Journal of Oleo Science
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Oils and Fats
  • Toshiharu Nagai, Keiko Ishikawa, Kazuaki Yoshinaga, Akihiko Yoshida, F ...
    Volume 66 (2017) Issue 12 Pages 1293-1299
    Released: December 01, 2017
    [Advance publication] Released: November 13, 2017
    JOURNALS FREE ACCESS

    The composition of triacylglycerol (TAG) positional isomer (-PI) and enantiomer (-E) in immature chicken egg yolk, mature chicken yolk, and chicken meat was examined. POO (consisting of one palmitic acid (P) and two oleic acids (Os)), PPO (consisting of two Ps and one O), and PPL (consisting of two Ps and one linoleic acid (L)) were treated as representative TAG molecular species in all the analytical samples because P, O, and L were the major fatty acids comprising egg and chicken meat. sn-POO (binding P at sn-1 position) was predominant in egg yolks, while sn-OOP and sn-OPO were present in chicken meat. This difference was ascribed to the different roles of these isomers as nutrients, because TAG in egg yolk is important for new born organisms and TAG in chicken meat is used for fat accumulation. The compositions of the TAG isomers in PPO and PPL in egg yolk were similar, and O and L did not bind at the sn-1 position. In contrast, all the isomers of PPO and PPL were found in chicken meat. These results imply that the TAG structure could be modified so that the nutrient requirement is fulfilled in egg yolk and chicken meat.

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  • Huanan Du, Xu Zhang, Ruchun Zhang, Lu Zhang, Dianyu Yu, Lianzhou Jiang
    Volume 66 (2017) Issue 12 Pages 1301-1310
    Released: December 01, 2017
    [Advance publication] Released: November 13, 2017
    JOURNALS FREE ACCESS

    Rosa acicularis seed oil was extracted from Rosa acicularis seeds by the ultrasonic-assisted aqueous enzymatic method using cellulase and protease. Based on a single experiment, Plackett-Burman design was applied to ultrasonic-assisted aqueous enzymatic extraction of wild rose seed oil. The effects of enzyme amount, hydrolysis temperature and initial pH on total extraction rate of wild rose seed oil was studied by using Box-Behnken optimize methodology. Chemical characteristics of a sample of Rosa acicularis seeds and Rosa acicularis seed oil were characterized in this work. The tocopherol content was 200.6±0.3 mg/100 g oil. The Rosa acicularis seed oil was rich in linoleic acid (56.5%) and oleic acid (34.2%). The saturated fatty acids included palmitic acid (4%) and stearic acid (2.9%). The major fatty acids in the sn-2 position of triacylglycerol in Rosa acicularis oil were linoleic acid (60.6%), oleic acid (33.6%) and linolenic acid (3.2%). According to the 1,3-random-2-random hypothesis, the dominant triacylglycerols were LLL (18%), LLnL (1%), LLP (2%), LOL (10%), LLSt (1.2%), PLP (0.2%), LLnP (0.1%), LLnO (0.6%) and LOP (1.1%). This work could be useful for developing applications for Rosa acicularis seed oil.

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Detergents, Surfactants, Interface and Colloid
  • Ketrawee Pantub, Paveena Wongtrakul, Wicharn Janwitayanuchit
    Volume 66 (2017) Issue 12 Pages 1311-1319
    Released: December 01, 2017
    JOURNALS FREE ACCESS

    Nanostructured lipid carriers loaded salicylic acid (NLCs-SA) were developed and optimized by using the design of experiment (DOE). Box-Behnken experimental design of 3–factor, 3-level was applied for optimization of nanostructured lipid carriers prepared by emulsification method. The independent variables were total lipid concentration (X1), stearic acid to Lexol® GT-865 ratio (X2) and Tween® 80 concentration (X3) while the particle size was a dependent variable (Y). Box-Behnken design could create 15 runs by setting response optimizer as minimum particle size. The optimized formulation consists of 10% of total lipid, a mixture of stearic acid and capric/caprylic triglyceride at a 4:1 ratio, and 25% of Tween® 80 which the formulation was applied in order to prepare in both loaded and unloaded salicylic acid. After preparation for 24 hours, the particle size of loaded and unloaded salicylic acid was 189.62±1.82 nm and 369.00±3.37 nm, respectively. Response surface analysis revealed that the amount of total lipid is a main factor which could affect the particle size of lipid carriers. In addition, the stability studies showed a significant change in particle size by time. Compared to unloaded nanoparticles, the addition of salicylic acid into the particles resulted in physically stable dispersion. After 30 days, sedimentation of unloaded lipid carriers was clearly observed. Absolute values of zeta potential of both systems were in the range of 3 to 18 mV since non-ionic surfactant, Tween® 80, providing steric barrier was used. Differential thermograms indicated a shift of endothermic peak from 55°C for α-crystal form in freshly prepared samples to 60°C for β´-crystal form in storage samples. It was found that the presence of capric/caprylic triglyceride oil could enhance encapsulation efficiency up to 80% and facilitate stability of the particles.

