Araiosamines A-D: tris-bromoindole cyclic guanidine alkaloids from the marine sponge Clathria (Thalysias) araiosa |
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Authors: | Wei Xiaomei Henriksen Niel M Skalicky Jack J Harper Mary Kay Cheatham Thomas E Ireland Chris M Van Wagoner Ryan M |
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Institution: | Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah 84112, United States. |
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Abstract: | Four new tris-bromoindole cyclic guanidine alkaloids, araiosamines A-D, were isolated from the methanol extract of a marine sponge, Clathria (Thalysias) araiosa, collected from Vanuatu. Their carbon skeletons delineate a new class of indole alkaloids apparently derived from a linear polymerization process involving a carbon-carbon bond formation. Comparison of the structures including the relative configurations suggests a common intermediate containing a dihydroaminopyrimidine moiety capable of undergoing various modalities of conjugate addition to yield unprecedented ring systems. |
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