Journal of Oleo Science
Online ISSN : 1347-3352
Print ISSN : 1345-8957
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Review
  • Miyashita Kazuo
    2019 Volume 68 Issue 1 Pages 1-11
    Published: January 01, 2019
    Released: January 01, 2019
    [Advance publication] Released: December 12, 2018
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    The benefit of fish oil to health has been widely recognized because of the high contents of functional EPA (20:5n-3) and DHA (22:6n-3) in the oil; however, the application of fish oil has been limited by its high susceptibility to oxidation. This review reports the characteristics of EPA and DHA oxidation compared with those of other fatty acids such as linoleic acid (18:2n-6). In addition, effective approaches to protect against oxidation are discussed, focusing on the unique antioxidant potential of amine compounds. Finally, the exceptionally high oxidative stability of EPA and DHA in biological systems is discussed. Understanding the protective mechanism against EPA and DHA oxidation in such systems may be useful for the development of an effective antioxidant procedure for fish oil that is rich in EPA and DHA.

Oils and Fats
  • Junmin Ji, Zhengfa Ge, Yeshen Feng, Xuede Wang
    2019 Volume 68 Issue 1 Pages 13-20
    Published: 2019
    Released: January 01, 2019
    [Advance publication] Released: December 12, 2018
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    To develop and use the hazelnut, the main composition, and the physicochemical characteristics, fatty acid compositions, triacylglycerol (TAG) distribution and tocol contents of Hazelnut (Corylus mandshurica Maxim.) which growing in Changbai mountain of Jilin province (HO1) and Anshan city of Liaoning province (HO2) in China were investigated, and the comparative study between the two hazelnut oils and American hazelnut / Turkish hazelnut were also explored. The content of crude lipid and protein in HO1 and HO2 were approximately 54% and 17%, 55% and 16%, respectively. The two hazelnut oils were abundant in unsaturated fatty acids, with the primary unsaturated fatty acids were oleic acid (78%-80%) and linoleic acid (14-16%), which accounted for above 90% of the oils. Therefore, both of the hazelnut oils were important sources of essential fatty acid. In addition, the main saturated fatty acid of the two hazelnut oils were palmitic acid (3%) and stearic acid (1-2%). The main triacylglycerols (TGA) profile were dioleolinolein (OOL), oleodilinolein (OLL) and triolein (OOO). The contents of tocol were 574.44 μg/g, 647.49 μg/g oil in HO1 and HO2, respectively, both of them were higher than that of grape seed oils (454 μg/g), olive oils (209 μg/g) and walnut oils (255 μg/g). The total phytosterol contents were over 2000μg/g and β-sitosterol was the most predominant sterol in two oils.

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  • Kazuo Mukai, Ayaka Ohara, Junya Ito, Masayuki Hirata, Eri Kobayashi, K ...
    2019 Volume 68 Issue 1 Pages 21-31
    Published: 2019
    Released: January 01, 2019
    [Advance publication] Released: December 12, 2018
    JOURNALS FREE ACCESS

    A kinetic study of the reaction of singlet oxygen (1O2) with eight vegetable oils 1–8 containing different concentrations of tocopherols (Tocs) and tocotrienols (Toc-3s) was performed. The second-order rate constants (kQ) for the reaction of 1O2 with vegetable oils 1–8 (rice bran, perilla, rape seed, safflower, grape seed, sesame, extra virgin olive, and olive oils) were measured in ethanol/chloroform/D2O (50:50:1, v/v/v) solution at 35°C using UV-vis spectrophotometry. Furthermore, comparisons of kQ values determined for the above oils 1-8 with the sum of the product {∑kQAO-i [AO-i]/105} of the kQAO-i values obtained for each antioxidant (AO-i) and concentration (in mg/100 g) ([AO-i]/105) of AO-i (Tocs and Toc-3s) contained in the oils 1-8 were performed. The observed kQ values were not reproduced by the kQ values calculated using only the concentrations of the four Tocs and Toc-3s. These results suggest that the contribution of fatty acids contained in the oils 1-8 is also necessary to fully explain the kQ values. Recently, the second-order rate constants (kS) for the reaction of aroxyl radical (ArO・) with the same vegetable oils 1–8 were measured in the same solvent at 25℃ using stopped-flow spectrophotometry (Ref. 23). The kS values obtained could be well explained as the sum of the product {Σ kSAO-i [AO-i]/105} of the kSAO-i and the [AO-i]/105 of AO-i (Tocs and Toc-3s) contained in the vegetable oils.

