The properties of aqueous mixtures of cationic species with alkyl dicarboxylic acid compounds have been studied. The cationic compounds used in this study were tertiary amine-type N-methyl-N-(2,3-dioxypropyl)hexadecylamine (C16amine) and quaternary ammonium-type N,N-dimethyl-N-(2,3-dioxypropyl)hexadecylammonium chloride (C16Q). The alkyl dicarboxylic acid compounds used were HOOC(CH₂)₁₀COOH (C12H) and its sodium salt (C12Na). Three aqueous mixtures were examined in this study: (System I) C16amine + C12H, (System II) C16Q + C12Na, and (System III) C16Q + C12H. The solution pH was set at 12 for System III. The combination of ¹H-NMR and mass spectroscopy data has suggested that a stoichiometric complex is formed in the aqueous solutions at a mole fraction of C12H (or C12Na) = 0.33. Here, the C12H (or C12Na) molecule added to the system bridges two cationic molecules, like a spacer of gemini surfactants. In fact, the static surface tensiometry has demonstrated that the stoichiometric complex behaves as gemini-like amphiphiles in aqueous solutions. Our current study offers a possible way for easily preparing gemini surfactant systems.

View full abstract

A heat-induced O/W emulsion gel that undergoes a phase transition from sol to gel on heating was formed from the addition of aqueous HCl to a toluene solution of a long-chain amidoamine derivative (C18AA). The heat induced O/W emulsions are highly sensitive to temperature, and the sol-gel transition temperature could be simply controlled by adjusting the C18AA concentration. Interestingly, the sol-gel transition of the O/W emulsions was also very sensitive to pH. Thus, we have successfully prepared a novel double-stimuli responsive gel based on O/W emulsions consisting of C18AA and HCl.

View full abstract

The physicochemical properties of nonionic surfactant mixtures in an aprotic, imidazolium-type room-temperature ionic liquid (RT-IL) have been studied using a combination of static surface tensiometry, dynamic light scattering (DLS), and cryogenic transmission electron microscopy (cryo-TEM). The surfactants used in this study are phytosterol ethoxylates (BPS-n, where n is an oxyethylene chain length of either 5 or 30) and the selected RT-IL is 1-butyl-3-methylimidazolium hexafluorophosphate (BmimPF₆). The shorter chain oxyethylene surfactant (BPS-5) exhibits greater surface activity in BmimPF₆ than BPS-30; hence, BPS-5 is a major component in driving the interfacial adsorption and molecular aggregation of the mixed system. The surface tension data demonstrate that an increased mole fraction of BPS-5 results in a decreased critical aggregation concentration (cac) and negatively increased Gibbs free energies estimated for molecular aggregation (ΔG⁰_agg) and interfacial adsorption (ΔG⁰_ads). Indeed, the compositions of the monolayer adsorbed at the air/solution interface and the molecular aggregate formed in the bulk solution are enriched with BPS-5. The combination of the DLS and cryo-TEM results demonstrates the spontaneous formation of multi-lamellar vesicles resulting from the BPS-5-rich composition of the molecular aggregates.

View full abstract

This article reports the preparation and properties of nanosized biodegradable polymer capsules synthesized using the electrocapillary emulsification method. The biodegradable polymers used were poly(ε-caprolactone) (PCL), which is a highly biodegradable and biocompatible polymer, and poly(lactide-co-glycolic acid) (PLGA). While the size of the capsules prepared using PCL alone was in the micrometer range, it decreased with an increase in the amount of PLGA added to PCL and eventually reached the nanometer level. When the electrocapillary emulsification applied potential was 2000 V, the sizes of the capsules (PCL:PLGA = 5:5) ranged from 50 to 80 nm. The percentage of glucose trapped in the PCL/PLGA nanocapsules was higher than 80% and the duration of glucose release from the nanocapsules was about two times longer than that from PCL capsules.

View full abstract

Microbial transformation studies conducted on isopimpinellin (1) by the fungus Glomerella cingulata have revealed that 1 was metabolized to give the corresponding reduced acid, 5,8-dimethoxy-6,7-furano-hydrocoumaric acid (2). The structure of metabolite 2 was elucidated by high-resolution mass spectrometry (HR-MS), extensive NMR techniques, including ¹H NMR, ¹³C NMR, ¹H-¹H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC) and heteonuclear multiple bond coherence (HMBC). The biotransformed product 2 showed weak a in vitro β-secretase (BACE1) inhibitory effect.

View full abstract

The antioxidative effects of rosemary and grape-seed extracts spiked in human plasma were examined using the thiobarbituric acid (TBA) method. The TBA values of plasma spiked with reagents to generate reactive oxygen species, such as singlet oxygen (¹O₂), hydroxyl radicals (^·OH), peroxynitrite (ONOO^–), and superoxide anions (O₂^·–), were measured by a flow injection analysis method with fluorescence (FL) detection. TBA values obtained by the addition of 50 mg/mL of rosemary extracts for ¹O₂, ^·OH, ONOO^–, and O₂^·– increased to 964 ± 65%, 1063 ± 61%, 758 ± 78%, and 698 ± 41%, respectively (n = 3, P < 0.01), whereas the values with 1 mg/mL of grape-seed extracts or tocopherol decreased (40.2 – 66.3%). Furthermore, the antioxidative effects of rosemary extract in rat plasma, spiked with reagents to generate ^·OH, were examined by high-performance liquid chromatography with FL detection. No peak, other than TBA–malondialdehyde, could be detected using wavelengths of 532 (λ_ex) and 553 nm (λ_em).

View full abstract

D-Glyceric acid (D-GA) calcium has been reported to accelerate ethanol oxidation in vivo in rats (Eriksson et al., Metabolism, 56, 895-898 (2007)). However, no other reports have shown that D-GA can reduce the harmful effects of ethanol. In this study, the effects of D-, L-, and DL-GA calcium on ethanol-dosed gastric cell viability were investigated using human gastric carcinoma cells (Kato III) and normal rat gastric mucosa cells (RGM1). Addition of 2% and 3 % ethanol to Kato III and RGM1 cells, respectively, decreased their cell viability by approximately 20-50 % after 24 or 72 h of cultivation. In 2 % ethanol-dosed Kato III cells cultivated for 24 h, addition of 0.002-20 μg/mL D- and L-GA calcium did not affect cell viability. Similarly, addition of less than 20 μg/mL DL-GA calcium did not affect cell viability. However, when 20 μg/mL DL-GA calcium was added, cell viability increased by 35.7 % after 72 h of incubation, compared to the viability of control cells without ethanol or GA. Addition of 20 μg/mL DL-GA calcium to 3 % ethanol-dosed RGM1 cells cultivated for 24 or 72 h also increased cell viability up to those observed in control cells. These results suggest that a racemic mixture of GA may have the strongest effect on enhancing the viability of ethanol-exposed cells.

View full abstract