• Title/Summary/Keyword: Methyl

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Antifungal Activity of Lower Alkyl Fatty Acid Esters against Powdery Mildews

  • Choi, Gyung-Ja;Jang, Kyoung-Soo;Choi, Yong-Ho;Yu, Ju-Hyun;Kim, Jin-Cheol
    • The Plant Pathology Journal
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    • v.26 no.4
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    • pp.360-366
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    • 2010
  • In the course of a searhing environmental friendly antifungal compounds, we found that mixture of methyl esters of fatty acids obtained from soybean oil had potent control efficacy against barley powdery mildew (Blumeria graminis f. sp. hordei). In this study, ten alkyl fatty acid esters (AFAEs) were tested for in vivo antifungal activity against five plant diseases such as rice blast, rice sheath blight, tomato gray mold, tomato late blight and barley powdery mildew. Some AFAEs showed the most control efficacy against barley powdery mildew among the tested plant diseases. By 5-hr protective and 1-day curative applications, six AFAEs ($3,000\;{\mu}g/ml$), including methyl and ethyl palmitates, methyl and ethyl oleates, methyl linoleate, and methyl linolenate demonstrated both curative and protective activities against barley powdery mildew. In contrary, methyl laurate strongly controlled the development of powdery mildew on barley plants by curative treatment at a concentration of $333\;{\mu}g/ml$, but did not show protective activity even at $3,000\;{\mu}g/ml$. Under greenhouse conditions, the seven AFAEs ($1,000\;{\mu}g/ml$) except for methyl and ethyl stearates, and methyl caprylate also effectively controlled cucumber powdery mildew caused by Podosphaera xanthii. Among them, methyl and ethyl palmitates ($333\;{\mu}g/ml$) represented the most control activity of more than 68% against the disease. The results are the first report on the antifungal activity of methyl and ethyl esters of fatty acids against plant pathogenic fungi.

Anti-Viral Hemorrhagic Septicemia Virus (VHSV) Activity of 3-Methyl Catechol (바이러스성출혈성패혈증 바이러스 감염에 대한 3-Methyl Catechol의 항바이러스성 활성)

  • Cho, Se-Young;Min, Na-Rae;Kim, Young O;Kim, Duwoon
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.54 no.5
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    • pp.644-651
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    • 2021
  • Viral hemorrhagic septicemia virus (VHSV) is a fish pathogen responsible for causing enormous economic loss to the aquaculture industry not only in Korea but worldwide. Thus, it is necessary to identify natural compounds that can be used to control the spread of VHSV. In this study, the anti-VHSV activities of five catechol derivatives, i.e., catechol, pyrogallol, 3-methyl catechol, veratrole, and 3-methyl veratrole-extracted from green tea-were assessed. The antiviral activities of these derivatives were found to be dependent on their structure, i.e., the hydroxyl or methoxyl group and their substituent groups-on the benzene ring. Catechol, pyrogallol, and 3-methyl catechol exhibited relatively high 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities than veratrole, and 3-methyl veratrole. Moreover, 3-methyl catechol harboring a methyl substituent group increased the viability of the virus-infected cells and resulted in a 2.86 log reduction in the gene copies of VHSV N (per mL) in real-time PCR analysis. In conclusion, the catechol derivatives harboring hydroxyl groups in their benzene ring exhibited higher antioxidant activities than those harboring the methoxyl groups. However, catechol derivatives with a methyl group at the 3'-position of the benzene ring exhibited higher antiviral activity than those harboring a hydroxyl group. To our knowledge, this is the first study to evaluate the relationship between the structure and the anti-VHSV activity of catechol derivatives.

