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

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

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- tetrahydroxy2α,20-epoxy-11(15→1)abeotaxa-11,15-diene (2) on the basis of ID, 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.

Original languageEnglish
Pages (from-to)1005-1011
Number of pages7
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume63
Issue number8
Publication statusPublished - Aug 2008
Externally publishedYes

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Alkaloids
Needles
Nuclear magnetic resonance spectroscopy
Carbon
Atoms
taxane

Keywords

  • Taxaceae
  • Taxane
  • Taxus canadensis

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

Cite this

A new pseudo-alkaloid taxane and a new rearranged taxane from the needles of Taxus canadensis. / Zhang, Manli; Huo, Changhong; Dong, Mei; Li, Ligeng; Sauriol, Françoise; Shi, Qingwen; Gu, Yucheng; Kiyota, Hiromasa; Cong, Bin.

In: Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, Vol. 63, No. 8, 08.2008, p. 1005-1011.

Research output: Contribution to journalArticle

Zhang, Manli ; Huo, Changhong ; Dong, Mei ; Li, Ligeng ; Sauriol, Françoise ; Shi, Qingwen ; Gu, Yucheng ; Kiyota, Hiromasa ; Cong, Bin. / A new pseudo-alkaloid taxane and a new rearranged taxane from the needles of Taxus canadensis. In: Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences. 2008 ; Vol. 63, No. 8. pp. 1005-1011.
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