Highly viscous hydrophobic isosorbide biobased polyester O/W emulsions are prepared through catastrophic phase inversion. The process is followed in situ with two different methods: torque and light backscattering (LBS). Considering high viscosity of the system, only discontinuous conductivity monitoring is performed for comparison. Torque and LBS allow to highlight the emulsion inversion point (EIP) with relatively close water weight fraction values (fw≈0.20). The torque and LBS signals are rather noisy before inversion (evolution of different structures) and more smooth after phase inversion (continuous aqueous phase). Torque gives a more macroscopic information, representative of the global state of the dispersion. Consistent conductivity and torque measurements suggest indeed an inversion pathway through multiple o/W/O emulsions leading to multiple complex structures before getting continuous aqueous final emulsion. This hypothesis is confirmed with continuous LBS monitoring and microscopic observations. LBS signal seems more complete because it combines the information of conductivity and torque and allows to clearly follow in situ the inversion from the beginning to the end of the process.
In this research, the palm oil ester (POE)- based nanoemulsion formulation containing quercetin for pulmonary delivery was developed. The nanoemulsion formulation was prepared by high energy emulsification method and then further optimized using D-optimal mixture design. The concentration effects of the mixture of POE:ricinoleic acid (RC), ratio 1:1 (1.50–4.50 wt.%), lecithin (1.50–2.50 wt.%), Tween 80 (0.50–1.00 wt.%), glycerol (1.50–3.00 wt.%), and water (88.0–94.9 wt.%) towards the droplet size were investigated. The results showed that the optimum formulation with 1.50 wt.% POE:RC, 1.50 wt.% lecithin, 1.50 wt.% Tween 80, 1.50 wt.% glycerol and 93.90 % water was obtained. The droplet size, polydispersity index (PDI) and zeta potential of the optimized formulation were 110.3 nm, 0.290 and －37.7 mV, respectively. The formulation also exhibited good stability against storage at 4℃ for 90 days. In vitro aerosols delivery evaluation showed that the aerosols output, aerosols rate and median mass aerodynamic diameter of the optimized nanoemulsion were 99.31%, 0.19 g/min and 4.25 µm, respectively. The characterization of physical properties and efficiency for aerosols delivery results suggest that POE- based nanoemulsion containing quercetin has the potential to be used for pulmonary delivery specifically for lung cancer treatment.
The analysis of lactones as an indicator of milk quality is important in food manufacturing. However, the extraction of lactones requires sensitive conditions due to their volatility. In this study, the parameters for resolution of lactone standards were evaluated by gas chromatography–electron ionization/mass spectrometry (GC–EI/MS) to develop a rapid and simple method for the quantification and compositional analysis of lactones in edible fats, especially milk fat. Fourteen lactone standards consisting of 6–16 carbon atoms were analyzed and their correction factors (CFs) were obtained by using δ-undecalactone as an internal standard. The CFs of the lactone standards followed the same trend for δ-lactones and γ-lactones. Three volume equivalents of organic solvent per unit sample yielded the best recovery in the lactone analysis. Notably, 91–114% lactone recovery for the standards was achieved with methanol as the extractant. This method was also applicable to other fat samples, such as virgin coconut oil that is thought to contain large amounts of lactones. The recovery of lactones from virgin coconut oil was in the range of 87–104%, indicating that the developed method is also applicable to solid or semi-solid fat samples. The lactone content of butter oil, coconut oil, and butter samples was calculated by using the obtained CFs and the results were in good agreement with those of previous reports. Consequently, the GC-EI/MS method developed in this study is deemed applicable for the quantification of lactones in fat samples.
Alkyldiethanolamides (fatty acid diethanolamides) synthesis from Terminalia catappa L. kernel oil was optimized using lypozyme as a catalyst. The result showed that the optimal reaction conditions were 2 hours reaction time, with a ratio of oil mass (g) to diethanolamine (mmol) of 1:5, a ratio of oil mass to enzyme (g) of 1: 0.075, and a temperature of 40°C. The percentage of alkyldiethanolamides at optimum condition was 56-60%. The synthesis results were also analyzed by FTIR. FTIR spectra revealed specific absorption at several wave numbers (3434 cm–1, 1655 cm–1, 1280 cm–1), indicating that amide and alcohol bonds (C=O, C-N, and O-H) were formed. GC-MS was employed to identify the types of fatty acid diethanolamides that were successfully synthesized. The fatty acid diethanolamides formed were palmitoyldiethanolamide (Rt = 32.96 min) and oleyldiethanolamide (Rt = 35.57 min). The total nitrogen content of alkyldietanolamides was 0.26%, or 0.19 mmol of the amide group in 1 g of sample.