Synthesis of Dimer Acid Methyl Ester Using Base-treated Montmorillonite (염기 처리된 montmorillonite를 이용한 다이머산 메틸에스테르의 합성)

  • Yuk, Jeong Suk;Shin, Jihoon;Kim, Young-Wun
    • Tribology and Lubricants
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    • v.35 no.2
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    • pp.132-138
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    • 2019
  • In this study, we demonstrate the effects of the acidic properties of montmorillonite (MMT), which is commonly used as a catalyst, on the conversion and selectivity of the dimer acid methyl ester (DAME) synthesis. We synthesize DAME by the dimerization of conjugated linoleic acid methyl ester (CLAME) and oleic acid methyl ester using MMT KSF. Incidentally, trimer acid methyl ester was formed as a by-product during the DAME synthesis. There is a necessity to adequately adjust the strength and quantity of the acid site to control the selectivity of DAME. Therefore, we vary the pH of the MMT acid by using various metal hydroxides. The purpose of this study is to increase the yield of monocyclic dimer acid methyl ester, which is a substance with adequate physical properties for industrial applications (e.g., lubricant and adhesive, etc.), using a heterogeneous catalyst. We report the dimerization of fatty acid methyl ester by using base treated-KSF, and apply it to conjugated soybean oil methyl ester. Then, we transmute the acid site properties of KSF, such as pH of 5 wt.% slurry KSF and various alkali metals (Li, Na, K, Ca). Characterization of base treated-KSF using a pH meter, x-ray diffraction, inductively coupled plasma-atomic emission spectrometer, Brunauer-Emmett-Teller surface analysis, and temperature-programmed desorption. We conduct an analysis of CLAME and DAME using nuclear magnetic resonance spectroscopy, gas chromatography, and gel permeation chromatography. Through these experiments, we demonstrate the effects of the acidic properties of KSF on the conversion and selectivity of the DAME synthesis, and evaluate its industrial potential by application to waste vegetable oil.

The Effect of Methyl Gallate Isolated from Paeonia suffruticosa on Inflammatory Response in LPS-stimulated RAW264.7 Cells (목단피(牧丹皮) Methyl Gallate 성분의 항염증효능에 대한 연구)

  • Park, Yong-Ki;Min, Ji-Young;Lee, Je-Hyun
    • The Korea Journal of Herbology
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    • v.24 no.4
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    • pp.181-188
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    • 2009
  • Objectives : In this study, we investigated the effect of methyl gallate of Paeonia suffruticosa(Moutan Cortex Radicis) on inflammatory response in activated macrophages. Methods : RAW264.7 cells were incubated with different concentrations of methyl gallate of Paeonia suffruticosa for 30 min and then stimulated with or without LPS at indicated times. Cell toxicity was determined by MTT assay. The concentrations of nitric oxide (NO), prostaglandin $E_2$ ($PGE_2$) and inflammatory cytokines (TNF-$\alpha$, IL-6) were measured in culture medium by Griess assay, enzyme-immuno assay, and ELISA, respectively. The expressions of iNOS, COX-2 and cytokine mRNA and protein were determined by RT-PCR and Western blot, respectively. The $I{\kappa}-B{\alpha}$ degradation in cytosol and NF-${\kappa}B$ p65 translocation into nuclear of the cells were determined by Western blot. Results : Methyl gallate was significantly inhibited LPS-induced production of NO and PGE2 in RAW264.7 cells. Methyl gallate was also suppressed LPS-induced expression of iNOS and COX-2 mRNA and protein in the cells. Methyl gallate was inhibited LPS-induced production of TNF-$\alpha$ and IL-6 via suppression of their mRNA expressions. Methyl gallate blocked the NF-${\kappa}B$ pathway in LPS-stimulated RAW264.7 cells. Conclusions : This study suggests that methyl gallate of Paeonia suffruticosa may have an antiinflammatory property through suppressing inflammatory mediator production in activated macrophages.

Translocation of Tolclofos-methyl from Ginseng Cultivated Soil to Ginseng (Panax ginseng C. A. Meyer) and Residue Analysis of Various Pesticides in Ginseng and Soil (토양 중 잔류된 Tolclofos-methyl의 인삼(Panax ginseng C. A. Meyer)에 대한 이행 및 잔류 특성)

