Journal of Oleo Science
Online ISSN : 1347-3352
Print ISSN : 1345-8957
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Volume 65 , Issue 2
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Review
  • Hiromichi Nakahara
    Volume 65 (2016) Issue 2 Pages 99-109
    Released: February 01, 2016
    JOURNALS FREE ACCESS
    Pulmonary surfactant (PS) preparations based mainly on bovine or porcine extracts are commonly administered to patients with neonatal respiratory distress syndrome (NRDS) for therapy. The preparations are sufficiently effective to treat NRDS; however, they are associated with a risk of infection and involve costly purification procedures to achieve batch-to-batch reproducibility. Therefore, we investigated the mechanism and interfacial behavior of synthetic PS preparations containing a mimicking peptide (KLLKLLLKLWLKLLKLLL, Hel 13-5). In particular, a hybrid PS formulation with fluorinated amphiphiles is reported from the perspective of surface chemistry. Fluorinated amphiphiles are characterized by exceptional chemical and biological inertness, high oxygen-dissolving capacity, low surface tension, excellent spreading ability, and high fluidity. These properties are superior to those for the corresponding hydrocarbon analogs. Indeed, a small amount of fluorinated long-chain alcohols enhances the effectiveness of the model PS preparation for in vitro pulmonary functions. Moreover, the mode of the improved efficacy differs depending on the hydrophobic chain length in the alcohols. For alcohols with a short fluorocarbon (FC) chain, the monolayer phase of the model PS preparation remains disordered (fluidization). However, the addition of alcohols containing a long FC chain reduces the disordered/ordered phase transition pressure and the growth of ordered domains of the monolayer (condensation). Furthermore, repeated compression-expansion isotherms of the monolayers, which can simulate respiration in the lung, suggest irreversible elimination of the short-FC alcohol into the subphase and enhancement of the squeeze-out phenomenon of certain PS components by solid-like monolayer formation induced by the long-FC alcohol. We demonstrated that fluorinated amphiphiles may be used as additives for synthetic or commercial PS preparations for RDS treatment.
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Oils and Fats
  • Małgorzata Tańska, Beata Roszkowska, Marta Skrajda, Grzegorz Dąbrowski
    Volume 65 (2016) Issue 2 Pages 111-121
    Released: February 01, 2016
    [Advance publication] Released: January 15, 2016
    JOURNALS FREE ACCESS
    The aim of the study was to determine quality and oxidative stability of selected cold pressed flaxseed oils, fresh (after producing, the beginning of shelf life) and stored at refrigerator temperature (after three months, the end of declared shelf life). The fresh oils were characterized by organoleptic assessment, fatty acids composition and bioactive compounds content (sterols, tocols, squalene, carotenoids, and phenols). For the fresh and stored oils oxidative stability in the Rancimat test, and the hydrolytic and oxidation degrees using standard methods were determined. It was found that fresh flaxseed oils were differentiated in fatty acid composition and content of bioactive compounds. Shares of saturated fatty acids, and content of squalene and phenolic compounds were most variable in the oils. At the end of shelf life flaxseed oils were characterized by 9-26% shorter induction time in compare to the initial state, and increased content of hydrolysis (acid value by 18-40%) and oxidation products (peroxide value by 16-37%, anisidine value by 13-41%, diene content by 10-21%, triene content by 23-42%) was detected.
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Detergents, Surfactants, Interface and Colloid
  • Keiko Gotoh, Kaori Horibe, Yang Mei, Toshiyuki Tsujisaka
    Volume 65 (2016) Issue 2 Pages 123-133
    Released: February 01, 2016
    [Advance publication] Released: January 15, 2016
    JOURNALS FREE ACCESS
    The effects of water hardness on textile detergency in aqueous solutions were systematically investigated using four surfactants: sodium oleate (OLNa), linear dodecylbenzene sulfonate (LAS), sodium dodecyl sulfate (AS), and polyoxyethylene (10) dodecyl ether (AE). Water hardness was adjusted according to the standard procedure described in IEC 60734:2012. As expected, by adding hardness salts the surface tension of the OLNa solution increased. Surprisingly, the addition of hardness salts lowers the surface tension for the LAS and AS solutions. In the case of the AE solution, hardness salt did not affect the surface tension. A decrease in transmittance and foamability after adding hardness salts was observed for every anionic surfactant solution, indicating that anionic surfactants can combine with divalent ions to form insoluble precipitates. Detergency experiments were performed using cotton plain-woven and towel fabrics soiled with a carbon black and oleic acid mixture. One piece each of untreated and soiled fabric were stacked and placed horizontally in detergent solution with or without hardness salts. As a mechanical action of soil removal, the shaking of 190 spm was applied. Soil removal and redeposition due to washing were evaluated from changes in values of the Kubelka–Munk function for both fabrics. With increasing water hardness, soil removal decreased and redeposition increased. In order of decreasing detergency, the surfactants were as follows: LAS > OLNa ≈ AS > AE. The results indicate that precipitates, formed by reaction of LAS or AS with hardness salts, are strongly adsorbed on the water surface because of their hydrophobicity, but they have no detergency power. The field emission scanning electron microscopic observation and X-ray photoelectron spectroscopic analysis showed that Ca(LAS)2 precipitation clung to fiber surfaces, and remained on the surfaces after washing. Significant changes in the cotton fabric due to washing were observed in mechanical properties and water absorbency.