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  • Yukina Takano, Tsuyoshi Asakawa, Mayumi Inai, Akio Ohta, Hitoshi Asaka ...
    Volume 66 (2017) Issue 12 Pages 1321-1328
    Released: December 01, 2017
    [Advance publication] Released: November 13, 2017
    JOURNALS FREE ACCESS

    Disulfide linked gemini surfactant having a long spacer chain, [C10H21N(CH3)2(CH2)11SS(CH2)11N(CH3)2C10H21]2Br (2C1011SS), was prepared by the hydrolysis and oxidation process of thioester group for [C10H21N(CH3)2(CH2)11SCOCH3]Br. The critical vesicle concentrations of double tailed surfactants such as dialkyldimethylammonium bromide were observed by the conductivity and light scattering methods. The disulfide bonds of gemini surfactant, [C12H25N(CH3)2CH2CH2SSCH2CH2N(CH3)2C12H25]2Br (2C12SS), were rapidly cleaved by the addition of water-soluble dithiothreitol. However, it took long time to cleave the disulfide bonds of so-called double tailed surfactants 2C1011SS due to vesicle formation. The dynamic light scattering method showed that the diameters of 2C12SS micelles were increased with the cleavage of disulfide bonds, whereas those of 2C1011SS aggregates remained almost constant at 17.6 ±1.3 nm in similar size with dialkyldimethylammonium bromide vesicles. The time course of disulfide cleavage was examined by the conductivity and HPLC analysis. The produced thiol surfactants were returned to their original gemini surfactants by the addition of H2O2.

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Biochemistry and Biotechnology
  • Nakyung Choi, Heejin Kim, Byung Hee Kim, Junsoo Lee, In-Hwan Kim
    Volume 66 (2017) Issue 12 Pages 1329-1335
    Released: December 01, 2017
    [Advance publication] Released: November 13, 2017
    JOURNALS FREE ACCESS

    The synthesis of phytosteryl ester via the lipase-catalyzed esterification of phytosterol with fatty acid from echium oil was performed in a recirculating packed bed reactor. A commercial lipase from Candida rugosa was immobilized and then used to optimize the reaction conditions for the synthesis of the phytosteryl ester. The parameters investigated were temperature, molar ratio of phytosterol to fatty acid, retention time, and amount of solvent. The optimum conditions were determined as the temperature of 40℃, the molar ratio of 1:3 (phytosterol to fatty acid), the retention time of 3 min, and the solvent amount of 40 mL. The maximum conversion of phytosteryl ester was ca. 90 mol% under the optimum conditions. The major fatty acid in phytosteryl ester synthesized was α-linolenic acid (ca. 38 mol%).

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  • Shinji Yamashita, Takuya Seino, Kazuhiko Aida, Mikio Kinoshita
    Volume 66 (2017) Issue 12 Pages 1337-1342
    Released: December 01, 2017
    JOURNALS FREE ACCESS

    To determine the mechanism underlying the anti-inflammatory effects of plant sphingolipids, especially plant glucosylceramide (GlcCer), the effects of plant sphingolipids on inflammatory stress in differentiated Caco-2 cells were compared to those of a sphingolipid of animal origin, galactosylceramide (GalCer). Addition of GlcCer or GalCer suppressed cell injury caused lipopolysaccharide (LPS)- and TNF-α-induced inflammatory stress and induction of apoptosis in differentiated Caco-2 cells. There was no difference in the suppressive effect between GlcCer and GalCer. The inflammatory cytokines and chemokines induced by LPS were suppressed by GlcCer. GlcCer remained on the cell surface. The results of this study can be summarized as follows: 1) sphingolipids such as GlcCer have potent anti-inflammatory effects; 2) GlcCer suppresses LPS-induced production of cytokines and apoptosis; 3) sphingolipids may remain on the surface of cells, and 4) the chemical properties of sphingolipids may prevent the interaction between LPS and its receptor.

