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Lipase-Catalyzed Synthesis, Antioxidant Activity, Antimicrobial Properties and Molecular Docking Studies of Butyl Dihydrocaffeate

Summary

This research developed an environmentally friendly way to create a new compound that could be useful in food preservation and medicine. Scientists modified a natural antioxidant to make it more effective and discovered it has strong antifungal properties. The study shows promise for developing safer food additives and potential treatments for fungal infections. Impacts on everyday life: • Could lead to better natural food preservatives • May help develop new treatments for dangerous fungal infections • Demonstrates environmentally friendly ways to create useful compounds • Could improve the shelf life of food products • Shows potential for creating safer alternatives to synthetic preservatives

Background

Dihydrocaffeic acid (DHCA) is a phenolic compound found in plants like Gynura bicolor and black olive pericarp, known for its antioxidant, anti-inflammatory and cytoprotective properties. However, phenolic acids have low solubility in organic solvents, limiting their application in lipid-based products. Lipophilization through enzymatic esterification is a promising approach to improve their solubility and biological properties.

Objective

To synthesize butyl dihydrocaffeate through lipase-catalyzed esterification and evaluate its antioxidant and antimicrobial activities, particularly its antifungal properties against Rhizopus oryzae. Additionally, to investigate potential protein targets and mechanisms of action through molecular docking studies.

Results

The enzymatic synthesis yielded approximately 67% butyl dihydrocaffeate after 72 hours. The ester retained significant antioxidant activity and showed notable antifungal activity against Rhizopus oryzae with MIC and MMC values of 1 and 2 mM respectively. Molecular docking studies revealed that the ester had comparable binding energy to the antifungal drug isavuconazole when targeting 14-α sterol demethylase B, though through different amino acid interactions.

Conclusion

Butyl dihydrocaffeate shows promise as a potential food additive with both antioxidant and antifungal properties. The enzymatic synthesis provides an environmentally friendly alternative to traditional chemical synthesis. The compound’s comparable binding energy to clinical antifungal drugs suggests a possible mechanism of action against R. oryzae, though further research is needed to fully understand its therapeutic potential.
  • Published in:Molecules,
  • Study Type:Laboratory Research,
  • Source: 10.3390/molecules27155024
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