A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity
Bioassay-guided fractionation of a cytotoxic EtOAc extract of the plant-associated fungal strain, Chaetomium globosum, afforded a new cytotoxic and cell cycle inhibitory xanthenone, globosuxanthone A, and several other structurally related inactive metabolites. Bioassay-guided fractionation of a cyt...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2006-12, Vol.14 (23), p.7917-7923 |
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| creator | Wijeratne, E.M. Kithsiri Turbyville, Thomas J. Fritz, Anne Whitesell, Luke Gunatilaka, A.A. Leslie |
| description | Bioassay-guided fractionation of a cytotoxic EtOAc extract of the plant-associated fungal strain, Chaetomium globosum, afforded a new cytotoxic and cell cycle inhibitory xanthenone, globosuxanthone A, and several other structurally related inactive metabolites.
Bioassay-guided fractionation of a cytotoxic EtOAc extract of the fungal strain, Chaetomium globosum, inhabiting the rhizosphere of the Christmas cactus, Opuntia leptocaulis, of the Sonoran desert afforded a new dihydroxanthenone, globosuxanthone A (1), a new tetrahydroxanthenone, globosuxanthone B (2), two new xanthones, globosuxanthone C (3) and D (4), 2-hydroxyvertixanthone (5), and two known anthraquinones (6 and 7). The structures of the new compounds 1–4 were elucidated by NMR and MS techniques, and the relative stereochemistry of 1 was determined by X-ray crystallographic analysis. Of the compounds encountered, 1 was found to exhibit strong cytotoxicity against a panel of seven human solid tumor cell lines, disrupt the cell cycle leading to the accumulation of cells in either G2/M or S phase, and induce classic signs of apoptosis. |
| doi_str_mv | 10.1016/j.bmc.2006.07.048 |
| format | Article |
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Bioassay-guided fractionation of a cytotoxic EtOAc extract of the fungal strain, Chaetomium globosum, inhabiting the rhizosphere of the Christmas cactus, Opuntia leptocaulis, of the Sonoran desert afforded a new dihydroxanthenone, globosuxanthone A (1), a new tetrahydroxanthenone, globosuxanthone B (2), two new xanthones, globosuxanthone C (3) and D (4), 2-hydroxyvertixanthone (5), and two known anthraquinones (6 and 7). The structures of the new compounds 1–4 were elucidated by NMR and MS techniques, and the relative stereochemistry of 1 was determined by X-ray crystallographic analysis. Of the compounds encountered, 1 was found to exhibit strong cytotoxicity against a panel of seven human solid tumor cell lines, disrupt the cell cycle leading to the accumulation of cells in either G2/M or S phase, and induce classic signs of apoptosis.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2006.07.048</identifier><identifier>PMID: 16904330</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Anthraquinones ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Apoptosis - drug effects ; Biological and medical sciences ; Cell Cycle - drug effects ; Cell Line, Tumor ; Cell-cycle disruptor ; Chaetomium - chemistry ; Chaetomium globosum ; Cytotoxicity ; Drug Screening Assays, Antitumor ; General pharmacology ; Globosuxanthones A–D ; Humans ; Medical sciences ; Molecular Structure ; Opuntia leptocaulis ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plant-associated fungus ; Stereoisomerism ; Xanthenes - isolation & purification ; Xanthenes - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry, 2006-12, Vol.14 (23), p.7917-7923</ispartof><rights>2006 Elsevier Ltd</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c447t-31d65f6b8ca6ba35997cbe1a0d46a9e9825bfcbf3ce818a171240d4900c321763</citedby><cites>FETCH-LOGICAL-c447t-31d65f6b8ca6ba35997cbe1a0d46a9e9825bfcbf3ce818a171240d4900c321763</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2006.07.048$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,782,786,3554,27933,27934,46004</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18256762$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16904330$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wijeratne, E.M. Kithsiri</creatorcontrib><creatorcontrib>Turbyville, Thomas J.</creatorcontrib><creatorcontrib>Fritz, Anne</creatorcontrib><creatorcontrib>Whitesell, Luke</creatorcontrib><creatorcontrib>Gunatilaka, A.A. Leslie</creatorcontrib><title>A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Bioassay-guided fractionation of a cytotoxic EtOAc extract of the plant-associated fungal strain, Chaetomium globosum, afforded a new cytotoxic and cell cycle inhibitory xanthenone, globosuxanthone A, and several other structurally related inactive metabolites.
