Journal of Oleo Science
Online ISSN : 1347-3352
Print ISSN : 1345-8957
ISSN-L : 1345-8957
Volume 71, Issue 1
Displaying 1-15 of 15 articles from this issue
Review
  • Dai Kitamoto, Tokuma Fukuoka, Azusa Saika, Tomotake Morita
    2021 Volume 71 Issue 1 Pages 1-13
    Published: 2021
    Released on J-STAGE: January 08, 2022
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    Biosurfactants produced by a variety of microorganisms show attractive properties (e.g., higher surface activity and biodegradability, lower toxicity, and environmental compatibility) compared to chemically synthesized counterparts. The numerous advantages of biosurfactants have prompted their application to not only the food, cosmetic, and pharmaceutical industries, but agriculture and environmental protection disciplines as well. Among different types of biosurfactants, glycolipids are the most practically useful, due to their high product titers from renewable resources and versatile interfacial and biochemical properties. Mannosylerythritol lipids (MELs) are characteristic glycolipid biosurfactants that are produced by different yeast strains of the genus Pseudozyma. MELs exhibit different lyotropic liquid crystalline phases, such as sponge (L3), reverse bicontinuous cubic (V2), or lamellar (Lα) phases; and they have high levels of surface activity at very low concentrations. MELs also show excellent moisturizing effects on human skin and hair, with comparable performance to natural ceramides. Today, MELs are commercially produced by a Japanese company and their use is rapidly expanding around the world. In this review, we will briefly describe the current R&D status of glycolipid biosurfactants, with a focus on the interfacial properties of MELs and their applications in cosmetic and personal care products.

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Oils and Fats
  • Kinuko Miyazaki, Yoshiyuki Takagishi, Kazuhiro Sakamoto, Yukiko Yamada ...
    2022 Volume 71 Issue 1 Pages 15-29
    Published: 2022
    Released on J-STAGE: January 08, 2022
    Advance online publication: December 08, 2021
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    For indirect determination of 3-chloro-1,2-propanediol fatty acid esters (3-MCPDEs) and glycidyl fatty acid esters (GEs) in thermally processed foodstuffs distributed in Japan, we modified two published methods, an enzymatic method (later approved as JOCS Standard Method for the Analysis of Fats, Oils, and Related Materials 2.4.14-2016 and Joint JOCS/AOCS Official Method Cd 29d-19) and EFSA method developed by the Joint Research Centre of the European Commission. The performance of these methods was demonstrated to be satisfactory. The partially modified enzymatic method showed mean recoveries of 93.7-98.5% for 3-MCPDEs, 94.4-98.4% for GEs, and HorRat(r) values of 0.06-0.78 in analyses of 6 types of foods including Japanese specific foods (fried rice cracker, fried instant noodle, biscuit, karinto, vegetable tempura, and frozen deep-fried chicken) spiked with 3-MCPD dioleate and glycidyl oleate at 0.02-0.04 mg/kg or 0.2-0.4 mg/kg. The partially modified EFSA method showed mean recoveries of 96.6-99.4% for 3-MCPDEs, 95.7-100.1% for GEs, and HorRat(r) values of 0.14-1.05 in analyses of 5 types of foods (not including karinto) spiked simultaneously with 3-MCPD dioleate and glycidyl oleate at either 0.02-0.04 mg/kg or 0.2-0.4 mg/kg. The results of analyses of 9 samples (fried rice cracker, biscuit, 2 potato crisps, fried potato snack, baked cracker, cracker dough, seafood tempura, and frozen deep-fried chicken) using these 2 methods were comparable. The 95% confidence intervals determined with weighted Deming regression analysis between the results of 3-MCPDEs or GEs in the same samples analyzed by the 2 methods showed: the slope around 1 (3-MCPDEs, 0.982-1.025; GEs, 0.887-1.078); and intercept close to 0 (3-MCPDEs, -0.002-0.003; GEs, -0.011-0.015). These data confirmed that the concentrations of 3-MCPDEs and GEs in food samples determined by 2 independent analytical methods were equivalent.