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Nutrition and Health Function
  • Nobuya Shirai
    Volume 66 (2017) Issue 12 Pages 1343-1348
    Released: December 01, 2017
    [Advance publication] Released: November 13, 2017
    JOURNALS FREE ACCESS

    This study investigated the in vitro and in vivo effects of Sunrouge (SR), which is an anthocyaninrich green tea. Hot and cold water extracts (CWEX) of Yabukita (YK; regular green tea), SR second crop (SR2), and SR third crop (SR3) were prepared. The 50% inhibitory concentrations for YK, SR2, and SR3 CWEXs against pancreatic lipase in vitro were 12.3±2.8, 6.2±0.3, and 4.0±1.1 mg/mL, respectively. Epigallocatechin gallate (EGCG) accounted for 4.3%, 6.0%, and 6.3% of YK, SR2, and SR3 CWEXs, respectively. SR2 had the highest anthocyanin content of these three samples. In vivo, the increase in the plasma triacylglycerol (TG) concentration following oral administration of oil to mice was significantly suppressed at 60 and 120 min in animals treated with SR2. No significant differences were observed between the plasma TG concentration in the YK and control groups. These results suggested that concomitant administration of SR with oil may suppress lipid absorption and that EGCG may exert this effect.

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Chemistry and Organic Synthesis
  • Mahmoud Ibrahiem Mohieeldin Darwish, Yuto Takenoshita, Toshiyuki Hamad ...
    Volume 66 (2017) Issue 12 Pages 1349-1354
    Released: December 01, 2017
    JOURNALS FREE ACCESS

    Preparation, characterization, and stability evaluation of gold nanoparticles stabilized by ω-sulfonylated alkylsulfanylaniline have been described. The particle solution was obtained by the spontaneous reaction of HAuCl4 and ω-sulfonylated alkylsulfanylaniline in boiling water. It showed a deep red color, owing to surface plasmon resonance of the resulting gold nanoparticles. The size and shape of the nanoparticles were pH-dependent, and pH 8 was found to be the most suitable condition to prepare stable nanoparticles with an average size of 11.2 ± 5.9 nm. The resulting particle solution was stable for a wide range of pH (3–13) and in phosphate-buffered saline (PBS) solution. The nanoparticles were storable as dried powder for at least two weeks, and were redispersible in water or PBS to give almost the same absorption spectra as the freshly prepared solution. Nanoparticle modification was achieved by simply adding thiol molecules to the particle solution.

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General Subjects
  • Chadaporn Krutpijit, Bunjerd Jongsomjit
    Volume 66 (2017) Issue 12 Pages 1355-1364
    Released: December 01, 2017
    JOURNALS FREE ACCESS

    Montmorillonite clay (MMT) is one of materials that can be “green material” due to its environmental safety. In this work, acid-activated MMT catalysts were prepared for the dehydration reaction of ethanol. To be the green process, the reaction with bioethanol was also studied. Ethanol concentrations in feed were varied in the range of 10-99.95 wt%. Moreover, the concentrations of hydrochloric acid activated MMT were investigated in range of 0.05-4 M. From the experiment, it reveals that different acid concentrations to activate MMT affect the catalytic activity of catalysts. The 0.3 M of HCl activated MMT exhibits the highest activity (under the best condition of 30 ml HCl aging for 1 h) with the Si/Al ratio of 7.4. It can reach the ethanol conversion and ethylene selectivity up to 95% and 98% at reaction temperature of 400°C, respectively. For the several ethanol feed concentrations, it does not remarkably affect in ethanol conversion. However, it has some different effect on ethylene selectivity between lower and higher reaction temperatures. It was found that at lower temperature reaction, ethylene selectivity is high due to the behavior of water in feed. In addition, the 0.3 M-MMT can be carried out under the hydrothermal effect.

