2,4,5-Tribromo-1H-imidazole in the egg masses of three muricid molluscs.
From analysis by gas chromatography/mass spectrometry (GC/MS), the presence of either 2,4,5-tribromo-1H-imidazole (1) or 3,4,5-tribromo-1H-pyrazole (2) was tentatively identified in lipophilic extracts from the egg masses of three muricid molluscs. Synthesis of these compounds, followed by comparison of the GC retention times and fragmentation patterns from electron impact MS, with those of the natural products, indicated that it was 2,4,5-tribromo-1H-imidazole rather than the pyrazole. This imidazole is likely to be responsible for some of the antimicrobial activity observed in the egg extracts. This is the first report of this compound from a natural source.
Benkendorff
Kirsten
K
Department of Chemistry and Institute for Biomolecular Science, University of Wollongong, NSW, Australia, 2522. kirsten.benkendorff@flinders.edu.au
Pillai
Ramesh
R
Bremner
John B
JB
D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology*; D004926:Escherichia coli / Q000187:drug effects; D008401:Gas Chromatography-Mass Spectrometry; D007093:Imidazoles / Q000737:chemistry* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008974:Mollusca / Q000737:chemistry*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects
D000890:Anti-Infective Agents; D007093:Imidazoles; C045039:2,4,5-tribromoimidazole