title: Polyhalogenated Indoles from the Red Alga Rhodophyllis membranacea: The First Isolation of Bromo-Chloro-Iodo Secondary Metabolites.
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.
authors.affiliation: Centre for Biodiscovery and School of Chemical and Physical Sciences and §Centre for Biodiscovery and School of Biological Sciences, Victoria University of Wellington , P.O. Box 600, Wellington, New Zealand.
authors.forename: Victoria H
authors.initials: VH
authors.lastname: Woolner
authors.affiliation: Centre for Biodiscovery and School of Chemical and Physical Sciences and §Centre for Biodiscovery and School of Biological Sciences, Victoria University of Wellington , P.O. Box 600, Wellington, New Zealand.
authors.forename: Cori M
authors.initials: CM
authors.lastname: Jones
authors.affiliation: Centre for Biodiscovery and School of Chemical and Physical Sciences and §Centre for Biodiscovery and School of Biological Sciences, Victoria University of Wellington , P.O. Box 600, Wellington, New Zealand.
authors.forename: Jessica J
authors.initials: JJ
authors.lastname: Field
authors.affiliation: Centre for Biodiscovery and School of Chemical and Physical Sciences and §Centre for Biodiscovery and School of Biological Sciences, Victoria University of Wellington , P.O. Box 600, Wellington, New Zealand.
authors.forename: Nazmi H
authors.initials: NH
authors.lastname: Fadzilah
authors.affiliation: Centre for Biodiscovery and School of Chemical and Physical Sciences and §Centre for Biodiscovery and School of Biological Sciences, Victoria University of Wellington , P.O. Box 600, Wellington, New Zealand.
authors.forename: Andrew B
authors.initials: AB
authors.lastname: Munkacsi
authors.affiliation: Centre for Biodiscovery and School of Chemical and Physical Sciences and §Centre for Biodiscovery and School of Biological Sciences, Victoria University of Wellington , P.O. Box 600, Wellington, New Zealand.
authors.forename: John H
authors.initials: JH
authors.lastname: Miller
authors.affiliation: Centre for Biodiscovery and School of Chemical and Physical Sciences and §Centre for Biodiscovery and School of Biological Sciences, Victoria University of Wellington , P.O. Box 600, Wellington, New Zealand.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Keyzers
authors.affiliation: Centre for Biodiscovery and School of Chemical and Physical Sciences and §Centre for Biodiscovery and School of Biological Sciences, Victoria University of Wellington , P.O. Box 600, Wellington, New Zealand.
authors.forename: Peter T
authors.initials: PT
authors.lastname: Northcote
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003603:Cytotoxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D006846:Hydrocarbons, Halogenated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D000461:Rhodophyta / Q000737:chemistry*; D012441:Saccharomyces cerevisiae / Q000187:drug effects
chemical_list: D000935:Antifungal Agents; D003603:Cytotoxins; D006846:Hydrocarbons, Halogenated; D007211:Indoles