Abstract
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.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Antifungal Agents / chemistry
-
Antifungal Agents / isolation & purification*
-
Antifungal Agents / pharmacology
-
Cytotoxins / chemistry
-
Cytotoxins / isolation & purification*
-
Cytotoxins / pharmacology
-
Drug Screening Assays, Antitumor
-
HL-60 Cells
-
Humans
-
Hydrocarbons, Halogenated / chemistry
-
Hydrocarbons, Halogenated / isolation & purification*
-
Hydrocarbons, Halogenated / pharmacology
-
Indoles / chemistry
-
Indoles / isolation & purification*
-
Indoles / pharmacology
-
Marine Biology
-
Molecular Structure
-
Nuclear Magnetic Resonance, Biomolecular
-
Rhodophyta / chemistry*
-
Saccharomyces cerevisiae / drug effects
Substances
-
Antifungal Agents
-
Cytotoxins
-
Hydrocarbons, Halogenated
-
Indoles