Chitosan-hydroxycinnamic acid conjugates: preparation, antioxidant and antimicrobial activity

Food Chem. 2014 Apr 1:148:97-104. doi: 10.1016/j.foodchem.2013.10.019. Epub 2013 Oct 12.

Abstract

In this study, the antioxidant and antimicrobial activities of chitosan-caffeic acid, chitosan-ferulic acid, and chitosan-sinapic acid conjugates with different grafting ratios were investigated. The synthesized chitosan-hydroxycinnamic acid conjugates were verified by performing (1)H NMR and differential scanning calorimetry analysis. The antioxidant activities of the conjugates were increased compared to the unmodified chitosan, by 1.79-fold to 5.05-fold (2,2-diphenyl-1-picrylhydrazyl scavenging assay), 2.44-fold to 4.12-fold (hydrogen peroxide scavenging assay), 1.34-fold to 3.35-fold (ABTS(+) radical scavenging assay), and also exhibited an increased reducing power. The conjugates also showed excellent lipid peroxidation inhibition abilities in a linoleic acid emulsion system. The conjugates exhibited antimicrobial activity against 15 clinical isolates, two standard methicillin-resistant Staphylococcus aureus (MRSA) and three standard methicillin-susceptible S. aureus strains, as well as eight foodborne pathogens. Additionally, the conjugates showed no cytotoxic activity towards human Chang liver and mouse macrophage RAW264.7 cells.

Keywords: Antimicrobial; Antioxidant; Chitosan; Cytocompatibility; Hydroxycinnamic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Cell Line
  • Chitosan / chemistry*
  • Chitosan / pharmacology
  • Coumaric Acids / chemistry*
  • Coumaric Acids / pharmacology
  • Humans
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Mice
  • Staphylococcus aureus

Substances

  • Anti-Bacterial Agents
  • Antioxidants
  • Coumaric Acids
  • Chitosan