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  • Abdul Hammed Kori, Sarfaraz Ahmed Mahesar, Abdul Rauf Khaskheli, Syed ...
    2022 Volume 71 Issue 1 Pages 31-41
    Published: 2022
    Released on J-STAGE: January 08, 2022
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    Pomegranate seed oil is a highly unsaturated fatty acid and liable to be oxidized; hence, oil was encapsulated to protect its bioactive materials and increase shelf life with the most common spray drying technique. Whey protein (WP) alone and in combination with Maltodextrin (MD) in the ratio 1:4 weight was utilized. Feed emulsion, droplet size, encapsulation efficiency (EE), moisture, bulk density, powder morphology, particle size, hygroscopicity, and solubility were also analyzed. The spray drying conditions were applied: inlet temperature 125 to 150°C and outlet 60 to 67°C, airflow rate 40-42 m3/mint, feed rate 5.2 g/m, and pump rate 40%. The shape of particles was spherical and round with dents on their surface. After encapsulation, the oxidative stability was monitored at 60°C for 15 days (8 h daily). The smaller droplet size of the emulsion was obtained at 35% total solid contents. WP alone showed better EE (90%) and oxidative stability than the combination of WP and MD as wall materials.

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  • Ying Qian, Anna Grygier, Arkadiusz Majewski, Dorota Walkowiak-Tomczak, ...
    2022 Volume 71 Issue 1 Pages 43-50
    Published: 2022
    Released on J-STAGE: January 08, 2022
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    The aim of this study was to examine olive oils purchased in Poland for their compliance with label declarations and EEC criteria. Statistical analysis was used to compare the olive oils in terms of their content and composition of essential constituents and color parameters. Fifty olive oils (extra virgin, bioextra virgin, cold-pressed, refined, and pomace) from different countries (Spain, Italy, Greece, Portugal, Germany, France, Israel, and the European Union), were purchased commercially in Poland. The contents of triacylglycerols, sterols, and tocopherols, the fatty acid composition, and the color parameters were determined using chromatographic and spectrophotometric methods. Statistical methods were used to divide the olive oils into clusters. Our results show that the composition and color parameters of olive oils available commercially in Poland, excluding pomace olive oils, are similar. It can thus be concluded that, irrespective of the type of olive oil stated on the label, their quality is the same or very similar.

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  • Amnart Soontornchatchawate, Supachai Chintanalert, Prakob Kitchaiya, A ...
    2022 Volume 71 Issue 1 Pages 51-55
    Published: 2022
    Released on J-STAGE: January 08, 2022
    Advance online publication: December 08, 2021
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    Vitamin E (VitE) production from crude palm oil (CPO) has been extensively studied and industrially conducted. VitE in CPO is in the range of 600 to 1,000 ppm, and is usually produced from one of the main by-products of edible palm oil production, namely palm fatty acid distillate (PFAD). PFAD contains 4,000 to 5,500 ppm of VitE, and is produced from deodorization process of palm oil purification. This paper presents an innovative process of VitE concentrate production from CPO. A scrubber was designed and installed between the deodorizer and conventional PFAD scrubber. The main objective of this new scrubber was a recovery of glycerides from PFAD. This new scrubber is operated at 150 to 160℃. The scrubbed oil is named as Scrubbed Palm Fatty Acid Distillate (S-PFAD). This simple and efficient modified process can retrieve glycerides as S-PFAD at 0.3% recovery and it enhances VitE concentration in S-PFAD to the range of 28,000 to 32,000 ppm, which is the highest concentration of VitE that has ever been produced in the palm oil production. Fatty acids and glycerides in S-PFAD were esterified and transesterified to methyl esters. The methyl esters were evaporated from S-PFAD, and S-PFAD residue oil contained 24.7% VitE.