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  • Tomokazu Yoshimura, Kazuki Akiba
    Volume 65 (2016) Issue 2 Pages 135-141
    Released: February 01, 2016
    [Advance publication] Released: January 15, 2016
    JOURNALS FREE ACCESS
    Dissymmetric and symmetric anionic gemini surfactants, N-alkyl-N’-alkyl-N,N’dipropanesulfonylethylenediamine (CmCnSul, where m and n represent alkyl chain lengths of m-n = 4-16, 6-14, 8-12, 10-10, and 12-12), were synthesized by two- or three-step reactions. Their physicochemical properties were characterized by equilibrium surface tension measurements, steady-state fluorescence spectroscopy of pyrene, and dynamic light scattering. The critical micelle concentration (CMC) of the dissymmetric surfactants C4C16Sul, C6C14Sul, and C8C12Sul was slightly lower than that of the symmetric surfactant C10C10Sul. The occupied area per molecule (A) of C8C12Sul was smaller than that of C10C10Sul, indicating that C8C12Sul has a high surface activity. However, the increase in the degree of dissymmetry from C8C12Sul to C6C14Sul and then to C4C16Sul resulted in high surface tension and large A. Based on the surface tension, the standard free energies of micellization (∆G°mic) and adsorption (∆G°ads), the efficiency of surface adsorption (pC20), and the effectiveness of surface adsorption (CMC/C20) were obtained. These parameters suggested that C8C12Sul formed micelles more readily than the other surfactants. The properties determined from the surface tension indicated that C8C12Sul’s ability is intermediate between those of C10C10Sul and C12C12Sul. The pyrene fluorescence and dynamic light scattering results revealed that the micelle size depends on the longer of the two alkyl chains in dissymmetric surfactants.
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  • Hideaki Watanabe, Atsunori Morigaki, Yukihiro Kaneko, Norio Tobori, Ke ...
    Volume 65 (2016) Issue 2 Pages 143-150
    Released: February 01, 2016
    JOURNALS FREE ACCESS
    α-Sulfonated fatty acid methyl ester salts (MES), which were made from vegetable sources, are attractive candidates for eco-friendly washing detergents because they have various special features like excellent detergency, favorable biodegradability, and high stability against enzymes. To overcome some disadvantages of powder-type detergents like caking, sorting, and dusting, we studied how temperature and humidity history, as a model for long-term storage conditions, can affect crystalline structures and reduce the brittleness of MES powder. We characterized the crystalline structure of MES grains using small-angle X-ray scattering, wide-angle X-ray scattering, differential scanning calorimetry, and Fourier transform infrared spectroscopy measurements and determined the yield values, which measure the brittleness of MES grains, in shear stress using dynamic viscoelasticity measurements. This study confirmed that MES crystals form three pseudo-polymorphs via thermal or humidity conditioning: metastable crystals (αsubcell), anhydrous crystals (β subcell), and dihydrate crystals (β’ subcell). Further, we found that the yield value increases upon phase transition from the β subcell to the β’ subcell and from the β’ subcell to the αsubcell. Therefore, controlling the thermal and humidity conditioning of MES grains is an effective way to decrease the brittleness of MES powders and can be used to overcome the above mentioned disadvantages of powder-type detergents in the absence of co-surfactants.
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Biochemistry and Biotechnology
  • Yongyun Lu, Xiaoqiang Zou, Wang Han, Yuanrong Jiang, Qiangzhe Jin, Li ...