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  • Masaaki Konishi, Tomotake Morita, Tokuma Fukuoka, Tomohiro Imura, Shin ...
    Volume 66 (2017) Issue 12 Pages 1365-1373
    Released: December 01, 2017
    [Advance publication] Released: November 13, 2017
    JOURNALS FREE ACCESS

    Biosurfactants (BSs) are produced in abundance from various feedstocks by diverse microorganisms, and are used in various applications. In this paper, we describe a new yeast isolate that produces glycolipid-BSs from glycerol, with the aim of enhancing the utilization of the surplus glycerol produced by the oleo-chemical industry. As a result of the screening, strain ZM1502 was obtained as a potential producer of BS from glycerol. Based on TLC analysis, the strain produced glycolipid BSs. According to structural analyses (NMR, MALDI-TOF MS, and GC-MS), the main component of the glycolipids was 6’,6”-di-O-acetylated acid-form sophorolipid (SL). Interestingly, the strain produced only acid-form SL, without lactone-form SLs, although the conventional SL-producing yeast, Starmerella bombicola, produces lactone-form SLs with small amounts of the acid-form. Based on taxonomy, the strain was identified as Candida floricola. It produced 3.5 g L–1 of acid-form SLs in 20% (w/v) glycerol. In addition, C. floricola CBS7290 and NBRC10700T also produced only acid-form SLs from glycerol. These results suggest that C. floricola would enhance the utilization of waste glycerol as a fermentation feedstock and facilitate a broad range of applications for SLs.

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  • Kouichi Nakagawa, Kazuhiro Matsumoto, Nattakan Chaiserm, Aroonsri Prip ...
    Volume 66 (2017) Issue 12 Pages 1375-1379
    Released: December 01, 2017
    JOURNALS FREE ACCESS

    We investigated stable organic radicals formed in response to cold stratification in ‘Fuji’ apple seeds using X-band (9 GHz) electron paramagnetic resonance (EPR) technique. This technique primarily detected two paramagnetic species in each seed. These two different radical species were assigned as a stable organic radical and Mn2+ species based on the g values and hyperfine components. Signal from the stable radicals was noted at a g value of about 2.00 and was strong and relatively stable. Significant radical intensity changes were observed in apple seeds on refrigeration along with water supplementation. The strongest radical intensity and a very weak Mn2+ signal were also observed for the seeds kept in moisture-containing sand in a refrigerator. Noninvasive EPR of the radicals present in each seed revealed that the stable radicals were located primarily in the seed coat. These results indicate that the significant radical intensity changes in apple seeds under refrigeration for at least 90 days followed by water supplementation for one week, can be related to cold stratification of the seeds.

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  • Aydan H. Yatmaz, Tetsuaki Kinoshita, Akio Miyazato, Masahiro Takagi, Y ...
    Volume 66 (2017) Issue 12 Pages 1381-1386
    Released: December 01, 2017
    [Advance publication] Released: November 13, 2017
    JOURNALS FREE ACCESS

    Vinegar is a widely used condiment in the world, and is produced from ethanol by acetic acid fermentation. Different fruits, vegetables, cereals, and wines can be used as ingredients for vinegar production. It is known that vinegar has many nutrient components such as organic acids, polyphenols, and aromatic compounds. Because of these bioactive components, it has many health benefits. China has a long history of producing vinegar and has been using it for health products and as medicine. Chinese aromatic Zhenjiang vinegar (Kozu) is produced from sticky rice. It is famous for its special flavor and health benefits. 5-Hydroxy-4-phenyl-butenolide (Fraglide-1) is a functional compound discovered in Kozu and has anti-fungal and anti-obesity effects. In this study, the Fraglide-1 content of different kinds of vinegars and ingredients, including Kozu samples and ingredients, was investigated. Fraglide-1 analysis was carried out via LC-MS/MS in multiple reaction monitoring mode. It was found that all the Kozu samples, as well as brown rice vinegar (Kurosu) samples, and the Chinese sticky rice husk used for the production of Kozu, contained Fraglide-1. Kozu production requires a 6-month- to 8-year-long aging process for its special flavor and aroma. Because of this long aging process, Fraglide-1 is thought to move from the sticky rice husk to Kozu.

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