  • Kim, Ji Yoon;Kim, Hea Na;Saravanan, Manoharan;Heo, Seong Jin;Jeong, Haet Nim;Kim, Jang Eok;Kim, Kwan Rae;Hur, Jang Hyun
    • The Korean Journal of Pesticide Science
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    • v.18 no.3
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    • pp.130-140
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    • 2014
  • Recently, some of the previous studies reported that tolclofos-methyl is still exist in ginseng cultivated soil, even though it is has been banned for ginseng. Therefore, the current study was aimed to examine the levels of absorption and translocation of tolclofos-methyl from ginseng cultivated soil to ginseng root and leaf stem for the period of 1 year. For this study, ginseng plants were transplanted in pots and treated with $5.0mg\;kg^{-1}$ of tolclofos-methyl (50% WP). At the end of each interval periods (every three months) the samples (soil, roots and leaf stems) were collected and analyzed the absorption and translocation levels of tolclofos-methyl using gas chromatography and mass spectrometry (GC-MS). The limit of quantitation of tolclofos-methyl was found to be $0.02mg\;kg^{-1}$ and 70.0~120.0% recovery was obtained with coefficient of variation of less than 10% regardless of sample types. In this study, a considerable amount of translocation of tolclofos-methyl residues were found in soil (4.28 to $0.06mg\;kg^{-1}$), root (7.09 to $1.54mg\;kg^{-1}$) and leaf stem (0.79 to $0.69mg\;kg^{-1}$). The results show that the tolclofos-methyl was absorbted and translocated from ginseng cultivated soil to ginseng root and ginseng leaf stem and found to be decreased time-coursely. Secondly, we were also analyzed soil, root and leaf stems samples from Hongcheon, Cheorwon, Punggi and Geumsan by GC-MS/MS (172 pesticides), LC-MS/MS (74 pesticides). In this study, 43 different pesticides were detected ($0.01{\sim}7.56mg\;kg^{-1}$) in soil, root and leaf stem. Further, tolclofos-methyl was detected 4 times separately in root sample alone which is less ($0.01{\sim}0.05mg\;kg^{-1}$) than their maximum residual limit (MRL) in ginseng. Consequently, the results from both studies indicate the residues of tolclofos-methyl found in ginseng cultivated soil and ginseng ensuring their safety level. Moreover, long-term evaluations are needed in order to protect the soil as well as ginseng free from tolclofos-methyl residues.

Antioxidative Effectiveness and Oxidized Products in Mixture of Methyl Linoleate and Phenolic Compounds (Methyl Linoleate에 대한 Phenol성 물질의 항산화성과 산화 생성물)

  • Kim, Jeong-Sook;Lee, Gee-Dong;Kwon, Joong-Ho;Yoon, Hyung-Sik
    • Korean Journal of Food Science and Technology
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    • v.25 no.4
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    • pp.379-385
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    • 1993
  • Antioxidative effectiveness and oxidized products in mixture of methyl linoleate(ML) and phenolic compounds were investigated under oxygen blowing at $37^{\circ}C$ for 9 days. Caffeic acid (3,4-dihydroxy cinnamate ; CML) and phloroglucinol(1,3,5-trihydroxy benzene ; PML) showed higher antioxidative effectiveness for methyl linoleate than 0.05% ${\alpha}-tocopherol$ (TML). Oxidized products in ML group 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 CML group the oxidized products were methyl-8-(2-furyl)-octanoate, 9-trans, cis hydroperoxide isomer and 9-trans, trans hydroperoxide isomer, but 13-hydroxy isomer was not identified. It was shown that CML were oxidized more slowly than ML group and at 6th day of oxidation, caffeic quinone was found to be major oxidized product of caffeic acid. Oxidixed Products in PML group were methyl-8-(2-furyl)-octanoate, 9-trans, cis hydroperoxide isomer, and 9-trans, trans hydroperoxide isomer but phloroglucinol was not oxidized even at the 9th day of reaction.

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Factors and Recovery of Herbicide Phytotoxicity on Direct - seeded Rice - 3. Phytotoxicity of Herbicide by Three Elements of Fertilizer (직파(直播) 벼의 제초제(除草劑) 약해(藥害) 요인(要因)과 회복(回復) 연구(硏究) - 3. 비료 3요소에 따른 약해 발생 특성)

