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Cytotoxic Falcarinol Oxylipins from Dendropanax arboreus
The crude organic extract of Dendropanax arboreus was selected as a candidate for bioassay-guided fractionation on the basis of its relatively selective cytotoxicity to a subset of cell lines within the National Cancer Institute's disease-oriented in vitro tumor-screening panel. The major compo...
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| Published in: | Journal of natural products (Washington, D.C.) D.C.), 1996-08, Vol.59 (8), p.748-753 |
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| Main Authors: | , , , , , |
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| container_end_page | 753 |
| container_issue | 8 |
| container_start_page | 748 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 59 |
| creator | Bernart, Matthew W Cardellina, John H Balaschak, Michael S Alexander, Mark R Shoemaker, Robert H Boyd, Michael R |
| description | The crude organic extract of Dendropanax arboreus was selected as a candidate for bioassay-guided fractionation on the basis of its relatively selective cytotoxicity to a subset of cell lines within the National Cancer Institute's disease-oriented in vitro tumor-screening panel. The major compound responsible for the in vitro cytotoxicity was falcarinol (1). Several other known compounds were isolated and found to be cytotoxic, including dehydrofalcarinol (2), a diynene (3), falcarindiol (4), and dehydrofalcarindiol (5). In addition, two novel polyacetylenes, dendroarboreols A (6) and B (7), were isolated and characterized by standard and inverse-detected NMR methods. Compounds were selected from this series for absolute stereochemical determination using the modified Mosher method and preliminary in vivo evaluation using a LOX melanoma mouse xenograft model. |
| doi_str_mv | 10.1021/np960224o |
| format | article |
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The major compound responsible for the in vitro cytotoxicity was falcarinol (1). Several other known compounds were isolated and found to be cytotoxic, including dehydrofalcarinol (2), a diynene (3), falcarindiol (4), and dehydrofalcarindiol (5). In addition, two novel polyacetylenes, dendroarboreols A (6) and B (7), were isolated and characterized by standard and inverse-detected NMR methods. Compounds were selected from this series for absolute stereochemical determination using the modified Mosher method and preliminary in vivo evaluation using a LOX melanoma mouse xenograft model.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np960224o</identifier><identifier>PMID: 8792622</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>agentes antineoplasticos ; Alkynes ; Animals ; antineoplastic agents ; araliaceae ; Biological and medical sciences ; Cell Division - drug effects ; chemical composition ; Chemical Fractionation ; chemical structure ; chemistry ; chimie ; Chromatography, Gel ; composicion quimica ; composition chimique ; Disease Models, Animal ; Diynes ; Dose-Response Relationship, Drug ; Drugs, Chinese Herbal - chemistry ; Drugs, Chinese Herbal - isolation & purification ; Drugs, Chinese Herbal - pharmacology ; espectrometria ; estructura quimica ; Fatty Alcohols - chemistry ; Fatty Alcohols - isolation & purification ; Fatty Alcohols - pharmacology ; Female ; feuille ; General pharmacology ; hidrocarburos ; hojas ; Humans ; hydrocarbons ; hydrocarbure ; leaves ; Magnetic Resonance Spectroscopy ; Medical sciences ; medicament cytostatique ; Melanoma - drug therapy ; Melanoma - pathology ; Mice ; Mice, Nude ; Panax ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plant Extracts - chemistry ; Plant Extracts - isolation & purification ; Plant Extracts - pharmacology ; Plants, Medicinal ; porto rico ; puerto rico ; quimica ; spectrometrie ; spectrometry ; structure chimique ; Structure-Activity Relationship ; substance toxique ; sustancias toxicas ; toxic substances ; Transplantation, Heterologous ; Tumor Cells, Cultured</subject><ispartof>Journal of natural products (Washington, D.C.), 1996-08, Vol.59 (8), p.748-753</ispartof><rights>Copyright © 1996 American Chemical Society and American Society of Pharmacognosy</rights><rights>1996 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a431t-25163237ead27f737e611d2225121c54fecea77e6d29dee09e556cd52035efb53</citedby><cites>FETCH-LOGICAL-a431t-25163237ead27f737e611d2225121c54fecea77e6d29dee09e556cd52035efb53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3200127$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8792622$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bernart, Matthew W</creatorcontrib><creatorcontrib>Cardellina, John H</creatorcontrib><creatorcontrib>Balaschak, Michael S</creatorcontrib><creatorcontrib>Alexander, Mark R</creatorcontrib><creatorcontrib>Shoemaker, Robert H</creatorcontrib><creatorcontrib>Boyd, Michael R</creatorcontrib><creatorcontrib>National Cancer Institute, Frederick, MD</creatorcontrib><creatorcontrib>General Directorate of Agricultural