• Title/Summary/Keyword: Ethyl pyruvate

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Asymmetric Hydrogenation of Ethyl Pyruvate over Bimetallic Rh-Pt/Al2O3 Catalysts Modified with Dihydrocinchonidine (Dihydrocinchonidine으로 개질된 Rh-Pt/Al2O3 이원금속 촉매를 이용한 Ethyl Pyruvate의 비대칭 수소화)

  • Cho, Hong-Baek;Kang, Joon-seok;Park, Yeung-Ho
    • Applied Chemistry for Engineering
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    • v.17 no.4
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    • pp.369-374
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    • 2006
  • $Rh-Pt/Al_{2}O_{3}$ catalysts were used for the first time to study its reaction characteristics in the asymmetric hydrogenation of ethyl pyruvate. The catalysts were prepared either by impregnation of Rh on a commercial $Pt/Al_{2}O_{3}$ or by sequential impregnation of Rh followed by impregnation of Pt on $Al_{2}O_{3}$. Reaction rate and enantiomeric excess (ee%) were compared according to the preparation method, Rh contents, and the reduction temperature of the catalyst. The physical characteristics of the catalysts were analyzed using XRD and TEM. Bimetallic $Rh-Pt/Al_{2}O_{3}$ catalysts showed an improved reaction rate and optical purity (63.6 ee%) with increasing the reduction temperature. The variation of the Rh contents as well as the preparation method elicited a big difference on the reaction rate, while enantiomeric excess (ee%) was lower (56~60%) with all bimetallic catalysts than with monometallic $Pt/Al_{2}O_{3}$ catalyst.

Studies on Cysteine desulfhydrase Produced by Bacteria(Part II) Enzymatic Preparation of L-Cysteine Derivatives by Cysteinedesulfhydrase from Aerobacter aerogenes. (Bacteria가 생산하는 Cysteinedesulfhydrase에 관한 연구(제이보) L-Cysteine 유도체의 효소적 합성에 관하여)

  • 최용진;양한철
    • Microbiology and Biotechnology Letters
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    • v.2 no.1
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    • pp.45-50
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    • 1974
  • 1 With cysteinedesulfhydrase (E. C.4.4.1.1.) from Aerobactor aerogenes, an enzyme which catalyzes the stoichiometric conversion of L-cysteine to pyruvate, ammonia and sulfide, reversibility of the degradation of L-cysteine was investigated. It was found that the enzyme also catalized the reverse reaction of $\alpha$, $\beta$-elimination to synthesize L-cysteine derivatives from pyruvate, ammonia and sulfides when large amounts of substrates were added to the reaction mixtures. 2. The synthetic reaction by cysteinedesulfhydrase proceeded linearly with incubation time and enzyme concentrations. The optimal pH for the synthetic reaction was 10.0. 3. The results of the isolation and identification of the products showed that the L-cysteine derivatives synthesized by this enzymatic method were identical with S-methyl-L-cysteine and S-ethyl-L-cysteine respectively.

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A Simple and Sensitive High Performance Liquid Chromatography-Electrospray Ionization/Mass Spectrometry Method for the Quantification of Ethyl Pyruvate in Rat Plasma

  • Kim, Hyun-Ji;Kim, Seung-Woo;Lee, Ja-Kyeong;Yoon, Sung-Hwa
    • Bulletin of the Korean Chemical Society
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    • v.32 no.4
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    • pp.1221-1227
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    • 2011
  • Ethyl pyruvate (EP) is known as a scavenger of reactive oxygen species (ROS) in the body through its role in the donation of diketone groups to metals to form an EP-metal complex. In order to develop a method for the quantification of EP in biological media, a sensitive and specific, high-performance liquid chromatographyelectrospray ionization-mass spectrometry (HPLC-ESI/MS) method is used to determine the EP-alkali metal ion binding species. The analyte was separated on a ZORBOX SB-C8 ($3.5{\mu}m$, $30mm{\times}2.1mm$ I.D.) column and analyzed in selected ion monitoring (SIM) mode with a positive ESI interface using the m/z 255 $[2M + Na]^+$ ion. The method was validated over the concentration range of $0.5-60.0\;{\mu}g$/mL under 1/9 (v/v) of acetonitrile/methanol solvent system with flow rate 0.05 mL/min. The limit of quantification (LOQ) was $0.5{\mu}g$/mL.

