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

Authors
  • Okoth, Dorothy A.1,
  • Hug, Joachim J.1,
  • Garcia, Ronald1,
  • Spröer, Cathrin
  • Overmann, Jörg
  • Müller, Rolf1,
  • 1 (R.G.)
Type
Published Article
Journal
Molecules
Publisher
MDPI AG
Publication Date
Jun 09, 2020
Volume
25
Issue
11
Identifiers
DOI: 10.3390/molecules25112676
PMID: 32527018
PMCID: PMC7321100
Source
PubMed Central
Keywords
Disciplines
  • Article
License
Green

Abstract

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.

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