Abstract
Chemical investigations of a marine sponge-associated Bacillus revealed six new imidazolium-containing compounds, bacillimidazoles A–F (1–6). Previous reports of related imidazolium-containing natural products are rare. Initially unveiled by timsTOF (trapped ion mobility spectrometry) MS data, extensive HRMS and 1D and 2D NMR analyses enabled the structural elucidation of 1–6. In addition, a plausible biosynthetic pathway to bacillimidazoles is proposed based on isotopic labeling experiments and invokes the highly reactive glycolytic adduct 2,3-butanedione. Combined, the results of structure elucidation efforts, isotopic labeling studies and bioinformatics suggest that 1–6 result from a fascinating intersection of primary and secondary metabolic pathways in Bacillus sp. WMMC1349. Antimicrobial assays revealed that, of 1–6, only compound six displayed discernible antibacterial activity, despite the close structural similarities shared by all six natural products.
Highlights
[19], we developed a natural streamlined discovery platform that inassociated bacteria
[19], we developed a streamlined discovery platform that includes strain cludes strain prioritization by metabolomics
WMMC1349 represent the discovery of a new class of marine-derived heterocyclic natural products
Summary
Heterocyclic scaffolds are commonly encountered in natural products isolated from both terrestrial and marine organisms [1,2,3,4]. Their vast structural diversity, drug-like features, and biological properties have inspired both intensive efforts to discover new heterocyclic compounds, as well as imaginative total syntheses [4]. Nitrogen-containing heterocycles, such as pyrroles, imidazoles, oxazoles, pyridines, and quinolones, exhibit a diverse array of biological activities; these include, but are by no means limited to, antibacterial [5], antifungal [6], and anticancer [7] activities.
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