biostudies-literatureYan JXSwiss National Science FoundationNIAID NIH HHSNational Institute of HealthUnited States Department of AgricultureUniversity of Wisconsin-MadisonNational Institutes of HealthNIH HHSNational Science Foundation43https://www.ebi.ac.uk/biostudies/studies/S-EPMC8779896biostudies-literatureUnknown20(1)Chemical investigations of a marine sponge-associated <i>Bacillus</i> revealed six new imidazolium-containing compounds, bacillimidazoles A-F (<b>1</b>-<b>6</b>). 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 <b>1</b>-<b>6</b>. 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 <b>1</b>-<b>6</b> result from a fascinating intersection of primary and secondary metabMarine drugsBacillimidazoles A-F, Imidazolium-Containing Compounds Isolated from a Marine <i>Bacillus</i>.PMC8779896multiple funds through School of Pharmacy & the Graduate Schoolmultiple funds through School of Pharmacy &amp; the Graduate SchoolRR02781Postdoctoral Mobility FellowshipOIA-9977484unknownU19AI141720DMB-8415048U19AI109673BIR-9214394U19 AI109673RR08438P41GM103399R01AT009874U19 AI142720Yan JXAnaniev GEHelfrich EJNClardy JChevrette MGHeyman HWu QCurrie CRBugni TSBraun DRRajski SRfalseBacillimidazoles A-F, Imidazolium-Containing Compounds Isolated from a Marine <i>Bacillus</i>.Chemical investigations of a marine sponge-associated <i>Bacillus</i> revealed six new imidazolium-containing compounds, bacillimidazoles A-F (<b>1</b>-<b>6</b>). 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 <b>1</b>-<b>6</b>. 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 <b>1</b>-<b>6</b> result from a fascinating intersection of primary and secondary metab2022-01-01T00:00:00Z2022 Jan2026-05-02T03:12:43.672Z2022-02-11T16:19:08.665ZS-EPMC87798963504989810.3390/md20010043