• Title/Summary/Keyword: Methyl Ester

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In Vitro Anticomplementary Activity of Phenylpropanoids from Agastache rugosa

  • Oh, Sei-Ryang;Jung, Keun Young;Lee, Hyeong-Kyu
    • Korean Journal of Pharmacognosy
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    • v.27 no.1
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    • pp.20-25
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    • 1996
  • In searching for anticomplementary compounds, three phenylpropanoids were isolated from the roots of Agastache rugosa and identified as rosmarinic acid (RA), rosmarinic acid methyl ester (RAM) and caffeic acid methyl ester (CAM) by NMR analyses. RA and RAM exhibited strong inhibitory activity on both the classical pathway (CP) and the alternative pathway (AP) of the complement system, in vitro, but CAM did far less than RA and RAM. $RAM-M1{\sim}-M5$, the methylated derivatives from the RAM, showed that the inhibitory activity was decreased in inverse proportion to the number of methylated groups and $RAM-M 2{\sim}-M4$, the isomers of two methylated hydroxyl groups, exhibited different inhibition activity.

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Production of Auxins and Auxin-like Compounds by Ginseng Growth-promoting Bacterium Pseudomonas fluorescens KGPP 207

  • Ten, Leonid N.;Lee, Mi Ja;Lee, Mee-Kyoung;Park, Hoon;Yoon, Jong Hyuk
    • Journal of Applied Biological Chemistry
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    • v.43 no.4
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    • pp.264-268
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    • 2000
  • High activity of acidic ethylacetate extract from the culture supernatant of ginseng growth-promoting bacterium Pseudomonas fluorescens KGPP 207 and its fractions were demonstrated through wheat coleoptile bioassay. The following auxins and auxin-like compounds were identified in these fractions by combined gas chromatography-mass spectrometry: indole-3-acetic acid, indole-3-acetic acid methyl and ethyl ester, indole-3-butyric acid, indole-3-lactic acid and its methyl ester, indole-3-propionic acid, indole-3-pyruvic acid, p-hydroxyphenyl acetic acid, p-hydroxyphenyl acetic acid methyl and ethyl ester, phenyl acetic acid and its methyl ester. The bacterium KGPP 207 belongs to the strain of P. fluorescens which produces plant growth regulators and its beneficial effect on the ginseng growth may be due to the formation of the identified compounds.

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Synthesis of Peptides Containing Optically Active 2-Amino-3-Phosphonopropionic Acid (광학 활성 2-Amino-3-Phosphonopropionic Acid의 새로운 합성 방법과 그를 포함하는 펩티드의 합성)

  • Kim Sang Bum;Cho Sung Ki;Han Jeong Sik;Kim Yong Joon;Hong Suk-In
    • Journal of the Korean Chemical Society
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    • v.38 no.7
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    • pp.516-520
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    • 1994
  • New synthetic method of optically active 2-amino-3-phosphonopropionic acid from L-serine was developed and their phosphonotripeptides, phthalylglycylglycyl-2-amino-3-(diethylphosphono)-propionic acid methyl ester and phthalylglycyl-L-phenylalanyl-2-amino-3-(diethylphosphono)propionic acid methyl ester, were synthesized by coupling reaction of amino acids with 2-amino-3-phosphonopropionic acid methyl ester.

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Benzylic Brominations with N-Bromosuccinimide in 1,2-Dichlorobenzene: Effective Preparation of (2-Bromomethyl-phenyl)-Methoxyiminoacetic Acid Methyl Ester

  • Lee, Sanghyuck;Ra, Choon Sup
    • Clean Technology
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    • v.22 no.4
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    • pp.269-273
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    • 2016
  • The benzylic bromination of methoxyimino-o-tolyl-acetic acid methyl ester (1) into (2-bromomethyl-phenyl)-methoxyimino-acetic acid methyl ester (2) using N-bromosuccinimide in the presence of 2,2'-azobisisobutyronitrile in various reaction solvents were investigated. The efficiency of the reaction was found to be sensitive to the kind of reaction solvents. We found the benzylic bromination of 1 to 2 can be performed in 1,2-dichlorobenzene as reaction solvent superior to the classic Wohl-Ziegler procedure in both reaction time and isolated yield (8 h vs 12 h, 92 vs 79%). This system provides clean, rapid, and high-yielding reactions with replacement of conventional solvents, such as tetrachloromethane, by less-toxic 1,2-dichlorobenzene.

