Journal of Oleo Science
Online ISSN : 1347-3352
Print ISSN : 1345-8957
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Volume 64 , Issue 8
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Preface
Application for Asian Foreign Country Membership to the Japan Oil Chemists’ Society (JOCS)
Detergents, Surfactants, Interface and Colloid
  • Kenji Aramaki, Minami Kimura, Kazuki Masuda
    Volume 64 (2015) Issue 8 Pages 801-807
    Released: August 01, 2015
    [Advance publication] Released: July 15, 2015
    JOURNALS FREE ACCESS
    Oil-in-cubic phase (O/I1) emulsions encapsulating the cosmetic UV absorbing agents 2-ethylhexyl 4-methoxycinnamate (EHMC), 2-ethylhexyl 2-cyano-3,3-diphenylacrylate (octocrylene, OCR) and 1-(4-tertbutylphenyl)-3-(4-methoxyphenyl)-1,3-propanedione (Avobenzone, TBMP) were prepared by vortex mixing accompanied by a heating-cooling process. A ternary phase diagram in a water/C12EO25/EHMC system at 25°C was constructed and the two-phase equilibrium of an oil phase and an I1 phase, which is necessary to prepare the O/I1-type emulsions, was confirmed. Also, the melting of the I1 phase into a fluid micellar solution phase was confirmed, allowing emulsification by a heating-cooling process. The O/I1-type emulsions were formulated in the ternary system as well as a quaternary system. The four-component system contained an additional cosolvent, isopropyl myristate (IPM). The use of the cosolvent allows the use of reduced amounts of EHMC, which is desirable because EHMC can cause temporary skin irritation. Formulation of the O/I1-type emulsions with other UV absorbing agents (OCR and TBMP) was also possible using the same emulsification method. When IPM was changed to tripalmitin, which has a melting point greater than room temperature, a solid-oil dispersion in I1 phase was formed. We have termed this a “solidin-cubic phase (S/I1) type dispersion”. These novel emulsions have not been reported previously. The UV absorbability of the O/I1-type emulsions and S/I1-type dispersions that encapsulate the UV absorbing agents was confirmed by measurement of UV absorption spectra.
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  • Hiromichi Sagitani, Masumi Komoriya
    Volume 64 (2015) Issue 8 Pages 809-816
    Released: August 01, 2015
    [Advance publication] Released: July 15, 2015
    JOURNALS FREE ACCESS
    Fatty acids, fatty acid potassium soaps, polyols and water are essential ingredients for producing stable cream soaps. The solution behavior of the above four components system has been studied to elucidate the effect of four sorts of polyols (glycerol, 1,3-butylene glycol, polyethylene glycol 400 and dipropylene glycol) on the stability of cream soaps. It has been revealed that the lamellar liquid crystalline one-phase converted to a two-phase of a lamellar phase and an isotropic aqueous solution by the addition of a few percent of 1,3-butylene glycol, polyethylene glycol 400 and dipropylene glycol, whereas the lamellar one-phase was remained by about 50 wt% of glycerol in the aqueous solution. The X-ray data at room temperature showed that the existence of 1:1 acid soap (1:1 mole ratio of potassium soap/fatty acid) crystals in the 1,3-butylene glycol, polyethylene glycol 400 and dipropylene glycol systems, whereas that the coexistence of 1:1 acid soap crystal and a lamellar gel phase (swelled lamellar gel structure) in the glycerol system. The phase transition peaks from coagel to gel (Tgel) and from gel to liquid state (Tc) were appeared in the above four polyol systems by DSC measurements. It was confirmed from the combined data of SAXS and DSC that the existence of anhydrous 1:1 acid soap gels (or with small amount of bound water) in the all polyol systems, whereas the coexistence of the anhydrate gel and the swelled gel with a lot of intermediate water in the only glycerol system. This swelled gel structure would be contributed to stabilize the dispersed anhydrate acid soap crystals in cream soaps.