  • Im, Il-Bin;Usui, K.;Cho, S.Y.
    • Korean Journal of Weed Science
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    • v.18 no.1
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    • pp.20-27
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    • 1998
  • This experiments were conducted to investigate the effects of fertilizer for herbicides phytotoxicity of rice(Oryza sativa L. japonica cv Dongjin). The shoot and root growth of rice were inhibited more by pyrazosulfuron-ethyl or pyrazosulfuronethyl+molinate than bensulfuron methyl or bensulfuron methyl+dimepiperate application in nitrogen or nitrogen mixed solution. In phosphate or phosphate mixed solution, rice growth were inhibited more by bensulfuron methyl or bensulfuron methyl+dimepiperate than pyrazosulfuron-ethyl or pyrazosulfuron-ethyl+molinate application. In solution mixed with nitrogen and phosphate or fertilizer three elements, rice shoots were more. inhibited by pyrazosulfuron-ethyl or pyrazosulfuron-ethyl+molinate treatments, roots were inhibited more relatively by bensulfuron methyl or bensulfuron methyl+dimepiperate treatments. In all fertilizer solutions, rice plant heights were reduced by dimepiperate and molinate applications, but root growth was reduced only by nitrogen and phosphate mixed solution. Rice growth in sulfonylurea or their mixed herbicide application were more inhibited in high :nitrogen concentration arid by phosphate exclusion than by nitrogen exclusion culture.

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Physiological Changes of Eleocharis Kuroguwai During Period of Growth Inhibition Caused by Bensulfuron-methyl (Bensulfuron-methyl처리(處理) 후 올방개 생육억제기간(生育抑制期間) 중의 생리적(生理的) 변화(變化))

  • Chun, J.C.;Shin, H.S.
    • Korean Journal of Weed Science
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    • v.14 no.3
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    • pp.171-175
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    • 1994
  • Physiological changes in Eleocharis kuroguwai Ohwi as affected by bensulfuron-methyl {Methyl 2-[[[[[(4, 6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino] sulfonyl]methyl]benzoate} was determined to relate the characteristics with regrowth behavior. There were no changes in relative growth rate(RGR) during the period of growth cessation after application of bensulfuron-methyl. RGR's of the growth ceseased plants caused at 39 and 51 g/ha began to increase in between 25 and 30 days after application (DAA) and between 30 and 35 DAA, respectively. In untreated plant tuber carbohydrate rapidly decreased right after emergence and almost consumed within 40 days. There was no carbohydrate consumption during the period of growth cessation in bensulfuron-methyl-applied plant, but the content started to rapidly decrease with regrowth. Tuber viability lasted for 30 days in untreated plant, while tubers were viable for 60 and 70 days after application of bensulfuron-methyl at 39 and 51 g/ha, respectively. During the period of growth cessation the plants kept minimum respiration and photosynthesis, but with regrowth respiration and photosynthesis were resumed and rapidly increased.

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Co(Ⅲ) Complexes of Glycine Methyl Ester (Ⅰ). Preparation and Characterization (Co(Ⅲ) Glycine Methyl Ester 착물에 관한 연구 (제1보). 착물의 합성과 구조규명)

  • Ja Hong Kim;Sang Chul Shim
    • Journal of the Korean Chemical Society
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    • v.24 no.5
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    • pp.356-360
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    • 1980
  • Octahedral Co(Ⅲ) complexes of the glycine methyl ester have been prepared and characterized by elemental analysis, infrared, and NMR spectrum. Co(Ⅲ) glycine methyl ester complex has been isolated from the reaction of glycine and glycine methyl ester in aqueous solution by cation exchange resin, Dowex 50W-X8 (hydrogen form). It has been observed that the complexes have $C_1-cis(0-0), C_2-cis(0-0), trans(0-0)$ geometry.

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Polymerization of Methyl Methacrylate with Nickel $\alpha$-Diimine Catalysts: Effect of the Methyl Position in the Ligand

  • Kim, Il;Kim, Jae-Sung;Han, Byeong-Heui;Ha, Chang-Sik
    • Macromolecular Research
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    • v.11 no.6
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    • pp.514-517
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    • 2003
  • In the solution polymerizations of methyl methacrylate with (${\alpha}$-diimine)nickel(II)/methylaluminoxane (MAO), we observed effects of the position of two methyl substituents in the ligand on both the activities of the catalysts and the polymer microstructure. ${\alpha}$-Diimine nickel(II) catalysts gave syndiotactic-rich poly(methyl methacrylate) with high molecular weight and narrow molecular weight distribution.