Isolation an Identification of the Active Compounds from Green Mustard Leaves against Oxidative Stress in Bovine Brain Tissue (청겨자채 추출물의 뇌조직 내 Oxidative Stree 억제활성물질의 동정)

  • 이근종;김미리;심재석;황재관
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.30 no.5
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    • pp.943-948
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    • 2001
  • Green mustard leves were found to effectively prevent lipid peroxidation of bovine-brain tissue by ascor-bate/Fe system, The 50% methanol extracts mustard leaves were separated into four solvent faction using n-hexane,. EtOAc, n-BiOH and water. Then n-BiOH fraction exclusively exhibited the antioxidative activities at concentration above 100 $\mu\textrm{g}$/mL/ The n-BuOH fraction was further isolated to a single compound using TLC analysis and silica gel chromatography. The active antiodidative compounds were identified as sinapic acid methyl ester and ferulic acid methyl ester by $^{1}$H-NMR and $^{13}$ C-NMR, The sinapic acid methyl ester and ferulic acid methyl ester were prepared by methylating of sinapic acid and ferulic acid with diazomethane. The results strongly suggested that sinapic acid and ferulic acid could be emplyed as a potential antioxiative agents for preventing the bovine brain lipid peroxidation. lipid peroxidation.

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Synthesis of Methyl 3-methyloctanoate, the Key Perfume Component of African Orchid Aerangis confusa (아프리카 난 Aerangis confusa의 향기성분 methyl 3-methyloctanoate의 합성)

  • Kim, Hyun-Ok;Kim, Young-Ju;Kim, Bieong-Kil;Seu, Young-Bae
    • Applied Biological Chemistry
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    • v.48 no.3
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    • pp.292-295
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    • 2005
  • Synthesis of methyl 3-methyloctanoate, a perfume component isolated from African orchid Aerangis confusa (or Aerangis kirkii) was achieved starting from itaconic acid in 9 steps. Itaconic acid is one of the cheapest organic compounds which is the fermentation product of microorganism Asp. terreus. As the key intermediate, 2-methyl-1,4-butanediol 4-acetate was obtained through the enzymatic regioselective hydrolysis of 2-methyl-1,4-butanediol diacetate with lipase. After Grignard reaction and oxidation, 3-methyloctanoic acid was obtained and converted to the various corresponding scented esters with a variety of alkyl alcohols, and the resulting fragrancy esters are expected to be utilized as the aroma additive materials in cosmetics, drinks and foods.

Synthesis and Crystal Structure of Asymmetric Dimer of 1,2-Benzothiazine Derivatives Using Silver Oxide (Silver Oxide를 이용한 1,2-벤조티아진 유도체의 비대칭 중합체 합성 및 결정 구조)

  • Park, Myung Suk
    • Journal of the Korean Chemical Society
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    • v.42 no.6
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    • pp.657-663
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    • 1998
  • New asymmetric dimer, 7,7'-substituted (or H)-4-oxo-2,2'- dialkyl-l,l',2,2'-dibenzothiazine-3,3'dicarboxylic acid methyl ester-1,1,1',1'-tetraoxide 3,4'-yl ethers 2a-d were synthesized through the oxidative dimerization of 7-substituted (or H)-4-hydroxy-2-alkyl-1,2-benzothiazine-3-carboxylic acid methyl ester 1,1-dioxides la-d using silver oxide($Ag_2O$). 4-Oxo-2,2'-dialkyl-1,1'2,2'-dibenzothiazine-3,3'-dicarboxylic acid methyl ester-1,1,1',l'-tetraoxide 3,4'-yl ether 2c was identified by X-ray crystal structure determination.

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Characteristics of Volatile Flavor Compounds in Kochujang Prepared with Commercial Enzyme During Fermentation (효소제를 사용한 개량식고추장의 숙성과정 중 휘발성 향기성분의 특성)

