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Isolation, Biosynthesis and Chemical Modifications of Rubterolones A–F: Rare Tropolone Alkaloids from Actinomadura sp. 5‐2
Author(s) -
Guo Huijuan,
Benndorf René,
Leichnitz Daniel,
Klassen Jonathan L.,
Vollmers John,
Görls Helmar,
Steinacker Matthias,
Weigel Christiane,
Dahse HansMartin,
Kaster AnneKristin,
de Beer Z. Wilhelm,
Poulsen Michael,
Beemelmanns Christine
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701005
Subject(s) - tropolone , chemistry , biosynthesis , isolation (microbiology) , stereochemistry , organic chemistry , biology , microbiology and biotechnology , enzyme
The discovery of six new, highly substituted tropolone alkaloids, rubterolones A–F, from Actinomadura sp. 5‐2, isolated from the gut of the fungus‐growing termite Macrotermes natalensis is reported. Rubterolones were identified by using fungus‐bacteria challenge assays and a HRMS‐based dereplication strategy, and characterised by NMR and HRMS analyses and by X‐ray crystallography. Feeding experiments and subsequent chemical derivatisation led to a first library of rubterolone derivatives (A–L). Genome sequencing and comparative analyses revealed their putative biosynthetic pathway, which was supported by feeding experiments. This study highlights how gut microbes can present a prolific source of secondary metabolites.