Ralfuranone is produced by an alternative aryl-substituted γ-lactone biosynthetic route in Ralstonia solanacearum.

Pauly J, Nett M, Hoffmeister D (2014) Ralfuranone is produced by an alternative aryl-substituted γ-lactone biosynthetic route in Ralstonia solanacearum. J Nat Prod 77, 1967-1971. PubMed

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.

Involved Units and Groups
Identifier

PMID: 25033087