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

Thiele, Wiebke; Froede, Rita; Steglich, Wolfgang und Müller, Michael (2020): Enzymatic Formation of Rufoschweinitzin, a Binaphthalene from the Basidiomycete Cortinarius rufoolivaceus. In: Chembiochem, Bd. 21, Nr. 10: S. 1423-1427

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.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1439-4227
• Sprache: Englisch