New regio- and stereoselective O-deacetylated and epoxy products of taxanes isolated from Taxus mairei

J Nat Prod. 2004 Dec;67(12):2136-40. doi: 10.1021/np040152y.

Abstract

Deacylation of a taxoid mixture isolated from the roots of Taxus mairei followed by chromatographic fractionation resulted in the isolation of three new taxoid derivatives, 2alpha,9alpha,10beta-triacetoxy-5alpha,14beta-dihydroxy-4(20),11(12)-taxadiene (1), 9alpha,10beta-diacetoxy-2alpha,5alpha,14beta-trihydroxy-4(20),11(12)-taxadiene (2), and 9alpha,10beta-diacetoxy-2alpha,5alpha,14beta-trihydroxy-4,20-epoxy,11(12)-taxene (3). Epoxidation of 2 afforded 9alpha,10beta-diacetoxy-2alpha,5alpha,14beta-trihydroxy-4,20:11,12-diepoxytaxane (6), while epoxidation of 4 yielded 9alpha,10beta-diacetoxy-5alpha,13alpha-dihydroxy-4,20-epoxy,11(12)-taxene (7) and 9alpha,10beta-diacetoxy-5alpha,13alpha-dihydroxy-4,20:11,12-diepoxytaxane (8). The structures were elucidated by detailed analysis of their NMR spectra. The structure and relative stereochemistry of 7 was confirmed by X-ray crystallography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Epoxy Compounds / chemistry*
  • Epoxy Compounds / isolation & purification*
  • Molecular Conformation
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Stereoisomerism
  • Taiwan
  • Taxoids / chemistry*
  • Taxoids / isolation & purification*
  • Taxus / chemistry*

Substances

  • Epoxy Compounds
  • Taxoids