Biologically active alkylated coumarins from Kayea assamica
Four coumarin derivatives, theraphins A ( 1), B ( 2), C ( 3), and D ( 4), along with three known xanthones, 2-hydroxyxanthone, 1,7-dihydroxyxanthone, and 5-hydroxy-1-methoxyxanthone, were isolated from the bark of Kayea assamica (Clusiaceae) native to Myanmar. Their structures were determined using...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2003-09, Vol.64 (2), p.535-541 |
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| container_title | Phytochemistry (Oxford) |
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| creator | Lee, Kyung-Hee Chai, Hee-Byung Tamez, Pamela A Pezzuto, John M Cordell, Geoffrey A Win, Khin Khin Tin-Wa, Maung |
| description | Four coumarin derivatives, theraphins A (
1), B (
2), C (
3), and D (
4), along with three known xanthones, 2-hydroxyxanthone, 1,7-dihydroxyxanthone, and 5-hydroxy-1-methoxyxanthone, were isolated from the bark of
Kayea assamica (Clusiaceae) native to Myanmar. Their structures were determined using spectroscopic and chemical techniques. The absolute configuration of
1 was established by the modified Mosher ester method. Theraphins A (
1), B (
2), and C (
3) exhibited good cytotoxicity against Col2, KB, and LNCaP human cancer cell lines. Theraphin D (
4) showed mild activity only against the KB cell line. The coumarins also exhibited mild antimalarial activities.
Theraphins A, B, C, and D, were isolated as cytotoxic principles from the bark of
Kayea assamica (Clusiaceae) native to Myanmar. |
| doi_str_mv | 10.1016/S0031-9422(03)00243-7 |
| format | Article |
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1), B (
2), C (
3), and D (
4), along with three known xanthones, 2-hydroxyxanthone, 1,7-dihydroxyxanthone, and 5-hydroxy-1-methoxyxanthone, were isolated from the bark of
Kayea assamica (Clusiaceae) native to Myanmar. Their structures were determined using spectroscopic and chemical techniques. The absolute configuration of
1 was established by the modified Mosher ester method. Theraphins A (
1), B (
2), and C (
3) exhibited good cytotoxicity against Col2, KB, and LNCaP human cancer cell lines. Theraphin D (
4) showed mild activity only against the KB cell line. The coumarins also exhibited mild antimalarial activities.
Theraphins A, B, C, and D, were isolated as cytotoxic principles from the bark of
Kayea assamica (Clusiaceae) native to Myanmar.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/S0031-9422(03)00243-7</identifier><identifier>PMID: 12943771</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Alkylated coumarins ; Alkylation ; Animals ; Antimalarial activity ; Antimalarials - isolation & purification ; Antimalarials - pharmacology ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Biological and medical sciences ; Chemical constitution ; Chloroquine - pharmacology ; Clusiaceae ; Clusiaceae - chemistry ; Coumarins - chemistry ; Coumarins - isolation & purification ; Coumarins - pharmacology ; Cytotoxicity ; Drug Screening Assays, Antitumor ; Fundamental and applied biological sciences. Psychology ; General pharmacology ; Humans ; Kayea assamica ; KB Cells ; Magnetic Resonance Spectroscopy ; Medical sciences ; Molecular Conformation ; Molecular Structure ; Myanmar ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plant Bark - chemistry ; Plant physiology and development ; Plants, Medicinal - chemistry ; Plasmodium falciparum - drug effects ; Plasmodium falciparum - genetics ; Tumor Cells, Cultured ; Xanthones</subject><ispartof>Phytochemistry (Oxford), 2003-09, Vol.64 (2), p.535-541</ispartof><rights>2003 Elsevier Ltd</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c512t-35fc8d14cffa61d7dd098f6f7b6349d25b3b39037f02053374ddb98412463003</citedby><cites>FETCH-LOGICAL-c512t-35fc8d14cffa61d7dd098f6f7b6349d25b3b39037f02053374ddb98412463003</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0031-9422(03)00243-7$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15086866$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12943771$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lee, Kyung-Hee</creatorcontrib><creatorcontrib>Chai, Hee-Byung</creatorcontrib><creatorcontrib>Tamez, Pamela A</creatorcontrib><creatorcontrib>Pezzuto, John M</creatorcontrib><creatorcontrib>Cordell, Geoffrey A</creatorcontrib><creatorcontrib>Win, Khin Khin</creatorcontrib><creatorcontrib>Tin-Wa, Maung</creatorcontrib><title>Biologically active alkylated coumarins from Kayea assamica</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Four coumarin derivatives, theraphins A (
1), B (
2), C (
3), and D (
4), along with three known xanthones, 2-hydroxyxanthone, 1,7-dihydroxyxanthone, and 5-hydroxy-1-methoxyxanthone, were isolated from the bark of
Kayea assamica (Clusiaceae) native to Myanmar. Their structures were determined using spectroscopic and chemical techniques. The absolute configuration of
1 was established by the modified Mosher ester method. Theraphins A (
1), B (
2), and C (
3) exhibited good cytotoxicity against Col2, KB, and LNCaP human cancer cell lines. Theraphin D (
4) showed mild activity only against the KB cell line. The coumarins also exhibited mild antimalarial activities.
