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

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• 作者：Julia Pauly ; Markus Nett ; Dirk Hoffmeister
• 刊名：Journal of Natural Products
• 出版年：2014
• 出版时间：August 22, 2014
• 年：2014
• 卷：77
• 期：8
• 页码：1967-1971
• 全文大小：285K
• ISSN：1520-6025

文摘

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