A New pseudo-Alkaloid Taxane and a New Rearranged Taxane from the Needles of Taxus canadensis

Manli Zhang, Changhong Huo, Mei Dong, Ligeng Li, Françoise Sauriol, Qingwen Shi, Yucheng Gu, Hiromasa Kiyota, Bin Cong

doi:10.1515/znb-2008-0814

A New pseudo-Alkaloid Taxane and a New Rearranged Taxane from the Needles of Taxus canadensis

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Manli Zhang

School of Pharmaceutical Sciences & College of Basic Medical Sciences, Hebei Medical University, 361 Zhongshan East Road, 050017, Shijiazhuang, Hebei Province, PR China
Changhong Huo

School of Pharmaceutical Sciences & College of Basic Medical Sciences, Hebei Medical University, 361 Zhongshan East Road, 050017, Shijiazhuang, Hebei Province, PR China
Mei Dong

School of Pharmaceutical Sciences & College of Basic Medical Sciences, Hebei Medical University, 361 Zhongshan East Road, 050017, Shijiazhuang, Hebei Province, PR China
Ligeng Li

School of Pharmaceutical Sciences & College of Basic Medical Sciences, Hebei Medical University, 361 Zhongshan East Road, 050017, Shijiazhuang, Hebei Province, PR China
Françoise Sauriol

Department of Chemistry, Queen’s University, Kingston, Ontario, K7L 3N6, Canada
Qingwen Shi

School of Pharmaceutical Sciences & College of Basic Medical Sciences, Hebei Medical University, 361 Zhongshan East Road, 050017, Shijiazhuang, Hebei Province, PR China
Yucheng Gu

Syngenta Jealott’s Hill International Reasearch Centre, Bracknell, Berkshire RG42 6EY, United Kingdom
Hiromasa Kiyota

Department of Bioscience and Biotechnology for Future Bioindustry, Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiya, Aoba-ku, Sendai, 981-8555 Japan
Bin Cong

School of Pharmaceutical Sciences & College of Basic Medical Sciences, Hebei Medical University, 361 Zhongshan East Road, 050017, Shijiazhuang, Hebei Province, PR China

抄録

<jats:p>A new taxane with an amino side chain on C-5 and a new 11(15→1)abeotaxane having a tetrahydrofuran ring along carbon atoms C-2, C-3, C-4, C-20 identified for the first time from the needles of the Canadian yew, Taxus canadensis. Their structures were characterized as 2α,7β ,9α,10β ,13-pentaacetoxy-11β -hydroxy-5α-(2´ -hydroxy,3'-N,N-dimethylamino-3´- phenyl)-propionyloxytaxa-4(20),12-diene (1) and 13α,20β -diacetoxy-5α,7β ,9α,10β -tetrahydroxy- 2α,20-epoxy-11(15→1)abeotaxa-11,15-diene (2) on the basis of 1D, 2D NMR spectroscopy and high-resolution FABMS analysis. Taxane 1 contains a rare C-12, C-13 double bond and a basic side chain, while taxane 2 bears a rare isopropenyl group at C-1. </jats:p>