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Pyonitrins A-D: Chimeric Natural Products Produced by . | LitMetric

Pyonitrins A-D: Chimeric Natural Products Produced by .

J Am Chem Soc

Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 240 Longwood Avenue , Boston , Massachusetts 02115 , United States.

Published: October 2019

AI Article Synopsis

Article Abstract

Bacterial symbionts frequently provide chemical defenses for their hosts, and such systems can provide discovery pathways to new antifungals and structurally intriguing metabolites. This report describes a small family of naturally occurring small molecules with chimeric structures and a mixed biosynthesis that features an unexpected but key nonenzymatic step. An insect-associated strain's activity in an murine candidiasis assay led to the discovery of a family of highly hydrogen-deficient metabolites. Bioactivity- and mass-guided fractionation led to the pyonitrins, highly complex aromatic metabolites in which 10 of the 20 carbons are quaternary, and 7 of them are contiguous. The genome revealed that the production of the pyonitrins is the result of a spontaneous reaction between biosynthetic intermediates of two well-studied metabolites, pyochelin and pyrrolnitrin. The combined discovery of the pyonitrins and identification of the responsible biosynthetic gene clusters revealed an unexpected biosynthetic route that would have prevented the discovery of these metabolites by bioinformatic analysis alone.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6823628PMC
http://dx.doi.org/10.1021/jacs.9b09739DOI Listing

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