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  • Sabeena Rizwan, Cinzia Benincasa, Khalid Mehmood, Shaista Anjum, Zahid ...
    2019 Volume 68 Issue 1 Pages 33-43
    Published: 2019
    Released: January 01, 2019
    [Advance publication] Released: December 12, 2018
    JOURNALS FREE ACCESS

    Mediterranean olive trees have been cultivated in Pakistan for decades to promote olive cultivation and use of olive oil. The qualitative characteristics of seven mono and one multi-varietal extra virgin olive oils (EVOOs) extracted from Italian cultivars grown in different areas of Balochistan a southwestern province of Pakistan were evaluated. Present study aims to assess the impact of bioclimatological change on biochemical profile of exotic cultivars. The dominating fatty acids found in analyzed EVOOs were oleic (65-72%), linoleic (10.61-18.33%) and palmitic acids (12-16%). The tocopherols α, (β+γ) and δ contents showed a great diversity which ranged from (60-408) mg/kg while, total phenol concentration ranged from (200-370) mg/kg. The analyses of phenolic compounds revealed the presence of phenolic acids, phenolic alcohols, secoiridoids, flavonoids, oleuropein and verbascosides. One-way ANOVA revealed significant differences (p < 0.05) regarding studied parameters. Principal component analysis (PCA) was applied to identify the main components and to classify samples into groups in terms of fatty acids and phenolic profiles. The first group (Frantoio, Moraiolo, Pendolino, Multi-varietal mixture) characterized by high amount of oleic acid and MUFAs/PUFAs ratio. The second group (Maurino and Leccino) correlates with SFAs and third (Ottobrattica, Coratina) with PUFAs. Based on the PCA of phenolic profile the studied cultivars were divided into two main groups. Morialo, Pendolino and Maurino correlated with (phenolic acids, hydroxytyrosol, flavonoids and secoiridoids). Frantoio, Ottobrattica, Coratina, multi-varietal and Leccino were correlated with oleuropein, tyrosol and ligstroside aglycon. The obtained data was compared with those obtained from same cultivars in their original and/or different growing area. Marked differences were observed in the composition of oleic, linoleic, palmitic acids, secoiridoids and total phenolic contents. These differences could be due to change in geographical location and climatical condition of Balochistan. The cultivar Moraiolo has shown best adaptation and preserved its biochemical composition among all studied cultivars.

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  • Yayoi Miyagawa, Mao Yoshida, Yudai Chizawa, Shuji Adachi
    2019 Volume 68 Issue 1 Pages 45-52
    Published: 2019
    Released: January 01, 2019
    JOURNALS FREE ACCESS

    The induction period for crystallization, defined as the time required to crystallize, was discussed during isothermal storage at –5 to –45°C for various vegetable oils; olive, safflower, rapeseed, corn, rice bran, soybean, and linseed oils. The induction periods, largely dependent on the oil type and storage temperature, were classified into two groups. The induction periods of corn, rice bran, soybean, and linseed oils were monotonically shortened as the storage temperature decreased. On the other hand, the induction periods for rapeseed, olive, safflower oils and the mixtures of rapeseed and soybean oils, and of olive and safflower oils did not simply change or elongate with a decrease in storage temperature. The induction periods could be formulated using two parameters. One was an expected value of the melting point of the oil, which was calculated from its fatty acid composition. The other was a molar fraction of triacylglycerol composed of the same fatty acids in the oil. The crystallization and melting processes of the oils under nonisothermal conditions were also analyzed by differential scanning calorimetry (DSC). It was suggested that the induction period was also predictable from the peak shape, peak number, onset temperature, and peak area in the DSC curve of the oil during the crystallization process.

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Detergents, Surfactants, Interface and Colloid
  • Satoshi Watanabe, Taiga Tominaga, Mutsuyoshi Matsumoto
    2019 Volume 68 Issue 1 Pages 53-60
    Published: 2019
    Released: January 01, 2019
    [Advance publication] Released: December 12, 2018
    JOURNALS FREE ACCESS

    Techniques for patterning hydrogels are important for fabrication of cell culture, analytical, and actuator devices at the micro- and nanometer length scales. In this study, we fabricated alginate hydrogels cross-linked by divalent cations on wettability-patterned substrates by alternate soaking of precursor solutions of sodium alginate and divalent cations. The wettability-patterned substrates were fabricated on hydrophilic glass plates modified with hydrophobic self-assembled monolayers of hexamethyldisilazane followed by exposure to an ultraviolet/ozone atmosphere through a metal mask. The film thickness of alginate gels with a width and length of 0.1 and 4 mm were tuned stepwise from 30 nm to 200 nm by adjusting the precursor conditions, including the pH, type of divalent metal ions, and sodium alginate concentration, and the alternate soaking conditions, including the dipping/withdrawal speed and number of alternate soaking cycles. This technique can be applied to other functional gels and will contribute to fabrication of hydrogel devices at the micro- and nanometer scales in the future.