Research, Ankara (Turkey)</creatorcontrib><title>Cytotoxic Falcarinol Oxylipins from Dendropanax arboreus</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>The crude organic extract of Dendropanax arboreus was selected as a candidate for bioassay-guided fractionation on the basis of its relatively selective cytotoxicity to a subset of cell lines within the National Cancer Institute's disease-oriented in vitro tumor-screening panel. The major compound responsible for the in vitro cytotoxicity was falcarinol (1). Several other known compounds were isolated and found to be cytotoxic, including dehydrofalcarinol (2), a diynene (3), falcarindiol (4), and dehydrofalcarindiol (5). In addition, two novel polyacetylenes, dendroarboreols A (6) and B (7), were isolated and characterized by standard and inverse-detected NMR methods. Compounds were selected from this series for absolute stereochemical determination using the modified Mosher method and preliminary in vivo evaluation using a LOX melanoma mouse xenograft model.</description><subject>agentes antineoplasticos</subject><subject>Alkynes</subject><subject>Animals</subject><subject>antineoplastic agents</subject><subject>araliaceae</subject><subject>Biological and medical sciences</subject><subject>Cell Division - drug effects</subject><subject>chemical composition</subject><subject>Chemical Fractionation</subject><subject>chemical structure</subject><subject>chemistry</subject><subject>chimie</subject><subject>Chromatography, Gel</subject><subject>composicion quimica</subject><subject>composition chimique</subject><subject>Disease Models, Animal</subject><subject>Diynes</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drugs, Chinese Herbal - chemistry</subject><subject>Drugs, Chinese Herbal - isolation & purification</subject><subject>Drugs, Chinese Herbal - pharmacology</subject><subject>espectrometria</subject><subject>estructura quimica</subject><subject>Fatty Alcohols - chemistry</subject><subject>Fatty Alcohols - isolation & purification</subject><subject>Fatty Alcohols - pharmacology</subject><subject>Female</subject><subject>feuille</subject><subject>General pharmacology</subject><subject>hidrocarburos</subject><subject>hojas</subject><subject>Humans</subject><subject>hydrocarbons</subject><subject>hydrocarbure</subject><subject>leaves</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>medicament cytostatique</subject><subject>Melanoma - drug therapy</subject><subject>Melanoma - pathology</subject><subject>Mice</subject><subject>Mice, Nude</subject><subject>Panax</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - isolation & purification</subject><subject>Plant Extracts - pharmacology</subject><subject>Plants, Medicinal</subject><subject>porto rico</subject><subject>puerto rico</subject><subject>quimica</subject><subject>spectrometrie</subject><subject>spectrometry</subject><subject>structure chimique</subject><subject>Structure-Activity Relationship</subject><subject>substance toxique</subject><subject>sustancias toxicas</subject><subject>toxic substances</subject><subject>Transplantation, Heterologous</subject><subject>Tumor Cells, Cultured</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><recordid>eNqFkdFr2zAQxsXoaNNsD_0DWvywFvbgTTpZlvVYsmYbC2TQFkpfxEWWi1PHciUbkv9-Cg55GvRJp_t-fNx9R8gFo98YBfa97VROATL3gUyYAJrGnzghE8pynvIiz87IeQhrSimnSpyS00IqyAEmpJjtete7bW2SOTYGfd26Jllud03d1W1IKu82yQ_blt512OI2Qb9y3g7hE_lYYRPs58M7JY_zu4fZr3Sx_Pl7drtIMeOsT0HEEYBLiyXISsYiZ6wEiH1gRmSVNRZl7JagSmupskLkpow7cGGrleBTcjP6dt69DTb0elMHY5sGW-uGoGXBqZT0fZCJAjLF9uDXETTeheBtpTtfb9DvNKN6H6c-xhnZy4PpsNrY8kge8ov6l4OOwWBTeWxNHY4YB0oZyIilI1aH3m6PMvpXncdMhH74e6_l0x-5KObPmkb-auQrdBpffLR8vGdKyXhAUIxH4HoE0AS9doNv4w3-M_8_24Sffg</recordid><startdate>19960801</startdate><enddate>19960801</enddate><creator>Bernart, Matthew W</creator><creator>Cardellina, John H</creator><creator>Balaschak, Michael S</creator><creator>Alexander, Mark R</creator><creator>Shoemaker, Robert H</creator><creator>Boyd, Michael R</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</scope><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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>19960801</creationdate><title>Cytotoxic Falcarinol Oxylipins from Dendropanax arboreus</title><author>Bernart, Matthew W ; Cardellina, John H ; Balaschak, Michael S ; Alexander, Mark R ; Shoemaker, Robert H ; Boyd, Michael R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a431t-25163237ead27f737e611d2225121c54fecea77e6d29dee09e556cd52035efb53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>agentes antineoplasticos</topic><topic>Alkynes</topic><topic>Animals</topic><topic>antineoplastic agents</topic><topic>araliaceae</topic><topic>Biological and medical sciences</topic><topic>Cell Division - drug effects</topic><topic>chemical composition</topic><topic>Chemical Fractionation</topic><topic>chemical structure</topic><topic>chemistry</topic><topic>chimie</topic><topic>Chromatography, Gel</topic><topic>composicion quimica</topic><topic>composition chimique</topic><topic>Disease