2,4,5-Tribromo-1H-imidazole in the egg masses of three muricid molluscs

Natural Product Research
Kirsten BenkendorffJohn B Bremner

Abstract

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.

References

Dec 1, 1984·Archives of Toxicology·R D VerschoyleC A Thompson
Jan 1, 1996·Toxicon : Official Journal of the International Society on Toxinology·M RoseghiniV Erspamer

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Citations

Apr 10, 2013·Asian Pacific Journal of Tropical Biomedicine·T KaviarasanA Yogamoorthi
Jan 29, 2010·Biological Reviews of the Cambridge Philosophical Society·Kirsten Benkendorff
Feb 3, 2006·Natural Product Reports·John W BluntMichèle R Prinsep

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