Somamides A and B, Two New Depsipeptide Analogues of Dolastatin 13 from a Fijian Cyanobacterial Assemblage of Lyngbya majuscula and Schizothrix Species

Journal of Natural Products
2001.0

Abstract

Somamides A (1) and B (2) were isolated from assemblages of the marine cyanobacteria Lyngbya majuscula and Schizothrix sp. from the Fijian Islands. These new depsipeptides are analogous in structure to the cyanobacterial metabolite symplostatin 2 (4) as well as dolastatin 13 (3), originally isolated from Dolabella auricularia, further demonstrating the cyanobacterial origin of the dolastatins. Marine cyanobacteria are known for their ability to produce a great diversity of unique secondary metabolites, especially lipopeptides which incorporate modified amino acid moieties, such as the majusculamides,1 lyngbyastatins,2 and hormothamnins.3 Similarly, the dolastatins are an intriguing group of polypeptides, frequently containing ketide extended residues, which possess exceptional cytostatic and antineoplastic activity.4 Although originally isolated in minute quantities from the herbivorous mollusc Dolabella auricularia, it has become evident that such metabolites truly originate in cyanobacteria.5 Examination of the lipid extracts from mixed assemblages of the marine cyanobacteria Lyngbya majuscula and Schizothrix species, collected in the Fijian Islands, led to the discovery of two new depsipeptides (1, 2) with strong structural homology to dolastatin 13 (3).6 Herein we report the isolation and structure elucidation of somamides A (1) and B (2).

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