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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.

Author information

1
Natural Products Discovery Group, Department of Chemistry and Biochemistry, Stephenson Life Sciences Research Center, University of Oklahoma, Norman, OK 73019, USA.

Abstract

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.

PMID:
22281750
DOI:
10.1039/c2ob06856g
[Indexed for MEDLINE]

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