Thermal and oxidative stability of the Ocimum basilicum L. essential oil/β-cyclodextrin supramolecular system

Kfoury M., Landy D., Auezova L., Greige-Gerges H., Fourmentin S.

The complexation abilities of five cyclodextrins (CDs) with seven phenylpropanoids (PPs) were evaluated by UV–visible spectroscopy, phase solubility studies and molecular modeling. Formation constants (Kf), complexation efficiency (CE), PP:CD molar ratio, increase in formulation bulk and complexation energy were assessed. All complexes exhibited a 1:1 stoichiometry but their stability was influenced by the nature and the position of the phenyl ring substituents. A relationship between the intrinsic solubility of guests (S0) and the solubilizing potential of CD was proposed. Molecular modeling was used to investigate the complementarities between host and guest. Finally, the antioxidant activity of encapsulated PPs was evaluated by scavenging of the stable DPPH radical.

Kim S., Lee D.

Two commercialized essential oils and their constituent compounds were investigated for fumigant and contact activities against two grain storage insects, adults of the maize weevil (Sitophilus zeamais) and the red flour beetle (Tribolium castaneum). The two commercialized basil and orange oils showed strong fumigant and contact activities against S. zeamais and T. castaneum. The constituents of the basil oil were linalool (21.83%), estragole (74.29%), and α-humulene (2.17%), and those of the orange oil were α-pinene (0.54%), sabinene (0.38%), β-myrcene (1.98%), limonene (96.5%), and linalool (0.6%). As a toxic fumigant, the basil oil was more effective (24-h LC50 = 0.014 and 0.020 mg cm− 3) than the orange oil (24-h LC50 = 0.106 and 0.130 mg cm− 3) against S. zeamais and T. castaneum adults, respectively. Among the constituents of the two essential oils, the toxicity of estragole was the highest (0.004 and 0.013), followed by linalool (0.016 and 0.023), limonene (0.122 and 0.171), α-pinene (0.264 and 0.273), and β-myrcene (0.274 and 0.275) based on 24-h LC50 values (mg cm− 3). Similar results were obtained in a contact toxicity test. The contact activity of basil oil was more toxic than orange oil, and estragole and linalool showed pronounced contact toxicity against S. zeamais and T. castaneum adults. Alpha-humulene had no activity as a fumigant at the tested doses, but it did have an effect as a contact poison, having 24-h LD50 values of 0.040 and 0.045 mg adult− 1 to S. zeamais and T. castaneum, respectively. Although basil oil, orange oil, and their components displayed both contact and fumigant toxicities, their effects were mainly exerted by fumigant action via the vapor phase. Thus, basil oil, orange oil, and their components could be potential candidates as new fumigants for the control of S. zeamais and T. castaneum adults.

Kfoury M., Auezova L., Fourmentin S., Greige-Gerges H.

In this study, we investigated the inclusion complexation of 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) and eight monoterpenes (eucalyptol, geraniol, limonene, linalool, α-pinene, β-pinene, pulegone, and thymol) in aqueous solution and solid state. The formation constants (K f) of inclusion complexes were determined using fluorescence spectroscopy and static headspace gas chromatography. The results indicated the formation of 1:1 inclusion complexes between HP-β-CD and all studied guests. A linear relationship was found between K f values and the hydrophobic character of the monoterpenes expressed as logP. Solid complexes were prepared by the freeze-drying method in a 1:1 (HP-β-CD:monoterpene) molar ratio. Physicochemical characterization of solid inclusion complexes was carried out using Fourier transform infrared spectroscopy and differential scanning calorimetry. Finally, the encapsulation efficiency (EE%) of HP-β-CD was determined using HPLC analysis. Noticeable difference in the EE% was observed between monoterpene hydrocarbons and oxygenated monoterpenes. These results suggested that complexation with HP-β-CD could be a promising strategy to enlarge the application of monoterpenes in cosmetic, pharmaceutical and food industries.

Filip S., Vidović S., Adamović D., Zeković Z.