Effects of Ethyl Pyruvate on Allodynia, TNF-${\alpha}$ Expression, and Apoptosis in the Dorsal Root Ganglion after Spinal Nerve Ligation Injury

  • Choi, Dae-Kee;Leem, Jeong-Gill;Shin, Jin-Woo;Suh, Jeong-Hun
    • The Korean Journal of Pain
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    • v.25 no.4
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    • pp.213-220
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    • 2012
  • Background: It has been demonstrated that the expression of tumor necrosis factor-${\alpha}$ (TNF-${\alpha}$) and apoptotic cell death in the dorsal root ganglion (DRG) following spinal nerve constriction injury play a role in the initiation and continuation of hyperalgesia and allodynia. The present study was designed to investigate the effects of ethyl pyruvate (EP) on mechanical and cold allodynia, TNF-${\alpha}$ expression, and apoptosis in DRG after spinal nerve ligation injury. Methods: Rats were divided into 3 groups: control, pre-EP, and post-EP. EP (50 mg/kg) was intraperitoneally injected 30 minutes before (pre-EP) or after (post-EP) surgery. Behavioral tests to determine mechanical and cold allodynia were conducted before surgery and 4 and 7 days after surgery. Seven days after surgery, TNF-${\alpha}$ protein levels in DRG were evaluated by enzyme-linked immunosorbent assay, and DRG apoptosis was determined by immunohistochemical detection of activated caspase-3. Results: Treatment with EP significantly reduced mechanical and cold allodynia following spinal nerve ligation injury. TNF-${\alpha}$ protein levels in the pre-EP ($4.7{\pm}1.2$ pg/200 ${\mu}g$; P < 0.001) and post-EP ($6.4{\pm}1.8$ pg/200 ${\mu}g$; P < 0.001) groups were 2-3 times lower than the control group ($14.4{\pm}1.2$ pg/200 ${\mu}g$). The percentages of neurons and satellite cells that co-localized with caspase-3 were also significantly lower in the pre-EP and post-EP groups than the control group. Conclusions: These results demonstrate that EP has a strong anti-allodynic effect that acts through the inhibition of TNF-${\alpha}$ expression and apoptosis in DRG after spinal nerve ligation injury.

Effect of Ethyl Pyruvate on Paclitaxel-Induced Neuropathic Pain in Rats

  • Choi, Seong Soo;Koh, Won Uk;Nam, Jae Sik;Shin, Jin Woo;Leem, Jeong Gill;Suh, Jeong Hun
    • The Korean Journal of Pain
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    • v.26 no.2
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    • pp.135-141
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    • 2013
  • Background: Although paclitaxel is a widely used chemotherapeutic agent for the treatment of solid cancers, side effects such as neuropathic pain lead to poor compliance and discontinuation of the therapy. Ethyl pyruvate (EP) is known to have analgesic effects in several pain models and may inhibit apoptosis. The present study was designed to investigate the analgesic effects of EP on mechanical allodynia and apoptosis in dorsal root ganglion (DRG) cells after paclitaxel administration. Methods: Rats were randomly divided into 3 groups: 1) a control group, which received only vehicle; 2) a paclitaxel group, which received paclitaxel; and 3) an EP group, which received EP after paclitaxel administration. Mechanical allodynia was tested before and at 7 and 14 days after final paclitaxel administration. Fourteen days after paclitaxel treatment, DRG apoptosis was determined by activated caspase-3 immunoreactivity (IR). Results: Post-treatment with EP did not significantly affect paclitaxel-induced allodynia, although it tended to slightly reduce sensitivities to mechanical stimuli after paclitaxel administration. After paclitaxel administration, an increase in caspase-3 IR in DRG cells was observed, which was co-localized with NF200-positive myelinated neurons. Post-treatment with EP decreased the paclitaxel-induced caspase-3 IR. Paclitaxel administration or post-treatment with EP did not alter the glial fibrillary acidic protein IRs in DRG cells. Conclusions: Inhibition of apoptosis in DRG neurons by EP may not be critical in paclitaxel-induced mechanical allodynia.

