Two new taxanes from the needles and branches bark of Taxus cuspidata

Chem Biodivers. 2006 Oct;3(10):1153-61. doi: 10.1002/cbdv.200690117.

Abstract

Two new taxanes were isolated from the MeOH extract of the needles and branches bark of the Japanese yew, Taxus cuspidata. The structures were established as (2alpha,5alpha,7beta,9alpha,10beta,13alpha)-5,10,13,20-tetraacetoxytax-11-ene-2,7,9-triol (1) and (2alpha,5alpha,9alpha,10beta)-2,9,10-triacetoxy-5-[(beta-D-glucopyranosyl)oxy]-3,11-cyclotax-11-en-13-one (2) on the basis of in-depth 1D- and 2D-NMR analyses. Compound 2 is the first example of a transannular taxane glycoside isolated from a natural source.

MeSH terms

  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plant Bark / chemistry
  • Plant Leaves / chemistry
  • Taxoids / chemistry
  • Taxoids / isolation & purification*
  • Taxus / chemistry*

Substances

  • (2alpha,5alpha,7beta,9alpha,10beta,13alpha)-5,10,13,20-tetraacetoxytax-11-ene-2,7,9-triol
  • (2alpha,5alpha,9alpha,10beta)-2,9,10-triacetoxy-5-((beta-D-glucopyranosyl)oxy)-3,11-cyclotax-11-en-13-one
  • Taxoids