Fractionation by supercritical fluid extraction (SFE) was used to obtain various extracts from Ocimum basilicum L. (sweet basil). The extractions were done at temperature of 40 °C and 50 °C, and at different pressure, which was increased successively from 100 bar (150 bar, 200 bar) to 300 bar. The identification and quantification of the extract compounds was done using gas chromatography–mass spectrometry (GC–MS) and gas chromatography with flame-ionization detector (GC–FID) analyses. The yield of basil SFE extracts varies from 0.138 to 1.008% (w/w). The major components identified in the extracts were linalool, eugenol, α-bergamotene, germacrene D, γ-cadinene, δ-cadinene, β-selinene and spathulenol. The highest extraction yield, in fractionation process, of linalool (167.03 mg per 100 g of basil) was achieved at pressure of 100 bar and temperature 50 °C (solvent density 0.378 kg/m 3 ).

López-Nicolás J.M., Andreu-Sevilla A.J., García-Carmona F., Carbonell-Barrachina Á.A.

The combination headspace solid phase micro-extraction + gas chromatography–mass spectrometry + gas chromatography with flame ionization detector was successfully used in quantitative determination of the instrumental odor of pear juice. Esters, aldehydes, alcohols, and terpenes were the major chemical families of the pear juice odor. Twenty-six were identified and quantified, with propyl acetate, hexyl acetate, 2-methyl-1-butanol, and butyl acetate being the major compounds. α-Cyclodextrins (CD) significantly improved the color of pear juice, leading to higher values of L* and lower of scores of a*, b*, and ΔE*. However, α-CD also reduced the total concentration of volatiles in the headspace of the juice by creating inclusion complexes with volatiles; after 40 min of oxidation, total volatiles were 8.2 and 3.4 mg L−1 in control and α-CD-treated juices, respectively. But in summary, the global quality (joint consideration of the main sensory attributes) was improved by the addition of α-CD (6.9 compared to 5.2).

Ghasemi Pirbalouti A., Mahdad E., Craker L.

Sweet basil, a plant that is extensively cultivated in some countries, is used to enhance the flavour of salads, sauces, pasta and confectioneries as both a fresh and dried herb. To determine the effect of drying methods on qualitative and quantitative characteristics of the plant and essential oil of basil, two landraces, Purple and Green, were dried in sunlight, shade, mechanical ovens at 40 °C and 60 °C, a microwave oven at 500 W and by freeze-drying. For comparison, the essential oils of all samples were extracted by hydrodistillation and analyzed using GC and GC-MS. The highest essential oil yields (v/w on dry weight basis) were obtained from shade-dried tissue in both landraces followed by the freeze-dried sample of the purple landrace and the fresh sample of green landrace. Increasing the drying temperature significantly decreased the essential oil content of all samples. Significant changes in the chemical profile of the essential oils from each of the landrace were associated with the drying method, including the loss of most monoterpene hydrocarbons, as compared with fresh samples. No significant differences occurred among several constituents in the extracted essential oils, including methyl chavicol (estragole), the major compound in the oil of both landraces, whether the plants were dried in the shade or sun, oven at 40 °C or freeze-dried, as compared with a fresh sample. The percentage methyl chavicol in the oil, however, decreased significantly when the plant material was dried in the oven at 60 °C or microwaved. In addition, linalool, the second major compound in the purple landrace, and geranial and neral, major compounds in the green landrace, decreased significantly when the plant tissue was dried in the oven at 60 °C or microwaved.

Bertoli A., Lucchesini M., Mensuali-Sodi A., Leonardi M., Doveri S., Magnabosco A., Pistelli L.

Exposure to stressful environmental conditions can induce severe metabolic variations in basil (Ocimum basilicum) aroma. The aromatic profiles of Dark Opal and Red Rubim varieties (in vivo plants, in vitro shoots, callus, and suspension cultures) were investigated for the first time. The established calli represented the most interesting miniaturised aromatic plant systems, as they were able to emit many typical basil volatiles with very low amounts of phenylpropanoids (1-2%). The hydrocarbon monoterpenes and oxygenated volatiles emitted from calli of both varieties were greatly and conversely affected by UV-C and UV-B, in comparison with the non-irradiated samples. As calli of both varieties still maintained very low levels of phenylpropanoids even after UV elicitation, they might be regarded not only as efficient in vitro plant models to study volatile compounds under UV stress conditions, but also as safe aromatic biomass in comparison with in vivo basil plants.

Menezes P.P., Serafini M.R., Quintans-Júnior L.J., Silva G.F., Oliveira J.F., Carvalho F.M., Souza J.C., Matos J.R., Alves P.B., Matos I.L., Hădărugă D.I., Araújo A.A.

