Synthesis and radical scavenging of novel magnolol derivatives

J Pharm Pharmacol. 2002 Dec;54(12):1697-703. doi: 10.1211/002235702360.

Abstract

We have investigated the developdment of potential antioxidants based on magnolol, a naturally occurring biphenolic obtained from the bark of Magnolia officinalis. A series of aminomethylated derivatives of magnolol were synthesized under the aromatic Mannich reaction. In-vitro testing for diphenyl-p-picrylhydrazyl (DPPH) scavenging and chemiluminescence assays in whole cell models revealed that the pyrrolidyl-containing magnolols (2b (5,5'-diallyl-3-(pyrrolidin-1-ylmethyl)-biphenyl-2,2'-diol), 3a (5,5'-diallyl-3,3'-bis-(pyrrolidin-1-ylmethyl)-biphenyl-2,2'-diol) and 4c (5,5'-diallyl-3-(morphorin-4-ylmethyl)-3'-(pyrrolidin-1-ylmethyl)-biphenyl-2,2'-diol)) displayed promising free radical scavenging effects as compared with magnolol. The results from compound 4c indicated that the naturally occurring component was suitable to be a lead compound toward promising antioxidants.

Publication types

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

MeSH terms

  • Biphenyl Compounds / chemical synthesis*
  • Biphenyl Compounds / chemistry*
  • Biphenyl Compounds / isolation & purification
  • Free Radical Scavengers / chemical synthesis*
  • Free Radical Scavengers / chemistry
  • Hydrazines / chemistry*
  • Lignans*
  • Luminescent Measurements
  • Magnolia / chemistry
  • Picrates
  • Plant Bark / chemistry
  • Plant Oils / chemistry

Substances

  • Biphenyl Compounds
  • Free Radical Scavengers
  • Hydrazines
  • Lignans
  • Picrates
  • Plant Oils
  • magnolol
  • 1,1-diphenyl-2-picrylhydrazyl