A taxane with an amino-side chain on C-5 was identified for the first time from rooted cuttings of the Canadian yew, Taxus canadensis. The structure was characterized as 2α,10β,13α-triacetoxy-5α-[3'-(N-formyl-Nmethylamino)-3'-phenylpropanoyloxy]taxa-4(20),12-dien-9α-ol (1) on the basis of 1D and 2D NMR data and HR-FAB-MS analyses. The spectra revealed that in CDCl3 solution 1 was composed of two rotamers (1a and 1b) in a ratio of approximately 1:1.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, and A. T. McPhail, J. Am. Chem. Soc., 93, 2325 (1971).
E. Baloglu and D. G. I. Kingston, J. Nat. Prod., 62, 1448 (1999).
V. S. Parmer, A. Jha, K. S. Bish, P. Taneja, S. K. Sight, A. Kumar, G. R. Poonam, and C. E. Olsen, Phytochemistry, 50, 1267 (1999).
Y.-F. Wang, Q.-W. Shi, M. Dong, H. Kiyota, Y.-C. Gu, and B. Cong, Chem. Rev., 111, 7652 (2011).
Q.-W. Shi, Y.-F. Wang, and H. Kiyota, Chem. Nat. Prod., Research Signpost, India, 43 (2006).
M.-L. Zhang, M. Dong, X.-L. Li, L.-G. Li, C.-H. Huo, Q.-W. Shi, Y.-C. Gu, B. Cong, and H. Kiyota, Tetrahedron Lett., 49, 3405 (2008).
G. Appendino, The Chemistry and Pharmacology of Taxol and Its Derivatives, Elsevier, Amsterdam, 1995, 22, pp. 1, 55.
D. G. I. Kingston, A. A. Molinero, and G. M. Rimoldi, Progress in the Chemistry of Organic Natural Products, Vol. 61, Springer, Wien, 1993.
Acknowledgment
We are grateful for financial support from the National Natural Science Foundation of China (81072551), the Scientific Research Foundation for the Returning Overseas Chinese Scholars of Hebei Province (2006-02), and the Scientific Research Foundation of Hebei Province (C2010000489). We also appreciate financial support from Syngenta Ltd. (2011-Hebei Medical University-Syngenta-03) and the Japan Society for the Promotion of Science (No. 22580112).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2012, pp. 914–916.
Rights and permissions
About this article
Cite this article
Zhang, HZ., Wang, YF., Zhang, ML. et al. A new alkaloid taxane composed of two N-formyl rotamers from the rooted cuttings of Taxus canadensis . Chem Nat Compd 48, 1035–1038 (2013). https://doi.org/10.1007/s10600-013-0458-7
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-013-0458-7