Dataset Information

Enzymatic Formation of Rufoschweinitzin, a Binaphthalene from the Basidiomycete Cortinarius rufoolivaceus.

ABSTRACT: Dimeric polyketides are widespread fungal secondary metabolites. They occur in both ascomycetes and basidiomycetes and, therefore, across fungal phyla. Here we report the isolation of a new binaphthalene, named rufoschweinitzin, from the basidiomycete Cortinarius rufoolivaceus. Rufoschweinitzin consists of two symmetrically 4,4'-coupled torachrysone-8-O-methyl ether moieties. Furthermore, we have identified a binaphthalene biosynthetic gene cluster in an unrelated fungus, the ascomycete Xylaria schweinitzii. Heterologous expression of the encoded cytochrome P450 enzyme verified its coupling activity: dimerization of torachrysone-8-O-methyl ether led to the formation of rufoschweinitzin alongside a hitherto unknown regioisomer, now named alloschweinitzin. We have thus demonstrated enzymatic formation of the basidiomycete's metabolite rufoschweinitzin and made the regiochemistry of alloschweinitzin accessible with an ascomycete-derived enzyme.

SUBMITTER: Thiele W

PROVIDER: S-EPMC7384108 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Enzymatic Formation of Rufoschweinitzin, a Binaphthalene from the Basidiomycete Cortinarius rufoolivaceus.

Thiele Wiebke W Froede Rita R Steglich Wolfgang W Müller Michael M

Chembiochem : a European journal of chemical biology 20200311 10

Dimeric polyketides are widespread fungal secondary metabolites. They occur in both ascomycetes and basidiomycetes and, therefore, across fungal phyla. Here we report the isolation of a new binaphthalene, named rufoschweinitzin, from the basidiomycete Cortinarius rufoolivaceus. Rufoschweinitzin consists of two symmetrically 4,4'-coupled torachrysone-8-O-methyl ether moieties. Furthermore, we have identified a binaphthalene biosynthetic gene cluster in an unrelated fungus, the ascomycete Xylaria ...[more]

PMID: 32159919

Similar Datasets

Project description:Biorefining of renewable feedstocks is one of the most promising routes to replace fossil-based products. Since many common fermentation hosts, such as Saccharomyces cerevisiae, are naturally unable to convert many component plant cell wall polysaccharides, the identification of organisms with broad catabolism capabilities represents an opportunity to expand the range of substrates used in fermentation biorefinery approaches. The red basidiomycete yeast Rhodosporidium toruloides is a promising and robust host for lipid- and terpene-derived chemicals. Previous studies demonstrated assimilation of a range of substrates, from C5/C6 sugars to aromatic molecules similar to lignin monomers. In the current study, we analyzed the potential of R. toruloides to assimilate d-galacturonic acid, a major sugar in many pectin-rich agricultural waste streams, including sugar beet pulp and citrus peels. d-Galacturonic acid is not a preferred substrate for many fungi, but its metabolism was found to be on par with those of d-glucose and d-xylose in R. toruloides A genomewide analysis by combined transcriptome sequencing (RNA-seq) and RB-TDNA-seq revealed those genes with high relevance for fitness on d-galacturonic acid. While R. toruloides was found to utilize the nonphosphorylative catabolic pathway known from ascomycetes, the maximal velocities of several enzymes exceeded those previously reported. In addition, an efficient downstream glycerol catabolism and a novel transcription factor were found to be important for d-galacturonic acid utilization. These results set the basis for use of R. toruloides as a potential host for pectin-rich waste conversions and demonstrate its suitability as a model for metabolic studies with basidiomycetes.IMPORTANCE The switch from the traditional fossil-based industry to a green and sustainable bioeconomy demands the complete utilization of renewable feedstocks. Many currently used bioconversion hosts are unable to utilize major components of plant biomass, warranting the identification of microorganisms with broader catabolic capacity and characterization of their unique biochemical pathways. d-Galacturonic acid is a plant component of bioconversion interest and is the major backbone sugar of pectin, a plant cell wall polysaccharide abundant in soft and young plant tissues. The red basidiomycete and oleaginous yeast Rhodosporidium toruloides has been previously shown to utilize a range of sugars and aromatic molecules. Using state-of-the-art functional genomic methods and physiological and biochemical assays, we elucidated the molecular basis underlying the efficient metabolism of d-galacturonic acid. This study identified an efficient pathway for uronic acid conversion to guide future engineering efforts and represents the first detailed metabolic analysis of pectin metabolism in a basidiomycete fungus.

Dataset Information

Enzymatic Formation of Rufoschweinitzin, a Binaphthalene from the Basidiomycete Cortinarius rufoolivaceus.

Publications

Enzymatic Formation of Rufoschweinitzin, a Binaphthalene from the Basidiomycete Cortinarius rufoolivaceus.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets