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Article

2-Hydroxysorangiadenosine: Structure and Biosynthesis of a Myxobacterial Sesquiterpene–Nucleoside

1
Department Microbial Natural Products, Helmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI) and Department of Pharmacy, Saarland University, Campus E8 1, 66123 Saarbrücken, Germany
2
German Center for Infection Research (DZIF), Partner Site Hannover-Braunschweig, 38124 Braunschweig, Germany
3
Leibniz Institute DSMZ-German Collection of Microorganisms and Cell Cultures, 38124 Braunschweig, Germany
*
Author to whom correspondence should be addressed.
These authors contributed equally.
Molecules 2020, 25(11), 2676; https://doi.org/10.3390/molecules25112676
Received: 20 May 2020 / Revised: 5 June 2020 / Accepted: 5 June 2020 / Published: 9 June 2020
Myxobacteria represent an under-investigated source for biologically active natural products featuring intriguing structural moieties with potential applications, e.g., in the pharmaceutical industry. Sorangiadenosine and the here-discovered 2-hydroxysorangiadenosine are myxobacterial sesquiterpene–nucleosides with an unusual structural moiety, a bicyclic eudesmane-type sesquiterpene. As the biosynthesis of these rare terpene–nucleoside hybrid natural products remains elusive, we investigated secondary metabolomes and genomes of several 2-hydroxysorangiadenosine-producing myxobacteria. We report the isolation and full structure elucidation of 2-hydroxysorangiadenosine and its cytotoxic and antibiotic activities and propose a biosynthetic pathway in the myxobacterium Vitiosangium cumulatum MCy10943T. View Full-Text
Keywords: myxobacteria; terpene–nucleoside; biosynthesis; antibiotics; sorangiadenosine; 2-hydroxysorangiadenosine; secondary metabolites; genome-mining; antibiotics; natural products discovery myxobacteria; terpene–nucleoside; biosynthesis; antibiotics; sorangiadenosine; 2-hydroxysorangiadenosine; secondary metabolites; genome-mining; antibiotics; natural products discovery
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MDPI and ACS Style

Okoth, D.A.; Hug, J.J.; Garcia, R.; Spröer, C.; Overmann, J.; Müller, R. 2-Hydroxysorangiadenosine: Structure and Biosynthesis of a Myxobacterial Sesquiterpene–Nucleoside. Molecules 2020, 25, 2676. https://doi.org/10.3390/molecules25112676

AMA Style

Okoth DA, Hug JJ, Garcia R, Spröer C, Overmann J, Müller R. 2-Hydroxysorangiadenosine: Structure and Biosynthesis of a Myxobacterial Sesquiterpene–Nucleoside. Molecules. 2020; 25(11):2676. https://doi.org/10.3390/molecules25112676

Chicago/Turabian Style

Okoth, Dorothy A., Joachim J. Hug, Ronald Garcia, Cathrin Spröer, Jörg Overmann, and Rolf Müller. 2020. "2-Hydroxysorangiadenosine: Structure and Biosynthesis of a Myxobacterial Sesquiterpene–Nucleoside" Molecules 25, no. 11: 2676. https://doi.org/10.3390/molecules25112676

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