Polyhalogenated Indoles from the Red Alga Rhodophyllis membranacea: The First Isolation of Bromo-Chloro-Iodo Secondary Metabolites

An unusual tetrahalogenated indole with the exceptionally rare inclusion of the three halogens bromine, chlorine, and iodine was found using mass spectrometry within a fraction of a semipurified extract obtained from the red alga Rhodophyllis membranacea. We report herein the isolation and structure...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2016-03, Vol.79 (3), p.463-469
Hauptverfasser: Woolner, Victoria H, Jones, Cori M, Field, Jessica J, Fadzilah, Nazmi H, Munkacsi, Andrew B, Miller, John H, Keyzers, Robert A, Northcote, Peter T
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Sprache:eng
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Zusammenfassung:An unusual tetrahalogenated indole with the exceptionally rare inclusion of the three halogens bromine, chlorine, and iodine was found using mass spectrometry within a fraction of a semipurified extract obtained from the red alga Rhodophyllis membranacea. We report herein the isolation and structure elucidation, using a combination of NMR spectroscopy and mass spectrometry, of 11 new tetrahalogenated indoles (1–11), including four bromochloroiodoindoles (5–7, 10). Several were evaluated for cytotoxic and antifungal activities against the HL-60 promyelocytic cell line and Saccharomyces cerevisiae, respectively.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.5b00831