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Phallusialides A–E, Pyrrole-Derived Alkaloids Discovered from a Marine-Derived Micromonospora sp. Bacterium Using MS-Based Metabolomics Approaches

Fan Zhang, Doug R. Braun, Shaurya Chanana, Scott R. Rajski, Tim S. Bugni
Journal of natural products 2019 v.82 no.12 pp. 3432-3439
Escherichia coli, Micromonospora, alkaloids, antibacterial properties, bacteria, liquid chromatography, metabolomics, methicillin-resistant Staphylococcus aureus, minimum inhibitory concentration, nuclear magnetic resonance spectroscopy, spectral analysis, tandem mass spectrometry
Integrating MS-based metabolomics approaches, LC–MS–PCA and molecular networking enabled the targeted isolation of five new pyrrole-derived alkaloids, phallusialides A–E (1–5), from a marine-derived Micromonospora sp. bacterium. The structures of 1–5 were elucidated by analysis of their HRMS, MS/MS, and NMR spectroscopic data. The absolute configuration of phallusialide A (1) was determined on the basis of comparisons of experimental and theoretically calculated ECD spectra. Compounds 1 and 2 exhibited antibacterial activity against methicillin resistant S. aureus (MRSA) and E. coli, with MIC values of 32 and 64 μg/mL, respectively, whereas 3–5 showed no antibacterial activity even at 256 μg/mL, yielding important SAR insights for this class of compounds.