(−)-Linalool is a monoterpene alcohol which is present in the essential oils of several aromatic plants. Recent studies suggest that (−)-linalool has antimicrobial, anti-inflammatory, anticancer, antioxidant, and antinociceptive properties in different animal models. The aim of this study was to prepare and characterize inclusion complexes of (−)-linalool with β-cyclodextrin (β-CD). Equimolar binary (−)-linalool/β-CD systems were prepared by physical mixture, paste (PM), and slurry methods (SC) and characterized by differential scanning calorimetry, thermogravimetric analysis, FT-IR spectroscopy, X-ray diffractometry, Karl Fisher titration, and scanning electron microscopy. Thermal characterization indicates the occurrence of complexation, mainly in paste complexes, which is present in the interval from 140 to 280 °C a gradual mass loss (4.6 %), probably related to (−)-linalool loss. FT-IR spectra showed changes that may be related to the formation of intermolecular hydrogen bonds between (−)-linalool and β-CD. The new solid-phase formed using the PM and SC methods, had a crystal structure which was different from the original morphology of β-CD.

Fourmentin S., Ciobanu A., Landy D., Wenz G.

The inclusion of volatile derivatives of benzene and cyclohexane in β-cyclodextrin (β-CD), hydroxypropyl-β-CD, and hydrophilic β-CD-thioethers was investigated by static headspace gas chromatography (HS-GC) and molecular modelling. The obtained binding constants strongly increase with the amount of space filling of the CD cavity and the salt concentration. β-CD thioethers show a 3–10 times higher binding potential than native β-CD.

Theodosiou E., Purchartová K., Stamatis H., Kolisis F., Křen V.

Over the past years, great advances have been made on the development of novel delivery systems for bioactive natural compounds, in parallel to their structural modification via chemical, chemo-enzymatic and enzymatic methodologies. These approaches give rise to novel formulations and derivatives that often display advantages over the parental molecule, such as enhanced bioavailability and pharmacological activity, due to improved dissolution and stability. Silymarin components suffer from poor solubility in water and lipid media and their resorption in the intestine is rather limited. Moreover, silybin undergoes intensive Phase II metabolism and is rapidly excreted in bile and urine, leading to low therapeutic efficacy. This work aims to present the current status of available silymarin formulations, and to highlight successful efforts for the biotransformation of its constituent flavonolignans towards the synthesis of novel derivatives. Herein, various pharmaceutical formulations that aim at the bioavailability improvement of these fascinating phytochemicals, i.e., liposomes, phytosomes, self-microemulsifying drug delivery systems, solid dispersions systems, dripping pills, nanosuspensions, floating tablets, and micronization, are reviewed. Silybin (semi)synthetic derivatives prepared by chemical or enzymatic methods, such as fatty acid conjugates, silybin bishemisuccinate, silybin glycosides, silybin sulfates, silybinic acid, and 2,3-dehydrosilybin, are also discussed in detail. Additionally, this work attempts to direct the attention towards the pharmacological implications of optically pure silybin A and silybin B and their biotransformation reactions, both Phase I and II, in relation to bioavailability.

Pingret D., Fabiano-Tixier A., Chemat F.

A new process employing ultrasound technology to improve hydrodistillation extraction was designed and developed. The extraction process (sono-Clevenger) was performed under simultaneous sonication using an ultrasonic horn in situ to provide rapid and complete recovery of analytes from the matrix. The extraction of essential oil from orange peels with conventional Clevenger extraction was compared with the sono-Clevenger process using physicochemical characterization and gravimetric analysis. The new procedure provided a substantial reduction in the extraction time when compared to conventional process without interfering on composition of target compounds.

Andrés M.F., González-Coloma A., Sanz J., Burillo J., Sainz P.

Plant parasitic nematodes are the most destructive group of plant pathogens worldwide and their control is extremely challenging. Plant Essential oils (EOs) and their constituents have a great potential in nematode control since they can be developed for use as nematicides themselves or can serve as model compounds for the development of derivatives with enhanced activity. This study reviews the plant EOs evaluated as potential nematicides and their toxic effects against pinewood nematode (Bursaphelenchus xylophilus) and root-knot nematodes (Meloidogyne spp.). Additionally, the nematicidal activity to M. javanica of several EOs from Spanish aromatic plants and their components is described.

Wenz G.

