Journal of Oleo Science
Online ISSN : 1347-3352
Print ISSN : 1345-8957
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Review
  • Dong Woog Lee
    2018 Volume 67 Issue 11 Pages 1361-1372
    Published: November 01, 2018
    Released: November 07, 2018
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    In this review, previous researches that measured intermembrane forces using the Surface Forces Apparatus are recapitulated. Different types of interaction forces are reported between two lipid bilayers including non-specific interactions (e.g., van der Waals, electrostatic, steric hydration, thermal undulation, and hydrophobic) and specific interactions (e.g., ligand-receptor). By measuring absolute distance and interaction forces at the sub-angstrom level and at a few nano-Newtons resolution, respectively, magnitudes, working ranges, and decay lengths of interaction between lipid bilayers are investigated. Utilizing recently developed fluorescence microscopy attachments, simultaneous fluorescence imaging of membrane proteins and lipid phases can be performed during approach/separation cycles of two lipid bilayer deposited surfaces, which can reveal cooperative effects between lipid phases and various types of membrane proteins.

Oils and Fats
  • Min-Yu Chung, In-Hwan Kim, Byung Hee Kim
    2018 Volume 67 Issue 11 Pages 1373-1379
    Published: 2018
    Released: November 07, 2018
    JOURNALS FREE ACCESS

    Pinolenic acid (PLA), which is a fatty acid (FA) exclusively found in the oils of edible pine nuts, has an appetite-suppression effect, thereby being effective to reduce body weight in humans. PLA concentrates would be suitable for use in functional foods and nutraceuticals due to the health benefits of PLA. PLA concentrates were prepared from free FA (FFA) obtained from pine nut oil using solvent fractionation. Siberian pine nut oil containing 18.3 wt% PLA was used as the starting material for the fractionation. The fractionation was performed in n-hexane at ultra-low temperatures down to −85°C. The PLA concentrates produced under the optimal conditions established in this study (temperature, −85°C; n-hexane-to-FFA ratio (v/w), 30:1; fractionation time, 36 h) contained 69.8 wt% PLA. The yield of PLA was 77.4 wt% of the initial PLA weight in the FFA. These results suggest that solvent fractionation is a more effective approach to prepare PLA concentrates with higher PLA contents at a particular yield of PLA than published methods using urea crystallization (e.g., PLA content = ~47 wt%, yield of PLA = ~77 wt%, Woo et al. (2016)) or lipase-catalyzed reactions (e.g., PLA content = ~30 wt%, yield of PLA = ~61 wt%, Lee et al. (2011)). The resulting PLA concentrates contained 11 of the 12 different species of FA present in the FFA, thereby indicating that the PLA concentrates prepared by solvent fractionation have more diverse FA profiles than those prepared by urea crystallization (e.g., 7 species of FA, Woo et al. (2016)).

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  • Soek Sin Teh, Siau Hui Mah
    2018 Volume 67 Issue 11 Pages 1381-1387
    Published: 2018
    Released: November 07, 2018
    JOURNALS FREE ACCESS

    The study was aimed at evaluating the effects of vegetable oils on emulsion stability. Palm olein (POo), olive oil (OO), safflower oil (SAF), grape seed oil (GSO), soybean oil (SBO) and sunflower oil (SFO) with different degree of saturation levels were chosen as major ingredient of oil phases. All the emulsions were stored at 4℃, 27℃ and 40℃ for 35 days and subjected to all the stability tests, including temperature variation, centrifuge test, cycle test, pH and slip melting point. The results indicated that POo exhibited the highest stability, followed by SAF, OO, GSO, SFO and SBO. In addition, the results implied that the degree of saturation levels of vegetable oils does give significant effect on emulsion stability based on the centrifuge testing for an approximate 30% usage level of oil. The POo-based emulsion exhibited good emulsion stability throughout the experimental period indicated that POo could be a good carrier oil for various applications in cosmetic industry.

