New Taxanes from the Needles of Taxus canadensis
Ten new taxanes were isolated from the methanol extract of the needles of the Canadian yew, Taxus canadensis. On the basis of their spectral analysis, their structures were established as 9α-hydroxy-2α,7α,10β-triacetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (1), 9α,10β-diacetoxy-5α-cinnamoy...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2003-04, Vol.66 (4), p.470-476 |
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| creator | Shi, Qing-Wen Sauriol, Françoise Mamer, Orval Zamir, Lolita O |
| description | Ten new taxanes were isolated from the methanol extract of the needles of the Canadian yew, Taxus canadensis. On the basis of their spectral analysis, their structures were established as 9α-hydroxy-2α,7α,10β-triacetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (1), 9α,10β-diacetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (2), 9α,20-dihydroxy-2α,10β,13α-triacetoxytaxa-4(5),11(12)-diene (3), 2α,9α,10β-triacetoxy-20-cinnamoyloxy-11,12-epoxytaxa-4-en-13-one (4), 9α-hydroxy-2α,10β,13α-triacetoxy-5α-(3‘-methylamino-3‘-phenyl)-propionyloxytaxa-4(20),11-diene (5), 2α,10β-diacetoxy-5α,9α-dihydroxytaxa-4(20),11-dien-13-one (6), 2α,9α-diacetoxy-5α,10β-dihydroxytaxa-4(20),11-dien-13-one (7), 5α,9α-dihydroxy-2α,10β,13α-triacetoxytaxa-4(20),11-diene (8), 5α,10β-dihydroxy-2α,9α,13α-triacetoxytaxa-4(20),11-diene (9), and 7β,11β-dihydroxy-2α,9α,10β,13-tetraacetoxy-5α-cinnamoyloxytaxa-4(20),12-diene (10). Taxane 1 is the first example of a 3,11-cyclotaxane with a 7-epi-α-oxygenated group. Taxane 4 is the first taxane with a C-11,12-epoxide ring as well as a C-4(5)-endo-double bond. Taxanes with a 12(13) double bond as in 10 instead of the usual 11(12) double bond have been found so far only in the needles, stem, and seeds of the Japanese yew. |
| doi_str_mv | 10.1021/np020361n |
| format | Article |
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On the basis of their spectral analysis, their structures were established as 9α-hydroxy-2α,7α,10β-triacetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (1), 9α,10β-diacetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (2), 9α,20-dihydroxy-2α,10β,13α-triacetoxytaxa-4(5),11(12)-diene (3), 2α,9α,10β-triacetoxy-20-cinnamoyloxy-11,12-epoxytaxa-4-en-13-one (4), 9α-hydroxy-2α,10β,13α-triacetoxy-5α-(3‘-methylamino-3‘-phenyl)-propionyloxytaxa-4(20),11-diene (5), 2α,10β-diacetoxy-5α,9α-dihydroxytaxa-4(20),11-dien-13-one (6), 2α,9α-diacetoxy-5α,10β-dihydroxytaxa-4(20),11-dien-13-one (7), 5α,9α-dihydroxy-2α,10β,13α-triacetoxytaxa-4(20),11-diene (8), 5α,10β-dihydroxy-2α,9α,13α-triacetoxytaxa-4(20),11-diene (9), and 7β,11β-dihydroxy-2α,9α,10β,13-tetraacetoxy-5α-cinnamoyloxytaxa-4(20),12-diene (10). Taxane 1 is the first example of a 3,11-cyclotaxane with a 7-epi-α-oxygenated group. Taxane 4 is the first taxane with a C-11,12-epoxide ring as well as a C-4(5)-endo-double bond. Taxanes with a 12(13) double bond as in 10 instead of the usual 11(12) double bond have been found so far only in the needles, stem, and seeds of the Japanese yew.