  • Choi, Jin-Young;Lee, Taik-Soo
    • Applied Biological Chemistry
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    • v.46 no.3
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    • pp.207-213
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    • 2003
  • Kochujang was prepared for this study with raw material inoculated by commercial enzyme of amylase and protease. Volati1e compounds of Kochujang were analyzed using a purge and trap method during fermentation and identified with GC-MSD. Total 54 kinds of volatile flavor components like 16 kinds of alcohol, 16 kinds of ester, 7 kinds of acid, 4 kinds of aldehyde, 2 kinds of alkane, 1 kind of benzene, 3 kinds of ketone, 1 kind of alkene, 2 kind of amine, 1 kind of phenol, other 1 were found. Total number of volatile flavor detected right after manufacturing were 23 kinds like 3 kinds of alcohol, 6 kinds of ester, 3 kinds of aldehyde. After 30 days storage, total number of volatile flavor went up to 31 kinds with addition of 4 kinds of alcohol, 1 kind of ester. The total number of volatile flavor after 120 days storage were increased to 49 kinds. Volatile flavor compounds detected during the storage period were total 20 kinds like 6 kinds of alcohol such as 2-methyl-1-propanol, ethanol, 3-methyl-1-butanol, 5 kinds of ester such as ethyl acetate, isoamyl acetate, ethyl butyrate, 3 kinds of aldehyde such as butanal, acetaldehyde and 6 kinds of others. Even though peak area % of flavor compound varied depends on fermentation period, ethanol, ethyl acetate, ethyl butyrate, ethenone, 2-methyl-1-propanol, 3-methyl-1-butanol were the main compounds that consisted of flavor from Kochujang which was made with enzyme treatment. Ethly acetate showed the highest result in the treatment of right after manufacturing, 3-methyl-1-butanol had up to 90th day and ether were the other days.

Detection of Antifungal Endolichenic Fungi and Antifungal Compound (항진균성 지의류 내생 곰팡이 및 항진균성 물질의 탐색)

  • Cheon, Da-Mi;Jang, Da Som;Kim, Hye Young;Choi, Kap Seong;Choi, Sang Ki
    • Korean Journal of Microbiology
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    • v.49 no.2
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    • pp.165-171
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    • 2013
  • To isolate a novel antifungal compound, we obtained 571 kinds of endolichenic fungi from Lichen Bioresources Center and examined their antifungal abilities. Four fungi Stereocaulon sp. (1429), Stereocaulon sp. (1430), Cryptosporiopsis sp. (0156), and Graphis sp. (1245) showed high antifungal activity against Candida albicans when they grew in both liquid and solid media. We extracted the culture supernatants of these fungi with chloroform and then ethyl acetate. The chloroform fraction exhibited the highest anti-fungal activities when those fractions were examined for the growth inhibition of Candida albicans with disc diffusion method. To see information for the inhibitor present in chloroform fraction we employed GC-MS for the fractions of Stereocaulon sp. (1429). We found that hexamethylcyclotrisiloxane, decanoic acid, hexadecanonic acid-methyl ester, 14-octadecenoic acid-methyl ester, and octadecenoic acid-methyl ester were present more in chloroform fraction than in ethylacetate fraction. This indicates that those compounds could be possible antifungal candidates since antifungal activity of chloroform extract was two times higher than that of ethyl acetate extract.

Changes of Volatile Flavor Compounds in Traditional Kochujang during Fermentation (재래식고추장 숙성과정 중의 휘발성 향기성분의 특성)

  • Choi, Jin-Young;Lee, Taik-Soo;Park, Sung-Oh;Noh, Bong-Soo
    • Korean Journal of Food Science and Technology
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    • v.29 no.4
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    • pp.745-751
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    • 1997
  • Volatile flavor components of kochujang made from a glutinuous rice by traditional method were analyzed by using purge and trap method during fermentation, and identified with GC-MSD. Fifty-one volatile components including 19 alcohols, 13 esters, 7 acids, 3 aldehydes, 1 alkanes, 2 ketones, 2 amines, 1 benzene, 1 alkene, 1 phenol and others were found in kochujang made by traditional method. The number of volatile components detected immediately after making kochujang were 22 and increased to 41 components after 30 day of fermentation. The most number 51 of volatile components were found after 120 day of fermentation. Twenty-two volatile components were commonly found through the fermentation period such as acetic acid ethyl ester, ethanol, butanoic acid ethyl ester, 1-butanol, 2-methyl-1-propanol, 3-methyl-1-butanol, butanoic acid and ethenone. Peak area(%) of 1-butanol was the highest one among the volatile components at immediately after mashing while ethanol showed the highest peak area after 30 day of fermentation. Although the various types of peak areas of volatile components were shown in kochujang during the fermentation days, acetic acid-ethyl ester, ethanol, butanoic acid-ethyl ester, 1-butanol, 3-methyl-1-butanol and 2-methyl-1-propanol were mainly detected during fermentation. Those might be the major volatile components in kochujang made by traditional method.

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