The objective of this investigation was to develop nanoemulsion formulations of Eucalyptus essential oil (EEO) and to evaluate its wound healing effects in comparison with standard gentamycin in rat model. Various nanoemulsionns of EEO were prepared using aqueous phase titration method and the zones of nanoemulsion were identified by the construction of phase diagrams. EEO nanoemulsions were investigated in terms of physical stability, self-nanoemulsification efficiency and physicochemical characterization. Optimized nanoemulsion of EEO was selected for wound healing study, collagen estimation and histopathological evaluation in rats in comparison with pure EEO and standard gentamycin. Optimized nanoemulsion presented significant would healing activity in rats as compared with pure EEO upon oral administration. The wound healing activity of optimized nanoemulsion was comparable with standard gentamycin. Optimized EEO nanoemulsion also presented significant enhancement in collagen content as compared with pure EEO and negative control. However, the collagen contents of optimized nanoemulsion treated animals were comparable with standard gentamycin-treated animals. Histopathological studies of optimized nanoemulsion treated rats showed no signs of inflammatory cells which suggested the safety and non-toxicity of EEO nanoemulsion. This study suggested the potential of nanoemulsion in enhancing the wound healing activity of EEO upon oral administration.
A series of cationic surfactants containing the thioacetate group, [CnH2n+1N(CH3)2(CH2)3SCOCH3] Cl (Cn3SAc, n = 12, 14, 16), were prepared and their properties in aqueous solution were investigated by conductivity, fluorescence, and dynamic light scattering measurements. The critical micelle concentrations (CMCs) of Cn3SAc decreased to about half the value of the corresponding alkyltrimethylammonium chloride. Thioacetate was eliminated with the addition of dithiothreitol (DTT) as well as NaOH. HPLC (high performance liquid chromatography) analysis and NMR (nuclear magnetic resonance) spectroscopy showed that thiol surfactants, [CnH2n+1N(CH3)2(CH2)3SH]Cl (Cn3SH), were generated upon the addition of DTT in aqueous solution via thiol-thioester exchange, whereas gemini surfactants, [CnH2n+1N(CH3)2(CH2)3SS(CH2)3N(CH3)2CnH2n+1]2Cl (2Cn3SS), were generated upon incubation in alkaline solution via hydrolysis and air oxidation.
In this study, we investigated the antioxidant activities of antheraxanthin-related carotenoids. Antheraxanthin and 9-cis-antheraxanthin were prepared from persimmon and orange fruit, respectively, and converted to other carotenoids under acidic conditions. Resulting carotenoids were purified using preparative silica gel HPLC, and their structures were analyzed in detail by NMR spectra. Both antheraxanthin and 9-cis-antheraxanthin were found to be converted to (8R)- and (8S)-mutatoxanthin at an approximate ratio of 3:2. High antioxidant activities were observed for antheraxanthin, 9-cis-antherxanthin, (8R)-mutatoxanthin, and (8S)-mutatoxanthin, with potent lipid peroxidation inhibitory and moderate 1O2-quenching activities.
Triglyceride deposit cardiomyovasculopathy (TGCV) is an intractable cardiovascular disease for which a specific treatment is urgently required. In TGCV, adipose triglyceride lipase (ATGL) deficiency results in the abnormal intracellular metabolism of long-chain fatty acid (LCFA) which leads to TG deposition. Medium-chain triglycerides have been used as an important functional food for various human diseases. To address the potential activities of tricaprin, a medium-chain triglyceride, on cardiac dysfunctions of TGCV, we examined the effects of tricaprin diet on Atgl knock out (KO) mice, an animal model for TGCV. Cardiac imaging tests showed that the tricaprin diet reduced TG accumulation, resulting from improvement of LCFA metabolism, and improved left ventricular function in Atgl KO mice compared to that in mice fed the control diet. In conclusion, tricaprin improved myocardial abnormality in the TGCV model, thus, it may be useful for the treatment of patients with TGCV.