Various heptasubstituted derivatives of β-cyclodextrin (β-CD) bearing 1, 2 and 3 methyl substituents per glucose unit were synthesized by regioselective methods. Binding free energies and binding enthalpies of these hosts towards 4-tert-butylbenzoate and adamantane-1-carboxylate were determined by isothermal titration microcalorimetry (ITC). It was found that methyl substituents at the secondary positions of β-CD lead to a tremendous reduction of the binding potential, while methylation at the primary positions significantly improved binding. Stabilizing intramolecular hydrogen bonds between the glucose units were made responsible for the high binding potentials of those β-CD derivatives that possess secondary hydroxy groups.

Calín-Sánchez Á., Lech K., Szumny A., Figiel A., Carbonell-Barrachina Á.A.

The influence of drying method on aroma compounds of sweet basil (Ocimum basilicum L.) was evaluated. The drying methods tested were convective (CD) and vacuum-microwave (VMD), as well as a combination of convective pre-drying and VM finish-drying (CPD–VMFD). Sweet basil's drying kinetics for CD was described by a two term exponential model, while VMD kinetics consisted of two periods: linear until a critical point and exponential beyond that point. Volatile compounds of basil samples were extracted by hydrodistillation and analyzed by GC/FID and GC/MS. Forty compounds were tentatively identified, with methyleugenol, eugenol, eucalyptol, and linalool being the major components. The total quantity of volatiles of fresh sweet basil, 32.1 g kg − 1 , decreased considerably during both CD and VMD, 14.4 g kg − 1 . The CPD-VMFD (40 °C and 360 W) was the best option for drying sweet basil, the time required was relatively short (≈ 250 min), and aroma quality was good according to instrumental data (total concentration of volatiles 16.7 g kg − 1 ) and sensory data (high intensities of fresh and floral notes).

Veronezi C.M., Costa T., Jorge N.

The antioxidant activity from basil ethanol extract, the effect on oxidative stability, total polar compounds, tocopherols levels and fatty acid profile in soybean oil under thermoxidation were evaluated. The basil leaves were dried in lyophilizer, ground and subjected to extraction with ethanol. The soybean oil (SO), soybean oil with 50 mg/kg of tert-butylhydroquinone (TBHQ), soybean oil with 3,000 mg/kg of extract (BE) and soybean oil with 3,000 mg/kg of extract and 50 mg/kg of TBHQ (mixture) treatments were subjected to 180 ± 5C for 20 h. Oil samples were taken at 0, 10 and 20 h and subjected to analysis. The addition of the basil extract increased oxidative stability and resulted in lower formation of total polar compounds. Although the content of tocopherols and polyunsaturated fatty acids decreased over the course of heating, their values remained higher than the SO treatments. Synergistic effect was not observed in the mixture treatment. Practical Applications Antioxidants are important ingredients in food processing because they have the capacity to protect foods containing oils and fats, from damage caused by free radicals and reactive oxygen species. Synthetic antioxidants are widely used in the food industry; however, their utilization has been questioned due to toxicity. Therefore, there is a growing interest in the use of natural antioxidants to reduce or replace the synthetic antioxidants. Several species of the Lamiaceae family are used in cooking, medicine and by the pharmaceutical industry, standing out is basil. Being rich in compounds with high antioxidant activity, basil extract can be used to replace synthetic antioxidants used in vegetable oils.

Naz S., Javaid S., Rehman S.U., Razzaq H.

Textile finishing is on the cusp of transformative change with the integration of the nanoencapsulation technique.

Muniz I.D., Santos J.B., de Oliveira R.M., Santos F.G., Souza Junior E.C., Oyama L., Fontan R.D., Bonomo R.C.

Devrnja N., Anđelković B., Ljujić J., Ćosić T., Stupar S., Milutinović M., Savić J.

β-cyclodextrin (β-CD) is a good host for the encapsulation of fennel and basil essential oils (FEO and BEO, respectively) and the formation of inclusion complexes (ICs) using the co-precipitation method. According to the results of the GC/MS analysis conducted in this study, monoterpenes and monoterpenoids were the dominant chemical groups in total FEO, while in BEO, these two groups occurred along with sesquiterpenes and sesquiterpenoids. The presence of dominant compounds from both EOs was validated using the FT-IR spectra of ICs, which indicated successful complexation. Analyses conducted using SPME/GC-MS showed the continuous emission of volatiles over 24 h from both ICs. Under SEM, particles of both ICs appeared to have a rectangular or rhomboid morphology and few aggregates. The insecticidal properties of EOs and ICs with β-CD were tested on the Colorado potato beetle (CPB) as a model pest. The inclusion complex of β-CD with FEO altered the developmental dynamic and body mass of the CPB. The initial increase in the proteolytic activity of CPB larvae fed with potato plants sprayed with ICs was not maintained for long, and the proteolytic efficacy of treated larvae remained in line with that of the control larvae. Future investigations will focus on manipulating the volume of EOs used and the treatment duration for optimal efficacy and potential application.

