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Structures and biosynthesis of the pyridinopyrones, polyenepyrones from a marine-derived Streptomyces species.

ABSTRACT: Three polyenylpyrone metabolites, pyridinopyrones A to C (1-3), have been isolated from the culture broth of a marine-derived Streptomyces sp., strain CNQ-301. The structures of the pyridinopyrones were assigned on the basis of chemical modification and combined spectroscopic methods, focusing on interpretation of 1D and 2D NMR data. Pyridinopyrones B and C (2, 3), examined as an inseparable mixture of methyl positional isomers, were ultimately defined by hydrogenation and NMR analysis of a saturated derivative. The biosynthesis of these metabolites was defined by the incorporation of stable isotope-labeled precursors, revealing that the biosynthetic starter unit is nicotinic acid, while the polyene chain and pendant methyl groups are acetate- and methionine-derived, respectively.

SUBMITTER: Fukuda T

PROVIDER: S-EPMC3163021 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Structures and biosynthesis of the pyridinopyrones, polyenepyrones from a marine-derived Streptomyces species.

Fukuda Takashi T Miller Eric D ED Clark Benjamin R BR Alnauman Ali A Murphy Cormac D CD Jensen Paul R PR Fenical William W

Journal of natural products 20110713 8

Three polyenylpyrone metabolites, pyridinopyrones A to C (1-3), have been isolated from the culture broth of a marine-derived Streptomyces sp., strain CNQ-301. The structures of the pyridinopyrones were assigned on the basis of chemical modification and combined spectroscopic methods, focusing on interpretation of 1D and 2D NMR data. Pyridinopyrones B and C (2, 3), examined as an inseparable mixture of methyl positional isomers, were ultimately defined by hydrogenation and NMR analysis of a satu ...[more]

PMID: 21751787

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