Synthesis of biologically active heterocyclic derivatives with the related fused systems incorporating a long chain of a fatty compound was described via the reactions of 5-amino-N-octadecyl-1H-pyrazole-4-carboxamide 4 with appropriate reagents namely, enaminones, and β-diketones. Hydroxylation of the synthesized compounds using a number of moles of propylene oxide gave nonionic surface-active agents having a good solubility in water, easy to handle, good biodegradability and announced surface properties that revealed the importance of their applications in avoiding pollution problems, and making them safe for humans and the environment. The surface properties and antimicrobial activity of these compounds were investigated, which showed low toxicity, high efficiency in the surface and biological activities. Therefore, these compounds may be exhibit capable potential in industry applications and can be used in the manufacture of cosmetics, textiles, moderate emulsifiers, dyes, pesticides and drugs.
This study aims to investigate the production of ethylene and diethyl ether from ethanol via catalytic dehydration using Si- and Al-based catalysts with Pd modification. First, six catalysts including H-beta zeolite (HBZ), mixed phases of γ-χ-Al2O3 (M-Al) and γ-Al2O3 (G-Al) with and without Pd modification (0.5 wt%) were prepared. The catalytic dehydration of vaporized ethanol at temperature ranging from 200 to 400°C was performed over the catalysts. For ethylene production, the most promising catalyst is HBZ (giving ethylene yield of ca. 99% at 400°C), whereas Pd modification has no significant effect on ethylene production. Considering the production of diethyl ether, it is produced at lower temperature (ca. 250°C) than that of ethylene. The most active catalyst to produce diethyl ether is HBZ with Pd modification (giving diethyl ether yield of ca. 48% at 250°C). Thus, increased diethyl ether yield can be achieved with Pd modification at low temperature for the HBZ catalyst. Other catalysts such as M-Al and G-Al can also produce significant amounts of ethylene. To elucidate the effect of Pd modification on these catalysts, different characterization techniques such as nitrogen physisorption (BET and BJH methods), scanning electron microscopy (SEM) and energy dispersive X-ray spectroscopy (EDX), X-ray photoelectron spectroscopy (XPS) and ammonia temperature-programmed desorption were performed and further discussed in more detail.
Salvia sclarea (SS) is characterized by its valuable essential oils (Eos) and potent biological activities. This study aimed at investigating the phytochemical composition of SS Eos collected in within the same week, from two different regions in Lebanon, Beirut (SS-Bt) and Taanayel (SS-Tl), utilizing GC-MS methods, and to explore their acute and subchronic antidiabetic potentials. Moreover, studying the phytochemical diversity of twenty SS Eos established on our work and literature descriptions in order to recognize the origin of the Lebanese active chemotype(s). The Eos have been obtained by hydro-distillation and identified via GC-MS analyses. Five chemotypes of SS Eos have been identified. The Lebanese Eos, SS-Bt and SS-Tl, studied here have shown evidence to belong to two different chemotypes 1 and 5, respectively. SS-Bt has shown to belong to chemotype 1, which is characterized by high linalool (LL) concentration (average 40.2%). On the other hand, SS-Tl has shown to belong to chemotype 5, which is characterized by high linalyl acetate (LA) concentration (average 50.4%). The acute and subchronic antidiabetic activities of these EOs have been monitored along with LL and LA, in order to find the most active chemotype. Chemotypes 1 (owned to high LL content), present at low altitude places of Lebanon and Poland, has shown significantly higher acute and subchronic antidiabetic activities than that of chemotype 5 (owned to high LA content). In conclusion, Salvia sclarea Eos have shown potential antidiabetic activities, and their Eos might be used in the future as a complementary or an alternative medicine in the management of diabetes and related complications.
