Journal of Oleo Science
Online ISSN : 1347-3352
Print ISSN : 1345-8957
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Volume 64 , Issue 9
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Review
  • Nihed Ben Halima, Rania Ben Saad, Bassem Khemakhem, Imen Fendri, Slim ...
    Volume 64 (2015) Issue 9 Pages 915-932
    Released: September 01, 2015
    [Advance publication] Released: August 06, 2015
    JOURNALS FREE ACCESS
    Oat is a promising plant for the future. It is edible and beneficial thanks to its nutritional, medicinal and pharmaceutical uses and, hence, recognized to be useful for a healthier world. The assessment of the vital functions of oat components is important for industries requiring correct health labelling, valid during the shelf life of any product. Oil, enzymes and other biomolecules of nutraceutic or dietary usage from oats would be valorized for this purpose. Although oats have a unique and versatile composition including antioxidants and biomolecules indispensable for health, they are undervalued in comparison with other staple cereals such as wheat, barley and rice. Furthermore, oats, apart from maize, comprise a high oil content used for a wide range of beneficial purposes. In addition, they contain beta glucan that has proven to be very helpful in reducing blood cholesterol levels and other cardiovascular diseases risks. In fact, there is diversity in the composition and content of the beneficial oat components within their genotypes and the different environmental conditions and, thus, oats are amenable to be enhanced by agronomic practices and genetic approaches.
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Oils and Fats
  • LiPing Chen, XuanRi Shen, GuoHua Chen, XianYing Cao, Jian Yang
    Volume 64 (2015) Issue 9 Pages 933-942
    Released: September 01, 2015
    [Advance publication] Released: August 06, 2015
    JOURNALS FREE ACCESS
    Three-Spot seahorse is a traditional medicine in Asian countries. However, the alcohol extract is largely unknown for its anti-inflammatory activity. This study aimed at elucidating fraction of potent anti-inflammatory activity of seahorse. A systematic solvent extraction method of liquid–liquid fractionation of ethanol crude extract gave four fractions petroleum ether (PE), and ethyl acetate (EtOAc), water saturated butanol (n-BuOH), water (H2O). In this study, PE extract was selected for further study after preliminary screening test, and was connected to silica column chromatography and eluted with different polarity of mobile phases, and obtained four active fractions (Fr I, Fr II, Fr III, Fr IV). Effect of separated fractions on inflammation was investigated in lipopolysaccharide (LPS) stimulated murine RAW264.7 cells in vitro. The result shows that seahorse extract was capable of inhibiting the production of nitric oxide (NO) significantly in a dose dependent manner and exhibited no notable cytotoxicity on cell viability. IC50 of fraction IV was 36.31 μg/mL, indicating that separated fraction possessed potent NO inhibitory activity against LPS-induced inflammatory response, thus, demonstrated its in vitro anti-inflammatory potentiality, it may be at least partially explained by the presence of anti-inflammation active substances, phenolic compounds, phospholipids and polyunsaturated fatty acids, especially phospholipids and polyunsaturated fatty acids. It could be suggested that seahorse lipid-soluble components could be used in functional food and anti-inflammatory drug preparations.
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  • Toshiharu Nagai, Natsuko Watanabe, Kazuaki Yoshinaga, Hoyo Mizobe, Koi ...
    Volume 64 (2015) Issue 9 Pages 943-952
    Released: September 01, 2015
    JOURNALS FREE ACCESS
    Bovine milk fat (BMF) is composed of triacylglycerols (TAG) rich in palmitic acid (P), oleic acid (O), and short-chain or medium-chain fatty acids (SCFAs or MCFAs). The composition and binding positions of the fatty acids on the glycerol backbone determine their physical and nutritional properties. SCFAs and MCFAs are known to characteristically bind to the sn-3 position of the TAGs in BMF; however, there are very few non-destructive analyses of TAG enantiomers binding the fatty acids at this position. We previously reported a method to resolve the enantiomers of TAGs, binding both long-chain saturated fatty acid and unsaturated fatty acid at the sn-1 and 3 positions, in palm oil, fish oil, and marine mammal oil using chiral HPLC. Here, we further developed a method to resolve several TAG enantiomers containing a dipalmitoyl (PP) glycerol backbone and one SCFA (or MCFA) in BMF. We revealed that the predominant TAG structure in BMF was homochiral, such as 1,2-dipalmitoyl-3-butyroyl-sn-glycerol. This is the first quantitative determination of many TAG enantiomers, which bind to a SCFA or MCFA, in BMF was evaluated simultaneously. Furthermore, the results indicated that the amount ratios of the positional isomers and enantiomers of TAGs consisting of a dipalmitoyl (PP) glycerol backbone and SCFA (or MCFA), resembled the whole TAG structures containing the other diacylglycerol backbones consisting of P, O, myristic acid, and/or stearic acid in BMF.