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  • Nagao Totani, Miho Yawata, Naoko Yasaki
    2018 Volume 67 Issue 11 Pages 1389-1395
    Published: 2018
    Released: November 07, 2018
    JOURNALS FREE ACCESS

    Polydimethylsiloxane (PDMS) was previously reported to show no protective effect in continuous deep-frying. In this study, we used canola oil with/without added PDMS to deep-fry shredded potato at 180°C either continuously or with 10-, 20-, or 30-min intervals between frying sessions for 6 h. In continuous deep-frying in canola oil not containing PDMS, far more oil vapor was generated from the oil and the water in the potato compared to frying with 20- and 30-min intervals between sessions and the oil in the fryer accordingly had a lower polar compound content (PC). The longer the oil was used to deep-fry potato, the more steam was generated from potato. Thus, polar compounds evaporated into the air in the steam, resulting in a low PC value of oil in the fryer. In contrast, both thermal deterioration and oil vaporization were remarkably inhibited in canola oil containing PDMS regardless of the frying pattern, and the PC value of the oil in the fryer increased in proportion to the amount of potato deep-fried. Canola oil with/without added PDMS was heated at 180°C for 6 h to confirm the effect of water released from potato on the oxidation of oil. A large increase in PC was observed in canola oil not containing PDMS when heated without water but this increase was inhibited to some extent when water was supplied continuously. On the other hand, the PC of canola oil containing PDMS was far lower than that of oil not containing PDMS, but the addition of water promoted an increase in PC. In conclusion, we observed superior protective effects of PDMS regardless of the deep-frying pattern employed, but the PC value nonetheless increased as the amount of food deep-fried increased. In addition, we confirmed that water in potato strongly correlates to PC increase of oil in the fryer.

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  • Alaina A. Esperón-Rojas, Cristóbal Torres-Palacios, Dalia Santos-Luna, ...
    2018 Volume 67 Issue 11 Pages 1397-1403
    Published: 2018
    Released: November 07, 2018
    JOURNALS FREE ACCESS

    Medium chain fatty acids (MCFAs), have gained nutritional relevance in the past few years. They are continuously used in obtaining structured lipids like medium chain acylglycerols (MCAs) for various purposes. However, because of their chemical structure pertaining carbon chain length and the presence of saturated and unsaturated fatty acids, sensitive detection techniques are required for their correct identification and separation. In the present work, a specific thin layer chromatography (TLC) method for MCAs was developed. The proposed method consisted of the use of a mixture of hexane: acetone (70:30 v/v) as mobile phase, since it proved effectiveness for the separation of compounds of interest (MCAs) as well as having the necessary sensitivity to separate different species of monoacylglycerols (MAGs), diacylglycerols (DAGs) and triacylglycerols (TAGs) of MCFAs. For observation of the compounds, a single oxidizing agent was not sufficient, thus a combination of visualization reagents was used (first a 10 % solution of sulphuric acid in methanol followed by a 10 % solution of phosphomolybdic acid in methanol) achieving the correct visualization of the desired compounds.

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  • Piraporn Sombutsuwan, Akkaradech Nakornsadet, Kornkanok Aryusuk, Saeng ...
    2018 Volume 67 Issue 11 Pages 1405-1415
    Published: 2018
    Released: November 07, 2018
    JOURNALS FREE ACCESS