The essential oils (EOs) extracted from Evodia lenticellata Huang and Evodia rutaecarpa (Juss.) Benth. leaves are screened to evaluate their contact toxicity and repellency towards Tribolium castaneum (Coleoptera: Tenebrionidae), Lasioderma serricorne (Coleoptera: Anobiidae) and Liposcelis bostrychophila (Psocoptera: Liposcelididae) adults. The EOs are obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry (GC-MS). The principal components in the E. lenticellata EO are identified to be caryophyllene oxide (28.5%), β-caryophyllene (23.1%), β-elemene (14.5%), and β-cubebene (4.7%), while the main components of the E. rutaecarpa EO are α-pinene (39.4%), β-elemene (13.5%), α-ocimene (7.6%), and α-selinene (4.0%). These two kinds of EOs and their individual compounds all showed different levels of contact toxicity and repellent activity against three stored-product insects.
Nanodiscs are self-assembled discoidal nanoparticles composed of amphiphilic α-helical scaffold proteins or peptides that accumulate around the circumference of a lipid bilayer. In this study, Pxt-5, which is an antimicrobial peptide isolated from the skin of Xenopus tropicalis, and its modified peptide (Modify-Pxt-5) were synthesized by solid-phase peptide synthesis (SPPS).Their surface properties, which are an important factor in inducing nanodisc formation, were investigated by circular dichroism (CD) spectroscopy, surface tension measurement, phospholipid vesicle clearance assay, and negative-staining transmission electron microscopy (NS-TEM). The α-helicity of Pxt-5 (8.4%) improved drastically to 45.6% by four amino-acid substitutions (Modify-Pxt-5). Both the peptides, having hydrophobic and hydrophilic faces, behaved like general surfactants, and the surface activity of Modify-Pxt-5 (CAC: 9.5×10–5 M, γCAC: 30.3 mN·m–1) was much higher than that of Pxt-5 (CAC: 7.9×10–5 M, γCAC: 38.1 mN·m–1). A turbid L-α-dimyristoylphosphatidylcholine (DMPC) vesicle solution (T = 0.3%) quickly turned transparent upon addition of Pxt-5 or Modify-Pxt-5. After twelve hours, the transmittance of vesicle solution with Modify-Pxt-5 (T = 96.2%) was found to be higher than that of vesicle solution with Pxt-5 (T = 83.5%), and then the micro-solubilized solutions were observed by NS-TEM. Interestingly, nanodisc structures were found in the vicinity of DMPC vesicles in both the images, and the average diameter of the nanodiscs was 11.2 ± 6.0 nm for those containing Pxt-5 and 10.8 ± 5.8 nm for those containing Modify-Pxt-5. It was also found that Modify-Pxt-5 effectively self-assembles into nanodiscs compared to Pxt-5 without any substitutions.
Lung surfactant, besides alveolar stability, also provides defence against pathogens by surfactant proteins (SP), SP-A and SP-D. The hydrophobic proteins SP-B and SP-C enhance surface activity. An unusual and paradoxical effect of bovine LS and synthetic model LS with SP-B/-C was bactericidal to Staphylococcus aureus and Escherichia coli. Bacterial proliferation were investigated with bovine lung surfactant extract (BLES), dipalmitoylphosphatdylcholine, palmitooleylglycerol, in combination with SP-B/-C using standard microbiological colony forming unit (CFU) counts and structural imaging. BLES and other surfactant-SP-B/-C mixtures inhibit bacterial growth in the concentration range of 0 -7.5 mg/mL, at > 10 mg/mL paradoxical growth of both the bacterial species suggest antibiotic resistance. The lipid only LS have no effect on bacterial proliferation. Smaller peptide mimics of SP-B or SP-B1-25, were less efficient than SP-Cff. Ultra structural studies of the bacterial CFU using electron and atomic force microscopy suggest some membrane damage of S. aereus at inhibitory concentration of BLES, and some structural alteration of E. coli at dividing zones, suggesting utilization and incorporation of surfactant lipid species by both bacteria. The results depicted from in vitro studies are also in agreement with protein-protein interactions obtained from PatchDock, FireDock and ClasPro algorithm. The MD-simulation decipher a small range fluctuation of gyration radius of the LS proteins and their peptide mimics. The studies have alarming implications in the use of high dosages (100 mg/mL/kg body weight) of exogenous surfactant for treatment of respiratory distress syndrome, genetic knock-out abnormalities associated with these proteins, and the novel roles played by SP-B/C as bactericidal agents.