Weisany W., Yousefi S., Soufiani S.P., Pashang D., McClements D.J., Ghasemlou M.

Essential oils (EOs) are biologically active and volatile substances that have found widespread applications in the food, cosmetics, and pharmaceutical industries. However, there are some challenges to their commercial utilization due to their high volatility, susceptibility to degradation, and hydrophobicity. In their free form, EOs can quickly evaporate, as well as undergo degradation reactions like oxidation, isomerization, dehydrogenation, or polymerization when exposed to light, heat, or air. Encapsulating EOs within mesoporous silica nanoparticles (MSNPs) could overcome these limitations and thereby broaden their usage. MSNPs may endow protection and slow-release properties to EOs, thereby extending their stability, enhancing their efficacy, and improving their dispersion in aqueous environments. This review explores and compares the design and development of different MSNP-based nanoplatforms to encapsulate, protect, and release EOs. Initially, a brief overview of the various types of available MSNPs, their properties, and their synthesis methods is given to better understand their roles as carriers for EOs. Several encapsulation technologies are then examined, including solvent-based and solvent-free methods. The suitability of each technology for EO encapsulation, as well as its impact on their stability and release, is discussed in detail. Opportunities and challenges for using EO-loaded MSNPs as preservatives, flavor enhancers, and antimicrobial agents in the food industry are then highlighted. Overall, this review aims to bridge a knowledge gap by providing a thorough understanding of EO encapsulation within MSNPs, which should facilitate the application of this technology in the food industry.

Roncero E., Delgado J., Morcuende D., Silva A., Andrade M.J.

One of the major hazards in cured meat is the ochratoxin A (OTA) accumulation, being the main producer Penicillum nordicum. Plant extracts can be used as biopreservative agents to its minimisation. The aim of this work was to evaluate the activity of essential oils from rosemary (REO), thyme (TEO) and oregano (OEO), and an acorn extract (AE) against three P. nordicum strains by analysing their inhibitory capacity on their growth and OTA biosynthesis in a dry-cured sausage-based agar. When evaluating their effect on the mould growth, the essential oils showed different activity, being concentration dependent. Concretely, the TEO and OEO activity was greater than that of REO, with a loss of activity throughout the incubation. As incubation time progressed, the plant extract ability to reduce the OTA content decreased. Additionally, differences at strain level were noticed depending on the plant extract, since some of them were able to trigger an overproduction of OTA. REO 500 μL/mL and OEO 50 μL/mL reduced the OTA production up to 93 and 98%, respectively, showing the best outcomes to be further explored as effective strategy to control the presence of OTA due to P. nordicum in dry-cured sausages.

Hădărugă N., Gârban Z., Baltă C., Muselin F., Hădărugă D., Riviş M.

It is well known that platinum-based antineoplastic agents, including cisplatin (CP), have side effects that limit their use. Nefrotoxicity, neurotoxicity, and hemolytic anemia are the most common side effects. There are few studies on the reduction in these effects that involves nanoencapsulation; however, almost none involve cyclodextrins (CDs). Changes in the hematological and biochemical parameters of healthy Wistar rats treated with solutions of γ-cyclodextrin/resveratrol/cisplatin (γ-CD/Rv/CP) ternary complexes are investigated for the first time. They are intraperitoneally injected with γ-CD/Rv/CP solutions containing 5 mg CP/kg.b.w. Single shots were administered to six groups of Wistar rats (six individuals for every group) using γ-CD/Rv/CP, γ-CD/CP, γ-CD/Rv complexes, as well as positive- and negative-control groups, respectively. Thirty-two hematological and biochemical parameters were evaluated from blood samples and used as input variables for the principal component analysis (PCA) discrimination of the groups. The best protection was obtained for the γ-CD/Rv/CP ternary complex, which determined closer biochemical values to the control group. These values significantly differ from those of the γ-CD/CP treated group, especially for the IP, UA, and T-Pro kidney-related biochemical parameters. This finding proves the beneficial influence of Rv during CP administration through CD-based carriers.