    A rapid and low energy consumption method for the recovery of γ-oryzanol from rice bran acid oil (RBAO), a byproduct of rice bran oil (RBO) refining, is presented. The RBAO was converted to the fatty acid ethyl ester (FAEE) and was used as the starting material. The dissolved γ-oryzanol was separated from the FAEE using an acid-base extraction method with alkaline aqueous ethanol and hexane as extraction media. A systematic investigation of the extraction yield was carried out by applying response surface methodology (RSM) based on central composite design (CCD) and Derringer’s desirability function. The concentration of NaOH, the percentage of ethanol in water, the hexane content and their interactions showed significant effects on the yield of γ-oryzanol and FAEE. The optimal extraction conditions were as follows: extraction time of 1 min at room temperature (28-32°C); extraction medium: 1.855 M NaOH; 75.91% ethanol in water and 20.59% hexane in the total volume of the extractant; and FAEE to extractant ratio of 1:10 corresponding to a maximum γ-oryzanol yield of 75.82±3.44% and the desired FAEE yield of 54.42±7.80%. The γ-oryzanol-rich fraction was further purified by washing with a 2% Na2CO3 solution, obtaining 69.94% recovery yield with 89.90% purity of γ-oryzanol. The purified γ-oryzanol showed good scavenging activity on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and the ABTS radical and was comparable to the commercial product, clearly suggesting that the presented process was efficient and feasible.

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Detergents, Surfactants, Interface and Colloid
  • Hideko Sahara, Shigeharu Harada
    2018 Volume 67 Issue 11 Pages 1417-1424
    Published: 2018
    Released: November 07, 2018
    JOURNALS FREE ACCESS

    Calorimetric measurements were conducted on aqueous solutions of n-alkylammonium chlorides (CnAC; H(CH2)nNH3Cl, n = 1 - 12) at 298.15 K. The solute partial molar enthalpy, Hs, was evaluated with reference to the infinitely diluted state. At low concentrations, the Hs increased with the molality, mt, until the critical micelle concentration (CMC) was reached. In the concentration range between the CMC and about three times the CMC, the Hs decreased linearly with increasing log mt. The Hs observed at the CMC was taken as the enthalpy of micelle formation, ΔHm, which was expressed as ΔHm / kJ mol–1 = 20.1 - 1.4n for CnAC with n from 7 to 12. The Gibbs energy of micelle formation, ΔGm, was estimated from the CMC values: ΔGm / kJ mol–1 = 4.1 - 3.3 n with n from 5 to 12. The entropy of micelle formation, ΔSm, was calculated as TΔSm / kJ mol–1 = 16.4 + 1.9 n with n from 7 to 12. The large positive entropy term was determined to be the driving force for micelle formation. It was inferred that the difference of the CMC of CnAC and sodium n-alkyl sulfate (SCnS;H(CH2)nOSO3Na, n = 5 - 13) homologs seemed to be caused by the difference in the number of possible hydrogen bonds to the head group of the micelle state. Based on an attempt to calculate the Hs for C12AC from the partial molar enthalpy and the concentrations of the constituent individual ions above the CMC, the increase in concentration of the micellar ions seemed to be the largest contribution to the concentration dependence of the Hs.

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Biochemistry and Biotechnology
  • Takashi Maoka, Yuki Kawashima, Mikihiro Takaki
    2018 Volume 67 Issue 11 Pages 1425-1433
    Published: 2018
    Released: November 07, 2018
    JOURNALS FREE ACCESS

    The dried powder of Paracoccus carotinifaciens (PANAFERD-AX®) contains (3S,3’S)-astaxanthin as a major carotenoid. Administration of PANAFERD-AX® for pigmentation of the prawn Penaeus japonicus was examined. Total carotenoid contents in the carapace, muscle, and head of the prawn were dose-dependently increased depending on the amount of PANAFERD-AX® administered. Furthermore, not only the amounts of astaxanthins (astaxanthin diester, astaxanthin monoester, and free astaxanthin) but also the amounts of yellow xanthophylls, isoastaxanthin (1), 5,6-dihydropenaeusxanthin (2), penaeusxanthin (3), tetrahydroxypirardixanthin (4), and curstaxanthin (5), were dose-dependently increased with the administration of PANAFERD-AX®. 5,6-Dihydropenaeusxanthin (2) and penaeusxanthin (3) are new carotenoids isolated from the prawn P. japonicus. These structures were determined to be (3R,4S,5R,6R,6’S)-5,6-dihydro-3,4,4’- trihydroxy-β,ε-caroten-3’-one (2) and (3R,4S,6’S)-3,4,4’-trihydroxy-β,ε-caroten-3’-one (3) by UV/vis, ESI TOF MS, 1H NMR, and CD spectral data. The metabolism of astaxanthin to these yellow xanthophylls in the prawn was discussed.

