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Antibiotics 2018, 7, 76 6 of 12 a transglycosylated compound, which includes the insoluble compounds. Transglycosylated materials have been reported to self-associate into particular micelle-like structures with a core-shell-like architecture, in which the hydrophobic skeleton is segregated from the aqueous exterior to form a novel drug-loading core, surrounded by a hydrophilic shell of sugar groups [48]. For instance, Kadota, Okamoto, Sato, Onoue, Otsu and Tozuka [24] found a 13000× increase in curcumin solubility when the tri-component system curcumin/α-glucosyl stevia/polyvinylpyrrolidone was used. In relation to the phenolic compounds, they have been reported to have toxic activities against fungi involved in the deterioration of agricultural products by interfering with the development of mycelia [49]. They affect membrane functions such as electron transport, nutrition, enzyme activity, protein and nucleic acid synthesis, and they interact with membrane proteins, causing disruption of the structures and functionality. For instance, curcumin’s efficacy would be influenced by its lipophilic nature, which leads to an adequate transmembrane permeability [16]. Its antifungal mechanism has been ascribed to the disruption of plasma membrane integrity, causing leakage of potassium ion from the cytosol and change in membrane potential [50]. On the other hand, gallic acid would exhibit both antioxidant as well as pro-oxidant characteristics, displaying a dual-edge sword behavior, which turns it into an efficient apoptosis inducing agent [51]. Regarding the inhibition mode of chitosan, three mechanisms have been proposed [52]: (1) Its positive charge can interact with negatively charged phospholipid components of fungi membrane, increasing its permeability and causing the leakage of cellular contents, which subsequently leads to cell death; (2) it can act as a chelating agent by binding to trace elements, causing the essential nutrients unavailable for normal growth of fungi; and (3) it may be able to penetrate the cell wall of fungi and bind to its DNA, inhibiting the synthesis of mRNA and, thus, affecting the production of essential proteins and enzymes. As far as DES are concerned, they would act as a plasticizer, affecting the apparent viscosity of the solutions and enhancing water vapor permeability, water solubility and water sorption capability, as reported by Almeida, Magalhães, Souza and Gonçalves [27]. Nonetheless, it worth noting that, while choline chloride and urea show no inhibition as individual materials, their final product as ChCl:U DES has been reported to show inhibition towards Candida cylindracea [53]. This behavior could be due to the synergistic effect of forming DES [54] and can be used to prove that occasionally DES have a higher toxicological behavior than its original components. The antimicrobial activity of DES is still not fully understood [55]. Some reports have noted that DES would increase the permeability of the lipid membrane of eukaryotic cells [56,57], as chitosan does. Since the mechanism for COS and DES would tentatively be similar, the differences in the performance of the composites presented herein in terms of fungal growth control should then be ascribed to differences in their ability to solubilize a wide range of solutes (e.g., components in the fungal cell membrane), pH, osmolality or chelation of membrane-bound divalent cations [58]. Since one of the possible mechanisms of action of silver requires that the silver ions enter the fungal cell for efficient killing, the enhancement of permeability driven by COS, DES and polyphenols would support that their interaction should be synergistic rather than simply additive. From our work, the best results of mycelial growth inhibition at the lowest concentration (125 mg·mL−1) in DES (GI 91.5%), attained for the composite based on gallic acid, may be ascribed to the fact that gallic acid is extremely well absorbed, and very soluble in water as compared with other polyphenols [51]. Moreover, the introduction of the hydroxyl group on the cation in the chloride of choline salt has also been reported to significantly improve the extraction capacity of ionic liquids for gallic acid [59]. 4. Materials and Methods 4.1. Reagents Stevioside standard was purchased from Wako (Osaka, Japan). Gallic acid, silymarin, ferulic acid, curcumin, choline chloride, urea, glycerol, and silver nanoparticles (40 nm particle sizePDF Image | Silver Nano Polyphenol Inclusion Compounds Composites
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