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  • Keiko Gotoh, Yu Kanasaki, Haruka Uchinomaru
    Volume 64 (2015) Issue 8 Pages 817-824
    Released: August 01, 2015
    [Advance publication] Released: July 15, 2015
    JOURNALS FREE ACCESS
    The effects of exposure of polymer surfaces to atmospheric pressure plasma (APP) on detergency were investigated from the viewpoint of pretreatment to cleaning in aqueous systems using three PET substrates: film, mesh, and fabric. The PET substrates were soiled with stearic acid as a model oily contaminant, and were treated with the APP jet immediately before cleaning. Stir washing in aqueous solutions with and without alkali or anionic surfactant was performed, and then the detergency was evaluated from the microscopic image analysis or surface reflectance measurement. For all PET samples and detergent solutions, APP exposure was found to promote the removal of stearic acid. Contact angle measurements showed that APP exposure enhanced the hydrophilicity of PET and stearic acid. The increase in the surface oxygen concentration on PET and stearic acid due to the APP exposure was also observed by XPS analysis. The simultaneous oxidation of the PET substrate and stearic acid soil by the APP pretreatment resulted in detergency improvement via surface hydrophilization. Furthermore, microscopic observations suggested that the collapse of crystallized stearic acid deposited on the PET substrate by APP heating facilitated its removal. In situ detergency evaluation by a quartz crystal microbalance technique confirmed that the removal of stearic acid from the PET substrate was promoted by the APP exposure. The experimental findings of this study demonstrate the effectiveness of the APP exposure before cleaning in aqueous solutions.
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Biochemistry and Biotechnology
  • Megumi Iwasa, Satoshi Nakaya, Yusuke Maki, Shinsuke Marumoto, Atsushi ...
    Volume 64 (2015) Issue 8 Pages 825-833
    Released: August 01, 2015
    [Advance publication] Released: July 15, 2015
    JOURNALS FREE ACCESS
    The chemical composition of essential oil extracted from Uncaria Hook (“Chotoko” in Japanese), the branch with curved hook of the herbal medicine Uncaria rhynchophylla has been investigated by GC and GC-MS analyses. Eighty-four compounds, representing 90.8% of the total content was identified in oil obtained from Uncaria Hook. The main components i were (E)-cinnamaldehyde (13.4%), α-copaene (8.0%), methyl eugenol (6.8%), δ-cadinene (5.3%), and curcumene (3.6%). The important key aroma-active compounds in the oil were detected by gas chromatography-olfactometry (GC-O) and aroma extract dilution analysis (AEDA), using the flavor dilution (FD) factor to express the odor potency of each compounds. Furthermore, the odor activity value (OAV) has been used as a measure of the relative contribution of each compound to the aroma of the Uncaria Hook oil. The GC-O and AEDA results showed that α-copaene (FD = 4, OAV = 4376), (E)-linalool oxide (FD = 64, OAV = 9.1), and methyl eugenol (FD = 64, OAV = 29) contributed to the woody and spicy odor of Uncaria Hook oil, whereas furfural (FD = 8, OAV = 4808) contributed to its sweet odor. These results warrant further investigations of the application of essential oil from Uncaria Hook in the phytochemical and medicinal fields.
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  • Fatma Hadrich, Zouhaier Bouallagui, Han Junkyu, Hiroko Isoda, Sami Say ...
    Volume 64 (2015) Issue 8 Pages 835-843
    Released: August 01, 2015
    JOURNALS FREE ACCESS
    To date, numerous studies have reported on the antidiabetic properties of various plant extracts through inhibition of carbohydrate-hydrolysing enzymes. The objective of this research was to evaluate the inhibitory effect of the hydroxytyrosol and the oleuropein against α-amylase and α-glucosidase. The hydroxytyrosol was purified from olive leaves. The result shows that the hydroxytyrosol had the strongest α-glucosidase inhibitory effect with IC50 values of 150 μM with mild inhibition against α-amylase. The enzyme kinetic studies, using Lineweaver–Burk indicated that, in the presence of the hydroxytyrosol, the Michaelis–Menton constant (Km) remained constant but the maximal velocity (Vmax) decreased, revealing a non-competitive type of inhibition with inhibition constants; Ki for the formation of the inhibitor-enzyme complex and Kis for the formation of the inhibitor-enzyme-substrate complex of 104.3 and 150.1 μM, respectively. On the other hand, oleuropein showedan uncompetitive inhibition. The concentrations used in this work were below cytotoxic levels observed at 400 μM. However, at 600 μM, the hydroxytyrosol significantly decreased viability of the Caco-2 cells (p < 0.05) and in the case of the oleuropein, there’s an increase in cell number compared to control (p < 0.05). These results suggest that the hydroxytyrosol and oleuropein are two potential effective α-glucosidase inhibitors for management of postprandial hyperglycemia.