The Effects of Ethyl Pyruvate on Lipopolysaccharide-induced Acute Lung Injury (리포다당질에 의한 급성폐손상에서 Ethyl Pyruvate의 효과)

  • Lee, Seung Hyeun;Yoon, Dae Wui;Jung, Jin Yong;Lee, Kyung Joo;Kim, Se Joong;Lee, Eun Joo;Kang, Eun Hae;Jung, Ki Hwan;Lee, Sung Yong;Lee, Sang Yeub;Kim, Je Hyeong;Shin, Chol;Shim, Jae Jeong;In, Kwang Ho;Kang, Kyung Ho;Yoo, Se Hwa
    • Tuberculosis and Respiratory Diseases
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    • v.61 no.4
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    • pp.374-383
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    • 2006
  • Background: Ethyl pyruvate (EP) is a derivative of pyruvate that has recently been identified by both various in vitro and in vivo studies to have antioxidant and anti-inflammatory effects. The aim of this study was to determine the effect of EP on lipopolysaccharide (LPS)-induced acute lung injury (ALI). Methods: 5 weeks old, male BALB/c mice were used. ALI was induced by an intratracheal instillation of LPS 0.5mg/Kg/$50{\mu}L$ of saline. The mice were divided into the control, LPS, EP+LPS, and LPS+EP groups. In the control group, balanced salt solution was injected intraperitoneally 30 minutes before or 9 hours after the intratracheal instillation of saline. In the LPS group, a balanced salt solution was also injected intraperitoneally 30 minutes before or 9 hours after instillation the LPS. In the EP+LPS group, 40mg/Kg of EP was injected 30 minutes before LPS instillation. In the LPS+EP group, 40mg/Kg of EP was injected 9 hours after LPS instillation. The TNF-$\alpha$ and IL-6 concentrations in the bronchoalveolar lavage fluid (BALF), and that of NF-$\kappa$B in the lung tissue were measured in the control, LPS and EP+LPS groups at 6 hours after instillation of saline or LPS, and the ALI score and myeloperoxidase (MPO) activity were measured in all four groups 24 and 48 hours after LPS instillation, respectively. Results: The TNF-$\alpha$ and IL-6 concentrations were significantly lower in the EP+LPS group than in the LPS group (p<0.05). The changes in the concentration of these inflammatory cytokines were strongly correlated with that of NF-$\kappa$B (p<0.01). The ALI scores were significantly lower in the EP+LPS and LPS+EP groups compared with the LPS group (p<0.05). In the EP+LPS group, the MPO activity was significantly lower than the LPS group (p=0.019). Conclusion: EP, either administered before or after LPS instillation, has protective effects against the pathogenesis of LPS-induced ALI. EP has potential theurapeutic effects on LPS-induced ALI.

A Convenient Allylation of 1,n-Dicarbonyl Compounds Using Organoindium Reagents

  • Lee, Pil Ho;DongSeo, Mun;Lee, Gu Yeon
    • Bulletin of the Korean Chemical Society
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    • v.22 no.12
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    • pp.1380-1384
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    • 2001
  • The chemoselective reactions of 1,n-dicarbonyl compounds with allyl halides using indium metal were investigated. $\alpha-Ketoesters$ such as ethyl pyruvate, ethyl 3-methyl-2-oxobutyrate and ethyl benzoylformate reacted with a variety of allyl halides i n the presence of indium to afford hydroxy unsaturated carbonyl compounds in good to excellent yields in MeOH/HCl at $25^{\circ}C.$ For the allyl bromide, the presence of various substituents at the $\alpha$ or $\gamma$ position exhibited little effects on both the reaction rates and yields. Ethyl acetoacetate or ethyl levulinate was treated with allylindium reagent to give hydroxy unsaturated carbonyl compounds in good yield. These results mean that both reactivity and selectivity are independent of the distance between carbonyl groups. 2,3-Butanedione or 1-phenyl-1,2-propanedione reacted with allylindium to produce monoallylation product as major compound.

Spectrophotometric, pH-metric and Conductometric Studies on Some 3-Arylhydrazone Derivatives of (2-Thenoyl) Ethylpyruvate) (2-Thenoyl Ethylpyruvate의 몇 가지 3-Arylhydrazone 유도체에 대한 분광광도법, pH 및 전도도법 연구)

  • El-Dossoki, F. I.;El-Seify, F. A.
    • Journal of the Korean Chemical Society
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    • v.50 no.2
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    • pp.99-106
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    • 2006
  • The electronic absorption spectra of [3-(2-thenoyl) 3-(p-NO2-phenylhydrazone) ethyl pyruvate] (I), p-Br (II) and p-CH3 (III) were studied in ethanol and the spectra comprise four absorption bands which assigned to the corresponding electronic transition. The pK values of these compounds have been determined spectrophotometrically and pH-metrically, the results shown that the interval range for color change of compound (I) is (8-10) similar to that of phenolphethalin indicator, indicating that this compound can be used as acid-base indicator. The successive stability constants of the compounds under study with some transition elements (Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), UO2(II), La(III) and Zr(IV) have been determined pH- metrically. Stoichiometric complexes with ratios 1:1 and 1:2 (M: L) were formed for all metals. The pK of the three derivatives and the values of the stability constant (logK) of the complexes have the order; III > II > I. Also conductometric titrations have been carried out and the results show that this titration can be used for determination of both the metal ion and the ligand concentrations by each others.

