Synthesis, spectroscopic characterization, density functional theory study, antimicrobial and antioxidant activities of curcumin and alanine-curcumin Schiff base

Abstract

In this work, a novel Schiff-base derived from curcumin and L-Alanine was synthesized under microwave conditions in excellent yield. The structural characterization has been carried out from their elemental analyses, FTIR, UV–Vis and ¹³C-NMR and ¹H-NMR spectral techniques. The Schiff base (Cur-Ala) and curcumin (Cur) have been screened for their antimicrobial activity toward some pathogens clinically important microorganisms: Bacillus subtilis, Escherichia coli and Staphylococcus aureus, Aspergillus niger and Candida albicans. Result found that the Schiff base was more active than the curcumin. The antibacterial and antifungal activities of Cur-Ala can be attributed to its greatest dipole moment, as shown by theoretical calculations. Also, the antioxidant activity of Schiff base and curcumin were studied by DPPH, cupric ion reducing antioxidant capacity and o-phenanthroline techniques. Results indicate that Cur-Ala and Cur show more antioxidant activities than the standard antioxidants (BHT and BHA). Quantum chemical parameter calculations of Cur-Ala and Cur have been investigated by DFT using B3LYP/6-31G (d,p) basis set method to calculate the optimized structure, atomic charges, MESP, global reactivity descriptors and thermomolecular proprieties of both molecules.

Communicated by Ramaswamy H. Sarma

Keywords:

• Schiff base
• curcumin
• L-alanine
• DFT
• antioxidant activity
• antimicrobial activity

Acknowledgement

The authors acknowledge the Department of Chemistry, Faculty of Sciences; UFAS1.

Disclosure statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this article.

Funding

The author(s) reported there is no funding associated with the work featured in this article.