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Chemistry and Organic Synthesis
  • Shiva Shanker Kaki, Konda Reddy Kunduru, Sanjit Kanjilal, Rachapudi Ba ...
    Volume 64 (2015) Issue 8 Pages 845-852
    Released: August 01, 2015
    [Advance publication] Released: July 15, 2015
    JOURNALS FREE ACCESS
    Ferulic acid was modified to produce a novel phenolipid containing butyl chains. Ferulic acid was esterified with butanol to produce butyl ferulate which was further dihydroxylated followed by esterification with butyric anhydride to produce the phenolipid containing butyric acid. IR, NMR and MS techniques confirmed the structure of the synthesized structured lipophilic phenolic compound. The synthesized compound was tested for in vitro antioxidant and antimicrobial activities. The produced phenolipid showed moderate antioxidant activity in DPPH (2, 2-diphenyl-1-picrylhydrazyl) radical scavenging assay but in linoleic acid oxidation method, it exhibited good activity compared with the parent compound and the reference compounds. The prepared derivative could find applications as antioxidant in lipophilic systems and also as a potential prodrug of butyric acid. It also showed antibacterial effect against the four bacterial strains studied. The drug-likeness properties of the prepared molecule calculated were in the acceptable ranges according to Lipinski’s rule of 5 and suggest that it has potential to cross the blood-brain barrier.
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  • Miho Yawata, Tohru Satoh, Maiko Iwahashi, Ryuji Hori, Shigeo Takeuchi, ...
    Volume 64 (2015) Issue 8 Pages 853-859
    Released: August 01, 2015
    [Advance publication] Released: July 15, 2015
    JOURNALS FREE ACCESS
    Strong and stable antioxidation effects of polydimethylsiloxane (PDMS) are widely accepted and utilized in commercial frying oil; however, the mechanism is not fully established. On the other hand, canola oil contains about 700 ppm (mg/kg-oil) of the natural antioxidant, tocopherol. Canola oil containing 0, 1 and 10 ppm added PDMS was heated at 180°C for 1 h under stirring, then left for 2-3 days at room temperature; this treatment was repeated 5 times. Compared to pure canola oil, PDMS-containing canola oil exhibited remarkably lower peroxide, p-anisidine and acid values, a lower decrease in tocopherol content but a higher oxygen content during the heating experiments, implicating low oxygen consumption for the oxidation. While PDMS has not been known to exhibit antioxidative effects at ambient temperatures, the present results show that PDMS prevents autoxidation as well as thermal oxidation. In addition, PDMS, not tocopherols, provided the major antioxidative effect during intermittent heating, and the decrease of tocopherols was significantly inhibited by PDMS. Phase contrast microscopy confirmed that PDMS contained in canola oil was suspended as particles. Also, the oxygen content in standing PDMS-containing canola oil decreased as the depth of oil increased, corresponding to the PDMS distribution, which also decreased as the depth of oil increased. Moreover, PDMS had a higher affinity for oxygen than canola oil in a mixture of canola oil/PDMS, 1:1 v/v. Thus, it is suggested that PDMS restricted the behavior of oxygen dissolved in canola oil by attracting oxygen in and around the PDMS particles, which is wholly different from the radical scavenging antioxidation of tocopherol.
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Essential Oils and Natural Products
  • Cheng-Fang Wang, Wen-Juan Zhang, Chun-Xue You, Shan-Shan Guo, Zhu-Feng ...
