Ralfuranone Is Produced by an Alternative Aryl-Substituted γ-Lactone Biosynthetic Route in Ralstonia solanacearum.

Basic Information

ID: ALA3351437

Journal: J Nat Prod

Title: Ralfuranone Is Produced by an Alternative Aryl-Substituted γ-Lactone Biosynthetic Route in Ralstonia solanacearum.

Authors: Pauly J, Nett M, Hoffmeister D.

Abstract: The aryl-substituted γ-lactones ralfuranones A and B were isolated after feeding L-[1-(13)C]-phenylalanine to a liquid culture of the plant pathogenic bacterium Ralstonia solanacearum. (13)C NMR analysis demonstrated specific enrichment of the label at position 2 of the γ-lactone. This labeling pattern is consistent with a biosynthetic mechanism that includes direct cyclization of two monomeric phenylpyruvate precursors into an α,β-substituted lactone, but incompatible with a terphenylquinone intermediate. As the latter was shown as an intermediate in allantofuranone biosynthesis, we conclude that aryl-substituted γ-lactones can be assembled via divergent biosynthetic routes.

CiteXplore: 25033087

DOI: 10.1021/np500263r

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