Synthesis, DFT study, theoretical and experimental spectroscopy of fatty amides based on extra-virgin olive oil and their antibacterial activity

Abstract

Medication products from natural materials are preferred due to their minimal side effects. Extra-virgin olive oil (EVOO) is a highly acclaimed Mediterranean diet and a common source of lipids that lowers morbidity and disease severity. This study synthesised two fatty amides from EVOO: hydroxamic fatty acids (FHA) and fatty hydrazide hydrate (FHH). The Density Functional Theory (DFT) was applied to quantum mechanics computation. Nuclear magnetic resonance (NMR), Fourier transforms infrared (FTIR), and element analysis were used to characterise fatty amides. Likewise, the minimum inhibitory concentration (MIC) and timing kill assay were determined. The results revealed that 82 % for FHA and 80 % for FHH conversion were achieved. The amidation reagent/EVOO ratio (mmol: mmol) was 7:1, using the reaction time of 12 h and hexane as an organic solvent. The results further revealed that fatty amides have high antibacterial activity with low concentration at 0.04 μg/mL during eight h of FHA and 0.3 μg/mL during ten h of FHH. This research inferred that FHA and FHH could provide an alternative and effective therapeutic strategy for bacterial diseases. Current findings could provide the basis for the modernisation/introduction of novel and more effective antibacterial drugs derived from natural products.

Keywords: Antibacterial activity; Extra virgin olive oil; Fatty amide; Fatty hydrazide hydrate; Fatty hydroxamic acids.