Fabrication of Novel Bioactive Cellulose-Based Films Derived from Caffeic Acid Phenethyl Ester-Loaded Nanoparticles via a Rapid Expansion Process: RESOLV

Abstract

Caffeic acid phenethyl ester (CAPE) nanoparticles (NPs) with an average size of ∼40 nm obtained from TEM and binomial average sizes of ∼90 and ∼400 nm obtained from DLS were successfully produced by rapid expansion of subcritical solutions into liquid solvents (RESOLV). The minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) of CAPE and CAPE-NPs were determined by plate count method against 12 pathogenic and spoilage bacteria and 3 strains of yeast. Total phenolic content (TPC) and antioxidant activities of CAPE-NPs were quantified and subsequently investigated using two assays, including 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and ferric reducing antioxidant power (FRAP). CAPE-NP-incorporated cellulose-based films were prepared and characterized. MICs and MBCs of CAPE-NPs against most bacteria and Candida albicans were 700 and 1400 μg/mL, respectively. CAPE-NPs yielded a TPC value of 426.74 μgGAE/mg and lower antioxidant activities than those of CAPE in ethanol (CAPE-EtOH), whereas BHT yielded lower FRAP than that of CAPE-NPs. The impregnation of CAPE into cellulose-based films was confirmed by FTIR spectra. Moreover, incorporation of only 0.5 wt % CAPE-NPs into the films resulted in an inhibitory effect against microorganisms. Fortunately, incorporation of higher concentration of CAPE-NPs-MC films led to a significantly higher antioxidant activity and vice versa. This indicated that CAPE-NPs significantly enhanced the antimicrobial and antioxidant activities of CAPE. The results show that the environmentally benign supercritical CO2 technique should be generally applicable to NP fabrication of other important bioactive ingredients, especially in liquid form. In addition, it is suggested that CAPE-NPs can be used to reduce the dosage of CAPE and improve their bioavailability and thus merit further investigation for bioactive packaging film and coating applications.

Enzymatic Synthesis and Antioxidant Activity of 1‐Caffeoylglycerol Prepared from Alkyl Caffeates and Glycerol

“…With ethyl acetate as an extracting agent, 1‐CG was easily separated from the reaction mixture, resulting from its high solubility in ethyl acetate and relative to its solubility in the reaction mixture, thereby leading to high purity of 1‐CG. The literature contains some reports related to purification of cinnamoyl transesterification products, including purification of feruloylated lipids through flash column chromatography using benzene/ether/dichloromethane/hexane (3:5:2:2, v/v/v/v) as the mobile phase (Saelo, Assatarakul, Sane, & Suppakul, ), separation of phenolic lipids using Thin Layer Chromatography (TLC) on preparative silica gel 60F plates (Zheng et al, ), and separation and enrichment of phenylpropenoid glycerides by high‐speed countercurrent chromatography (Karboune, St‐Louis, & Kermasha, ). However, these procedures are not suitable for the industrial production due to large eluent and equipment requirements.…”

Antifungal Activity of the Phenolic Compounds Ellagic Acid (EA) and Caffeic Acid Phenethyl Ester (CAPE) against Drug-Resistant Candida auris

“…Some studies have proposed different carriers for these compounds without interfering with their inhibitory effect against Candida spp. [76][77][78]. Sampaio et al (2021) evaluated ellagic acid-cyclodextrin complexes for antifungal activity.…”

Supercritical Fluid Applications in the Design of Novel Antimicrobial Materials

“…Saelo et al [112] applied Rapid Expansion of a Supercritical Solution into a Liquid Solvent (RESOLV) process to obtain caffeic acid phenethyl ester (CAPE) nanoparticles. The mixture of CAPE, ethanol, and scCO 2 at 17.3 MPa and 50 • C was expanded through a nozzle at 80 • C into distilled water.…”

“…The obtained CAPE NPs were incorporated into methylcellulose films in the process of film preparation by the solvent casting method. Films containing 0.5% of CAPE NPs exhibited antimicrobial properties against P. aeruginosa, C. albicans, and Listeria monocytogenes [112].…”