Suvarna V., Chippa S.

Background: Volatile oils and their constituents have been considered as major bioactive natural compounds due to their wide therapeutic and biological activities in the field of pharmaceuticals in human healthcare. However, due to their poor solubility, their applications are limited. Inclusion complexation of volatile oils and their volatile constituents with cyclodextrins has emerged as a promising approach for the improvement of aqueous solubility, bioavailability, and stability. Objective: The present review summarizes various research investigations highlighting the complexation of volatile oils and their constituents with cyclodextrins and their derivatives. Additionally, we present the glimpses of patents published between 1998-2021to highlight the significance of inclusion of volatile oil in cyclodextrins. Methods: The selection of articles for the current review was carried out by using keywords ‘Cyclodextrin’, ‘Essential oil’, ‘Inclusion Complex’, ‘Encapsulation’ and ‘Essential oils/ volatile oils constituents’ in certain specific databases such as Elsevier (Science direct), Pubmed Medical subject headings (MeSH) and Medline. Result: 199 studies published were included in the review. Invitro and invivo studies revealed the efficacy of EOs and their VCs complexed with various types of CD when compared to free forms. Conclusion: This review shows the impact of cyclodextrin complexation on the solubility, bioavailability, stability, and biological activities of volatile oils and their constituents.

Horablaga A., Şibu (Ciobanu) A., Megyesi C.I., Gligor (Pane) D., Bujancă G.S., Velciov A.B., Morariu F.E., Hădărugă D.I., Mişcă C.D., Hădărugă N.G.

This is the first study on the modeling of the controlled release of the estimated antioxidants (flavonoids or flavonolignans) from β-cyclodextrin (β-CD)/hydrophilic vegetable extract complexes and the modeling of transdermal pharmaceutical formulations based on these complexes using an overall estimation by the spectrophotometric method. The Korsmeyer–Peppas model was chosen for evaluating the release mechanisms. β-CD/chamomile (Matricaria chamomilla L., Asteraceae) ethanolic extract and β-CD/milk thistle (Silybum marianum L., Asteraceae) ethanolic extract complexes were obtained by the co-crystallization method with good recovering yields of 55–76%, slightly lower than for β-CD/silibinin or silymarin complexes (~87%). According to differential scanning calorimetry (DSC) and Karl Fischer water titration (KFT), the thermal stability of complexes is similar to β-CD hydrate while the hydration water content is lower, revealing the formation of molecular inclusion complexes. In the Korsmeyer–Peppas model, β-CD/M. chamomilla flower extract complexes reveal Case II transport mechanisms, while the corresponding complexes with leaf extracts indicate non-Fickian diffusion for the controlled release of antioxidants in ethanol 60 and 96%. The same non-Fickian diffusion was revealed by β-CD/S. marianum extract and β-CD/silibinin complexes. On the contrary, almost all model transdermal pharmaceutical formulations based on β-CD/M. chamomilla extract complexes and all those based on β-CD/S. marianum extract complexes revealed non-Fickian diffusion for the antioxidant release. These results indicate that H-bonding is mainly involved in the diffusion of antioxidants into a β-CD based matrix, while the controlled release of antioxidants in model formulations is mainly due to hydrophobic interactions. Results obtained in this study can be further used for studying the particular antioxidants (namely rutin or silibinin, quantified, for example, by liquid chromatographic techniques) for their transdermal transport and biological effects in innovatively designed pharmaceutical formulations that can be obtained using “green” methods and materials.

Hădărugă N.G., Popescu G., Gligor (Pane) D., Mitroi C.L., Stanciu S.M., Hădărugă D.I.

