• The Korean Journal of Physiology and Pharmacology
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• v.22 no.1
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• pp.53-61
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• 2018

Ethyl linoleate is an unsaturated fatty acid used in many cosmetics for its various attributes, such as antibacterial and anti-inflammatory properties and clinically proven to be an effective anti-acne agent. In this study, we investigated the effect of ethyl linoleate on the melanogenesis and the mechanism underlying its action on melanogenesis in B16F10 murine melanoma cells. Our results revealed that ethyl linoleate significantly inhibited melanin content and intracellular tyrosinase activity in ${\alpha}$-MSH-induced B16F10 cells, but it did not directly inhibit activity of mushroom tyrosinase. Ethyl linoleate inhibited the expression of microphthalmia-associated transcription factor (MITF), tyrosinase, and tyrosinase related protein 1 (TRP1) in governing melanin pigment synthesis. We observed that ethyl linoleate inhibited phosphorylation of Akt and glycogen synthase kinase $3{\beta}$ ($GSK3{\beta}$) and reduced the level of ${\beta}-catenin$, suggesting that ethyl linoleate inhibits melanogenesis through $Akt/GSK3{\beta}/{\beta}-catenin$ signal pathway. Therefore, we propose that ethyl linoleate may be useful as a safe whitening agent in cosmetic and a potential therapeutic agent for reducing skin hyperpigmentation in clinics.

• Journal of the Korean Applied Science and Technology
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• v.9 no.2
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• pp.175-179
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• 1992

In order to investigate the effect of tannic acid and ${\alpha}$-tocopherol on methyl linoleate autoxidation and on inhibition activity of lipoxygenase in phospholipid, the rate of formation of methyl linoleate hydroperoxide was measured by HPLC. The reaction mixture contained methyl linoleate 70mM, radical initiator AMVN 0.7mM, tannic acid and ${\alpha}$-tocopherol 0.7mM, each, in a mixture of hexane/isopropanol(1 : 1, v/v). Under this reaction condition, tannic acid was good enough antioxidant. The tannic acid and ${\alpha}$-tocopherol for the inhibition activivity of lipoxygenase were measured at the reaction conditions: phospholipid $1{\mu}M$. tannic acid and ${\alpha}$-tocopherol were reacted as an inhibitor of lipoxygenase in phospholipid, especialy in phosphatidy lcholine.

• Tuberculosis and Respiratory Diseases
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• v.77 no.5
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• pp.203-208
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• 2014

Background: In this study, we investigated whether lobetyolin, lobetyol, and methyl linoleate derived from Codonopsis pilosula affect MUC5AC mucin secretion, production, and gene expression from airway epithelial cells. Methods: Confluent NCI-H292 cells were pretreated with lobetyolin, lobetyol, or methyl linoleate for 30 minutes and then stimulated with phorbol 12-myristate 13-acetate (PMA) for 24 hours. The MUC5AC mucin gene expression, and mucin protein production and secretion were measured by reverse transcription polymerase chain reaction and enzyme-linked immunosorbent assay, respectively. Results: Lobetyolin, lobetyol, and methyl linoleate inhibited the gene expression of MUC5AC mucin induced by PMA; lobetyolin did not affect PMA-induced MUC5AC mucin production. However, lobetyol and methyl linoleate inhibited the production of MUC5AC mucin; lobetyolin and lobetyol did not significantly affect PMA-induced MUC5AC mucin secretion from NCI-H292 cells. However, methyl linoleate decreased the MUC5AC mucin secretion. Conclusion: These results suggest that among the three compounds, methyl linoleate can regulate gene expression, production, and secretion of MUC5AC mucin by directly acting on the airway epithelial cells.

• Korean Journal of Food Science and Technology
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• v.28 no.3
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• pp.440-445
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• 1996

An attempt was made to study the relative composition of Monohydroperoxide isomers of methyl linoleate oxidized to different peroxide values at 60, 90, 120 and $150^{\circ}C$, respectively. HPLC was used to analyze and isolate the monohydroperoxide isomers fractionated by silica gel column after reduction with NaBH.. GC-MS was used to identify four monnhydroperoxide isomers as trimethylsilyl (TMS) in mixtures of oxidized methyl linoleate In the geometrical isomers, the proportions of 9/13-OOH-trans, trant-diene were higher than those of 9/13-OOH-cis, trans-diene at $60^{\circ}C$ and $90^{\circ}C$. However in the initial stage at $150^{\circ}C$, the proportions of 9/13-OOH-cis, trans-diene were slightly higher than those of 9/13-OOH-trans, trans-diene. In case of positional isomers, equal proportions of 9-OOH-10, 12-diene and 13-OOH-9, 11-diene were found in all samples of methyl linoleate oxidized at different temperatures and peroxide levels.

• Korean Journal of Food Science and Technology
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• v.25 no.6
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• pp.614-619
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• 1993

Oxidation mechanisms of methyl linoleate with ${\alpha}-Tocopherol$(TML) were investigated by determining oxidized products using GC-MS during oxidation at $37^{\circ}C$ for 9 days. Oxidized products of TML were found to be methyl octanoate, methyl-8-(2-furyl)-octanoate, 9,13-trans, cis isomer and 9,13-trans, trans isomer. In previous report, oxidation products of methyl linoleate(ML) were methyl-8-(2-furyl)octanoate, 9,13-trans, cis hydroperoxide isomer, 9,13-trans, trans hydroperoxide isomer, and 9-TMSO-12,13-epoxy-10-octadecenoate. In the case of ML, 9-TMSO-12,13-epoxy-l0-octadecenoate was produced instead of methyl octanoate in TML. ${\alpha}-Tocopherol$ quinone, as a major oxidized product of ${\alpha}-Tocopherol$ was formed at the 6th day of oxidation. ${\alpha}-Tocopherol$ quinone was produced rather quickly in lipid media than aqueous media. In oxidation of methyl linoleate, it was shown that the first oxidized product was methyl-9,13-hydroxy-octadecadienoate. As second products, methyl-8-(2-furyl)-octanoate, 9-TMSO-12,13-epoxy-10-octadenoate, and methyl octanoate were oxidized from methyl-9-hydroxy-10-trans, 12-trans-octadecadienoate.