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  • Shunya Yamamoto, Akio Ohta, Faisal Hossain, Gemala Anjani, Hitoshi Asa ...
    2019 Volume 68 Issue 1 Pages 61-66
    Published: 2019
    Released: January 01, 2019
    [Advance publication] Released: December 12, 2018
    JOURNALS FREE ACCESS

    Water-insoluble genistein was solubilized in aqueous medium by using phospholipid vesicles composed of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and 1,2-dioleoyl-sn-glycerophosphocholine (DOPC) with 0-30% cholesterol. For each vesicle, the maximum solubilization amount of genistein was investigated by X-ray scattering measurement. In addition, the antioxidant capacity of the solubilized genistein was evaluated by the ABTS assay. Genistein was found to be solubilized by 10-20% and 40-50% of the vesicle concentrations of pure DPPC and DOPC respectively. The maximum solubilization amount of genistein decreased to 0-10% and 20-30% when 30% of cholesterol is present in the respective vesicles. Cholesterol is solubilized in a hydrophobic core whereas genistein is solubilized in the polar head region or in the polar-apolar interface. The overlapping of solubilizing sites affected the solubilization of genistein when cholesterol was present in the vesicles. Moreover, the lamellar interval was largely affected by cholesterol in compared to the little impact of genistein because the later can indirectly affect the acyl chains. Genistein solubilized in DOPC showed the same degree of antioxidant capacity as that of vesicle-free genistein system. On the other hand, genistein solubilized in DPPC had lower antioxidant activity than the former systems. The distinction of antioxidant activity at different systems probably related to the difference of accessibility of ABTS radical cation to solubilized genistein through different vesicles. Finally, cholesterol-free DOPC vesicles were found to be the best solubilizer for genistein among the investigated systems.

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  • Hirotaka Tanabe, Minako Kaido, Motoko Kawashima, Reiko Ishida, Masahik ...
    2019 Volume 68 Issue 1 Pages 67-78
    Published: 2019
    Released: January 01, 2019
    [Advance publication] Released: December 12, 2018
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    Purpose: To investigate the efficacy of eyelid margin cleansing with lid hygiene detergent in patients with obstructive meibomian gland dysfunction (MGD). Methods: As a pilot study, we investigated the safety and efficacy of lid hygiene using tap water and/or lid hygiene shampoo in fourteen eyes of 7 normal subjects. All subjects were instructed to cleanse the eyelid margin with tap water and/or lid hygiene shampoo. As a main prospective clinical study, thirty-four eyes of 34 patients with obstructive MGD were enrolled. All subjects were instructed to cleanse the eyelid margin with lid hygiene shampoo at least once daily for 1 month. Ocular surface conditions were observed before and 1 month after study initiation. Results: A significant exacerbating change (p < 0.05) was not detected after either method in the pilot study. In the main study, significant improvements were observed in tear break-up time (TBUT), lid margin lissamine green staining scores, vascular dilatation, and meibum status (p < 0.05). No significant improvements in corneal or conjunctival fluorescein staining scores, the mucocutaneous junction, lid margin deformation, or plugging were observed (p ≥ 0.05). Subjective improvements were observed in 27 subjects. Meibography revealed that 28 subjects had normal meibomian glands, and 6 subjects had meibomian gland atrophy. Significant improvements were observed in TBUT, vascular dilatation, and meibum status only in the group with normal meibomian glands (p < 0.05), but subjective symptoms and lid margin lissamine green staining scores improved in both groups (p < 0.05). No subjects experienced any problems throughout the study. Conclusion: Daily routine use of lid hygiene detergent can alleviate the symptoms of MGD regardless of meibomian gland atrophy.

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Nutrition and Health Function
  • Hirona Kugo, Chie Miyamoto, Ayaka Sawaragi, Kiyoto Hoshino, Yuka Hamat ...
    2019 Volume 68 Issue 1 Pages 79-85
    Published: 2019
    Released: January 01, 2019
    JOURNALS FREE ACCESS

    Abdominal aortic aneurysm (AAA) is a vascular disease characterized by the weakening of the vascular walls and the progressive dilation of the abdominal aorta. Nicotine, a primary component of cigarette smoke, is associated with AAA development and rupture. Nicotine induces AAA development by weakening vascular walls. However, little is known about preventive methods using functional food factors for nicotine-induced vascular destruction. Sesamin and sesamolin are functional food factors that are fat-soluble lignans found in Sesamum indicum seeds. Previous reports indicated that sesamin and sesamolin have anti-oxidative and anti-inflammatory effects. In this study, we evaluated the effects of sesamin and sesamolin-rich sesame extract on the weakening of vascular walls in nicotine-administered mice. Sesame extract attenuated the degradation of collagen and elastin fibers caused by nicotine. In addition, sesame extract decreased the area positive for matrix metalloproteinase 12 (MMP-12) and oxidative stress in the vascular walls. These results suggest that sesame extract may decrease the weakening of vascular walls by suppressing the nicotine-induced degradation of collagen and elastin fibers. Sesame extract may be effective in preventing AAA development by decreasing both, MMP-12 expression and oxidative stress in vascular walls.

