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

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  • Yong Li
  • Man-Li Zhang
    School of Pharmaceutical Sciences, Hebei Medical University, 361 Zhongshan East Road, 050017 Shijiazhuang, Hebei Province, China
  • Yu-Fang Wang
    School of Pharmaceutical Sciences, Hebei Medical University, 361 Zhongshan East Road, 050017 Shijiazhuang, Hebei Province, China
  • Mei Dong
    Department of Forensic Medicine, Hebei Key Laboratory of Forensic Medicine, Hebei Medical University, 050017 Shijiazhuang, Hebei Province, China
  • Françoise Sauriol
    Department of Chemistry, Queen’s University, Kingston, Ontario, K7L 3N6 Canada
  • Qing-Wen Shi
  • Hiromasa Kiyota
    Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiya, Aoba-ku, Sendai 981-8555, Japan
  • Yu-Cheng Gu
    Jealott’s Hill International Research Centre, Syngenta, Berkshire RG42 6EY, UK
  • Bin Cong
    Department of Forensic Medicine, Hebei Key Laboratory of Forensic Medicine, Hebei Medical University, 050017 Shijiazhuang, Hebei Province, China

抄録

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

収録刊行物

  • hc

    hc 18 (2), 57-60, 2012-04-01

    Walter de Gruyter GmbH

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