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 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Woolner, Victoria H Jones, Cori M Field, Jessica J Fadzilah, Nazmi H Munkacsi, Andrew B Miller, John H Keyzers, Robert A Northcote, Peter T |
| description | 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. |
| doi_str_mv | 10.1021/acs.jnatprod.5b00831 |
| format | Article |
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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). 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Nat. Prod</addtitle><description>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.</description><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - isolation & purification</subject><subject>Antifungal Agents - pharmacology</subject><subject>Cytotoxins - chemistry</subject><subject>Cytotoxins - isolation & purification</subject><subject>Cytotoxins - pharmacology</subject><subject>Drug Screening Assays, Antitumor</subject><subject>HL-60 Cells</subject><subject>Humans</subject><subject>Hydrocarbons, Halogenated - chemistry</subject><subject>Hydrocarbons, Halogenated - isolation & purification</subject><subject>Hydrocarbons, Halogenated - pharmacology</subject><subject>Indoles - chemistry</subject><subject>Indoles - isolation & purification</subject><subject>Indoles - pharmacology</subject><subject>Marine Biology</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Rhodophyta - chemistry</subject><subject>Saccharomyces cerevisiae - drug effects</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1v1DAQhi0EokvhHyDkI5cs_ojthFtZ0bJSUatSzpEdj5tUTmaxs4e98stx2S1HTpZGz_uO5yHkPWdrzgT_ZPu8fpztskvo18ox1kj-gqy4EqzSTKiXZMW4lpVsdH1G3uT8yBiTrFWvyZnQRumWNSvy-xbjYbARH6B0gafb2WOETEPCiS4D0LsyvIgPlt4N6HE3HGIcM51gcsnOtgf7md4X7HJMeaHbjNEuI84UA_1SKrDaDBETVtsSpj-gx9nbdKDfYbEO47hAfkteBRszvDu95-Tn5df7zbfq-uZqu7m4rqysm6UKvRCmNeCNA-ecqH3duppLH7wTKsigHPc9aBOclrwVIpgAzHNvgzK1D_KcfDz2FmO_9pCXbhpzDzHaGXCfO26MZo02TBW0PqJ9wpwThG6Xxqn8u-Ose7LfFfvds_3uZL_EPpw27N0E_l_oWXcB2BH4G8d9msvB_-_8A2vZl9M</recordid><startdate>20160325</startdate><enddate>20160325</enddate><creator>Woolner, Victoria H</creator><creator>Jones, Cori M</creator><creator>Field, Jessica J</creator><creator>Fadzilah, Nazmi H</creator><creator>Munkacsi, Andrew B</creator><creator>Miller, John H</creator><creator>Keyzers, Robert A</creator><creator>Northcote, Peter T</creator><general>American Chemical Society and American Society of Pharmacognosy</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20160325</creationdate><title>Polyhalogenated Indoles from the Red Alga Rhodophyllis membranacea: The First Isolation of Bromo-Chloro-Iodo Secondary Metabolites</title><author>Woolner, Victoria H ; Jones, Cori M ; Field, Jessica J ; Fadzilah, Nazmi H ; Munkacsi, Andrew B ; Miller, John H ; Keyzers, Robert A ; Northcote, Peter T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-fc22797ed7bebbb24d49b413dfdb25f3f5b1dce67fb631922f7fe0d1daf574df3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - isolation & purification</topic><topic>Antifungal Agents - pharmacology</topic><topic>Cytotoxins - chemistry</topic><topic>Cytotoxins - isolation & purification</topic><topic>Cytotoxins - pharmacology</topic><topic>Drug Screening Assays, Antitumor</topic><topic>HL-60 Cells</topic><topic>Humans</topic><topic>Hydrocarbons, Halogenated - chemistry</topic><topic>Hydrocarbons, Halogenated - isolation & purification</topic><topic>Hydrocarbons, Halogenated - pharmacology</topic><topic>Indoles - chemistry</topic><topic>Indoles - isolation & purification</topic><topic>Indoles - pharmacology</topic><topic>Marine Biology</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Rhodophyta - chemistry</topic><topic>Saccharomyces cerevisiae - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Woolner, Victoria H</creatorcontrib><creatorcontrib>Jones, Cori M</creatorcontrib><creatorcontrib>Field, Jessica J</creatorcontrib><creatorcontrib>Fadzilah, Nazmi H</creatorcontrib><creatorcontrib>Munkacsi, Andrew B</creatorcontrib><creatorcontrib>Miller, John H</creatorcontrib><creatorcontrib>Keyzers, Robert A</creatorcontrib><creatorcontrib>Northcote, Peter T</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Woolner, Victoria H</au><au>Jones, Cori M</au><au>Field, Jessica J</au><au>Fadzilah, Nazmi H</au><au>Munkacsi, Andrew B</au><au>Miller, John H</au><au>Keyzers, Robert A</au><au>Northcote, Peter T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Polyhalogenated Indoles from the Red Alga Rhodophyllis membranacea: The First Isolation of Bromo-Chloro-Iodo Secondary Metabolites</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. 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| ispartof | Journal of natural products (Washington, D.C.), 2016-03, Vol.79 (3), p.463-469 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | 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 |
| title | Polyhalogenated Indoles from the Red Alga Rhodophyllis membranacea: The First Isolation of Bromo-Chloro-Iodo Secondary Metabolites |
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