Trikentramides A–D: Indole Alkaloids from the Australian Sponge Trikentrion flabelliforme
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Chemical investigations of two specimens of Trikentrion flabelliforme collected from Australian waters have resulted in the identification of four new indole alkaloids, trikentramides A-D (9-12). The planar chemical structures for 9-12 were established following analysis of 1D/2D NMR and MS data. The relative configurations for 9-12 were determined following comparison of 1H NMR data with previously reported and related natural products. The application of a quantum mechanical modeling method, density functional theory, confirmed the relative configurations and also validated the downfield carbon chemical shift observed for one of the quaternary carbons (C-5a) in the cyclopenta[g]indole series. The indole-2,3-dione motif present in trikentramides A-C is rare in nature, and this is the first report of these oxidized indole derivatives from a marine sponge.
Journal of Natural Products
This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Natural Products, copyright 2013 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/np400617h.
Natural Products Chemistry