Bioassay-guided fractionation of a cytotoxic EtOAc extract of the fungal strain, Chaetomium globosum, inhabiting the rhizosphere of the Christmas cactus, Opuntia leptocaulis, of the Sonoran desert afforded a new dihydroxanthenone, globosuxanthone A (1), a new tetrahydroxanthenone, globosuxanthone B (2), two new xanthones, globosuxanthone C (3) and D (4), 2-hydroxyvertixanthone (5), and two known anthraquinones (6 and 7). The structures of the new compounds 1–4 were elucidated by NMR and MS techniques, and the relative stereochemistry of 1 was determined by X-ray crystallographic analysis. Of the compounds encountered, 1 was found to exhibit strong cytotoxicity against a panel of seven human solid tumor cell lines, disrupt the cell cycle leading to the accumulation of cells in either G2/M or S phase, and induce classic signs of apoptosis.</description><subject>Anthraquinones</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Apoptosis - drug effects</subject><subject>Biological and medical sciences</subject><subject>Cell Cycle - drug effects</subject><subject>Cell Line, Tumor</subject><subject>Cell-cycle disruptor</subject><subject>Chaetomium - chemistry</subject><subject>Chaetomium globosum</subject><subject>Cytotoxicity</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General pharmacology</subject><subject>Globosuxanthones A–D</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Opuntia leptocaulis</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant-associated fungus</subject><subject>Stereoisomerism</subject><subject>Xanthenes - isolation & purification</subject><subject>Xanthenes - pharmacology</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE2P0zAQhi0EYsvCD-CCfIFbwjh2nVicVhVf0kpc4Gw59njrKomL7Sz03-OqlfbGySPPM69mHkLeMmgZMPnx0I6zbTsA2ULfghiekQ0TUjScK_acbEDJoYFByRvyKucDAHRCsZfkhkkFgnPYkNMdXfAPdWF_cin-NUvZ4xIXpD7FmRp6nOpXY3KONpiCjuaSTFho9LSS1K_Lw5rpbm-wxDmsM32Y4hhzLRzOcTnTBTOtIcGaxWKixpbwGMrpNXnhzZTxzfW9Jb--fP65-9bc__j6fXd331gh-tJw5uTWy3GwRo6Gb5Xq7YjMgBPSKFRDtx29HT23OLDBsJ51ovYUgOUd6yW_JR8uuccUf6-Yi55DtjjVwzCuWctB9aKTZ5BdQJtizgm9PqYwm3TSDPTZtz7o6luffWvodfVdZ95dw9dxRvc0cRVcgfdXwGRrJp-qhJCfuLq-7GVXuU8XDquKx4BJZxuwCnMhoS3axfCfNf4BJwagJg</recordid><startdate>20061201</startdate><enddate>20061201</enddate><creator>Wijeratne, E.M. Kithsiri</creator><creator>Turbyville, Thomas J.</creator><creator>Fritz, Anne</creator><creator>Whitesell, Luke</creator><creator>Gunatilaka, A.A. Leslie</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><scope>IQODW</scope><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>20061201</creationdate><title>A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity</title><author>Wijeratne, E.M. Kithsiri ; Turbyville, Thomas J. ; Fritz, Anne ; Whitesell, Luke ; Gunatilaka, A.A. Leslie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c447t-31d65f6b8ca6ba35997cbe1a0d46a9e9825bfcbf3ce818a171240d4900c321763</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Anthraquinones</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Apoptosis - drug effects</topic><topic>Biological and medical sciences</topic><topic>Cell Cycle - drug effects</topic><topic>Cell Line, Tumor</topic><topic>Cell-cycle disruptor</topic><topic>Chaetomium - chemistry</topic><topic>Chaetomium globosum</topic><topic>Cytotoxicity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General pharmacology</topic><topic>Globosuxanthones A–D</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Opuntia leptocaulis</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant-associated fungus</topic><topic>Stereoisomerism</topic><topic>Xanthenes - isolation & purification</topic><topic>Xanthenes - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wijeratne, E.M. Kithsiri</creatorcontrib><creatorcontrib>Turbyville, Thomas J.</creatorcontrib><creatorcontrib>Fritz, Anne</creatorcontrib><creatorcontrib>Whitesell, Luke</creatorcontrib><creatorcontrib>Gunatilaka, A.A. 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Leslie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2006-12-01</date><risdate>2006</risdate><volume>14</volume><issue>23</issue><spage>7917</spage><epage>7923</epage><pages>7917-7923</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Bioassay-guided fractionation of a cytotoxic EtOAc extract of the plant-associated fungal strain, Chaetomium globosum, afforded a new cytotoxic and cell cycle inhibitory xanthenone, globosuxanthone A, and several other structurally related inactive metabolites.
Bioassay-guided fractionation of a cytotoxic EtOAc extract of the fungal strain, Chaetomium globosum, inhabiting the rhizosphere of the Christmas cactus, Opuntia leptocaulis, of the Sonoran desert afforded a new dihydroxanthenone, globosuxanthone A (1), a new tetrahydroxanthenone, globosuxanthone B (2), two new xanthones, globosuxanthone C (3) and D (4), 2-hydroxyvertixanthone (5), and two known anthraquinones (6 and 7). The structures of the new compounds 1–4 were elucidated by NMR and MS techniques, and the relative stereochemistry of 1 was determined by X-ray crystallographic analysis. Of the compounds encountered, 1 was found to exhibit strong cytotoxicity against a panel of seven human solid tumor cell lines, disrupt the cell cycle leading to the accumulation of cells in either G2/M or S phase, and induce classic signs of apoptosis.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16904330</pmid><doi>10.1016/j.bmc.2006.07.048</doi><tpages>7</tpages></addata></record> |
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| subjects | Anthraquinones Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Apoptosis - drug effects Biological and medical sciences Cell Cycle - drug effects Cell Line, Tumor Cell-cycle disruptor Chaetomium - chemistry Chaetomium globosum Cytotoxicity Drug Screening Assays, Antitumor General pharmacology Globosuxanthones A–D Humans Medical sciences Molecular Structure Opuntia leptocaulis Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant-associated fungus Stereoisomerism Xanthenes - isolation & purification Xanthenes - pharmacology |
| title | A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity |
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