Investigation of the metabolome of the ascomycete Annulohypoxylon truncatum led to the identification of novel oxygenated brasilane glycosides and the revision of the stereochemistry of the brasilane A octahydro-1H-indene core scaffold to trans. The bra biosynthetic gene cluster containing five genes (braA-braE) was identified and verified by heterologous expression experiments in Aspergillus oryzae demonstrating that BraC is a multifunctional P450 monooxygenase. In vitro studies of BraB revealed it to be a very rare fungal UDP-GlcNAc dependent N-acetylglucosamine transferase. UDP-glucose is also accepted as a donor, and a broad acceptor substrate tolerance for various primary and secondary alcohols was observed.
biosynthesis, P450 monooxygenase, brasilane terpene glycosides, Annulohypoxylon truncatum, N-acetylglucosamine transferase
NCBI PubMed ID: 32936132Publication DOI: 10.1039/d0cc03950kJournal NLM ID: 9610838Publisher: Cambridge: Royal Society of Chemistry
Correspondence: eric.kuhnert@oci.uni-hannover.de
Institutions: Institute for Organic Chemistry and Centre for Biomolecular Drug Research (BMWZ), Leibniz University Hannover, Hannover, Germany, Department Microbial Drugs, Helmholtz Centre for Infection Research (HZI), Braunschweig, German
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, cell growth, HPLC-MS, enzymatic assay, cytotoxicity assay, gene expression, antimicrobial assay, HPLC-DAD
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