Enzymatic Formation of Rufoschweinitzin, a Binaphthalene from the Basidiomycete Cortinarius rufoolivaceus.
Chembiochem
; 21(10): 1423-1427, 2020 05 15.
Article
em En
| MEDLINE
| ID: mdl-32159919
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.
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MEDLINE
Assunto principal:
Ascomicetos
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Proteínas Fúngicas
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Sistema Enzimático do Citocromo P-450
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Cortinarius
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Policetídeos
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Naftalenos
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Naftóis
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article