Canataxpyran A, a novel 3,8-secotaxane with a 13,17-ether bridge from needles of Taxus canadensis

Heterocyclic communications

article

Yong Li¹  Man-Li Zhang³  Yu-Fang Wang³  Mei Dong¹  Françoise Sauriol⁴  Qing-Wen Shi¹  Hiromasa Kiyota⁵  Yu-Cheng Gu⁶  Bin Cong¹ 

[1] Department of Forensic Medicine, Hebei Key Laboratory of Forensic Medicine, Hebei Medical University;Department of Thoracic, Fourth Hospital of Hebei Medical University;School of Pharmaceutical Sciences, Hebei Medical University;Department of Chemistry, Queen’s University;Graduate School of Agricultural Science, Tohoku University;Jealott’s Hill International Research Centre

关键词: isolation;    needle;    3;    8-secotaxane;    Taxaceae;    Taxus canadensis;   

DOI  :  10.1515/hc-2012-0035

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

A novel 6/12-membered bicyclic taxane with a 13,17-ether bridge, named canataxpyran A, was isolated from the needles of Taxus canadensis . The structures were characterized as 7β,9,10β,20-tetracetoxy-13β,17-epoxy-3,8-secotaxa-3 E ,8 E ,11-triene-2α,5α-diol (designated as canataxpyran A, 1 ). This bicyclic taxane gradually decomposed in CDCl 3 to give the corresponding enones, 10β,20-diacetoxy-13β,17-epoxy-4α,5α-dihydroxy-3,8-secotaxa-2 E ,7 E ,11-trien-9-one (canataxpyran B, 2 ) and 5α,10β,20-triacetoxy-13β,17-epoxy-4α-hydroxy- 3,8-secotaxa-2 E ,7 E ,11-trien-9-one (canataxpyran C, 3 ). Compound 1 is the first example of a natural 3,8-secotaxane with 13,17-oxygen bridge.

【 授权许可】

CC BY|CC BY-NC-ND