abeo-taxane diterpenoids from the Taiwanese Yew Taxus sumatrana

Chem Biodivers. 2009 Dec;6(12):2255-62. doi: 10.1002/cbdv.200900003.

Abstract

Chemical investigation of the acetonic extract of the leaves and twigs of Taxus sumatrana (Taxaceae) led to the isolation of four new taxane diterpene esters, taiwantaxins A-D (1-4, resp.). Their structures were determined primarily on the basis of 1D- and 2D-NMR techniques as well as MS. Compound 1 is a rearranged taxane diterpenoid possessing an opened oxetane ring moiety containing C(4), C(5), and C(20). The metabolites 2 and 3 belong to a 5/6/6 taxene system having a rare five-membered gamma-lactone ring comprising C(8), C(9), C(10), and C(19). Compound 4 is an example of a taxane diterpene containing a 6/8/6 ring system with a tetrahydrofuran ring comprising C(2), C(3), C(4), and C(20). The 11(15-->1)abeo-taxane diterpenoids, taiwantaxins A-C (1-3, resp.) are lacking an O-bearing functionality at either C(13) or C(14). Compound 2 showed significant cytotoxic activity against human PC-3 tumor cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / toxicity
  • Bridged-Ring Compounds / chemistry*
  • Cell Line, Tumor
  • Diterpenes / chemistry*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Taiwan
  • Taxoids / chemistry*
  • Taxoids / isolation & purification
  • Taxoids / toxicity*
  • Taxus / chemistry*

Substances

  • 5a-acetoxy-20-(benzoyloxy)-2a,4a,7b,9a,15-pentahydroxy-10- oxo-10,19-epoxy-11(15-1)abeo-tax-11(12)-ene
  • Antineoplastic Agents, Phytogenic
  • Bridged-Ring Compounds
  • Diterpenes
  • Taxoids
  • taxane