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  • Chenling Qu, Zhuozhen Li, Qiankui Yang, Xueke Wang, Dianxuan Wang
    2022 Volume 71 Issue 1 Pages 57-66
    Published: 2022
    Released on J-STAGE: January 08, 2022
    Advance online publication: December 08, 2021
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    Storage is an important step after peanut harvest and drying. Many factors could affect the peanut quality during storage. The quality change differences of peanut after being dried by solar radiation and at 35°C, 40°C, 45°C, 50°C during later storage were investigated, including moisture content (MC) and germination percentage (GP) of peanut kernels, acid value (AV), peroxide value (PV), iodine value (IV), vitamin E (VE) content and fatty acid composition (FAC) of extracted peanut oil. And the impact of four storage conditions, air-room temperature (A-RT), air-low temperature (A-LT), vacuum-room temperature (V-RT) and nitrogen-room temperature (N-RT) on peanut quality after 10 months’ storage were also studied in this paper. The results revealed that drying conditions had only a little influence on peanut quality during later storage. Peanut dried by solar radiation was more easily oxidized than that dried under other drying conditions. The effects of storage time were much greater. The GP, AV, PV, VE content and FAC, showed significantly changes along with storage. GP and VE content decreased, AV and PV increased, and some linoleic acid was oxidized to oleic acid after 10 months’ storage. In addition, A-LT exhibited best performance in keeping peanut quality than A-RT, V-RT and N-RT, which demonstrated that low temperature was more advantageous for peanut storage than controlled atmosphere. These results above would provide useful information and reference for the peanut storage to apply in food industry.

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Detergents, Surfactants, Interface and Colloid
  • Kotaro Kaneko, Aki Nakazato, Akihiro Ishikawa, Nobuhiro Kaneko, Akira ...
    2022 Volume 71 Issue 1 Pages 67-74
    Published: 2022
    Released on J-STAGE: January 08, 2022
    Advance online publication: December 08, 2021
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    Supplementary material

    Surface pressure (π)-area (A) isotherms were studied to analyze the interactions between a hydrophilic ionic liquid (IL) (ethyl(2-hydroxyethyl)dimethylammonium methanesulfonate) and a pure dipalmitoylphosphatidylcholine (DPPC) film or a DPPC-cholesterol mixed film. When the hydrophilic IL was added to an underlayer solution, the isotherm shifted toward higher areas. Intriguingly, when the hydrophilic IL was added, the packing of the film materials became loose and the elastic modulus decreased, resulting in increased flexibility. This phenomenon was most evident under a cholesterol mole fraction of 0.2. This composition resembles that of cell membranes, which typically comprise phospholipids and cholesterol, suggesting that this hydrophilic IL may be able to interact significantly with biological membranes.

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  • Kazuo Takei, Masaru Watanabe, Keita Kawasaki, Toshio Sakai
    2022 Volume 71 Issue 1 Pages 75-81
    Published: 2022
    Released on J-STAGE: January 08, 2022
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    Supplementary material

    Herein, we report the colloidal stability of emulsifier-free (EF-) triolein-in-water (TO/W) emulsions prepared by mixing TO and water using a high-powered bath-type ultrasonicator (HPBath-US; 28 kHz, 300 W) in the absence of emulsifiers such as surfactants. In particular, the effect of the temperature (15-60℃) on the colloidal stability of EF-TO/W emulsions was examined because this is important for the practical application of EF-TO/W emulsions, for example, in foods, pharmaceuticals, and cosmetics. We found that the colloidal stability of the EF-TO/W emulsions decreased with increase in the temperature from 15 to 25°C, whereas it increased with increase in temperature from 25 to 40°C, and the high colloidal stability of the EF-TO/W emulsions was maintained above 40°C. The reduction in the colloidal stability of EF-TO/W emulsions between 15 and 25°C is likely a result of the TO droplets formed by thermal motion, as well as enhanced Ostwald ripening at higher temperatures. On the other hand, the increase in the colloidal stability of the EF-TO/W emulsions from 25 to 40°C and their high colloidal stability above 40℃ is attributed to the reduction in the interfacial tension between TO and water at higher temperatures. This decrease in the interfacial tension between TO and water with temperature increase is related to the transformation of short-range ordered domains (clusters) of TO molecules in the liquid state, which increases the colloidal stability of the EF-TO/W emulsions.