Theraphins A, B, C, and D, were isolated as cytotoxic principles from the bark of
Kayea assamica (Clusiaceae) native to Myanmar.</description><subject>Alkylated coumarins</subject><subject>Alkylation</subject><subject>Animals</subject><subject>Antimalarial activity</subject><subject>Antimalarials - isolation & purification</subject><subject>Antimalarials - pharmacology</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Chemical constitution</subject><subject>Chloroquine - pharmacology</subject><subject>Clusiaceae</subject><subject>Clusiaceae - chemistry</subject><subject>Coumarins - chemistry</subject><subject>Coumarins - isolation & purification</subject><subject>Coumarins - pharmacology</subject><subject>Cytotoxicity</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General pharmacology</subject><subject>Humans</subject><subject>Kayea assamica</subject><subject>KB Cells</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Myanmar</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Bark - chemistry</subject><subject>Plant physiology and development</subject><subject>Plants, Medicinal - chemistry</subject><subject>Plasmodium falciparum - drug effects</subject><subject>Plasmodium falciparum - genetics</subject><subject>Tumor Cells, Cultured</subject><subject>Xanthones</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0E1PHCEYwHFi2uhq_Qht51LTHqZ94BlgSA_GGvuSmvSgngnDi6GdWRRmTfbbl3U3evTE5fcAz5-QtxQ-U6DiyxUA0lZ1jH0E_ATAOmzlHlnQXmKLEuAVWTyRA3JYyl8A4FyIfXJAmepQSrogX7_FNKbbaM04rhtj5_jgGzP-W49m9q6xaTWZHJelCTlNzW-z9qYxpZipTrwhr4MZiz_enUfk-vvF9fnP9vLPj1_nZ5et5ZTNLfJge0c7G4IR1EnnQPVBBDkI7JRjfMABFaAMwIAjys65QfUdZZ3AusIROdlee5fT_cqXWU-xWD-OZunTqmiJXEmJ9EXIQCiuQFbIt9DmVEr2Qd_lWPdcawp6U1c_1tWbdBpQP9bVm7l3uwdWw-Td89QuZwUfdsCUWjRks7SxPDsOveiFqO791gWTtLnN1dxcMaAIlDKmKK_idCt8DfsQfdbFRr-03sXs7axdii989j86L526</recordid><startdate>20030901</startdate><enddate>20030901</enddate><creator>Lee, Kyung-Hee</creator><creator>Chai, Hee-Byung</creator><creator>Tamez, Pamela A</creator><creator>Pezzuto, John M</creator><creator>Cordell, Geoffrey A</creator><creator>Win, Khin Khin</creator><creator>Tin-Wa, Maung</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</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>M7N</scope><scope>7X8</scope></search><sort><creationdate>20030901</creationdate><title>Biologically active alkylated coumarins from Kayea assamica</title><author>Lee, Kyung-Hee ; Chai, Hee-Byung ; Tamez, Pamela A ; Pezzuto, John M ; Cordell, Geoffrey A ; Win, Khin Khin ; Tin-Wa, Maung</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c512t-35fc8d14cffa61d7dd098f6f7b6349d25b3b39037f02053374ddb98412463003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Alkylated coumarins</topic><topic>Alkylation</topic><topic>Animals</topic><topic>Antimalarial activity</topic><topic>Antimalarials - isolation & purification</topic><topic>Antimalarials - pharmacology</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Chemical constitution</topic><topic>Chloroquine - pharmacology</topic><topic>Clusiaceae</topic><topic>Clusiaceae - chemistry</topic><topic>Coumarins - chemistry</topic><topic>Coumarins - isolation & purification</topic><topic>Coumarins - pharmacology</topic><topic>Cytotoxicity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General pharmacology</topic><topic>Humans</topic><topic>Kayea assamica</topic><topic>KB Cells</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Myanmar</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Bark - chemistry</topic><topic>Plant physiology and development</topic><topic>Plants, Medicinal - chemistry</topic><topic>Plasmodium falciparum - drug effects</topic><topic>Plasmodium falciparum - genetics</topic><topic>Tumor Cells, Cultured</topic><topic>Xanthones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lee, Kyung-Hee</creatorcontrib><creatorcontrib>Chai, Hee-Byung</creatorcontrib><creatorcontrib>Tamez, Pamela A</creatorcontrib><creatorcontrib>Pezzuto, John M</creatorcontrib><creatorcontrib>Cordell, Geoffrey A</creatorcontrib><creatorcontrib>Win, Khin Khin</creatorcontrib><creatorcontrib>Tin-Wa, Maung</creatorcontrib><collection>AGRIS</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>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>MEDLINE - Academic</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lee, Kyung-Hee</au><au>Chai, Hee-Byung</au><au>Tamez, Pamela A</au><au>Pezzuto, John M</au><au>Cordell, Geoffrey A</au><au>Win, Khin Khin</au><au>Tin-Wa, Maung</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biologically active alkylated coumarins from Kayea assamica</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2003-09-01</date><risdate>2003</risdate><volume>64</volume><issue>2</issue><spage>535</spage><epage>541</epage><pages>535-541</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Four coumarin derivatives, theraphins A (
1), B (
2), C (
3), and D (
4), along with three known xanthones, 2-hydroxyxanthone, 1,7-dihydroxyxanthone, and 5-hydroxy-1-methoxyxanthone, were isolated from the bark of
Kayea assamica (Clusiaceae) native to Myanmar. Their structures were determined using spectroscopic and chemical techniques. The absolute configuration of
1 was established by the modified Mosher ester method. Theraphins A (
1), B (
2), and C (
3) exhibited good cytotoxicity against Col2, KB, and LNCaP human cancer cell lines. Theraphin D (
4) showed mild activity only against the KB cell line. The coumarins also exhibited mild antimalarial activities.
Theraphins A, B, C, and D, were isolated as cytotoxic principles from the bark of
Kayea assamica (Clusiaceae) native to Myanmar.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>12943771</pmid><doi>10.1016/S0031-9422(03)00243-7</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0031-9422 |
| ispartof | Phytochemistry (Oxford), 2003-09, Vol.64 (2), p.535-541 |
| issn | 0031-9422 1873-3700 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Alkylated coumarins Alkylation Animals Antimalarial activity Antimalarials - isolation & purification Antimalarials - pharmacology Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Biological and medical sciences Chemical constitution Chloroquine - pharmacology Clusiaceae Clusiaceae - chemistry Coumarins - chemistry Coumarins - isolation & purification Coumarins - pharmacology Cytotoxicity Drug Screening Assays, Antitumor Fundamental and applied biological sciences. Psychology General pharmacology Humans Kayea assamica KB Cells Magnetic Resonance Spectroscopy Medical sciences Molecular Conformation Molecular Structure Myanmar Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Bark - chemistry Plant physiology and development Plants, Medicinal - chemistry Plasmodium falciparum - drug effects Plasmodium falciparum - genetics Tumor Cells, Cultured Xanthones |
| title | Biologically active alkylated coumarins from Kayea assamica |
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