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Detergents, Surfactants, Interface and Colloid
  • Chika Endo, Yoshiko Ito, Chika Akabane, Yukihiro Kaneko, Hideki Sakai
    Volume 64 (2015) Issue 9 Pages 953-962
    Released: September 01, 2015
    [Advance publication] Released: August 06, 2015
    JOURNALS FREE ACCESS
    A new mechanism of spontaneous emulsification without any salts or co-solvents is described, and is related to the dilatational behavior. Spontaneous emulsification can reduce the time required to remove oily soils from hard surfaces and enhance the detergency, because this type of emulsification requires no external mechanical work. In this paper, we focused on triolein, the main component of food oils and human sebum soil, and tried to induce spontaneous emulsification by using mixed micellar solutions of sodium polyoxyethylene alkyl ether sulfate and N, N-dimethyldodecylamine oxide (AES/DDAO). We characterized the dilatation of the oil/water interface using dynamic interfacial tension and elasticity measurements. This study confirmed that the degree of spontaneous emulsification can be enhanced by controlling the molar ratio of DDAO to AES. This enhancement can be attributed to an increased rate of decrease in the dynamic interfacial tension (i.e., a decreased interface dilatational elasticity), allowing for much greater suppression of the Marangoni effect. Further, we determined that one of the reasons for the decrease in the interface dilatational elasticity is the increasing number of micelles near the oil drop interface, which results from a decrease in the electrostatic repulsion between the micelles and the drop interface. Therefore, controlling the molar ratio of a mixed anionic/amphoteric surfactant solution is an effective way to induce spontaneous emulsification in the absence of salts or co-solvents.
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  • Toshinari Mizuhashi, Tsuyoshi Asakawa, Akio Ohta
    Volume 64 (2015) Issue 9 Pages 963-969
    Released: September 01, 2015
    [Advance publication] Released: August 06, 2015
    JOURNALS FREE ACCESS
    We examined the “micelle-vesicle transition” through the mixing effect of single–tailed thiol surfactants produced by the cleavage of gemini surfactants, [C12H25N(CH3)2CH2CH2SSCH2CH2N(CH3)2C12H25] 2Cl (C12SSC12), which have a disulfide bond in the spacer chain. Phase diagrams of C12H25N(CH3)2CH2CH2SHCl-didodecyldimethylammonium chloride (C12SH-DDAC) and C12SSC12-DDAC were determined by conductivity and pyrene fluorescence probe methods. The aggregate diameters were evaluated by dynamic light scattering (DLS). The critical vesicle concentration (CVC) was confirmed by the abrupt increase in the intensity of light scattering with excitation at 335 nm. Vesicle formation was confined to the DDAC-rich region of the C12SSC12-DDAC system, while the vesicle formation region for the C12SH-DDAC system spread out with the addition of dithiothreitol (DTT) to C12SSC12-DDAC. This implies that single–tailed surfactants can induce a more favorable environment for molecular packing of the vesicular surface. The micelle-vesicle transition occurs with disulfide spacer chain cleavage of gemini surfactants at a particular specific concentration range.
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  • Tokuzo Kawase, Mami Nakagawa, Yuuya Higuchi, Tatsuo Oida
    Volume 64 (2015) Issue 9 Pages 971-986
    Released: September 01, 2015
    JOURNALS FREE ACCESS
    In this study, a series of all-hydrocarbon anionic gemini surfactants containing COOH (adipic acid-type and suberic acid-type), SO3Na, OSO3Na, and OP=O(OH)2 functional groups was developed from 1,4-diol and 1,4-diketone as a key block material. The effect of the surfactant head groups on the surface properties was investigated by surface tension and surface pressure-area (π-A) measurements. We found that the critical micelle concentrations (CMC) of the studied geminis were smaller by one order of magnitude than those of the corresponding 1+l-type surfactants. From π-A measurements, the limiting areas of COOH-type geminis were less than twofold of the area of the corresponding 1+1-type, which indicates that the gemini structure enabled tighter packing than is possible in surfactants of the 1+l-type. In contrast, the limiting area of the OP=O(OH)2-type gemini was larger than those of the COOH-type geminis. Furthermore, the suberic acid-type gemini showed a smaller limiting area than that of adipic acid-type gemini. Therefore, we can conclude that the flexibility of the gemini at the connecting position has a significant effect on formation of the monolayer at the air/water interface.