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General Subjects
  • Fernando Sánchez-Albarrán, Rafael Salgado-Garciglia, Jorge Molina-Torr ...
    2019 Volume 68 Issue 1 Pages 87-94
    Published: 2019
    Released: January 01, 2019
    [Advance publication] Released: December 12, 2018
    JOURNALS FREE ACCESS

    Studies on avocado oil have focused on the most common commercial cultivars, Hass, Fuerte, and Bacon, rather than the less common varieties, P. americana var. drymifolia and P. americana var. americana, even though the drymifolia variety has a higher oil content and the americana variety is the most common avocado grown in the tropics. The most abundant storage structures for plant oils are the oleosomes, and the aim of this study was to determine the oleosome size, oil yield, and fatty acid composition of the americana and drymifolia varieties, using the Hass cultivar as a reference. Differences were found between the three avocado types for 1) oil yield, with drymifolia having higher and americana lower oil content (p < 0.05%), 2) oleosome size, with Hass having a larger (41.53 µm) and americana a smaller (11.96 µm) size, and 3) fatty acid composition, with the americana and drymifolia varieties showing less monounsaturated fatty acids (oleic) and more polyunsaturated fatty acids (linoleic) and saturated fatty acids (palmitic); while Hass had a high level (60%) of monounsaturated fatty acids. Small but significant differences were also found between oleosome and mesocarp oils isolated from the drymifolia and Hass types.

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  • Piriya Pinthong, Piyasan Praserthdam, Bunjerd Jongsomjit
    2019 Volume 68 Issue 1 Pages 95-102
    Published: 2019
    Released: January 01, 2019
    [Advance publication] Released: December 12, 2018
    JOURNALS FREE ACCESS

    Oxidative dehydrogenation of ethanol to acetaldehyde over Mg-Al layered double hydroxides (LDH) and their differently calcined derivative catalysts was investigated in this study. The Mg-Al catalysts were synthesized via co-precipitation method and calcined at different temperatures at 450°C, 600°C and 900°C. It revealed that the calcination temperature affected the physicochemical properties and the catalytic activity of these catalysts toward the oxidative dehydrogenation of ethanol. It was found that ethanol conversion increased with increasing reaction temperature from 200 to 400°C, whereas acetaldehyde selectivity decreased. At low reaction temperature (200-300°C), the non-calcined catalyst (Mg-Al-000) showed the highest ethanol conversion, which can be attributed to the hydroxyl groups on surface having acetaldehyde as a major product. The calcination process led to formation of mixed oxide phase in Mg-Al catalysts as proven by the XRD and FT-IR results. The catalyst calcined at 450°C (Mg-Al-450) exhibited the highest basicity as measured by the CO2-TPD with ethanol conversion of 45.8% and acetaldehyde yield of 29.7% at 350°C.

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  • Kensuke Nakajima, Narumi Maeda, Shigeru Oiso, Hiroko Kariyazono
    2019 Volume 68 Issue 1 Pages 103-109
    Published: 2019
    Released: January 01, 2019
    [Advance publication] Released: December 12, 2018
    JOURNALS FREE ACCESS

    Ghrelin is a stomach-derived peptide hormone with an appetite-stimulating effect. Octanoylation on the serine-3 residue of ghrelin by ghrelin O-acyl transferase (GOAT) is essential for its orexigenic effect. Mature octanoylated ghrelin is generated by the C-terminal cleavage of octanoylated proghrelin via prohormone convertases (furin, PC1/3, or PC2). We previously established an AGS-GHRL8 cell line that produces octanoylated ghrelin in the presence of octanoic acid, and found that oleanolic acid suppresses octanoylated ghrelin production in AGS-GHRL8 cells. Here, we investigated the effects of oleanolic acid in C57BL/6J mice fed a standard, high-fat, or high-glucose diet. Oral administration of oleanolic acid for seven days (20 or 40 mg/kg) reduced plasma octanoylated ghrelin levels and body weight gain in the standard diet-fed mice but not in other two diet-fed mice. There were no significant differences in ghrelin, GOAT, furin, PC1/3, and PC2 gene expression levels between the vehicle- and oleanolic acid-treated mice fed a standard diet. Octanoyl-CoA is a substrate for ghrelin octanoylation by GOAT. We found that oleanolic acid did not affect octanoyl-CoA production in vitro. Hence, the inhibitory effect of oleanolic acid on octanoylated ghrelin production may not be related to the decrease in octanoyl-CoA. The results of this study may provide valuable knowledge for the development of anti-obesity agents with an inhibitory effect on octanoylated ghrelin production.

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