Novel taxa-4(20),12-diene and 2(3→20)abeotaxane from needles of Taxus canadensis

Biosci Biotechnol Biochem. 2011;75(9):1698-701. doi: 10.1271/bbb.110223. Epub 2011 Sep 7.

Abstract

A novel 6/8/6-membered taxane with a rare C-12(13)-double bond and rare 2(3→20)abeotaxane were isolated from the needles of Taxus canadensis. Their structures were characterized as 7β,9α,10β-triacetoxytaxa-4(20),12-diene-2α,5α,11β-triol (1) and 2α,7β,10β-triacetoxy-5α-hydroxy-2(3→20)abeotaxa-4(20),11-diene-9,13-dione (2) on the basis of 1D and 2D spectroscopic data. 1 is the first example of a natural taxane without substitution at both C-13 and C-14.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / analysis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Breast Neoplasms / drug therapy
  • Breast Neoplasms / pathology
  • Cell Line, Tumor
  • Female
  • Humans
  • Magnetic Resonance Spectroscopy
  • Male
  • Molecular Structure
  • Plant Extracts / analysis*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Plant Leaves / chemistry
  • Prostatic Neoplasms / drug therapy
  • Prostatic Neoplasms / pathology
  • Taxoids / analysis*
  • Taxoids / chemistry
  • Taxoids / isolation & purification
  • Taxoids / pharmacology
  • Taxus / chemistry*
  • Treatment Failure
  • Uterine Cervical Neoplasms / drug therapy
  • Uterine Cervical Neoplasms / pathology

Substances

  • Antineoplastic Agents
  • Plant Extracts
  • Taxoids