Chemical Studies on Taxus canadensis

• Published in: Chemistry & biodiversity 2013-10, Vol.10 (10), p.1729-1753
• Main Authors: Li, Yong, Qin, Fang, Wang, Si-Ming, Guo, Rui-Xia, Zhang, Yue-Feng, Gu, Yu-Cheng, Shi, Qing-Wen
• Format: Article
• Language: English
• Subjects: Cell Survival - drug effects; Diterpenoids; Drug Resistance, Neoplasm - drug effects; Generic drugs; Humans; Isomerism; MCF-7 Cells; Microtubule polymerization; Molecular Conformation; Plant Extracts - chemistry; Propellanes; Semisynthesis; Taxaceae; Taxanes; Taxoids - chemistry; Taxoids - isolation & purification; Taxoids - toxicity; Taxol; Taxus - chemistry; Taxus - metabolism; Taxus canadensis; Yew
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.201200032

A series of new taxanes, 1–93, have been isolated, together with 37 known taxoids including Taxol® (paclitaxel) and cephalomannine, from the Canadian yew, Taxus canadensis (Taxaceae) in the past 30 years. These new taxoids possess various skeletons containing 5/7/6, 6/10/6, 6/5/5/6, 6/8/6, and 6/12 ring systems and six new taxanes with four novel skeletons, i.e., a taxane with a 6/6/8/6 ring system, a taxane with a [3.3.3] propellane skeleton, three taxanes with [3.3.3] [3.4.5] dipropellane sytems, as well as a novel taxane with a unique 5/5/4/6/6/6 hexacyclic skeleton, containing a unique [3.3.2] propellane, were isolated for the first time from natural sources. It should be emphasized that 13‐acetyl‐9‐dihydrobaccatin III, a very useful starting material for the semisynthesis of Taxol® and Taxotere®, represents the most abundant taxane in the needles of this yew tree. These findings establish the above mentioned yew tree as significantly different from the remaining species. On the other hand, some chemical modifications on the taxanes isolated from this plant were carried out.