Haskap (Lonicera caerulea L.) fruit contains some bioactive phenolic phytochemicals, mainly cyanidin-3-glucoside (cy3-glc) and chlorogenic acid. The purpose of this study was to investigate the effects of anthocyanin-rich phenolic phytochemical (containing 13.2% anthocyanin) purified from a Haskap fruit (named Haskap phytochemical) on postprandial serum triglyceride and blood glucose levels. The Haskap phytochemical (containing cy 3-glc at 300 mg/kg of body weight) was administered orally to rats fasted for 24 h and 30 min later, a corn oil emulsion was administered to these rats. After the administration, serum triglyceride concentration was measured. An increase in serum triglyceride concentration and the AUC significantly lowered in the Haskap phytochemical-administered group than in the saline-administered group. To evaluate the effect of serum glucose levels, the Haskap phytochemical was orally administered to rats fasted for 24 h and sucrose solution (2 g/kg of body weight) was administered to these rats after 30 min. After the administration, blood glucose level was measured. The Haskap phytochemical significantly reduced the increase in blood glucose levels and AUC in the Haskap phytochemical-administered group than in the saline-administered group. Furthermore, to investigate the long-term effects of Haskap phytochemical intake, high-fat diet (HF diet) with 1.5% or 3.0% Haskap phytochemical was administered to rats for four weeks. The investigation of chronological changes in the serum components of the rats fed HF diets in addition to the administration of Haskap phytochemical showed that the increase in serum triglyceride concentrations, total cholesterol concentrations and blood glucose were significantly suppressed compared to the HF diet-fed control (HF-control). These results suggest that the decrease in postprandial blood lipids and blood glucose by short or long-term Haskap phytochemical ingestion is due to anthocyanin and other polyphenols contained in the Haskap phytochemical.
The chemical composition of essential oils from four Piper species, Piper retrofractum Vahl., P. boehmeriaefolium (Miq.) C. DC., P. sarmentosum Roxb., and P. maclurei Merr., were analysed by gas chromatography-flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Nineteen to sixty-four compounds representing 92.0%-98.4% of the total contents were identified in the oil samples. The major constituents identified in P. retrofractum leaf oil were benzyl benzoate (14.4%), myrcene (14.4%), bicycloelemene (9.9%), bicyclogermacrene (7.0%) and β-caryophyllene (5.3%). On the other hand, the main constituents of P. boehmeriaefolium were α-copaene (28.3%), α-pinene (7.4%) and 1, 8-cineole (5.7%). P. sarmentosum showed a very different chemical profile characterized mainly by aromatic compounds and devoid of monoterpene hydrocarbons. The major constituents were benzyl benzoate (49.1%), benzyl alcohol (17.9%), 2-hydroxy-benzoic acid phenylmethyl ester (10.0%) and 2-butenyl-benzene (7.9%). The leaf of P. maclurei was characterized by higher amount of (E)-cinnamic acid (37.4%) and (E)-nerolidol (19.4%). Moreover, (Z)-9-octadecanoic acid methyl ester (28.0%), (E)-cinnamyl acetate (17.2%), phytol (12.2%) and (E)-cinnamaldehyde (8.8%) were the major compounds identified in the stem oil.
Arachidonic acid (ARA) is an n-6 PUFA and is thought to have an important role in various physiological and psychological functions. Recently, supplementation with ARA-enriched TAG was shown to improve age-related decreases in cognitive function in healthy elderly men. To investigate the influence of baseline serum ARA status on cognitive function and its improvement, we analyzed cognitive function stratified by serum ARA level. The stratified analysis was also conducted for the effects of ARA-enriched TAG supplementation on cognitive improvement. Cognitive function was evaluated by measuring event-related potentials (ERPs), including P300 latency and amplitude. When participants were stratified by baseline serum ARA level, P300 latency was significantly longer and P300 amplitude was generally lower in the low-ARA group than in the high-ARA group. No significant difference in P300 components was observed when participants were stratified by serum levels of any other fatty acid. ARA-enriched TAG supplementation significantly shortened P300 latency and increased P300 amplitude in the low-ARA group, although no significant differences were observed in the high-ARA group. These findings suggest that lower serum ARA levels were associated with cognitive function in elderly men and that ARA-enriched TAG supplementation is more effective in improving cognitive function in healthy elderly men with low serum ARA levels than in those with high serum ARA levels.
It is reported that mixing polyglycerol polyricinoleate (PGPR) and polyglycerol laurilester has a great emulsifying capacity, and consequently fine oil-in-water (o/w) emulsions can be formed. However, the role of PGPR is not clear. The objective of this research is to investigate the phase behavior of vegetable oil/mixture of PGPR and polyglycerol fatty acid ester/water systems, and to clarify the role of PGPR in making a fine emulsion. Phase diagrams were constructed to elucidate the optimal process for preparing fine emulsions. In all the systems examined in this study, the phases, including the liquid crystal phase (Lc) and sponge phase (L3), spread widely in the phase diagrams. We examined droplet size of the emulsions prepared from each phase and found that o/w nano-emulsions with droplet sizes as small as 50 nm were formed by emulsifying either from a single L3 phase or a two-phase region, Lc + L3. These results indicate that a sponge phase L3 or liquid crystal phase Lc or both is necessary to form an o/w nano-emulsion whose average droplet diameter is less than 50 nm for PGPR and polyglycerin fatty acid ester mixtures used as surfactant.
