Molecular and Chemical Characterization of the Biosynthesis of the 6-MSA-Derived Meroterpenoid Yanuthone D in Aspergillus niger.

Dorte Koefoed Holm, Lene Maj Petersen, Andreas Klitgaard, Peter Boldsen Knudsen, Zofia Dorota Jarczynska, Kristian Fog Nielsen, Charlotte Held Gotfredsen, Thomas Ostenfeld Larsen, Uffe Hasbro Mortensen

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Abstract

Secondary metabolites in filamentous fungi constitute a rich source of bioactive molecules. We have deduced the genetic and biosynthetic pathway of the antibiotic yanuthone D from Aspergillus niger. Our analyses show that yanuthone D is a meroterpenoid derived from the polyketide 6-methylsalicylic acid (6-MSA). Yanuthone D formation depends on a cluster composed of ten genes including yanA and yanI, which encode a 6-MSA polyketide synthase and a previously undescribed O-mevalon transferase, respectively. In addition, several branching points in the pathway were discovered, revealing five yanuthones (F, G, H, I, and J). Furthermore, we have identified another compound (yanuthone X1) that defines a class of yanuthones that depend on several enzymatic activities encoded by genes in the yan cluster but that are not derived from 6-MSA.
Original languageEnglish
JournalChemistry & Biology
Volume21
Issue number4
Pages (from-to)519-529
Number of pages11
ISSN1074-5521
DOIs
Publication statusPublished - 2014

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