Synthesis and Biological Evaluation of New Natural Phenolic (2E,4E,6E)-Octa-2,4,6-trienoic Esters

Chem Biodivers. 2017 Dec;14(12). doi: 10.1002/cbdv.201700294. Epub 2017 Dec 5.

Abstract

In the present study the esterification of the OH groups of resveratrol, caffeic acid, ferulic acid, and β-sitosterol with an antioxidant polyconjugated fatty acid, (2E,4E,6E)-octa-2,4,6-trienoic acid, was achieved. As the selective esterification of OH groups of natural compounds can affect their biological activity, a selective esterification of resveratrol and caffeic acid was performed by an enzymatic approach. The new resulting compounds were characterized spectroscopically (FT-IR, NMR mono, and bidimensional techniques); when necessary the experimental data were integrated by quantum chemical calculations. The antioxidant, anti-inflammatory and proliferative activity was evaluated. The good results encourage the use of these molecules as antioxidant and/or anti-inflammatory agents in dermocosmetic application.

Keywords: Anti-inflammatory activity; Antioxidant activity; Biocatalysis; Natural products; Selective esterification.

MeSH terms

  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Caffeic Acids / chemical synthesis
  • Caffeic Acids / chemistry
  • Cell Line
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Esters / chemical synthesis
  • Esters / chemistry*
  • Esters / pharmacology
  • Humans
  • Hydrogen Peroxide / toxicity
  • Keratinocytes / cytology
  • Keratinocytes / drug effects
  • Keratinocytes / metabolism
  • Lipopolysaccharides / toxicity
  • Magnetic Resonance Spectroscopy
  • Oxidative Stress / drug effects
  • Phenols / chemical synthesis
  • Phenols / chemistry
  • Phenols / pharmacology
  • Quantum Theory
  • Spectroscopy, Fourier Transform Infrared
  • Stereoisomerism

Substances

  • Antioxidants
  • Caffeic Acids
  • Esters
  • Lipopolysaccharides
  • Phenols
  • Hydrogen Peroxide
  • caffeic acid