Nicrophorusamides A and B, antibacterial chlorinated cyclic peptides from a gut bacterium of the carrion beetle nicrophorus concolor

Abstract

Nicrophorusamides A and B (1 and 2) were discovered from a rare actinomycete, Microbacterium sp., which was isolated from the gut of the carrion beetle Nicrophorus concolor. The structures of the nicrophorusamides were established as new chlorinated cyclic hexapeptides bearing uncommon amino acid units mainly based on 1D and 2D NMR spectroscopic analysis. The absolute configurations of the amino acid residues S-chloro-L-tryptophan, D-threo-beta-hydroxyasparagine/D-asparagine, L-omithine, L-allo-isoleucine, D-leucine, and D-valine were determined using Marfey's method and chemical derivatization with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate followed by LC/MS analysis. Nicrophorusamide A (1) showed antibacterial activity against several Gram-positive bacteria.