This study aimed to elucidate the physico-chemical characteristics of EO–BCD inclusion complexes and their resulting antimicrobial activity. Cinnamon bark extract, trans-cinnamaldehyde, clove bud extract, eugenol, and a 2:1 (trans-cinnamaldehyde:eugenol) mixture were microencapsulated by the freeze-drying method. EO–BCD complexes were characterized for particle size, morphology, polydispersity index, entrapment efficiency, and phase solubility. All particles showed a spherical shape, smooth surface, no significant differences in size distribution and strong tendency to agglomerate. The entrapment efficiencies ranged from 41.7 to 84.7%, where pure compounds were higher (p < 0.05) than extracts. The oils and their BCD complexes were analyzed for their antimicrobial activity against Salmonella enterica serovar Typhimurium LT2 and Listeria innocua. All antimicrobials effectively inhibited bacterial growth within the concentration range tested, except free eugenol. The EO–BCD complexes were able to inhibit both bacterial strains at lower active compound concentrations than free oils, likely due to their increased water solubility that led to increased contact between pathogens and essential oils. The cinnamon bark and clove bud extract BCD complexes were the most powerful antimicrobials, despite showing the lowest entrapment efficiencies amongst the oils. Results suggest that the application of these antimicrobial complexes in food systems may be effective at inhibiting pathogens.

Characterization of beta-cyclodextrin inclusion complexes containing essential oils (trans-cinnamaldehyde, eugenol, cinnamon bark, and clove bud extracts) for antimicrobial delivery applications

Water-insoluble β-cyclodextrin-based fibers were synthesized by electrospinining followed by thermal cross-linking. The fibers were characterized by field-emission scanning electron microscopic (FE-SEM) and Fourier transformed infrared spectrometer (FT-IR). The highly insoluble fraction obtained from different pH values (3-11) indicates successful cross-linking reactions and their usability in aqueous solution. After the cross-linking reaction, the fibers' tensile strength increases significantly and the BET surface area is 19.49 m(2)/g. The cross-linked fibers exhibited high adsorption capacity for cationic dye methylene blue (MB) with good recyclability. The adsorption performance can be fitted well with pseudo-second-order model and Langmuir isotherm model. The maximum adsorption capacity is 826.45 mg/g according to Langmuir fitting. Due to electrostatic repulsion, the fibers show weak adsorption toward negatively charged anionic dye methyl orange (MO). On the basis of the selective adsorption, the fiber membrane can separate the MB/MO mixture solution by dynamic filtration at a high flow rate of 150 mL/min. The fibers can maintain good fibrous morphology and high separation efficiency even after five filtration-regeneration cycles. The obtained results suggested potential applications of β-cyclodextrin-based electrospun fibers in the dye wastewater treatment field.

https://pubs.acs.org/doi/pdf/10.1021/acsami.6b15624

Synthesis of β-Cyclodextrin-Based Electrospun Nanofiber Membranes for Highly Efficient Adsorption and Separation of Methylene Blue

Polyvinyl alcohol (PVA) nanofibers encapsulating eugenol (EG)/cyclodextrin (CD) inclusion complexes (IC) (EG/CD-IC) were produced via electrospinning technique in order to achieve high thermal stability and slow release of EG In order to find out the most favorable CD type for the stabilization of EG, three types of native cyclodextrins (α-CD, β-CD, and γ-CD) were used for the formation of EG/CD-IC In the case of PVA/EG/α-CD nanofibers, uncomplexed EG was detected indicating that α-CD is not a proper host for EG/CD-IC formation However, for PVA/EG/β-CD-IC and PVA/EG/γ-CD-IC nanofibers, enhanced durability and high thermal stability for EG were achieved due to the inclusion complexation The electrospun nanofibers encapsulating CD-IC of active compounds such as eugenol may be quite useful in the food industry due to the extremely large surface area of nanofibers along with specific functionality, enhanced thermal stability, and slow release of the active compounds by CD inclusion complexation

/pdf/enhanced-thermal-stability-of-eugenol-by-cyclodextrin-1543yyioso.pdf

Enhanced Thermal Stability of Eugenol by Cyclodextrin Inclusion Complex Encapsulated in Electrospun Polymeric Nanofibers

Physico-chemical characterization and evaluation of bio-efficacies of black pepper essential oil encapsulated in hydroxypropyl-beta-cyclodextrin