This paper reports a method to control the formation and disruption of vesicles from a novel single-tailed surfactant (11-ferrocenylundecylammonium bromide, 11-FAB), which contains two stimuli-responsive groups corresponding to pH variation and redox reaction conditions, by external stimuli. Although 11-FAB is a single-tailed surfactant, pure 11-FAB spontaneously forms vesicles in water. Microscopic observations of 2.5 mM aqueous solutions of pure 11-FAB (pH = 5.2) show that a number of 11-FAB vesicles are giant, with diameters of 10–30 μm. The disruption of vesicles is observed in aqueous 11-FAB solutions under basic conditions. The vesicles are then reformed under acidic conditions. Reduced 11-FAB also forms large vesicles in electrolyte solutions. These vesicles are disrupted by electrochemical oxidation and reformed by subsequent chemical reduction. This reversible disruption and reformation of vesicles is attributed to the drastic change in the molecular structure of 11-FAB. To our knowledge, this is the first report of control over the formation and disruption of vesicles using two stimuli responses.
We studied the effects of the spacer chain length of amino acid-based gemini surfactants on the formation of wormlike micelles in aqueous solutions. The surfactants used were synthesized by reacting dodecanoylglutamic acid anhydride with diamine compounds (ethylenediamine, pentanediamine, and octanediamine), and were abbreviated as 12-GsG-12 (s: the spacer chain length of 2, 5, and 8 methylene units). These surfactants yielded viscoelastic wormlike micellar solutions at pH 9 upon mixing with a cationic monomeric surfactant, hexadecyltrimethylammonium bromide (HTAB). We found that the rheological behavior was strongly dependent on the spacer chain length and HTAB concentration. When the shortest spacer chain analogue (12-G2G-12) was used, an increased HTAB concentration resulted in the following structural transformations of the micelles: (i) spherical or rodlike micelles; (ii) anionic wormlike micelles exhibiting a transient network structure; (iii) anionic wormlike micelles with a micellar branching or interconnected structure; and (iv) cationic wormlike micelles. Similarly, when the middle spacer chain analogue (12-G5G-12) was used, a structural transformation from anionic to cationic wormlike micelles occurs; however, molecular aggregates with a lower positive curvature were also formed in this transition region. When the longest spacer analogue (12-G8G-12) was used, the formation of cation-rich molecular aggregates was not observed. These transition behaviors were attributed to the packing geometry of the gemini surfactants with HTAB. Additionally, as the spacer chain length increased, the zero-shear viscosity in the anionic wormlike micellar region decreased, suggesting limited one-dimensional micellar growth of spherical, rodlike, or anionic wormlike micelles.
We have developed oleic acid-based partially fluorinated gemini surfactants with carboxylic acid headgroups. The fluorocarbon chain is covalently bound to the terminal carbonyl group of oleic acid via a -CH2CH2OCO- unit, and the carboxylic acid headgroups are introduced to the cis double bond of oleic acid via -OCOCH2CH2- units. The aqueous solution properties of these surfactants were studied at pH 9 in the presence of 10 mmol dm–3 NaCl by means of static surface tension, pyrene fluorescence, and dynamic light scattering measurements. The resulting surface tension data demonstrate that the partially fluorinated gemini surfactants exhibit excellent surface activity in their dilute aqueous solutions. In addition, the surfactants are suggested to form micellar aggregates 2–4 nm in diameter. We also studied the aqueous temperature-concentration phase diagrams of the partially fluorinated gemini surfactants (disodium salts) on the basis of visual observations (through a crossed polarizer), polarized optical microscopy, and small angle X-ray scattering measurements. Several phase states including micellar solution phase, hexagonal phase, bicontinuous cubic phase, and lamellar phase were observed along with the coexistence of these phases in certain regions. Assemblies with lesser positive curvature tend to be formed with increasing surfactant concentration, increasing temperature, and increasing fluorocarbon chain length. A comparison of the phase diagrams of the partially fluorinated and hydrogenated surfactant systems suggests that close molecular packing is inhibited within the assemblies of the partially fluorinated surfactants because of the limited miscibility between the fluorocarbon and hydrocarbon units. To the best of our knowledge, this is the first systematic report focusing on the temperature-concentration phase diagrams of (partially) fluorinated gemini surfactants over a wide range of compositions and temperatures.
