Using a small-angle X-ray scattering technique, shape and size, and internal structure of diglycerol polyisostearate nonionic surfactant micelles in nonpolar oil n-hexadecane (HD) were investigated at 25°C. Furthermore, the effect of added water on the structure of host reverse micelles was also investigated. The scattering data were evaluated by the generalized indirect Fourier transformation (GIFT) method and model fittings. It was found that diglycerol polyisostearate (abbreviated as (iso-C18)nG2, where n=2-4 represent the number of isostearate chain per surfactant molecule) spontaneously form reverse micelles in HD at 25°C and their geometry (shape and size, and internal structure) could flexibly be controlled by a small change in the lipophilic tail architecture of the surfactant, temperature, and water addition. Increasing number of isostearate chain per surfactant molecule decreases the micelles size favoring prolate-to-sphere type transition. This phenomenon could be best understood due to voluminous lipophilic part of the surfactant. Increasing temperature decreases the size of the reverse micelles due to enhanced interpenetration of the surfactant chain and the oil and also due to dominant hydrophobic character of the surfactant at higher temperatures. In the studies of effect of added water on the structure of micelles, it was found that the reverse micelles swell with water causing two dimensional micellar growths.
The content and composition of triterpene alcohol fractions of the non-saponifiable lipids (NSL) along with the fatty acid composition of the kernel fats (n-hexane extracts) of the shea tree (Vitellaria paradoxa; Sapotaceae) were determined for 36 samples from seven sub-Saharan countries: Cote d’ Ivoire, Ghana, Nigeria, Cameroun, Chad, Sudan, and Uganda. The fat content of the kernels, proportion of NSL in the fats, and triterpene alcohols in the NSL are in the range of 30–54, 2–12, and 22–72%, respectively. The triterpene alcohol fractions contained α-amyrin (1), β-amyrin (2), lupeol (3), and butyrospermol (4) as the major constituents along with minor or trace amounts of ψ-taraxasterol (5), taraxasterol (6), parkeol (7), 24-methylene-24-dihydroparkeol (8), 24-methylenecycloartanol (9), dammaradienol (10), and 24-methylenedammarenol (11). Fatty acid composition is dominated by stearic (28–56%) and oleic (34–61%) acids. Shea butters from West African provenances contained in general higher levels of triterpene alcohols and stearic acid than those from East African provenances. Both stearic acid and total triterpene alcohol contents were significantly correlated to the latitude and elevation of the source population, indicating that higher levels of these compounds are found at higher ambient temperatures.
Water-distilled essential oils from aerial parts of Tanacetum argenteum ssp. argenteum and T. densum ssp. amani from Turkey were analyzed by GC and GC/MS. The essential oil of T. argenteum ssp. argenteum was characterized with α-pinene 36.7%, β-pinene 27.5% and 1,8-cineole 9.8%. T. densum ssp. amani was characterized with β-pinene 27.2%, 1,8-cineole 13.1%, α-pinene 9.7% and p-cymene 8.9%. Antibacterial activity of the oils were evaluated for five Gram-positive and five Gram-negative bacteria by using a broth microdilution assay. The highest inhibitory activity was observed against Bacillus cereus for T. argenteum ssp. argenteum oil (125 μg/mL) when compared with positive control chloramphenicol it showed the same inhibition potency. However, the same oil showed lower inhibitory activity against B. subtilis when compared. The oil of T. densum ssp. amani did not show significant activity against the tested microorganisms. DPPH radical scavenging activity of the T. argenteum ssp. argenteum oil was investigated for 15 and 10 mg/mL concentrations. However, the oil did not show significant activity when compared to positive control α-tocopherol. Both oils showed toxicity to Vibrio fischeri in the TLC-bioluminescence assay.
Monoazacryptand [20.18.18] (1), monoaza-15-crown-5 (2a), and monoaza-18-crown-6 (2b) with a partially fluorinated sidearm were newly prepared and their transport abilities were estimated in a supported liquid membrane containing a mixture of 2- (perfluorohexyl) ethyl alcohol and 2- (perfluorooctyl) ethyl alcohol. In competitive passive transport of K+, Na+, and Li+ under neutral conditions, the K+ selectivity increased in the order: ionophore 2a<ionophore 2b<ionophore 1; whereas, the transport velocity increased in the order: ionophore 2a<ionophore 1<ionophore 2b. On the other hand, only ionophore 1 successfully transported K+ in the transport from the neutral source phase to the acidic receiving phase. This result was reasonably explained by considering the excellent K+ complexing ability of monoazacryptand (1) in comparison with that of monoazacrown ethers (2a and 2b).
Enzymatic synthesis of phospholipids (PLs) containing polyunsaturated fatty acids (PUFAs) was studied. The main purpose was to establish an efficient production method for PLs containing docosahexaenoic acid or eicosapentaenoic acid using only food-compatible reagents. Phospholipase A2 (PLA2)-mediated ester synthesis was employed to introduce the PUFAs into the sn-2 position of lysophospholipid (LPL) to yield PUFA-containing PLs. When LPL and the fatty acids were reacted in glycerol in the presence of porcine pancreas PLA2, the reaction was not very effective. However, it was found that addition of certain kinds of amino acids such as glycine or L-alanine in the reaction mixture improved the reaction. After the reaction, the synthesized PLs were extracted selectively with ethanol and n-hexane, leaving the unreacted LPL, amino acids and the enzyme remained in the glycerol layer. It was confirmed that the enzyme remained in the glycerol layer could be reused by adding fresh substrates for the subsequent reactions.
Novel double-chain nonionic surfactants with an acid decomposition function were prepared by acid-catalyzed condensation of chloroacetone with fatty alcohols (octyl, decyl, and dodecyl), followed by a Williamson reaction with polyethylene glycol without any expensive reagents and special equipment. These surfactants showed easy micelle formation compared to those of polyoxyethylene (n=9) dodecyl ether (C12EO9), and good foaming properties. The emulsion stability of these surfactants was almost the same as that of C12EO9. They decomposed completely after 30 min at pH 1. After 28 days they were more than 60% biodegradable and were almost the same as sodium dodecanoate.
Liquid chromatography-mass spectrometry is one of the most powerful methods for the identification and detection of chemical structures of lipids. In this study, we attempted to identify the chemical structures of glucosylceramides from maize, rice, mushroom (maitake) and sea cucumber by liquid chromatography-ion trap mass spectrometry. For structural analysis of glucosylceramides, [M+H]+, [M+H-18]+ or [M+H-162]+ in the positive scan mode was used for MS/MS analysis to obtain product ion spectra. The typical signals which are characteristic for the sphingoid base moieties were observed while the isomers could not be distinguished. This method should be useful for the structural determination of diverse glucosylceramide molecular species.
This study sets out to investigate the in vitro permeation of ketoprofen from the formulated nanoemulsions through excised rat skin. In vitro permeation of ketoprofen nanoemulsion through rat skin was evaluated in Franz diffusion cells and compared with marketed product (Fastum gel®). Limonene which has been reported to be a good enhancer for ketoprofen was selected. Moreover the effects of limonene which was added to the nanoemulsion formulations at levels of 1%, 2%, 3% and on rat skin permeation of ketoprofen were also evaluated. The selected optimized formulation was further studied for skin irritation. Utilization of limonene as a penetration enhancer increased the permeation of ketoprofen from the formulated nanoemulsion with increasing concentrations of limonene. The results obtained showed that nanoemulsion with 3% limonene produced similar and comparable skin permeation of ketoprofen with marketed formulation and the skin irritation study on rats showed the optimized formulation prepared was safe.