Abstract
The development of inclusion complexes is used to encapsulate nonpolar compounds and improve their physicochemical characteristics. This study aims to develop complexes made up of Euterpe oleracea Mart oil (EOO) and β-cyclodextrin (β-CD) or hydroxypropyl-β-cyclodextrin (HP-β-CD) by either kneading (KND) or slurry (SL). Complexes were analyzed by molecular modeling, Fourier-transform infrared spectroscopy, scanning electron microscopy, powder X-ray diffraction, thermogravimetry analysis and differential scanning calorimetry. The antibacterial activity was expressed as Minimum Inhibitory Concentration (MIC), and the antibiotic resistance modulatory activity as subinhibitory concentration (MIC/8) against Escherichia coli, Streptomyces aureus, Pseudomonas aeruginosa and Enterococcus faecalis. Inclusion complexes with β-CD and HP-β-CD were confirmed, and efficiency was proven by an interaction energy between oleic acid and β-CD of −41.28 ± 0.57 kJ/mol. MIC values revealed higher antibacterial activity of complexes compared to the isolated oil. The modulatory response of EOO and EOO-β-CD prepared by KND as well as of EOO-β-CD and EOO-HP-β-CD prepared by SL showed a synergistic effect with ampicillin against E. coli, whereas it was not significant with the other drugs tested, maintaining the biological response of antibiotics. The antimicrobial response exhibited by the complexes is of great significance because it subsidizes studies for the development of new pharmaceutical forms.
Highlights
Vegetable oils are a target of studies due to their many pharmacological applications
The açai pulp was dried at a temperature of 60 ◦C and subjected to mechanical pressing (LDS R 135/2008, 240 kg·h−1) at a temperature of 40 ◦C. β-cyclodextrin (β-CD), hydroxypropyl-β-cyclodextrin (HP-β-CD) and resazurin were purchased from Sigma-Aldrich
The results of molecular modeling, Fourier Transform Infrared Spectroscopy (FT-IR), Scanning Electron Microscopy (SEM), Powder X-ray Diffraction (PXRD), TG and Differential Scanning Calorimetry (DSC) analyses revealed that E. oleracea Mart oil (EOO) was able to successfully form inclusion complexes, especially with β-cyclodextrin (β-CD), confirming the expectations arisen by the estimated interaction energy between oleic acid and β-CD (∆G = −41.28 ± 0.57 kJ/mol)
Summary
Vegetable oils are a target of studies due to their many pharmacological applications. According to Martins da Silva et al [1], the chemical constituents present in a variety of oils exhibit different biological activities. The resin oil of Copaifera multijuga, commonly used as an anti-inflammatory [2], the essential oil of Ocimum basilicum, applied as an antihyperalgesic [3], and the Allium sativum oil, displaying antioxidant and antimicrobial activities [4] similar to those of Euterpe oleracea oil [5,6], are a few examples. Among the phytosteroids present in the oil, the most important are β-sitosperol, stigmasterol and campesterol. Their ability to improve cell metabolism and reduce inflammatory processes are the reasons why these compounds are widely used by the cosmetic industry to prevent skin aging [10]
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