Models, Animal</topic><topic>Diynes</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drugs, Chinese Herbal - chemistry</topic><topic>Drugs, Chinese Herbal - isolation & purification</topic><topic>Drugs, Chinese Herbal - pharmacology</topic><topic>espectrometria</topic><topic>estructura quimica</topic><topic>Fatty Alcohols - chemistry</topic><topic>Fatty Alcohols - isolation & purification</topic><topic>Fatty Alcohols - pharmacology</topic><topic>Female</topic><topic>feuille</topic><topic>General pharmacology</topic><topic>hidrocarburos</topic><topic>hojas</topic><topic>Humans</topic><topic>hydrocarbons</topic><topic>hydrocarbure</topic><topic>leaves</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>medicament cytostatique</topic><topic>Melanoma - drug therapy</topic><topic>Melanoma - pathology</topic><topic>Mice</topic><topic>Mice, Nude</topic><topic>Panax</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - isolation & purification</topic><topic>Plant Extracts - pharmacology</topic><topic>Plants, Medicinal</topic><topic>porto rico</topic><topic>puerto rico</topic><topic>quimica</topic><topic>spectrometrie</topic><topic>spectrometry</topic><topic>structure chimique</topic><topic>Structure-Activity Relationship</topic><topic>substance toxique</topic><topic>sustancias toxicas</topic><topic>toxic substances</topic><topic>Transplantation, Heterologous</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bernart, Matthew W</creatorcontrib><creatorcontrib>Cardellina, John H</creatorcontrib><creatorcontrib>Balaschak, Michael S</creatorcontrib><creatorcontrib>Alexander, Mark R</creatorcontrib><creatorcontrib>Shoemaker, Robert H</creatorcontrib><creatorcontrib>Boyd, Michael R</creatorcontrib><creatorcontrib>National Cancer Institute, Frederick, MD</creatorcontrib><creatorcontrib>General Directorate of Agricultural Research, Ankara (Turkey)</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</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>Bernart, Matthew W</au><au>Cardellina, John H</au><au>Balaschak, Michael S</au><au>Alexander, Mark R</au><au>Shoemaker, Robert H</au><au>Boyd, Michael R</au><aucorp>National Cancer Institute, Frederick, MD</aucorp><aucorp>General Directorate of Agricultural Research, Ankara (Turkey)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cytotoxic Falcarinol Oxylipins from Dendropanax arboreus</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>1996-08-01</date><risdate>1996</risdate><volume>59</volume><issue>8</issue><spage>748</spage><epage>753</epage><pages>748-753</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>The crude organic extract of Dendropanax arboreus was selected as a candidate for bioassay-guided fractionation on the basis of its relatively selective cytotoxicity to a subset of cell lines within the National Cancer Institute's disease-oriented in vitro tumor-screening panel. The major compound responsible for the in vitro cytotoxicity was falcarinol (1). Several other known compounds were isolated and found to be cytotoxic, including dehydrofalcarinol (2), a diynene (3), falcarindiol (4), and dehydrofalcarindiol (5). In addition, two novel polyacetylenes, dendroarboreols A (6) and B (7), were isolated and characterized by standard and inverse-detected NMR methods. Compounds were selected from this series for absolute stereochemical determination using the modified Mosher method and preliminary in vivo evaluation using a LOX melanoma mouse xenograft model.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>8792622</pmid><doi>10.1021/np960224o</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 1996-08, Vol.59 (8), p.748-753 |
| issn | 0163-3864 1520-6025 |
| language | eng |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | agentes antineoplasticos Alkynes Animals antineoplastic agents araliaceae Biological and medical sciences Cell Division - drug effects chemical composition Chemical Fractionation chemical structure chemistry chimie Chromatography, Gel composicion quimica composition chimique Disease Models, Animal Diynes Dose-Response Relationship, Drug Drugs, Chinese Herbal - chemistry Drugs, Chinese Herbal - isolation & purification Drugs, Chinese Herbal - pharmacology espectrometria estructura quimica Fatty Alcohols - chemistry Fatty Alcohols - isolation & purification Fatty Alcohols - pharmacology Female feuille General pharmacology hidrocarburos hojas Humans hydrocarbons hydrocarbure leaves Magnetic Resonance Spectroscopy Medical sciences medicament cytostatique Melanoma - drug therapy Melanoma - pathology Mice Mice, Nude Panax Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Extracts - chemistry Plant Extracts - isolation & purification Plant Extracts - pharmacology Plants, Medicinal porto rico puerto rico quimica spectrometrie spectrometry structure chimique Structure-Activity Relationship substance toxique sustancias toxicas toxic substances Transplantation, Heterologous Tumor Cells, Cultured |
| title | Cytotoxic Falcarinol Oxylipins from Dendropanax arboreus |
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