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Biochemistry and Biotechnology
  • Mudassar Hussain, Iram Liaqat, Muhammad Mubin, Bushra Nisar, Khurram S ...
    2022 Volume 71 Issue 1 Pages 83-93
    Published: 2022
    Released on J-STAGE: January 08, 2022
    Advance online publication: December 08, 2021
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    The extremely difficult and challenging process is identifying pheretimoid species, genus Metaphire and Amynthas involving increased homoplasy in various morphological characteristics. The molecular identification, phylogenetic relationships, and evolutionary divergence time of earthworms belonging to the pheretimoid complex were investigated in this study using partial mitochondrial COI (cytochrome C oxidase subunit I) gene sequences ranging from 550-680 bp. Results revealed that 86 pheretimoid earthworms were morphologically different from a total of 342 mature worms. Moreover, 11 pheretimoid species were molecularly identified, including Metaphire posthuma (02), M. anomala (01), M. houlleti (02), M. californica (01), M. birmanica (02), Amynthas minimus (01), A. morrisi (01), and M. bununa (01). A phylogenetic tree was constructed with bootstrap values of 95%, which supported a monophyletic lineage of two well-supported clades formed by 12 partial COI sequences and 48 GenBank sequences using Hirudo medicinalis as an outgroup. The monophyly of these obtained genera indicated overall similarity at species level. Today, species like Amynthas, Metaphire and Pheretima have worm diversity in the form of pheretimoid earthworms, which dates to the Late Miocene (11.2-5.3 Mya) and the Pliocene (5.3-2.4 Mya). Compared to all relevant pheretimoid species, genetic p-distance values ranged from 0.0% to 0.57% (less than 1%). These low range values demonstrated that both genera Metaphire and Amynthas, supported the theory, which states that there are shared similarities among the species, despite different morphology. The current study is the first attempt in Pakistan to identify earthworms through DNA barcoding thus providing a genomic stamp. The work explored the significance of COI gene sequences to construct molecular tools that will be useful to overcome the different obstacles in morphologically similar earthworm identification and their phylogenetic study.

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  • Runzhou Sun, Ruixin Xiao, Pengfei Lv, Feifei Guo, Yanling Gong, Meixin ...
    2022 Volume 71 Issue 1 Pages 95-104
    Published: 2022
    Released on J-STAGE: January 08, 2022
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    Pink lotus essential oil (PLEO) is the volatile components extracted from lotus flowers and there are few relevant research. The purpose of this study was to observe the effect of PLEO on NAFLD in vitro model and its possible mechanism. The ingredients of PLEO were determined by gas chromatography-mass spectrometry (GS-MS) and its lipid-lowering and hepatoprotective activities were investigated. HepG2 cells were treated with free fatty acid (FFA) to establish a cell model of NAFLD. Cell viability was evaluated by 3-(4,5-dimethyl thiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) method. Total cholesterol (TC), triglyceride (TG), tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), and interleukin-6 (IL-6) were determined by Enzyme-Linked Immune Sorbent Assay (ELISA). Oil red O staining was performed to observe the lipid accumulation in the HepG2 cells. Lipid metabolism enzymes including fatty acid synthase (FAS), acetyl-coA carboxylase (ACC), stearoyl-CoA desaturase 1 (SCD-1), and carnitine palmitoyltransferase-1 (CPT-1), insulin signaling pathways including phosphatidylinositol 3 kinase (PI3K) and protein kinase B Akt, inflammatory signaling pathways such as nuclear factor kappa-B (NF-κB), were determined by Western blotting. There were 46 components determined in PLEO with many terpenoids compounds. PLEO decreased TC and TG contents in the FFA-treated HepG2 cells. Furthermore, PLEO inhibited TNF-α, IL-6 and IL-1β excretion, decreased NF-κB, FAS, ACC and SCD-1 while increased phosphorylation of NF-κB, PI3K, Akt, and CPT-1 expression. It is the first time to reveal that PLEO alleviates FFA-induced steatosis in HepG2 cells by regulating lipid metabolism, inhibiting inflammatory response, and improving insulin sensitivity.

