cologne/Bonn, Germany
3   Institute for Pharmaceutical Microbiology, University of Bonn, Germany
,
Jan Schrör
1   Institute for Pharmaceutical Biology, University of Bonn, Germany
,
Michaele Josten
2   German Center for Infection Research (DZIF) Partner Site Cologne/Bonn, Germany
3   Institute for Pharmaceutical Microbiology, University of Bonn, Germany
4   Institute of Medical Microbiology, Immunology and Parasitology, University of Bonn, Germany
,
Stefan Kehraus
1   Institute for Pharmaceutical Biology, University of Bonn, Germany
,
Max Crüsemann
1   Institute for Pharmaceutical Biology, University of Bonn, Germany
,
Wiebke Hanke
1   Institute for Pharmaceutical Biology, University of Bonn, Germany
,
Tanja Schneider
2   German Center for Infection Research (DZIF) Partner Site Cologne/Bonn, Germany
3   Institute for Pharmaceutical Microbiology, University of Bonn, Germany
,
Till F. Schäberle
2   German Center for Infection Research (DZIF) Partner Site Cologne/Bonn, Germany
5   Institute for Insect Biotechnology, Justus Liebig University Giessen, Germany
,
Gabriele M. König
1   Institute for Pharmaceutical Biology, University of Bonn, Germany
2   German Center for Infection Research (DZIF) Partner Site Cologne/Bonn, Germany
› Author Affiliations
Further Information

Publication History

received 27 April 2018
revised 21 June 2018

accepted 26 June 2018

Publication Date:
10 July 2018 (online)

Abstract

Zobellia galactanivorans has been reported as a seaweed-associated or marine-derived species with largely unknown secondary metabolites. The combination of bioinformatic analysis and MS- and bioactivity guided separation led to the isolation of a new antibiotically active dialkylresorcin from the marine bacterium Z. galactanivorans. The antibiotic profile of the new dialkylresorcin zobelliphol (1) was investigated and compared with related and naturally occurring dialkyresorcins (i.e., stemphol (2) and 4-butyl-3,5-dihydroxybenzoic acid (3)) from the marine-derived fungus Stemphylium globuliferum. Bacterial reporter strain assays provided insights into the mode of action of this antibiotic compound class. We identified an interference with bacterial DNA biosynthesis for the dialkylresorcin derivative 1. In addition, the putative biosynthetic gene cluster corresponding to production of 1 was identified and a biosynthetic hypothesis was deduced.

Supporting Information

 
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