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  • Heejin Kim, Nakyung Choi, Hak-Ryul Kim, Junsoo Lee, In-Hwan Kim
    2018 Volume 67 Issue 11 Pages 1435-1442
    Published: 2018
    Released: November 07, 2018
    JOURNALS FREE ACCESS

    Δ5-Olefinic acids have been characterized in gymnosperm plants and have been reported to have several biological health benefits. Δ5-Olefinic acids from pine nut oil were effectively concentrated by repeated lipase-catalyzed esterification. The pine nut oil contained three major Δ5-olefinic acids, namely taxoleic acid (C18:2 Δ5,9), pinolenic acid (C18:3 Δ5,9,12), and sciadonic acid (C20:3 Δ5,11,14). The fatty acids present in pine nut oil were selectively esterified with ethanol using Lipozyme RM IM from Rhizomucor miehei as a biocatalyst. The Δ5-olefinic acids were concentrated in the unesterified fatty acid fraction. The optimum molar ratio of the substrates (fatty acid:ethanol), temperature, the enzyme loading, and the reaction time were 1:7, 25°C, 5% of total substrate weight, and 6 h, respectively. There was no significant effect in the concentration of Δ5-olefinic acids when water was added in the reaction mixture. The same protocol and optimum conditions were employed for two times repeated lipase-catalyzed esterifications. In first lipase-catalyzed esterification, the Δ5-olefinic acids content in the pine nut oil increased from 17 mol% to 51 mol% with a yield of 40 mol%. In a second lipase-catalyzed esterification, with the Δ5-olefinic acids-concentrated fatty acids obtained from the first reaction as the substrate, the Δ5-olefinic acids content increased to 86 mol% with a yield of 15 mol%. Finally, a maximum Δ5-olefinic acids content of ca. 96 mol% with a yield of 6 mol% was obtained via a third lipase-catalyzed esterification.

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Medical Chemistry
  • Xu Jiang, Mukesh Kumar, Yonglin Zhu
    2018 Volume 67 Issue 11 Pages 1443-1453
    Published: 2018
    Released: November 07, 2018
    JOURNALS FREE ACCESS

    The current investigation aimed to scrutinize the neuro-protective effect of hyperforin on β‑amyloid peptide (Aβ)1-42 and H2O2 induced injury in PC12 cells and colchicine induced Alzheimer’s disease (AD). PC12 cells were treated with H2O2 and (Aβ)1-42 in the presence of hyperforin. The cell viability was determined via suing the MTT assay; malondialdehyde (MDA) and lactate dehydrogenase (LDH) levels were also scrutinized. Colchicine induced the destruction of memory and learning which was exhibited in neurobehavioral theory (passive avoidance and Morris water maze) connected with reduced activity of acetylcholinesterase (AChE). Anti‑oxidant and inflammatory parameters also estimated. Hyperforin dose dependently increased the cell viability and reduced the MDA and LDH release via PC12 cell injured with H2O2 and (Aβ)1-42. Hyperforin treatment lead to a considerable enhance in TLT in the retention trials as comparisian to acquisition trial suggesting as boosting memory and learning in rats. Hyperforin treatments significantly increase the AChE and reduced the superoxide dismutase, glutathione, MDA, protein carbonyl, glutathione peroxdiase, catalase, NF‑kB and IL‑1β at dose dependent manner. In summary, the model of H2O2 and (Aβ)1-42 induced PC12 cell injury was successfully developed and dose dependently treatment of hypoforin showed the neuroprotective effect against the H2O2 and (Aβ)1-42 induced cell damage. These finding clearly exhibited that hyperforin reverted the colchicine induced neuro‑chemical and behavioural alteration via potent anti‑inflammatory and anti‑oxidant activity.