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Biochemistry and Biotechnology
  • Antaram Sarve, Mahesh N. Varma, Shriram S. Sonawane
    Volume 64 (2015) Issue 9 Pages 987-997
    Released: September 01, 2015
    JOURNALS FREE ACCESS
    In the present study, the low-cost non-edible kusum (Schleichera triguga) oil with a substantial amount of free fatty acid (FFA) was utilized for biodiesel synthesis. In pretreatment step, FFA was reduced by the acid catalyzed esterification method. Then, response surface method (RSM) in conjunction with centre composite design (CCD) containing 30 experimental runs were statistically employed for process optimization and kinetic study for the base catalyzed transesterification process. A statistical model predicted highest fatty acid methyl ester (FAME) yield of 97.37% at the optimal values of process parameters as follows: sodium methoxide concentration 0.9 wt% of oil, Methanol to oil molar ratio 9:1, temperature 58.9℃ and reaction time 58.5 min. Using these optimal parameters under experimental conditions in three independent replicates an actual FAME content of 98.14% was obtained which was in reasonable agreement with predicted one. The developed kinetic model suggested a 1.8th order reaction with activation energy of 31.42 kcal mol–1 and frequency factor of 5.53×1019 L mol–1min–1. Furthermore, Important fuel properties of kusum oil biodiesel (KOB) was compared with ASTM 6751 and DIN EN 14214. The viscosity was found to be 5.34 Cst at 40°C and the flash point was 152°C.
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  • Mitsuo Miyazawa, Yoshimi Nakashima, Hiroshi Nakahashi, Nobuyuki Hara, ...
    Volume 64 (2015) Issue 9 Pages 999-1007
    Released: September 01, 2015
    [Advance publication] Released: August 06, 2015
    JOURNALS FREE ACCESS
    The present study focuses on the volatile compounds with characteristic odor of essential oil from the leaves of Magnolia obovata by hydrodistillation (HD) and solvent-assisted flavor evaporation (SAFE) method. Eighty-seven compounds, representing 98.0% of the total oil, were identified using HD. The major compounds of HD oil were (E)-β-caryophyllene (23.7%), α-humulene (11.6%), geraniol (9.1%), and borneol (7.0%). In SAFE oil, fifty-eight compounds, representing 99.7% of the total oil, were identified. The main compounds of SAFE oil were (E)-β-caryophyllene (48.9%), α-humulene (15.7%), and bicyclogermacrene (4.2%). In this study, we newly identified eighty-five compounds of the oils from M. obovata leaves. These oils were also subjected to aroma evaluation by gas chromatography-olfactometry (GC-O) and aroma extract dilution analysis (AEDA). As a result, twenty-four (HD) and twenty-five (SAFE) aroma-active compounds were detected. (E)-β-Caryophyllene, α-humulene, linalool, geraniol, 1,8-cineole, and bicyclogermacrene were found to impart the characteristic odor of M. obovata leaves. These results imply that the oils of M. obovata leaves must be investigated further to clarify their potential application in the food and pharmaceutical industries.
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Chemistry and Organic Synthesis
  • Shiro Komba, Eiichi Kotake-Nara, Sachiko Machida
    Volume 64 (2015) Issue 9 Pages 1009-1018
    Released: September 01, 2015
    [Advance publication] Released: August 06, 2015
    JOURNALS FREE ACCESS
    Novel fucoxanthin derivatives that could change the size of mixed micelles were synthesized. The mixed micelles under consideration consist of a bile acid and some additives. To change the affinity against a bile acid, we designed the synthesis of a fucoxanthin-lithocholic acid complex. Lithocholic acid is one of the bile acids. The 3-OH on lithocholic acid was protected by a levulinyl group, and the protected lithocholic acid was selectively coupled via an ester linkage to the 3-OH on fucoxanthin to obtain levulinyl-protected lithocholyl fucoxanthin (LevLF). The levulinyl group was then selectively deprotected using hydrazine to obtain a lithocholyl fucoxanthin (LF). The average sizes of the micelles that contained these compounds (fucoxanthin, LevLF, and LF) with a bile acid (sodium taurocholate) were measured. The LevLF induced larger micelles than fucoxanthin or LF. Interestingly, the addition of 1-oleoyl-rac-glycerol induced a more efficient change in the micelle size. The large micelles grew larger, and the small micelles became smaller. Triple-mixed micelles with LevLF, sodium taurocholate, and 1-oleoyl-rac-glycerol formed the largest micelle with a diameter of 68 nm. On the other hand, triple-mixed micelles using LF, sodium taurocholate, and 1-oleoyl-rac-glycerol made the smallest micelles with diameters as low as 12 nm. We also investigated the hydrolysis of these compounds with enzymes (esterase from porcine liver, lipase from porcine pancreas, and cholesterol esterase from Pseudomonas sp.). The ester linkage between the lithocholic acid and fucoxanthin of LevLF was hydrolyzed with cholesterol esterase. In addition, the intestinal absorption was examined with Caco-2 cells, and no advantageous change in absorption efficiency was observed by chemically modifying the fucoxanthin unless different micelles sizes and increasing hydrophobicity are induced.
