Novel fluoro- and hydroxyl-containing jasmonate derivatives as highly efficient elicitors in suspension cultures of Taxus chinensis

Bioorg Med Chem Lett. 2004 Sep 20;14(18):4755-8. doi: 10.1016/j.bmcl.2004.06.082.

Abstract

To develop more effective abiotic elicitors for cell suspension cultures of T. chinensis to meet the needs for paclitaxel as anti-tumor drug, some fluoro- or hydroxyl-containing groups are introduced to the ester moiety of jasmonic acid by the esterification or acylation with bis(trichloromethyl) carbonate and corresponding alcohol. Some of them are found to be novel and effective elicitors, which can enhance the production of taxuyunnanine C (Tc) up to 60% more than that by methyl jasmonate (MJA) in T. chinensis cell cultures.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Cells, Cultured
  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / chemistry
  • Cyclopentanes / pharmacology*
  • Esterification
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Esters / pharmacology*
  • Hydrocarbons, Fluorinated / chemical synthesis
  • Hydrocarbons, Fluorinated / chemistry
  • Hydrocarbons, Fluorinated / pharmacology*
  • Oxylipins
  • Stereoisomerism
  • Structure-Activity Relationship
  • Taxoids / metabolism
  • Taxus / drug effects*
  • Taxus / growth & development
  • Taxus / metabolism
  • Time Factors

Substances

  • 2,3-dihydroxypropyl jasmonate
  • Cyclopentanes
  • Esters
  • Hydrocarbons, Fluorinated
  • Oxylipins
  • Taxoids
  • pentafluoropropyl jasmonate
  • taxuyunnanine C
  • jasmonic acid