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np020361n</identifier><identifier>PMID: 12713395</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Biological and medical sciences ; Bridged-Ring Compounds - chemistry ; Bridged-Ring Compounds - isolation & purification ; Canada ; Chromatography, High Pressure Liquid ; General pharmacology ; Medical sciences ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plants, Medicinal - chemistry ; Stereoisomerism ; Structure-Activity Relationship ; Taxoids ; Taxus - chemistry</subject><ispartof>Journal of natural products (Washington, D.C.), 2003-04, Vol.66 (4), p.470-476</ispartof><rights>Copyright © 2003 American Chemical Society and American Society of Pharmacognosy</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-d0434af3a301e9d576c63e0f44d933d3b022f571d25c6869ce4c1de9563e4a683</citedby><cites>FETCH-LOGICAL-a445t-d0434af3a301e9d576c63e0f44d933d3b022f571d25c6869ce4c1de9563e4a683</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np020361n$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np020361n$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14771701$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12713395$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shi, Qing-Wen</creatorcontrib><creatorcontrib>Sauriol, Françoise</creatorcontrib><creatorcontrib>Mamer, Orval</creatorcontrib><creatorcontrib>Zamir, Lolita O</creatorcontrib><title>New Taxanes from the Needles of Taxus canadensis</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Ten new taxanes were isolated from the methanol extract of the needles of the Canadian yew, Taxus canadensis. On the basis of their spectral analysis, their structures were established as 9α-hydroxy-2α,7α,10β-triacetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (1), 9α,10β-diacetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (2), 9α,20-dihydroxy-2α,10β,13α-triacetoxytaxa-4(5),11(12)-diene (3), 2α,9α,10β-triacetoxy-20-cinnamoyloxy-11,12-epoxytaxa-4-en-13-one (4), 9α-hydroxy-2α,10β,13α-triacetoxy-5α-(3‘-methylamino-3‘-phenyl)-propionyloxytaxa-4(20),11-diene (5), 2α,10β-diacetoxy-5α,9α-dihydroxytaxa-4(20),11-dien-13-one (6), 2α,9α-diacetoxy-5α,10β-dihydroxytaxa-4(20),11-dien-13-one (7), 5α,9α-dihydroxy-2α,10β,13α-triacetoxytaxa-4(20),11-diene (8), 5α,10β-dihydroxy-2α,9α,13α-triacetoxytaxa-4(20),11-diene (9), and 7β,11β-dihydroxy-2α,9α,10β,13-tetraacetoxy-5α-cinnamoyloxytaxa-4(20),12-diene (10). Taxane 1 is the first example of a 3,11-cyclotaxane with a 7-epi-α-oxygenated group. Taxane 4 is the first taxane with a C-11,12-epoxide ring as well as a C-4(5)-endo-double bond. Taxanes with a 12(13) double bond as in 10 instead of the usual 11(12) double bond have been found so far only in the needles, stem, and seeds of the Japanese yew.</description><subject>Biological and medical sciences</subject><subject>Bridged-Ring Compounds - chemistry</subject><subject>Bridged-Ring Compounds - isolation & purification</subject><subject>Canada</subject><subject>Chromatography, High Pressure Liquid</subject><subject>General pharmacology</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plants, Medicinal - chemistry</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>Taxoids</subject><subject>Taxus - chemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1Lw0AQBuBFFFs_Dv4ByUXBQ3R2Zz-aoxS1SvEDqx6XdXeD0TSpuwnqvzfS0F48Dcw8vAwvIQcUTikwelYtgAFKWm2QIRUMUglMbJIhUIkpjiQfkJ0Y3wEAIRPbZECZooiZGBK49V_JzHybysckD_U8ad58cuu9K7tFnf_d2phYUxnnq1jEPbKVmzL6_X7ukqfLi9l4kk7vrq7H59PUcC6a1AFHbnI0CNRnTihpJXrIOXcZosNXYCwXijomrBzJzHpuqfOZ6BQ3coS75HiZuwj1Z-tjo-dFtL4su0_rNmqFDBFQdPBkCW2oYww-14tQzE340RT0Xz16VU9nD_vQ9nXu3Vr2fXTgqAcmWlPmwVS2iGvHlaIKaOfSpSti479XdxM-tFSohJ7dP-rJ1fPlywNyfbPONTbq97oNVdfdPw_-Ao-6hXw</recordid><startdate>20030401</startdate><enddate>20030401</enddate><creator>Shi, Qing-Wen</creator><creator>Sauriol, Françoise</creator><creator>Mamer, Orval</creator><creator>Zamir, Lolita O</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><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>7X8</scope></search><sort><creationdate>20030401</creationdate><title>New