Isolation, Biosynthesis and Chemical Modifications of Rubterolones A-F: Rare Tropolone Alkaloids from Actinomadura sp. 5-2.

Guo H, Benndorf R, Leichnitz D, Klassen JL, Vollmers J, Görls H, Steinacker M, Weigel C, Dahse HM, Kaster AK, de Beer ZW, Poulsen M, Beemelmanns C (2017) Isolation, Biosynthesis and Chemical Modifications of Rubterolones A-F: Rare Tropolone Alkaloids from Actinomadura sp. 5-2. Chemistry , PubMed

ILRS Authors

René Benndorf

Projects

Investigation of secondary metabolites from insect-associated microbes and their contribution to insect homeostasis and defense
Details

Abstract

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.

Identifier

doi: 10.1002/chem.201701005 PMID: 28463423

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