Taxanes from Rooted Cuttings of Taxus c anadensis
A 3,11-cyclotaxane (1), a new epoxytaxane (2), an abeo-taxane (3), and 26 known taxanes were isolated in rooted cuttings of the Canadian yew (Taxus canadensis) for the first time. Their chemical structures were characterized as 1β,2α,9α-trihydroxy-10β-acetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-...
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Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2004-11, Vol.67 (11), p.1864-1869 |
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container_title | Journal of natural products (Washington, D.C.) |
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creator | Petzke, Tracy L Shi, Qing Wen Sauriol, Françoise Mamer, Orval Zamir, Lolita O |
description | A 3,11-cyclotaxane (1), a new epoxytaxane (2), an abeo-taxane (3), and 26 known taxanes were isolated in rooted cuttings of the Canadian yew (Taxus canadensis) for the first time. Their chemical structures were characterized as 1β,2α,9α-trihydroxy-10β-acetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (1), 2α,9α,10β-triacetoxy-11,12-epoxy-20-hydroxytaxa-4-en-13-one (2), and 7β,9α,10β,13α-tetraacetoxy-11(15→1)abeo-taxa-4(20),11-diene-5α,15-diol (3). Metabolite 2 is a new taxane, metabolite 1 has been reported previously in the needles of Taxus baccata, , and metabolite 3 was previously discovered as a biotransformation product but is now reported as a natural product for the first time. |
doi_str_mv | 10.1021/np049836w |
format | Article |
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Their chemical structures were characterized as 1β,2α,9α-trihydroxy-10β-acetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (1), 2α,9α,10β-triacetoxy-11,12-epoxy-20-hydroxytaxa-4-en-13-one (2), and 7β,9α,10β,13α-tetraacetoxy-11(15→1)abeo-taxa-4(20),11-diene-5α,15-diol (3). Metabolite 2 is a new taxane, metabolite 1 has been reported previously in the needles of Taxus baccata, , and metabolite 3 was previously discovered as a biotransformation product but is now reported as a natural product for the first time.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np049836w</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Journal of natural products (Washington, D.C.), 2004-11, Vol.67 (11), p.1864-1869</ispartof><rights>Copyright © 2004 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a104w-69f424b5c8a38b1a0bc10c0f59e0a78e717db9350ea0048bf2110d581fd51cbe3</citedby><cites>FETCH-LOGICAL-a104w-69f424b5c8a38b1a0bc10c0f59e0a78e717db9350ea0048bf2110d581fd51cbe3</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/np049836w$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np049836w$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Petzke, Tracy L</creatorcontrib><creatorcontrib>Shi, Qing Wen</creatorcontrib><creatorcontrib>Sauriol, Françoise</creatorcontrib><creatorcontrib>Mamer, Orval</creatorcontrib><creatorcontrib>Zamir, Lolita O</creatorcontrib><title>Taxanes from Rooted Cuttings of Taxus c anadensis</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>A 3,11-cyclotaxane (1), a new epoxytaxane (2), an abeo-taxane (3), and 26 known taxanes were isolated in rooted cuttings of the Canadian yew (Taxus canadensis) for the first time. Their chemical structures were characterized as 1β,2α,9α-trihydroxy-10β-acetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (1), 2α,9α,10β-triacetoxy-11,12-epoxy-20-hydroxytaxa-4-en-13-one (2), and 7β,9α,10β,13α-tetraacetoxy-11(15→1)abeo-taxa-4(20),11-diene-5α,15-diol (3). Metabolite 2 is a new taxane, metabolite 1 has been reported previously in the needles of Taxus baccata, , and metabolite 3 was previously discovered as a biotransformation product but is now reported as a natural product for the first time.</description><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNptj01LxDAURYMoWEcX_oNsXLiovtckbbqU4hcMCDKuy0uaSAcnGZKW0X_vyIgrV3dxD5d7GLtEuEGo8DZsQbZa1LsjVqCqoKyhUsesAKxFKXQtT9lZzmsAENCqguGKPim4zH2KG_4a4-QG3s3TNIb3zKPn-37O3HIKNLiQx3zOTjx9ZHfxmwv29nC_6p7K5cvjc3e3LAlB7sq69bKSRllNQhskMBbBgletA2q0a7AZTCsUOAKQ2vgKEQal0Q8KrXFiwa4PuzbFnJPz_TaNG0pfPUL_49r_ue7ZqwNLNvfrOKewf_YP9w1NF1Ig</recordid><startdate>20041129</startdate><enddate>20041129</enddate><creator>Petzke, Tracy L</creator><creator>Shi, Qing Wen</creator><creator>Sauriol, Françoise</creator><creator>Mamer, Orval</creator><creator>Zamir, Lolita O</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20041129</creationdate><title>Taxanes from Rooted Cuttings of Taxus c anadensis</title><author>Petzke, Tracy L ; Shi, Qing Wen ; Sauriol, Françoise ; Mamer, Orval ; Zamir, Lolita O</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a104w-69f424b5c8a38b1a0bc10c0f59e0a78e717db9350ea0048bf2110d581fd51cbe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Petzke, Tracy L</creatorcontrib><creatorcontrib>Shi, Qing Wen</creatorcontrib><creatorcontrib>Sauriol, Françoise</creatorcontrib><creatorcontrib>Mamer, Orval</creatorcontrib><creatorcontrib>Zamir, Lolita O</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Petzke, Tracy L</au><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>Taxanes from Rooted Cuttings of Taxus c anadensis</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2004-11-29</date><risdate>2004</risdate><volume>67</volume><issue>11</issue><spage>1864</spage><epage>1869</epage><pages>1864-1869</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>A 3,11-cyclotaxane (1), a new epoxytaxane (2), an abeo-taxane (3), and 26 known taxanes were isolated in rooted cuttings of the Canadian yew (Taxus canadensis) for the first time. Their chemical structures were characterized as 1β,2α,9α-trihydroxy-10β-acetoxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (1), 2α,9α,10β-triacetoxy-11,12-epoxy-20-hydroxytaxa-4-en-13-one (2), and 7β,9α,10β,13α-tetraacetoxy-11(15→1)abeo-taxa-4(20),11-diene-5α,15-diol (3). Metabolite 2 is a new taxane, metabolite 1 has been reported previously in the needles of Taxus baccata, , and metabolite 3 was previously discovered as a biotransformation product but is now reported as a natural product for the first time.</abstract><pub>American Chemical Society</pub><doi>10.1021/np049836w</doi><tpages>6</tpages></addata></record> |
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title | Taxanes from Rooted Cuttings of Taxus c anadensis |
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