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5-epi-Canadensene and other novel metabolites of Taxus canadensis |
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| Authors: | Lolita O Zamir Junzeng Zhang Kristina Kutterer Françoise Sauriol Orval Mamer Abdesslem Khiat Yvan Boulanger |
| Institution: | a Université du Québec, Institut Armand-Frappier, 531 boul. des Prairies, Laval, Québec, Canada, H7N 4Z3 b Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Québec, Canada H3A 2K6 Biomedical Mass Spectrometry Unit, McGill University, 1130 Pine Avenue West, Montreal, Québec, Canada H3A 1A3 Département de Radiologie, Centre Hospitalier de l'Université de Montréal, Campus Saint-Luc, 1058 St-Denis, Montréal, Québec, Canada H2X 3J4 |
| Abstract: | The Canadian yew distinguishes itself from other yews by the nature of its taxane metabolites. We are now reporting a new canadensene taxane whose stereochemistry is rigorously established. The three-dimensional structures of canadensene, 5-epi-canadensene and three other related bicyclic taxanes isolated from other yews were calculated using distance constraints derived from NMR data. The stereochemistry of the substituents, the polar acetate groups and the double bonds determine the 3D models. In addition, three new taxanes were also characterized and some biosynthetic speculations are presented. |
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