Enzymatic synthesis of a dihydrobenzofuran neolignan by oxidative coupling

Arch Pharm Res. 1999 Jun;22(3):306-8. doi: 10.1007/BF02976368.

Abstract

The oxidative dimerization of ferulic acid has been carried out using horse-radish peroxidase as catalyst to give a dihydrobenzofuran neolignan (1), the structure of which was elucidated as (2SR,3RS)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-n-buto xycarbonyl-5-(2E-carboxyethenyl)-7-methoxybenzofuran by spectroscopic analyses. This compound showed more potent cytotoxicity against several tumor cell lines than the starting material.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemical synthesis*
  • Acrylates / pharmacology*
  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology*
  • Benzofurans / chemical synthesis*
  • Benzofurans / pharmacology*
  • Coumaric Acids / pharmacology*
  • Drug Evaluation
  • Free Radical Scavengers / pharmacology*
  • Horseradish Peroxidase / chemistry*
  • Humans
  • Mice
  • Oxidation-Reduction
  • Tumor Cells, Cultured

Substances

  • Acrylates
  • Antineoplastic Agents
  • Benzofurans
  • Coumaric Acids
  • Free Radical Scavengers
  • dogwalker1
  • ferulic acid
  • Horseradish Peroxidase