Taxanes with C-5-amino-side chains from the needles of Taxus canadensis
| Autor: | Alain Lesimple, Lolita O. Zamir, Xiuhong Ji, Francoise Sauriol, Qing-Wen Shi |
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| Rok vydání: | 2004 |
| Předmět: |
Magnetic Resonance Spectroscopy
Taxane Molecular Structure biology Stereochemistry Metabolite Plant Science General Medicine Spectrometry Mass Fast Atom Bombardment Horticulture Fast atom bombardment biology.organism_classification Biochemistry chemistry.chemical_compound chemistry Taxus canadensis Side chain Taxoids Taxus Molecular Biology Taxus cuspidata |
| Zdroj: | Phytochemistry. 65:3097-3106 |
| ISSN: | 0031-9422 |
| Popis: | Five taxanes with an amino-side chain on C-5 were identified for the first time in the needles of the Canadian yew, Taxus canadensis. Their structures were characterized as 2alpha,7beta,9alpha,10beta,13-pentaacetoxy-11beta-hydroxy-5alpha-(3'-N,N-dimethylamino-3'-phenyl)-propionyloxytaxa-4(20),12-diene (1), 2alpha,9alpha-dihydroxy-10beta,13alpha-diacetoxy-5alpha-(3'-methylamino-3'-phenyl)-propionyloxytaxa-4(20),11-diene (2), 2alpha17-dihydroxy-9alpha,10beta,13alpha-triacetoxy-5alpha-(3'-N,N-dimethylamino-3'-phenyl)-propionyloxytaxa-4(20),11-diene (3), 2alpha-hydroxy-7beta,9alpha,10beta,13alpha-tetraacetoxy-5alpha-(2'-hydroxy-3'-N,N-dimethylamino-3'-phenyl)-propionyloxytaxa-4(20),11-diene (4), and 9alpha-hydroxy-2alpha,10beta,13alpha-triacetoxy-5alpha-(3'-N,N-dimethylamino-3'-phenyl)-propionyloxytaxa-4(20),11-diene (5) on the basis of 1D-, 2D-NMR spectroscopic data and high-resolution fast atom bombardment MS analyses. Metabolite (1) was isolated from the needles of the Canadian yew for the first time but had previously been detected in the stems of the Japanese yew, whereas taxanes (2-5) are only now reported. Metabolite (3) is the first reported nitrogen-containing taxane with a 17-hydroxyl substitution. |
| Databáze: | OpenAIRE |
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