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The first chemical study of the common species Terrazoanthus onoi, present off the coast of Ecuador, led to the identification of a new family of 2-aminoimidazole alkaloids named terrazoanthines A-C (1-3). Homologues 1 and 2 feature an unprecedented 6-(imidazol-5-yl)benzo[d]imidazole. Acyl substitution pattern and complete configurational assignments were deduced from comparison between experimental and theoretical 13 C NMR and ECD data, respectively. These compounds may represent key derivatives in the biosynthesis of zoanthoxanthins.

Terrazoanthines, 2-Aminoimidazole Alkaloids from the Tropical Eastern Pacific Zoantharian Terrazoanthus onoi