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  • Hanaa Mohamad Soliman, Amany M. Basuny, Shaker M. Arafat
    Volume 64 (2015) Issue 9 Pages 1019-1032
    Released: September 01, 2015
    [Advance publication] Released: August 06, 2015
    JOURNALS FREE ACCESS
    Olive Pomace was firstly dried, then pomace olive oil was extracted, and the obtained oil was hydrolyzed to produce glycerol and mixture of fatty acids1). Fatty acids mixture was separated, this mixture was then cooled, where the all saturated fatty acids were solidified, and then they were filtered off. These saturated fatty acids were identified by GC mass after esterification, and were identified as stearic, palmitic and myristic acids. Stearic acid was extracted using supercritical CO2 extractor2). The stearic acid was confirmed by means of GC mass after its esterification, and it was used as starting material for preparation of a variety of heterocyclic compounds, which were then tested for their antimicrobial activities.
    Thus the long-chain fatty acid hydrazide (2) was prepared from the corresponding long-chain fatty ester with hydrazine hydrate3). Reacting 2 with phenyl isothiocyanate afforded the corresponding thiosemicarbazide 4. The later 4 underwent intramolecular cyclization in basic medium, and gave the s-triazole derivative 5, which was methylated and afforded 3-heptadecanyl-5-(methylthio)-4-phenyl-4H-1,3,4-triazole (7), which was then treated with hydrazine hydrate and afforded the corresponding 1-(5-heptadecanyl-4-phenyl-4H-1,2,4-triazol-3-yl) hydrazine (8).On the other hand, thiosemicarbazide 4 underwent intramolecular cyclization in acid medium and afforded the corresponding thiadiazole derivative 6.Treatment of thiosemicarbazide 4 with ethyl chloro(arylhydrazono) acetate derivatives 9a-b, furnished a single product 13 (Scheme 6). Similarly, when the thiosemicarbazide 4 was treated with the phenylcarbamoylarylhydrazonyl chloride 10a-c, it afforded (3-Aryl-N-5-(phenylcarbamoyl)-1,3,4-thiadiazol-2(3H)-ylidene)octadecanehydrazide 15a-c (Scheme 7). Also the reaction of thiosemicarbazide 4 with 2-oxo-N-arylpropanehydrazonoyl chlorides 11a-c and N-phenylbenzohydrazonoyl chloride 11d gave the corresponding thiadiazole derivatives 16a-d as shown in Scheme 8.
    A solution of thiosemicarbazide 4 was treated with the haloketones 17a-c, afforded the thiadiazine derivatives 20a-c, as shown in Scheme 9. Analogously, the thiosemicarbazide 4 was reacted with α-haloketones 21a-b and afforded the corresponding products 22a-b (Scheme 9). The structure elucidation of all synthesized compounds is based on the elemental analysis and spectral data (IR, 1H NMR, 13C NMR and MS).
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  • Masayoshi Hisama, Sanae Matsuda, Junichi Arai, Katsunobu Masui, Haruo ...
    Volume 64 (2015) Issue 9 Pages 1033-1041
    Released: September 01, 2015
    JOURNALS FREE ACCESS
    A novel amphiphilic hydroquinone derivative having a C18 alkyl chain phosphate attached to the hydroquinone (HQ) moiety was chemically synthesized. The thermal stability, distribution between organic and aqueous phases, and in vitro skin permeability were evaluated. This HQ derivative was identified as disodium p-phenylene diisostearyl diphosphate (HQ-2P2IS) by UV, infrared, mass, and nuclear magnetic resonance spectroscopies. Product HQ-2P2IS was obtained in good yield (56%), and it exhibited satisfactory stability in neutral solution, comparable to that of HQ. Its skin permeability was also higher than that of HQ. HQ-2P2IS is susceptible to enzymatic hydrolysis by tissue phosphatase, which releases HQ in the skin tissues. Thus, these characteristics indicate that the novel hydroquinone derivative presented herein, i.e., HQ-2P2IS, may serve as an effective pro-hydroquinone for skin care applications.
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