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Antimicrobial and Antioxidant Activities of N-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff Bases

Summary

This research developed improved versions of a marine-derived compound called chitosan by adding specific chemical groups to enhance its ability to fight harmful bacteria and fungi while also acting as an antioxidant. Here’s how this impacts everyday life: • Could lead to development of safer, more effective natural preservatives for food products • May help create new environmentally-friendly pesticides for crop protection • Could provide alternatives to synthetic antimicrobial chemicals in agriculture • Has potential applications in developing new food packaging materials • May contribute to reducing crop losses due to fungal infections in agriculture

Background

Chitosan, obtained by hydrolyzing N-alkyl ethanamide from chitin, is the only natural basic polysaccharide and has certain antibacterial and antifungal activities. N-2-hydroxypropyltrimethyl ammonium chloride chitosan (HACC) is a cationic quaternary ammonium salt polymer with good water solubility, but its antimicrobial and antioxidant activities need improvement.

Objective

To synthesize and evaluate a series of N-2-hydroxypropyltrimethyl ammonium chitosan derivatives bearing amino acid Schiff bases (HACGM, HACGB, HACGD, HACGS) to improve the biological activity of chitosan quaternary ammonium salt.

Results

The modified compounds showed significantly improved antimicrobial and antioxidant activities compared to HACC. HACGB demonstrated 99.87% and 92.95% inhibition rates against S. aureus and E. coli at 0.1 mg/mL concentration. Both HACGM and HACGB achieved 100% inhibition of B. cinerea and F. oxysporum at 0.5 mg/mL concentration. The compounds also showed enhanced DPPH and superoxide radical scavenging abilities.

Conclusion

The insertion of amino acid Schiff bases into HACC framework successfully improved its biological activity. The modified compounds, especially HACGM and HACGB, demonstrated superior antimicrobial and antioxidant properties compared to unmodified HACC. This discovery provides valuable reference for further development and applications of chitosan derivatives in agriculture.
  • Published in:Marine Drugs,
  • Study Type:Laboratory Research,
  • Source: 10.3390/md20020086
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