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Bacillimidazoles A−F, Imidazolium-Containing Compounds Isolated from a Marine Bacillus

Pharmaceutical Sciences Division, University of Wisconsin-Madison, 777 Highland Ave, Madison, WI 53705, USA
Harvard Medical School, Harvard University, 240 Longwood Ave, Boston, MA 02115, USA
Department of Bacteriology, University of Wisconsin-Madison, 1550 Linden Ave, Madison, WI 53706, USA
Bruker Daltonics, Bruker Scientific LLC., 40 Manning Rd, Billerica, MA 01821, USA
The Small Molecule Screening Facility (SMSF), University of Wisconsin-Madison, 600 Highland Ave, Madison, WI 53792, USA
Author to whom correspondence should be addressed.
Current addresses: Merck & Co. LLC., 126 E. Lincoln Ave, Rahway, NJ 07065, USA.
These authors contributed equally to this work.
Current addresses: Departments of Chemistry & Microbial Pathogenesis, Institute of Biomolecular Design & Discovery, Yale University, West Haven, CT 06516, USA.
Current address: LOEWE Centre for Translational Biodiversity Genomics, Institute of Molecular Bio-Science, Goethe University Frankfurt, 60487 Frankfurt am Main, Germany.
Current address: Department of Plant Pathology, Wisconsin Institute for Discovery, University of Wisconsin-Madison, 425 G Henry Mall, Madison, WI 53706, USA.
Current address: Metabolon Inc., 617 Davis Drive. Suite 100, Morrisville, NC 27560, USA.
Academic Editor: Asunción Barbero
Mar. Drugs 2022, 20(1), 43;
Received: 6 December 2021 / Revised: 22 December 2021 / Accepted: 22 December 2021 / Published: 1 January 2022
(This article belongs to the Special Issue Heterocyclic Compounds from Marine Organisms)
Chemical investigations of a marine sponge-associated Bacillus revealed six new imidazolium-containing compounds, bacillimidazoles A–F (16). 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 16. 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 16 result from a fascinating intersection of primary and secondary metabolic pathways in Bacillus sp. WMMC1349. Antimicrobial assays revealed that, of 16, only compound six displayed discernible antibacterial activity, despite the close structural similarities shared by all six natural products. View Full-Text
Keywords: marine-derived Bacillus; antibacterial; biosynthetic gene cluster; isotopic enrichment; heterocycles; imidazolium marine-derived Bacillus; antibacterial; biosynthetic gene cluster; isotopic enrichment; heterocycles; imidazolium
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MDPI and ACS Style

Yan, J.-X.; Wu, Q.; Helfrich, E.J.N.; Chevrette, M.G.; Braun, D.R.; Heyman, H.; Ananiev, G.E.; Rajski, S.R.; Currie, C.R.; Clardy, J.; Bugni, T.S. Bacillimidazoles A−F, Imidazolium-Containing Compounds Isolated from a Marine Bacillus. Mar. Drugs 2022, 20, 43.

AMA Style

Yan J-X, Wu Q, Helfrich EJN, Chevrette MG, Braun DR, Heyman H, Ananiev GE, Rajski SR, Currie CR, Clardy J, Bugni TS. Bacillimidazoles A−F, Imidazolium-Containing Compounds Isolated from a Marine Bacillus. Marine Drugs. 2022; 20(1):43.

Chicago/Turabian Style

Yan, Jia-Xuan, Qihao Wu, Eric J.N. Helfrich, Marc G. Chevrette, Doug R. Braun, Heino Heyman, Gene E. Ananiev, Scott R. Rajski, Cameron R. Currie, Jon Clardy, and Tim S. Bugni. 2022. "Bacillimidazoles A−F, Imidazolium-Containing Compounds Isolated from a Marine Bacillus" Marine Drugs 20, no. 1: 43.

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