Title

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

Document Type

Article

Publication details

Benkendorff, K, Pillai, R & Bremner, JB 2004, '2,4,5-Tribromo-1H-Imidazole in the egg masses of three muricid molluscs', Natural Product Research, vol. 18, no. 5, pp. 427-431.

Publisher's version of this article is available at http://dx.doi.org/10.1080/1478641031000620682

Peer Reviewed

Peer-Reviewed

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.