    Volume 64 (2015) Issue 8 Pages 861-868
    Released: August 01, 2015
    [Advance publication] Released: July 15, 2015
    JOURNALS FREE ACCESS
    In the course of our search for natural bioactive chemicals and investigations on their insecticidal activities from some medicinal plants growing in China, the essential oil derived from the twigs of Zanthoxylum armatum (Rutaceae) was found to possess strong insecticidal activities against two stored-product insects, Lasioderma serricorne and Tribolium castaneum. A total of 32 constituents of the essential oil were identified by GC and GC-MS analysis, and it revealed (E)-anethole (20.5%), 1,8-cineole (14.0%), 2-tridecanone (12.5%), limonene (9.0%) and piperitone (8.0%) as major components, followed by β-phellandrene (6.3%), β-pinene (5.1%) and 4-terpineol (4.4%). From the essential oil, five compounds were isolated and identified as (E)-anethole, 1,8-cineole, 2-tridecanone, limonene and piperitone. The results of insecticidal bioassays showed that the essential oil of Z. armatum exhibited strong fumigant toxicity towards L. serricorne and T. castaneum with LC50 values of 13.83 and 4.28 mg/L air, respectively, and also possessed contact toxicity against two insect species with LD50 values of 18.74 and 32.16 μg/adult, respectively. Among the active compounds, piperitone performed the strongest fumigant toxicity against L. serricorne (LC50 = 1.21 mg/L air) and contact toxicity against T. castaneum (LD50 = 3.16 μg/adult). 1,8-Cineole, limonene and piperitone showed similar fumigant toxicity against T. castaneum with LC50 values of 5.47, 6.21 and 7.12 mg/L air, respectively. Meanwhile, L. serricorne was the most sensitive to 2-tridecanone (LD50 = 5.74 μg/adult) in the progress of contact toxicity assay.
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  • Imen Touihri, Maher Boukhris, Naziha Marrakchi, José Luis, Belgacem Ha ...
    Volume 64 (2015) Issue 8 Pages 869-879
    Released: August 01, 2015
    [Advance publication] Released: July 15, 2015
    JOURNALS FREE ACCESS
    Allium roseum L. (Alliaceae) endemic mediterranean specie was represented in the North Africa by 12 different taxa. In the present study, chemical composition, antiproliferative, antioxidant and antimicrobial activities of the essential oil extracted from A. roseum var. grandiflorum Briq. bulbs collected in the North of Tunisia were investigated. Chemical characterization has shown methyl methanethiosulfinate as major sulphurous compounds. A. roseum bulbs essential oil provides interesting antiproliferative activity against two human colonic adenocarcinoma HT29 and CACO2 cell lines in dose-dependent manner with a half-maximal inhibition (IC50) of 4.64 µg/mL and 8.22 µg/mL respectively. The antioxidant activity, as determined by FRAP assay, was 285 µmol equivalent Trolox/g of essential oil. The scavenging effect on DPPH radicals of essential oil was estimated as IC50 values at 156 µg/mL. The inhibition of superoxide anion production in a model of cancer cell lines was significant for both lines HT29 and CACO2 with IC50 of 20.25 µg/mL and 29.12 µg/mL respectively. Allium roseum essential oil exhibited antibacterial and antifungal activities with a high effectiveness against Candida albicans given by an MIC value of 0.019 mg/mL. This biological effect appears to be related mainly to the presence of organosulfur compounds.
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  • Kaan Polatoğlu, Ömer Cem Karakoç, Betül Demirci, Nezhun Gören, Kemal H ...