Effects of Alanine and Glutamine on Alcohol Oxidation and Urea Nitrogen Production in Perfused Rat Liver

  • Yim, Jungeun;Chyun, Jonghee;Cha, Youngnam
    • Nutritional Sciences
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    • v.6 no.4
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    • pp.189-194
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    • 2003
  • Most of the ethyl alcohol consumed by humans is oxidized to acetaldehyde in the liver by the cytoplasmic alcohol dehydrogenase (ADH) system. For this ADH-catalyzed oxidation of alcohol, $NAD^+$ is required as the coenzyme and $NAD^+$becomes reduced to NADH. As the $NAD^+$becomes depleted and NADH accumulates, alcohol oxidation is reduced. For continued alcohol oxidation, the accumulated NADH must be quickly reoxidized to $NAD^+$, and it is this reoxidation of NADH to $NAD^+$that is known to be the rate-limiting step in the overall oxidation rate of alcohol The reoxidation of NADH to $NAD^+$is catalyzed by lactate dehydrogenase in the cytoplasm of hepatocytes, with pyruvate being utilized as the substrate. The pyruvate may be supplied from alanine as a result of amino acid metabolism via the urea cycle. Also, glutamine is thought to help with the supply of pyruvate indirectly, and to activate the urea cycle by producing $NH_3$. Thus, in the present study, we have examined the effects of alanine and glutamine on the alcohol oxidation rate. We utilized isolated perfused liver tissue in a system where media containing alanine and glutamine was circulated. Our results showed that when alanine (5.0mM) was added to the glucose-free infusion media, the alcohol oxidation rate was increased by 130%. Furthermore, when both glutamine and alanine were added together to the infusion media, the alcohol oxidation rate increased by as much as 190%, and the rate of urea nitrogen production increased by up to 200%. The addition of glutamine (5.0mM) alone to the infusion media did not accelerate the alcohol oxidation rate. The increases in the rates of alcohol oxidation and urea nitrogen production through the addition of alanine and glutamine indicate that these amino acids have contributed to the enhanced supply of pyruvate through the urea cycle. Based on these results, it is concluded that the dietary supplementation of alanine and glutamine could contribute to increased alcohol detoxification through the urea cycle, by enhancing the supply of pyruvate and $NAD^+$to ensure accelerated rates of alcohol oxidation.

Effects of modified atmosphere packaging (MAP) and vaporized ethyl pyruvate (EP) treatment for the shelf life of 'Seolhyang' strawberries (딸기 '설향' 품종의 MAP 및 ethyl pyruvate 처리의 유통기한 연장 효과 연구)

  • Kim, Jinse;Park, Jong Woo;Park, Seok Ho;Choi, Dong Soo;Kim, Yong Hoon;Lee, Soo Jang;Park, Chun Wan;Lee, Jung Soo;Cho, Byoung-Kwan
    • Food Science and Preservation
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    • v.24 no.3
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    • pp.351-360
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    • 2017
  • We have studied the technology to extend the storage period of 'Seolhyang' strawberries using modified atmosphere package (MAP) and ethyl pyruvate (EP) treatment for domestic distribution and export. The selected ripe strawberries harvested on December 28, 2016 at the Sancheong farmhouse were transported to the laboratory for 2 h and tested. After a day's precooling at $4^{\circ}C$, the strawberries were divided into seven experimental groups. These groups were control, active MAP using low density polyethylene (LDPE), active MAP using polyamide (PA), active MAP using PA with EP treatment, passive MAP using LDPE, passive MAP using PA and passive MAP using PA with EP treatment. Quality analysis was carried out every 4 days during the storage period of 16 days. During the storage period of 16 days, MAP decreased from 3.5% to less than 1.1% in weight loss ratio compared with control, and decreased from 36% to less than 7% in fungal incidence. In the case of fungi in the EP treatment group, hyphae did not grow on the outside of the strawberry but grew to the inside. This tendency was similar to that in the low oxygen and high carbon dioxide environment of the MAP, the mycelium of the fungus did not grow outside of the strawberry. Fungi are the biggest problem in the distribution and export of strawberries, and these results suggest that MAP alone could inhibit mold and increase shelf life.