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  • Peng Feng, Shijun Shu, Feifei Zhao
    2022 Volume 71 Issue 1 Pages 105-118
    Published: 2022
    Released on J-STAGE: January 08, 2022
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    Supplementary material

    Osteoporosis is a bone related disease that is characterised by bone loss that further increases the susceptibility to bone fractures and bone frailty due to disturbances in the micro-architecture of bone tissue. Fisetin (flavonoids) exhibited anti-inflammatory and antioxidative stress effects against various diseases. In this protocol, we make an effort to comfort the anti-osteoporosis effect of fisetin against ovariectomy (OVX) induced osteoporosis. A docking study of fisetin and alendronate on the estrogen (α and β) and vitamin D receptors was carried out. SaOS-2 (osteoblast like human) cells were used for the estimation of cell proliferation. The OVX induced OVX model was used and three doses of fisetin and alendronate was given to rats till 16 weeks. The hormone levels, bone turnover markers and biochemical parameters were estimated. Fisetin was docked into estrogen (α and β) and vitamin D receptors, resulting in stable complexes with lower binding scores. Fisetin significantly (p < 0.001) exhibited the induction of cell proliferation against the SaOS-2 cells. OVX induced osteoporosis rats exhibited a suppression of body weight and uterus index, after the Fisetin treatment. Fisetin treatment significantly (p < 0.001) improved the level of bone mineral content (BMC), bone mineral density (BMD) and biochemical parameters such as energy, maximum load, stiffness, young modules, maximum stress and reduced the level of 1,25(OH) 2 D3 and E 2 . Fisetin treatment significantly (p < 0.001) declined the level of phosphorus (P), calcium (Ca) and boosted the level of VitD. Fisetin treatment significantly (p < 0.001) reduced the malonaldehyde (MDA) level and enhanced the glutathione (GSH), catalase (CAT), superoxide dismutase (SOD) level in the bone, intestine and hepatic tissue. Fisetin treatment suppressed the cytokines, RANKL/OPG ratio, receptor activator of nuclear factor-κB ligand (RANKL) and improved the level of osteoprotegerin (OPG). The findings suggest that fisetin could be a beneficial phytoconstituent for the treatment and prevention of postmenopausal osteoporotic complications.

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  • Keisuke Wada, Azusa Saika, Kazunori Ushimaru, Shun Sato, Tokuma Fukuok ...
    2022 Volume 71 Issue 1 Pages 119-125
    Published: 2022
    Released on J-STAGE: January 08, 2022
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    Moesziomyces antarcticus is a basidiomycetous yeast that produces mannosylerythritol lipids (MELs), which have potential applications as bio-based functional materials in various oleochemical industries, the cosmetics, toiletry, agriculture, and pharmaceutical industries. To better understand the MEL producer, we characterized the central metabolic pathways of M. antarcticus strain T-34 grown on glucose or olive oil via metabolomics. The relative fatty acid content was higher in the cells cultured in olive oil compared to glucose, while the acetyl-CoA content was lower in cells cultured in olive oil. The levels of the tricarboxylic acid cycle metabolites citrate/isocitrate, α-ketoglutarate, and succinate were lower in olive oil compared to glucose, while fumarate and malate levels exhibited the opposite pattern. Pyruvate was not detected in olive oil compared to glucose culture. The levels of glycerol, as well as trehalose, myo-inositol, threitol/erythritol, and mannitol/sorbitol, were higher in olive oil compared to glucose cultures. The ATP level was lower in olive oil compared to glucose culture, although the assimilation of fatty acids produced by digestion of olive oil should promote large amounts of ATP production. The possibility that ATP regeneration by respiratory chain complex promote oil utilization and MEL production in M. antarcticus T-34 was found based on the results of this metabolomic analysis.