    Volume 64 (2015) Issue 8 Pages 881-893
    Released: August 01, 2015
    [Advance publication] Released: July 15, 2015
    JOURNALS FREE ACCESS
    Insecticides of the natural origin are an important alternative to the synthetic insecticides that are being employed for the preserving stored products. The volatiles obtained from T. cinerariifolium (=Pyrethrum cinerariifolium) is being used for many types of insecticidal applications; however there is a very little information on the insecticidal activity of the essential oils of other Tanacetum species. The main purpose of the present study is to determine the chemical composition of T. macrophyllum (Waldst. & Kit.) Schultz Bip. essential oils and evaluate their insecticidal activity against S. granarius as well as its other beneficial biological activities. Highest contact toxicity was observed in the leaf oil of (88.93%) against S. granarius. The flower oil showed considerable fumigant toxicity against L. minor at 10 mg/mL application concentration (61.86 %) when compared with other samples at the same concentration. The highest DPPH (2,2-Diphenyl-1-picrylhydrazyl) scavenging activity (47.7%) and phosphomolybdenum reducing activity was observed also for the flower oil of T. macrophyllum at 10 mg/mL concentration. The essential oils were analyzed by GC, GC/MS. The flower and leaf oils were characterized with γ-eudesmol 21.5%, (E)-sesquilavandulol 20.3%, copaborneol 8.5% and copaborneol 14.1%, 1,8-cineole 11%, bornyl acetate 9.6%, borneol 6.3% respectively. AHC analysis of the qualitative and quantitative data obtained from the essential oil composition of the T. macrophyllum essential oil from the present research and previous reports pointed out that two different chemotypes could be proposed with current findings which are p-methyl benzyl alcohol/ cadinene and eudesmane chemotypes.
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  • S. Zafar Haider, Manindra Mohan, Abhay K. Pandey, Pooja Singh
    Volume 64 (2015) Issue 8 Pages 895-903
    Released: August 01, 2015
    JOURNALS FREE ACCESS
    The repellent and fumigant toxicity of essential oils of Tanacetum nubigenum Wallich. ex DC collected from three different habitats (Gothing, Burphu and Glacier) of Uttarakhand Himalayas, India named as TNG, TNB and TNM respectively, were investigated against the adults of red flour beetle Tribolium castaneum (Herbst). Among the three samples tested, TNG was found to more potent exhibiting more repellent effect towards the insects and with LC50 values by fumigant bioassay were 13.23 and 8.32 µl per 0.25 L air at 24 and 48 h exposure of insects to the essential oil respectively. In between other two oil samples, TNM was superior in potency showed LC50 value of 14.22 (24 h) & 8.82 µl per 0.25 L air (48 h). During in vivo study all the essential oil samples significantly protected 500 g of wheat grains for 6 months from insect infestation as compared to non fumigated grains and order of efficacy was TNG>TNM>TNB. There were no side effects of essential oils on germination rate of grains (<85%) exposed for 6 months after fumigation. The present study suggests that essential oil of T. nubigenum can be explored as novel natural fumigants for the control of stored product insects.
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General Subjects
  • Isao Yamazaki, Fumiko Kimura, Kiyotaka Nakagawa, Kunihiko Nakai, Takah ...
    Volume 64 (2015) Issue 8 Pages 905-914
    Released: August 01, 2015
    [Advance publication] Released: July 15, 2015
    JOURNALS FREE ACCESS
    Analysis of the placenta can be a useful way to determine the fatty acid (FA) status of pregnant women and neonates since this large organ can be obtained easily and non-invasively. Although several studies have been conducted on using placental tissue for FA analysis, the sampling methods have not been thoroughly examined. The aim of the present study was to determine a suitable method of sampling human placentae by focusing on their heterogeneity. Twenty-four placentae were collected from healthy pregnant Japanese women in the Miyagi Prefecture of Japan. Five of them were used to compare the FA composition between the peripheral area and the central area of the placentae. The other 19 were examined to determine differences in the FA composition between the fetal and maternal side. Placental tissue crude lipid was saponified, and methyl was esterified with 14% sodium boron trifluoride methanol for gas chromatography with flame ionization detector analysis. Fifty-six peaks were detected from the methyl esters of the placental total lipid, and 33 of those were identified as FA methyl esters. There were considerable variations in the FA composition, as the variation was low in the central parts and high in the peripheral parts of the placentae. The 18:1n-9 and 18:2n-6 levels were higher in the fetal side, whereas the 20:3n-6, 20:4n-6, and 22:6n-3 levels were higher in the maternal side. These findings indicate the presence of heterogeneity in the FA composition of human placenta, and they suggest the necessity for standardizing the sampling method so that the placental tissue can be used to determine the FA status.
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