A new bromoindolesulfonic acid derivative, echinosulfonic acid D (1) was isolated from the New-Caledonian sponge Psammoclemma sp. in a minute quantity. The structure of the alkaloid was established by spectroscopic methods and, in particular, by ESI MSn experiments. Echinosulfonic acid D was cytotoxic to KB cells (IC50 2 microg/mL).
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Synthesis and Cheminformatics-Directed Antibacterial Evaluation of Echinosulfonic Acid-Inspired Bis-Indole Alkaloids.
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School of Environment and Science, Griffith University, Southport, QLD 4222, Australia.
Synthetic efforts toward complex natural product (NP) scaffolds are useful ones, particularly those aimed at expanding their bioactive chemical space. Here, we utilised an orthogonal cheminformatics-based approach to predict the potential biological activities for a series of synthetic bis-indole alkaloids inspired by elusive sponge-derived NPs, echinosulfone A () and echinosulfonic acids A-D (-). Our work includes the first synthesis of desulfato-echinosulfonic acid C, an α-hydroxy bis(3'-indolyl) alkaloid (), and its full NMR characterisation.
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J Nat Prod
August 2022
Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Kita-ku, Okayama 7008530, Japan.
Echinosulfonic acid D, a sponge metabolite whose structure was recently reassigned, was synthesized for the first time. The key step is the double indolization of dimethylbarbituric acid using the umpolung indole reagent, followed by a hydrolysis/decarboxylation/esterification sequence.
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Environmental Futures Research Institute, Griffith University, Southport 4222, Queensland, Australia.
The structures of the sponge-derived dibrominated bis-indole alkaloids, namely, echinosulfone A () and the echinosulfonic acids A to D (-), have been revised based upon reanalysis of their NMR spectroscopic and MS spectrometric data, comparison of this data with those reported for structurally related compounds, and based on their common biogenesis. The reinterpreted spectroscopic evidence has been corroborated by the total synthesis of the revised structure of echinosulfone A (). This was achieved by bis-carbonylation at C-3 of the magnesium salt of 6-bromoindole with triphosgene to afford the new dibrominated bis-indole ketone, bis(6-bromo-1-indol-3-yl)methanone (), followed by N-sulfonation of one indole moiety to furnish 6-bromo-3-(6-bromo-1-indole-3-carbonyl)-1-indole-1-sulfonate ().
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J Nat Prod
January 2020
School of Molecular Sciences , The University of Western Australia, Crawley , WA 6009 , Australia.
Two previously reported bis-indole alkaloids, echinosulfone A and echinosulfonic acid B, have been isolated for the first time from a Western Australian marine sponge, sp. (order: Poecilosclerida, family: Crellidae). Single-crystal X-ray diffraction of a decomposition product of echinosulfone A prompted our investigation and subsequent structure reassignment of the echinosulfonic acid natural product family, which we report here.
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Nat Prod Res
January 2005
Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, 91198 Gif-sur-Yvette Cedex, France.
A new bromoindolesulfonic acid derivative, echinosulfonic acid D (1) was isolated from the New-Caledonian sponge Psammoclemma sp. in a minute quantity. The structure of the alkaloid was established by spectroscopic methods and, in particular, by ESI MSn experiments.
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