The neutral glycosphingolipids, mono-, di-, tri- and tetraglycosylceramides (GL-1, GL-2, GL-3, GL-4a and GL-4b), were identified from whole tissues of the marine crab Erimacrus isenbeckii by successive column chromatography with ion exchange Sephadex (QAE-Sephadex), magnesium silicate (Florisil) and silicic acid (Iatrobeads) resins. Through component analysis, sugar analysis, methylation studies, exoglycosidase cleavage, and various chromatographic and spectrometric techniques, their structures were proposed to be as follows: GL-1, Glcβ1-1Cer; GL-2, Manβ1-4Glcβ1-1Cer; GL-3, Galβ1-3Manβ1-4Glcβ1-1Cer; and GL-4a and GL-4b, Gal3Meα1-4Galβ1-3Manβ1-4Glcβ1-1Cer. The main molecular species of the aliphatic moiety in each purified glycolipid were 18:0, 22:0, 22:1-d14:1 (fatty acid-sphingoid) and 18:0-d16:1 for GL-1; 18:0-d16:1 and 22:1-d14:1, d16:1 for GL-2; 22:1, 24:1-d16:1 for GL-3; 22:1, 24:1-d16:1 for GL-4a; and h22:1, h24:1-d16:1 for GL-4b, respectively. By immunological detection, an arthro-series glycosphingolipid (At3Cer; GlcNAcβ1-3Manβ1-4Glcβ1-1Cer) was also detected as a minor component. The characteristic arthro-series glycosphingolipid has been observed in most animals belonging to the phylum Arthropoda.
Fatty acids are fundamental cellular components, and provide essential building blocks for membrane biosynthesis. Although the use of gene knockout mutants is a robust method for examining the function of specific cellular metabolic networks, fatty acid synthase knockout mutants are extremely difficult to isolate. In the Dictyostelium discoideum genome, we found two putative fatty acid synthase genes, and we created a knockout mutant for one of them to examine the physiological consequences. In this study, we found that a continuous fatty acid supply was necessary for normal development, and the fatty acid synthase knockout mutant showed severe developmental delay. This developmental defect was corrected in chimeras composed of wild type cells and knockout mutant cells (3:7, respectively). The knockout mutant also showed aberrant expression of fatty acid biosynthesis genes. These results showed that D. discoideum needs correct fatty acid synthesis for normal development.
In this study, the anti-degranulation effects of fifteen carotenoids were evaluated using RBL-2H3 rat basophilic leukemia cell line as a mast cell model. Nine carotenoids, fucoxanthin, zeaxanthin, β-carotene, astaxanthin, 3-hydroxyechinenone, fucoxanthinol, lycopene, β-cryptoxanthin, and siphonaxanthin significantly suppressed antigen-induced mast cell degranulation. Under the same conditions, the cellular carotenoid contents were quantified using high performance liquid chromatography-photodiode array (HPLC-PDA). There was no correlation between the cellular carotenoid contents and their anti-degranulation activities. These results indicate that the differences in the anti-degranulation activities of carotenoids were not related to their uptake by the cells.
Lipase Thermomyces lanuginosa has shown potential in modifying oils and fats through interesterification. Analyzing the physicochemical properties of the modified oils is important to determine the effectiveness of lipase in catalyzing interesterification. In this study, the effectiveness of the immobilized lipase (Lipozyme® TL IM) in catalyzing interesterification of palm olein in pilot-scale batch reactor was determined. The evaluation was done by analyzing the changes of triacylglycerol (TAGs) composition, sn-2 position fatty acids composition and the physical properties of the palm olein after the interesterifications. The pilot-scale batch reaction was conducted for 8 hours with 5 %w/w enzyme dosage based on the results of TAGs composition of the laboratory-scale interesterified products. The pilot-scale results showed that Lipozyme® TL IM act as an effective enzyme in converting TAGs, in which 4.5% of trisaturated TAGs (PPP and PPS) were produced in the batch reaction. The formation of these new TAGs had also altered the thermal and physical properties of the palm olein. These interesterified products showed a broad peak and shoulder at high temperature, ranging from 10°C to 40°C, indicating the formation of some new TAGs with high melting points. However, the enzyme did not perform perfectly as a 1,3-specific enzyme in the reaction as a significant reduction of oleic acid and an increment of palmitic acid at the sn-2 position was observed.
While some isothiocyanate (ITCs) are attractive targets for the agricultural and pharmaceutical industries, the presence of goitrin and ITCs has hampered the widespread utilization of rapeseed meal. ITCs are the products of the myrosinase-mediated hydrolysis of glucosinolate (GSLs). As such, a study was conducted in order to gain a better understanding into the identity of the GSLs contained in rapeseed meal. Extraction of the GSLs was carried out with 20% ethanol, affording 3.0% GSL content. The resulting GSL extracts were purified via silica gel column chromatography resulting in the isolation of main three pure GLSs (GSL A, B, and C) and a final GSL content of 39.8%. The indirect-identification of the GSLs in rapeseed meal was also carried out via GC/MS analysis of ITCs. The GSLs, progoitrin and gluconapin, were present in the highest concentration in these extracts. Interestingly, only goitrin was produced when GSL A was the substrate for the defatted rapeseed meal mediated hydrolysis reaction. This indicates GSL A is a progoitrin. Conversely, 3-butenyl ITC was produced only when GSL B was used as substrate, indicating GSL B is gluconapin. These results will be helpful for opening the doors for the use of rapeseed meal in the agricultural or pharmaceutical sectors.