Taxanes from Rooted Cuttings of Taxus canadensis
- 1 November 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 67 (11) , 1864-1869
- https://doi.org/10.1021/np049836w
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 1 beta,2 alpha,9 alpha-trihydroxy-10 beta-acetoxy-5 alpha-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (1), 2 alpha,9 alpha,10 beta-triacetoxy-11,12-epoxy-20-hydroxytaxa-4-en-13-one (2), and 7 beta,9 alpha,10 beta,13 alpha-tetraacetoxy-11(15-->1)abeo-taxa-4(20),11-diene-5 alpha,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.Keywords
This publication has 10 references indexed in Scilit:
- Five Novel Taxanes from Taxus canadensisJournal of Natural Products, 1999
- Taxuspines U, V, and W, new taxane and related diterpenoids from the Japanese yew Taxus cuspidataTetrahedron, 1996
- Taxus canadensis taxanes: structures and stereochemistryCanadian Journal of Chemistry, 1995
- Isolation of 9-Dihydro-13-acetylbaccatin III from Taxus canadensisJournal of Natural Products, 1992
- Triterpenes from the frond exudate of the fern Notholaena greggiiPhytochemistry, 1992
- Highly efficient, practical approach to natural taxolJournal of the American Chemical Society, 1988
- Mise en Évidence de Nouveaux Analogues du Taxol Extraits de Taxus baccataJournal of Natural Products, 1984
- 19-Hydroxybaccatin III, 10-Deacetylcephalomannine, and 10-Deacetyltaxol: New Antitumor Taxanes From Taxus wallichianaJournal of Natural Products, 1981
- Photocyclization of aryl-substituted acetylenesi application of di-.pi.-methane-like rearrangements to arylcyclopropene synthesesJournal of the American Chemical Society, 1971
- Synthesis of Nitrofuran Derivatives. IYAKUGAKU ZASSHI, 1965