Taxanes from the Needles of Taxus canadensis</title><author>Shi, Qing-Wen ; Sauriol, Françoise ; Mamer, Orval ; Zamir, Lolita O</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-d0434af3a301e9d576c63e0f44d933d3b022f571d25c6869ce4c1de9563e4a683</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Biological and medical sciences</topic><topic>Bridged-Ring Compounds - chemistry</topic><topic>Bridged-Ring Compounds - isolation & purification</topic><topic>Canada</topic><topic>Chromatography, High Pressure Liquid</topic><topic>General pharmacology</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plants, Medicinal - chemistry</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><topic>Taxoids</topic><topic>Taxus - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shi, Qing-Wen</creatorcontrib><creatorcontrib>Sauriol, Françoise</creatorcontrib><creatorcontrib>Mamer, Orval</creatorcontrib><creatorcontrib>Zamir, Lolita O</creatorcontrib><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>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>Shi, Qing-Wen</au><au>Sauriol, Françoise</au><au>Mamer, Orval</au><au>Zamir, Lolita O</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New Taxanes from the Needles of Taxus canadensis</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2003-04-01</date><risdate>2003</risdate><volume>66</volume><issue>4</issue><spage>470</spage><epage>476</epage><pages>470-476</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Ten new taxanes were isolated from the methanol extract of the needles of the Canadian yew, Taxus canadensis. On the basis of their spectral analysis, their structures were established as 9α-hydroxy-2α,7α,10β-triacetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (1), 9α,10β-diacetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (2), 9α,20-dihydroxy-2α,10β,13α-triacetoxytaxa-4(5),11(12)-diene (3), 2α,9α,10β-triacetoxy-20-cinnamoyloxy-11,12-epoxytaxa-4-en-13-one (4), 9α-hydroxy-2α,10β,13α-triacetoxy-5α-(3‘-methylamino-3‘-phenyl)-propionyloxytaxa-4(20),11-diene (5), 2α,10β-diacetoxy-5α,9α-dihydroxytaxa-4(20),11-dien-13-one (6), 2α,9α-diacetoxy-5α,10β-dihydroxytaxa-4(20),11-dien-13-one (7), 5α,9α-dihydroxy-2α,10β,13α-triacetoxytaxa-4(20),11-diene (8), 5α,10β-dihydroxy-2α,9α,13α-triacetoxytaxa-4(20),11-diene (9), and 7β,11β-dihydroxy-2α,9α,10β,13-tetraacetoxy-5α-cinnamoyloxytaxa-4(20),12-diene (10). Taxane 1 is the first example of a 3,11-cyclotaxane with a 7-epi-α-oxygenated group. Taxane 4 is the first taxane with a C-11,12-epoxide ring as well as a C-4(5)-endo-double bond. Taxanes with a 12(13) double bond as in 10 instead of the usual 11(12) double bond have been found so far only in the needles, stem, and seeds of the Japanese yew.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>12713395</pmid><doi>10.1021/np020361n</doi><tpages>7</tpages></addata></record> |
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| subjects | Biological and medical sciences Bridged-Ring Compounds - chemistry Bridged-Ring Compounds - isolation & purification Canada Chromatography, High Pressure Liquid General pharmacology Medical sciences Molecular Structure Nuclear Magnetic Resonance, Biomolecular Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plants, Medicinal - chemistry Stereoisomerism Structure-Activity Relationship Taxoids Taxus - chemistry |
| title | New Taxanes from the Needles of Taxus canadensis |
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