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Medical Chemistry
  • Maulidiyah Maulidiyah, Akhmad Darmawan, Wahyu Wahyu, Andi Musdalifah, ...
    2022 Volume 71 Issue 1 Pages 127-134
    Published: 2022
    Released on J-STAGE: January 08, 2022
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    Lichen Usnea sp. is potential as a new natural medicine. This study report isolation of secondary metabolites from lichen Usnea sp. and α-glucosidase inhibitory, which is potential as an antidiabetic agent. Lichen powder was macerated using methanol, separated using column chromatography gravity and thin-layer chromatography. The crystalline was isolated and purified by the recrystallization process for obtaining pure compound. The isolated compound was determined using FTIR and NMR spectroscopy (1H and 13C). The results showed that the isolated compound was yellow needle crystals. Based on the spectra data interpretation, it was obtained usnic acid compound with the molecular formula of C18H16O7. The α-glucosidase inhibitory activity test showed that the usnic acid had activity in inhibiting the α-glucosidase enzyme with an IC50 value of 106.78 µg/mL. The usnic acid from Usnea sp. has a very good impact on the source of natural compounds as an antidiabetic drug in the future.

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Nutrition and Health Function
  • Eiichi Kotake-Nara, Megumi Hase, Ryosuke Hoshina, Mayumi Hidan, Hideak ...
    2022 Volume 71 Issue 1 Pages 135-140
    Published: 2022
    Released on J-STAGE: January 08, 2022
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    We investigated the effect of neutral lipids, polar lipids, and an emulsified formulation (EMF) on carotenoid bioaccessibility in an in vitro digestion assay of vegetables. These reagents enhanced carotenoid bioaccessibility. Contrary to our previous report, they also exhibited effects on lutein. Bile extracts/pancreatin concentrations also participated in the bioaccessibility. The EMF, which consisted of lower amounts of oil, had the same effect on lutein as rapeseed oil. These reagents also showed effects in the aging model, with more reduced bile extract/pancreatin concentrations, suggesting that lipids and EMF contributed to carotenoid bioaccessibility in bile/pancreatic juice secretions due to aging and disease.

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General Subjects
  • Patchaporn Seekhiaw, Piriya Pinthong, Piyasan Praserthdam, Bunjerd Jon ...
    2022 Volume 71 Issue 1 Pages 141-149
    Published: 2022
    Released on J-STAGE: January 08, 2022
    Advance online publication: December 08, 2021
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    The MgAlO catalyst was obtained from thermal decomposition of the MgAl-LDH catalyst having Mg/Al molar ratio of 5. The catalytic Guerbet reaction of ethanol was investigated to determine the effect of WHSV and nitrogen flow rate on butanol production and product distribution. It was performed in a fixed-bed microreactor under continuous flow of vaporized ethanol mixed with N2. The MgAlO catalyst had high total basic sites and high total acid sites that were crucial for ethanol Guerbet reaction. The MgAlO catalyst showed the highest butanol selectivity at 300℃ under WHSV = 3.10 h-1 and nitrogen flow rate = 3,600 mL/h, and the highest butanol yield at 400℃ under WHSV = 3.10 h-1 and nitrogen flow rate = 900 mL/h. It can be summarized that in order to enhance the butanol yield, the low WHSV is preferred to increase the contact time of ethanol and catalyst under moderate temperature.

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