Antioxidant and antimicrobial properties of encapsulated guava leaf oil in hydroxypropyl-beta-cyclodextrin

A solid state eugenol/β-cyclodextrin inclusion complex (EG/β-CD) was prepared by lyophilization method and characterized by Powder X-ray Diffraction (XRD) and Fourier Fransform Infrared Spectroscopy (FTIR). UV–Vis spectrometer was used to determine the EG content encapsulated in the complex. In order to estimate the release characteristics of the EG/β-CD powder, Avrami’s equation and Thermogravimetric (TG) analyzer were, respectively, used. The loss percentage of EG was no more than 10 wt% for 4 week exposing at 25 °C and 75% humidity, and the release of EG is controlled by a combination mechanism of diffusion and first-order mode. TG results not only proved the thermo stability of the EG in EG/β-CD complex, but also clarified the thermal decomposition behaviors of the EG/β-CD. The antibacterial activity of the EG/β-CD complex was investigated using agar cup-plate diffusion method and bacterial strains of Escherichia coli, Salmonella paratyphi B, and Staphyloccocus aureus were used. The results indicated that EG/β-CD had a selective antimicrobial active against Escherichia coli.

Release characteristics and antibacterial activity of solid state eugenol/β-cyclodextrin inclusion complex

The preparation, characterization, and environmental application of β-cyclodextrin/citric acid/wood flour (β-CD/CA/WF) graft copolymer wood-based biosorbent for methylene blue (MB) biosorption were investigated in this paper. The Fourier transform infrared spectroscopy and the technique of phenolphthalein probe were used to characterize the grafting β-CD. Furthermore, the biosorption behavior of MB on β-CD/CA/WF graft copolymer was studied under various conditions of pH, contact time, and initial MB concentration. The results indicated that the biosorption of MB was dependent on both the initial MB concentration and the initial pH. Langmuir isotherm model fitted the isotherm data better than the Freundlich model. The adsorption kinetics followed the pseudo-second-order kinetic model, and intraparticle diffusion was one of the effective rate-controlling steps for the entire biosorption period. Equilibrium and kinetic results have implied that β-CD/CA/WF graft copolymer could be considered as a promising material for the adsorption of dye from aqueous solutions.

Biosorption of methylene blue from aqueous solutions on β-cyclodextrin grafting wood flour copolymer: kinetic and equilibrium studies

Poplar wood flour, a low-cost and abundantly available material, was modified by grafting β-cyclodextrin (β-CD) in the presence of citric acid or 1,2,3,4-Butanetetracarboxylic acid, aiming to expand the application of wood flour. The products were characterized by Fourier transform infrared spectroscopy and the technique of phenolphthalein probe. The grafting conditions of β-CD onto wood flour including curing temperature, β-CD concentration in impregnation solution and catalyst were also evaluated by the technique of phenolphthalein probe. Besides, eugenol (EG), an antibacterial fragrant guest molecule, was loaded on the modified wood flour by lyophilization, and its release characteristics were investigated by Thermo-gravimetric. The results revealed that the modified wood flour material had a thermo-protective effect on the volatilization of EG and the encapsulated EG content was reached to 1.31 %, which could demonstrate a potential application in the finishing and packing areas.

Preparation of cyclodextrin grafting wood flour and investigation of the release characteristics of eugenol

A novel functional material of β-cyclodextrin (β-CD) grafting cellulose beads containing immobilized silver nanoparticles (AgNPs) is presented in this paper The morphology was characterized by scanning electron microscopy, energy-dispersive X-ray, and X-ray photoelectron spectroscopy Phenolphthalein probe molecule technique was used to detect the activity of the grafting β-CD, and the results demonstrated that the deposition of AgNPs had no influence on its encapsulation ability Acid resistance of the AgNPs on the bead material was studied by atomic absorption spectrometry The stability of the AgNPs was enhanced due to the grafting of β-CD Tube dilution method was applied to study the bacteriostatic effect, and the minimal inhibitory doses of the novel material against Escherichia coli and Staphylococcus aureus were 125 and 25 mg, respectively The minimal bactericidal doses for the two bacteria were 25 and 25 mg, respectively

Preparation, Characterization, and Bacteriostasis of AgNP-Coated β -CD Grafting Cellulose Beads

Method for preparing nanometer silver in-site loaded beta-cyclodextrin grafting cellulose microsphere material by using equipment for preparing microsphere material

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