    Volume 65 (2016) Issue 2 Pages 151-159
    Released: February 01, 2016
    JOURNALS FREE ACCESS
    Diacylglycerol-enriched rice bran oil (RBO-DAG) was produced by deacidification of high-acid rice bran oil (RBO) with glycerol (Gly) using Lipozyme RM IM by continuous dehydration by combination of two enzyme columns (column 1 and 3, used for deacidification) with one molecular sieves column (column 2, used for dehydration). The conditions for three columns were respectively optimized. Response surface methodology (RSM) was used to optimize the conditions of column 1. The content of DAG and conversion of free fatty acid (FFA) were used as indicators and the effects of the enzyme load (8-12 g), flow rate (0.3-0.6 mL/min), substrate molar ratio (4-6) and reaction temperature (55-75°C) were investigated. The content of DAG and conversion of FFA were significantly correlated to the flow rate and substrate molar ratio. Most desirable conditions of the reaction with respect to the maximal DAG content and FFA conversion was attained under the residence time of 40 min, substrate molar ratio of 5.52 (Gly: RBO) and temperature of 66°C. The conditions for column 2 were investigated by varying molecular sieves load and flow rate, and the maximal dehydration rate of 85.22% was obtained under the optimal conditions. For column 3, the optimum conditions were obtained as: flow rate, 0.2mL/min; temperature, 65°C, and the content of DAG and FFA were 38.99% and 3.04%, respectively under these conditions. The catalytic activity of the lipase was stable in twelve continuous operations with 83.22% of its original ability, demonstrating its potential in the continuous packed-bed reactors (PBRs) system. These results showed that packed-bed reactors combined with continuous deacidification and dehydration in one system had great value in industrial production for high-acid RBO with the improved conversion rate.
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  • Kenshi Watanabe, Makoto Ohno, Tsunehiro Aki
    Volume 65 (2016) Issue 2 Pages 161-167
    Released: February 01, 2016
    [Advance publication] Released: January 15, 2016
    JOURNALS FREE ACCESS
    Membrane-bound fatty acid desaturases acting on acyl-CoA contribute to the biosynthesis of unsaturated fatty acids, such as arachidonic acid and docosahexaenoic acid in higher organisms. We propose a simplified method for measuring the desaturase activity that combines the in vitro reaction by desaturase-expressing yeast cell homogenate and the detection of acyl-CoA product as butylamide derivatives by gas chromatography. To set up the in vitro reaction, we traced the in vivo activity of rat liver ∆6 fatty acid desaturase (D6d) expressed in the yeast, Saccharomyces cerevisiae, and determined the time taken for the D6d activity to reach its maximum level. The cell homogenate of yeast expressing the maximum D6d activity was made to react in vitro with linoleoyl-CoA to generate the D6d product, γlinolenoyl-CoA. This product was successfully detected as a peak corresponding to γ-linolenoyl butylamide on gas chromatography. This procedure, with low background expression, using non-labeled acyl-CoA as substrate, will contribute toward developing a simple in vitro desaturase assay. It will also help in elucidating the functions of membrane-bound fatty acid desaturases with various substrate specificities and regioselectivities.
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Chemistry and Organic Synthesis
  • Tetsushi Yamamoto, Kentaro Uemura, Yuki Sawashi, Kuniko Mitamura, Atsu ...
    Volume 65 (2016) Issue 2 Pages 169-175
    Released: February 01, 2016
    [Advance publication] Released: January 15, 2016
    JOURNALS FREE ACCESS
    Soft-shelled turtles (Pelodiscus sinensis) are widely distributed in some Asian countries, and parts of this turtle contain abundant collagen. In this study, we optimized a method for extracting collagen from the soft-shelled turtle. We used three types of solvent and four extraction conditions to determine an effective collagen extraction method, which was extraction at 37°C with acetic acid after hydrochloric acid pretreatment. Next, we extracted collagen from three regions in the soft-shelled turtle: muscle, skin, and an area of soft tissue in the periphery of the turtle shell known in Japan and China as the “emperor.” We determined that emperor tissue yielded the highest concentration and purity of collagen. We then optimized the pretreatment method for extraction from emperor tissue by using formic acid instead of hydrochloric acid, and the amount of extracted collagen increased by approximately 1.3-fold. Finally, we identified the optimal solvent out of four types of organic acid for collagen extraction from emperor tissue; the amount of extracted collagen from emperor tissue increased approximately 3-fold when citric acid was used as the extraction solvent instead of acetic acid. Emperor tissue can regenerate; thus, it is possible to obtain collagen from the emperor repeatedly without killing the turtle. Our findings suggest that the emperor tissue of softshelled turtles may be a good source of collagen for pharmaceutical and cosmetic applications.
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  • Refat El-Sayed, Ismail Althagafi
    Volume 65 (2016) Issue 2 Pages 177-192
    Released: February 01, 2016
    JOURNALS FREE ACCESS
    Some functionalized pyridine and fused system derivatives were synthesized using enaminonitrile derivative 5 as a starting material for the reaction, with various reagents under different conditions. Propoxylation of these compounds using different moles of propylene oxide (3, 5 and 7 moles) leads to a novel group of surface active agents. The antimicrobial and surface activities of the synthesized compounds were investigated. Most of the evaluated compounds proved to be active as antibacterial and antifungal agents and showed good surface activity, which makes them suitable for diverse applications such as the manufacturing of emulsifiers, cosmetics, drugs, pesticides, etc. Additionally, biodegradation testing exhibits significant breakdown within six to seven days, and hence, lowers the toxicity to human beings and becomes environmentally friendly.
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