• Korean Journal of Food Science and Technology
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• v.31 no.3
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• pp.600-605
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• 1999

Methyl linoleate was oxidized at 60, 90, 120 and $150^{\circ}C$, respectively, with sparging oxygen for different periods of time. On the basis of the peroxide values determined at four temperatures, four heating times were chosen for the analysis of physicochemical parameters, such as peroxide value, total oxidation products, polymer content, viscosity, refractive index and characteristics of thermal degradation by DSC (Differential Scanning Calorimeter). The content of peroxide linkage (C-O-O-C) polymer and ether or carbon to carbon linkage (C-O-C/C-C) polymer were analyzed by High Performance Size Exclusion Chromatography (HPSEC). The polymer formed at four temperatures was qualitatively identified as dimer. The polymer with peroxide linkage (C-O-O-C) were detected from methyl linoleate oxidized at $60^{\circ}C\;and\;90^{\circ}C$, but they were not detected from methyl linoleate oxidized at $120^{\circ}C\;and\;150^{\circ}C$. The enthalpy changes increased as peroxide value increased whereas maximum degradation temperature decreased. The highest correlation coefficients were obtained between maximum degradation temperature $(T_m)$, exothermic enthalpy changes and peroxide value, peroxide linkage (C-O-O-C) polymer content.

• Preventive Nutrition and Food Science
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• v.1 no.2
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• pp.244-251
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• 1996

Molecular weight and partial amino acid sequence of the cis, 9-cis, 12-octadecadienoate isomerase(linoleate isomerase) of Butyrivibrio fibrisovens A-38 were determined. Linoleate isomerase was isolated from the bac-teria cultured anaerobically and purified by ultracentrifugation in conjunction with Sepharose 6B column chro-matography, Phenyl sepharose 4B column chromatography and fast performance liquid chromatography (EPLC). The isomerase was single polypeptide with 19KD of molecular weight, when determined by SDS-PAGE. Fourteen amino acids sequence of N-terminal of the linoleate isomerase was N-GEIDKYPRIIKQQ determined by Edman method.

• Journal of the Korean Society of Food Science and Nutrition
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• v.13 no.4
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• pp.444-450
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• 1984

Effects of muscle extracts of five species of fish and shell-fish, mackerel, jack mackerel, yellow corvenia, shrimp and baby-neck clam, on lipid oxidation were investigated using a model system consisting of methyl linoleate absorbed in micro crystalline cellulose and extracts of fishes. Ethanol extracts of both mackerel and jack mackerel apparently showed inhibitory effect on the oxidation of methyl linoleate, while the extract of yellow corvenia, and baby-neck clam showed a slight catalyzed effect on contrary. The ethanol extract of shrimp, however, revealed no effect on the oxidation of methyl linoleate. When the ethanol extracts were dialyzed, the outer fractions of dark fleshed fish had a strong inhibitory effect on the oxidation of methyl linoleate, while the inner fractions did not. The outer fraction of yellow corvenia showed catalyzed effect, but the inner fraction inhibited the oxidation slightly. The outer fraction of shrimp had a strong inhibitory action, but the inner fraction showed no effect. The methanol-water fraction of chloroform-methanol extract of shrimp showed a quite strong inhibitory effect on the oxidation, whereas that of four other samples did the same levels of effect as ethanol extracts.

• Journal of the East Asian Society of Dietary Life
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• v.5 no.1
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• pp.87-93
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• 1995

The oxidized mixture of lipid(methyl linoleate) and phenolics(phloroglucinol) at 37$^{\circ}C$, 82$m\ell$ O/min., for 9 days were separated each by C cartridge and silica cartridge making use of different eluting solvent. And the oxidation products were analyzed by HPLC. In conclusion, the oxidized mixture were separated into methyl linoleate and phloroglucinol by cartridge on HPLC. and also in this experiment, separated methyl linoleate and phloroglucinol could be analyzed in the common eluant, water and acetonitrile on HPLC. SEP-PAK cartridges were used almost sample purification until now, but under the various eluting solvents and conditions, cartridge will be expected to mini columns which can separate different polarity materials.

• Journal of the Korean Society of Food Science and Nutrition
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• v.12 no.2
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• pp.84-92
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• 1983

In order to investigate the effect of autoxidized oil on the enzyme activity in the mouse liver, we administered the fixed dosage of autoxidized methyl linoleate (AOML) to mice once per day for 20 days by using stomach tube and investigated the enzyme activity with the histochemical staining method and biochemical analysis. The following results were obtained: The POV, COV and TBA value in the liver of AOML group were significantly increased than those of normal group. The phospholipid, triglyceride and total cholesterol in the liver of AOML group were slightly increased than those of normal group. The activities of acid phosphatase and alkaline phosphatase in the liver of AOML group were increased than those of normal group but ATPase activity was decreased in the AOML group. The decrease of RNA, accumulation of fat and damage of liver cells were observed as the morphological changes in the liver of AOML group. From the results obtained we conclude that the autoxidized methyl linoleate influenced upon the various enzyme activity and the morphological changes in the mouse liver.