The goal of the study was the discrimination of β-cyclodextrin (β-CD)/hazelnut (Corylus avellana L.) oil/antioxidant ternary complexes through Fourier-transform infrared spectroscopy coupled with principal component analysis (FTIR–PCA). These innovative complexes combine the characteristics of the three components and improve the properties of the resulting material such as the onsite protection against oxidative degradation of hazelnut oil unsaturated fatty acid glycerides. Also, the apparent water solubility and bioaccessibility of the hazelnut oil components and antioxidants can be increased, as well as the controlled release of bioactive compounds (fatty acid glycerides and antioxidant flavonoids, namely hesperidin, naringin, rutin, and silymarin). The appropriate method for obtaining the ternary complexes was kneading the components at various molar ratios (1:1:1 and 3:1:1 for β-CD hydrate:hazelnut oil (average molar mass of 900 g/mol):flavonoid). The recovering yields of the ternary complexes were in the range of 51.5–85.3% and were generally higher for the 3:1:1 samples. The thermal stability was evaluated by thermogravimetry and differential scanning calorimetry. Discrimination of the ternary complexes was easily performed through the FTIR–PCA coupled method, especially based on the stretching vibrations of CO groups in flavonoids and/or CO/CC groups in the ternary complexes at 1014.6 (± 3.8) and 1023.2 (± 1.1) cm−1 along the second PCA component (PC2), respectively. The wavenumbers were more appropriate for discrimination than the corresponding intensities of the specific FTIR bands. On the other hand, ternary complexes were clearly distinguishable from the starting β-CD hydrate along the first component (PC1) by all FTIR band intensities and along PC2 by the wavenumber of the asymmetric stretching vibrations of the CH groups at 2922.9 (± 0.4) cm−1 for ternary complexes and 2924.8 (± 1.4) cm−1 for β-CD hydrate. The first two PCA components explain 70.38% from the variance of the FTIR data (from a total number of 26 variables). Other valuable classifications were obtained for the antioxidant flavonoids, with a high similarity for hesperidin and naringin, according to FTIR–PCA, as well as for ternary complexes depending on molar ratios. The FTIR–PCA coupled technique is a fast, nondestructive and cheap method for the evaluation of quality and similarity/characteristics of these new types of cyclodextrin-based ternary complexes having enhanced properties and stability.

Taleuzzaman M., Chauhan S., Tomar D.S., Singh P.K., Talwar I., Javed M.N.

Cai Q., Zhang Y., Fang X., Lin S., He Z., Peng S., Liu W.

In this study, a novel emulsion, thymol (Thy) and lauric acid (LA) emulsion (Thy/LA-Emulsion) was prepared by homogenizing eutectic solvent (Thy/LA mixture) and caseinate solution. The effects of different thymol and lauric acid mass ratio on the formation, stability, and antibacterial activity of emulsions were studied. Compared with thymol alone, adding lauric acid (25, 50, and 75%) could enhance the antibacterial efficacy of the emulsions. Among them, Thy/LA25%-Emulsion could be stored at room temperature for a month without the increase of particle size, indicating that the addition of LA had not impacted the stability of emulsions. Meanwhile, Thy/LA25%-Emulsion exhibited a greater inhibition zone (3.06 ± 0.12 cm) and required a lower concentration (0.125 mg/mL) to completely inhibit the growth of Listeria monocytogenes. Consequently, Thy/LA25%-Emulsion demonstrated the best antibacterial activity and physicochemical stability due to its long-term storage stability. Our results suggest that Thy/LA25%-Emulsion may become a more functional natural antibacterial agent with greater commercial potential owing to its cheaper raw materials, simpler production processes, and better antibacterial effect in the food industry.

Tangpao T., Charoimek N., Teerakitchotikan P., Leksawasdi N., Jantanasakulwong K., Rachtanapun P., Seesuriyachan P., Phimolsiripol Y., Chaiyaso T., Ruksiriwanich W., Jantrawut P., Van Doan H., Cheewangkoon R., Sommano S.R.

Basils of the genus Ocimum are aromatic plants grown widely throughout the tropical and temperate regions. The essential oils obtained from their aerial parts are enriched with volatile organic compounds with high market demand for food and pharmaceutical industries. The volatile organic compounds have been shown to exhibit biological activities. Therefore, their novel applications have been extensively explored in the last few decades. The most widely available basils in the tropical areas include white holy basil (O. sanctum var. Shyama), red holy basil (O. sanctum var. Rama), Thai basil (O. basilicum var. thyrsiflorum), lemon basil (O. citriodorum), and tree basil (O. gratissimum). Over 60 volatiles of different classes have been exclusively described, and some of them could be useful as biomarkers for genotype specification. The major volatile ingredient is the phenylpropanoids, such as methyl eugenol, which has the potential as a natural product for mitigating Oriental fruit fly (Bactrocera dorsalis) during tropical fruit production. Moreover, basil essential oils are also used to control diseases of the fruits during post-harvest storage. As a result, the application of basil essential oils as a sustainable defect control strategy for tropical fruit value chains seems intriguing. This review provides comprehensive information on plant taxonomy and volatile compositions of the essential oil fractions from different basil species. Their biological activities and applications are also discussed, mainly during the pre- and post-production of tropical fruits. Additionally, the available techniques to enhance the efficacy of the volatile active compounds are also described.

