Bioactive quinic acid derivatives from Ageratina adenophora

Molecules. 2013 Nov 14;18(11):14096-104. doi: 10.3390/molecules181114096.

Abstract

A novel quinic acid derivative, 5-O-trans-o-coumaroylquinic acid methyl ester (1), together with three known ones, chlorogenic acid methyl ester (2), macranthoin F (3) and macranthoin G (4), were isolated from the aerial parts of the invasive plant Ageratina adenophora (Spreng.). The structure of new compound 1 was elucidated on the basis of extensive spectroscopic analysis, including 1D- and 2D-NMR techniques. Compounds 2-4 were isolated from plant A. adenophora for the first time. All the compounds showed in vitro antibacterial activity toward five assayed bacterial strains, especially 3 and 4, which showed in vitro antibacterial activity against Salmonella enterica with MIC values of 7.4 and 14.7 μM, respectively. Compound 1 was further found to display in vitro anti-fungal activity against spore germination of Magnaporthe grisea with an IC₅₀ value 542.3 µM. These four compounds were also tested for their antioxidant activity against DPPH (1,1-diphenyl-2-picrylhydrazyl) radical.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ageratina / chemistry*
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology
  • Biphenyl Compounds / chemistry
  • Free Radical Scavengers / chemistry
  • Magnaporthe / drug effects
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Picrates / chemistry
  • Quinic Acid / chemistry*
  • Quinic Acid / pharmacology
  • Salmonella enterica / drug effects
  • Saponins / chemistry
  • Saponins / pharmacology

Substances

  • Anti-Infective Agents
  • Biphenyl Compounds
  • Free Radical Scavengers
  • Picrates
  • Saponins
  • macranthoin F
  • Quinic Acid
  • 1,1-diphenyl-2-picrylhydrazyl