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Org Biomol Chem. 2012 Mar 14;10(10):2044-50. doi: 10.1039/c2ob06856g. Epub 2012 Jan 27.

Fungal biofilm inhibitors from a human oral microbiome-derived bacterium.

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Natural Products Discovery Group, Department of Chemistry and Biochemistry, Stephenson Life Sciences Research Center, University of Oklahoma, Norman, OK 73019, USA.


The human mouth is home to a rich assortment of native and transient microorganisms. One of the commonly encountered bacterial species, Streptococcus mutans, was shown to generate the novel hybrid polyketide-nonribosomal peptide metabolite mutanobactin A (1). We have characterized three new analogues, mutanobactins B-D (2-4), and subjected these compounds to further biomedical evaluation. Metabolites 1, 2, and 4 were found to inhibit biofilm formation by the fungal oral-pathogen Candida albicans. Compound 4 was the most potent metabolite with an IC(50) value of 5.3 ± 0.9 μM. Using a combination of Marfey's analysis, proton spin-spin coupling, and (1)H-(1)H NOESY data, we proposed absolute configuration assignments in toto for 1-3 and a partial assignment for 4. In addition, feeding studies with isotopically labeled precursor metabolites (acetate and amino acids) have helped to determine the biosynthetic origins of this unique natural product family.

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