Lee M.H., Lee I.Y., Chun Y.G., Kim B.

In the present study, β-caryophellene (BCP) was encapsulated using five different carrier lipids composed of FAs with different chain lengths and degrees of saturation: medium-chain triglyceride (MCT), coconut, olive, and soybean oils, and cocoa butter. In order to investigate effects of type of carrier lipids on physical stability, various food processing treatments including thermal, freeze-thaw, and ionic strength treatments were inflicted to the lipid nanocarriers containing BCP. The initial droplet sizes and PDI of all lipid nanocarriers were maintained after thermal (LTLT, HTST, and autoclave) and salt treatments. Additionally, more than 96% of encapsulated BCP remained even after autoclave treatment. Although the droplet sizes and PDI increased after freeze-thaw treatment, the lipid nanocarriers with MCT oil maintained their high dispersion stability (PDI < 0.3) even after 3 freeze-thaw cycles. For determining storage stability, the laser scanning turbidimetry assay was carried out at 4 and 25 °C. The creaming formation caused by coalescence during storage was remarkable in the lipid nanocarriers with olive oil and soybean oil, while the lipid nanocarriers with MCT oil composed of only saturated FAs exhibited high dispersion stability. Moreover, the fasted lipid digestion was observed in the lipid nanocarrier with MCT oil. • β-caryophellene (BCP) was encapsulated using five different carrier lipids. • Initial stability of lipid nanocarriers were kept after various thermal treatments. • BCP-loaded lipid nanocarrier with MCT oil shows the highest freeze-thaw stability. • Coalescence was distinct in BCP-loaded lipid nanocarriers with olive and soybean oils. • The fasted lipid digestion occurred in the BCP-loaded lipid nanocarriers with MCT oil.

Gonzalez Pereira A., Carpena M., García Oliveira P., Mejuto J.C., Prieto M.A., Simal Gandara J.

Cyclodextrins (CDs) are cyclic oligomers broadly used in food manufacturing as food additives for different purposes, e.g., to improve sensorial qualities, shelf life, and sequestration of components. In this review, the latest advancements of their applications along with the characteristics of the uses of the different CDs (α, β, γ and their derivatives) were reviewed. Their beneficial effects can be achieved by mixing small amounts of CDs with the target material to be stabilized. Essentially, they have the capacity to form stable inclusion complexes with sensitive lipophilic nutrients and constituents of flavor and taste. Their toxicity has been also studied, showing that CDs are innocuous in oral administration. A review of the current legislation was also carried out, showing a general trend towards a wider acceptance of CDs as food additives. Suitable and cost-effective procedures for the manufacture of CDs have progressed, and nowadays it is possible to obtain realistic prices and used them in foods. Therefore, CDs have a promising future due to consumer demand for healthy and functional products.

Faghihi K., Soleimani M.

This study aimed to develop new thermally stable synthetic polyester network containing β-cyclodextrin (β-CD) cavities with good absorbent behavior to remove organic pollutants such as parabens derivatives (methyl and propyl parabens) from aqueous solution. β-Cyclodextrin polyester network (β-CDPN) was synthesized by the reaction of β-CD with N,N′-(4,4′-diphenylether) bis trimellitimide diacid chloride as a cross-linker agent in the presence of sodium hydride. Diimide acid chloride as a synthetic cross-linker agent was prepared by two-step reactions. The sorbent process was optimized by four different parameters, such as pH, the temperature of the solution, contact time, β-CDPN ratio. After adsorbed of parabens in aqueous solution, the β-CDPN precipitates were gathered, and the solution was analyzed by using the high-performance liquid chromatography (HPLC) technique. The results show the high absorbent capacity of parabens (about 99%) by β-CDPN cavities. Furthermore, the kinetic data were measured using the pseudo-first-order and pseudo-second-order equation. The pseudo-second-order showed the best fit for the kinetic studies (methyl and propyl parabens R2: 0.9979 and 0.9998, respectively). The adsorption equilibrium of methyl paraben using β-CDPN could be well defined with the Langmuir isotherm model. The adsorption ability of β-CDPN kept nearly unchanged after five filtration-regeneration cycles, further TGA and DTG experiments show β-CDPN has excellent thermal stability and can be used in a wide range of temperatures.