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Antibiotics 2018, 7, 76 7 of 12 (TEM), 0.02 mg·mL−1 in aqueous buffer, with sodium citrate as a stabilizer) were purchased from Sigma-Aldrich/Merck KGaA (Darmstadt, Germany). Chitosan oligomers were obtained from medium molecular weight chitosan (supplied by Hangzhou Simit Chemical Technology Co., Ltd., Hangzhou, China), dissolving 10 g in 500 mL of acetic acid (1%) under constant stirring at 60 ◦C. Once dissolved, hydrogen peroxide (0.3 mol·L−1) was added for the degradation of the polymer chains, obtaining oligomers of less than 2000 Da [60]. Liquefaction of the choline chloride and urea (1:2 v/v) eutectic mixture occurred at 80 ◦C under stirring in a hot-plate magnetic stirrer for 10 min, in good agreement with Biswas et al. [61]. 4.2. Microwave-Assisted Preparation of the Polyphenol Inclusion Compounds The aqueous biphasic system separation technique was used for the formation of the inclusion compounds. This technology is a liquid-liquid extraction system for bioseparation and is frequently used to process all types of biotechnological materials, such as proteins, enzymes, phytochemicals, nucleic acids and pigments [62]. In the case under study, the inclusion complexes formed with stevioside were recovered from the upper part of the reactor. 4.3. Chitosan Oligomers (COS)-Based Composites In each of the four jars with screw caps, 1 g of chitosan oligomers of 2000 Da (COS), 0.06 g of stevioside and 0.01 g of one of the polyphenols (either gallic acid, silymarin, ferulic acid or curcumin) were added to 40 mL of hydroalcoholic solution (1:1 v/v distilled water and ethanol), followed by treatment in a microwave (Milestone Ethos-One, Sorisole, BG, Italy) at 80 ◦C for 20 min under stirring. The resulting solutions were centrifuged at 2500 rpm and stored at 4 ◦C. For the incorporation of the silver nanoparticles to the nanocomposite, 0.1 mL of commercial AgNPs (0.02 mg·mL−1) were added dropwise to 0.9 mL of the previously centrifuged microwave fractions, and the final solution (with pH 7.5) was stirred at room temperature. 4.4. Deep Eutectic Solvent-Based Composites To prepare the DES-based composites, 20 mL of choline chloride and urea (1:2 v/v) DES and 10 mL of glycerol were added to each of the four jars with screw caps, together with 0.03 g of stevioside and 0.01 g of the respective polyphenol (gallic acid, silymarin, ferulic acid or curcumin). The mixture was heated at 80 ◦C in the microwave, under stirring, for 20 min. Then, 0.1 mL of AgNPs (0.02 mg·mL−1) were added dropwise to 0.9 mL of the microwave fractions (previously centrifuged at 2500 rpm). The mixture, with pH 7.5, was subjected to vigorous stirring for 5 min at room temperature. 4.5. Silver Nanoparticles-Only Treatments Two additional treatments consisting of 0.1 mL of AgNPs (0.02 mg·mL−1) added dropwise to 0.9 mL of the dispersion medium (either COS or DES), without the polyphenol inclusion compounds, were prepared for control purposes. The mixtures were vigorously stirred for 5 min at room temperature. 4.6. Characterization of the Nanocomposites The structure and properties of the nanocomposites obtained through the synthetic procedures described above were characterized using Fourier-Transform Infrared spectroscopy (FTIR), scanning electron microscopy (SEM) and transmission electron microscopy (TEM). Results were recently reported in patent P201731489 [36]. 4.7. Fungal Isolates and Growth Conditions The fungal species used in the experiment was Phytophthora cinnamomi isolate MYC43, supplied by Centro de Investigaciones Científicas y Tecnológicas de Extremadura—Instituto del Corcho, la MaderaPDF Image | Silver Nano Polyphenol Inclusion Compounds Composites
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