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Nutrition and Health Function
  • Naohisa Nosaka, Yoshie Suzuki, Hiromi Suemitsu, Michio Kasai, Kazuhiko ...
    2018 Volume 67 Issue 11 Pages 1455-1462
    Published: 2018
    Released: November 07, 2018
    JOURNALS FREE ACCESS

    Medium-chain triglycerides (MCT) are useful for increasing fat utilization during exercise. The highest rate of fat oxidation during submaximal exercise tends to precede the lactate threshold in untrained adults. In our previous study, blood lactate concentration was more than 4 mmol/L (onset of blood lactate) in recreational athletes during exercise at a workload corresponding to 60% peak O2 uptake (Vo2), which was below ventilation threshold. In the present study, we investigated the effect of 2 week of ingestion of food containing 6 g MCT on substrate oxidation during moderate-intensity (50% peak Vo2) exercise and high-intensity (70% peak Vo2) exercise in recreational athletes. For comparison, two experimental trials were conducted after participants had been administered isoenergic test foods (MCT-supplemented food with mainly maltodextrin-containing carbohydrate (MCT + CHO) or CHO) for 2 weeks, with a washout period between trials. Participants were instructed to perform cycle ergometer exercise at a workload corresponding to 50% peak Vo2 for 40 min followed by a workload corresponding to 70% peak Vo2 until exhaustion. Fat oxidation was significantly increased in the MCT + CHO trial (13.3 ± 2.7 g/40 min, mean ± SD, p < 0.05) during moderate-intensity exercise and the duration was extended significantly (23.5 ± 19.4 min, p < 0.05) during subsequent high-intensity exercise, compared with that observed in the CHO trial (fat oxidation; 11.7 ± 2.8 g/40 min, duration; 17.6 ± 16.1 min). In conclusion, continuous ingestion of 6 g MCT with maltodextrin could increase fat oxidation during moderate-intensity exercise and extend the duration of subsequent high-intensity exercise in recreational athletes, compared with the ingestion of isoenergic maltodextrin alone.

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Chemistry and Organic Synthesis
Essential Oils and Natural Products
  • Rakia Saidi, Ferdaws Ghrab, Rim Kallel, Abdelfattah El Feki, Tahya Bou ...
    2018 Volume 67 Issue 11 Pages 1483-1499
    Published: 2018
    Released: November 07, 2018
    JOURNALS FREE ACCESS

    The aerial part of Clematis flammula (Ranunculaceae) has been traditionally used in the treatment of skin diseases including mycotic infection in the Tunisian traditional medicine. The study was undertaken to extract and determine the essential oil chemical composition of Clematis flammula aerial parts and to assess the potential of anemonin in wound healing on mechanically wounded wistar rats. The essential oil was obtained by hydrodistillation and analyzed by GC-MS. Anemonin was isolated and then incorporated as active in a cream for which the cytotoxicity was evaluated by methyl thiazolyl tetrazolium (MTT)-based colorimetric assay. Then, its potential in wound healing on mechanically wounded wistar rats was assessed. The GC-MS analysis showed that the major compound was protoanemonin (86.74%) which spontaneously dimerised in part to form the anemonin. The wound healing activity of anemonin cream exhibited a non toxic potential of anemonin at a concentration of 25 µg/mL with a cell migration efficiency that reaches more than 80% after 48 hours of treatment. Wound healing efficiency was evaluated by monitoring morphological and skin histological analyses. Comparable wound surface reduction of the group treated by anemonin cream (p ≥ 0.05) when compared to the reference treated group. The skin histological analysis showed the completely wound closure. Antioxidant activity was assessed by the malondialdehyde (MDA) rates and antioxidant enzymes (glutathione peroxidase (GPx) and catalase) determination. The results provided strong support for the effective wound healing activity of anemonin cream, making it a promising candidate as a therapeutic agent in tissue repairing processes.

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