• 제목/요약/키워드: free radical reaction

검색결과 240건 처리시간 0.018초

New Radical Allylation Reactions Using 2-Bromo-3-(phenylthio)propene and Their Application to the Synthesis of Carbocyclic Compounds

  • 유병우;Dennis P. Curran
    • Bulletin of the Korean Chemical Society
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    • 제17권11호
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    • pp.1009-1018
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    • 1996
  • A study on the application of vinyl radical cyclization via free radical allylation reaction in the synthesis of various carbocyclic compounds is described. In connection with this study, a new allyl transfer reagent, 2-bromo-3-(phenylthio)propene 1 is developed and it was shown that vinyl radical cyclization through free radical allylation reaction using reagent 1 provides a valuable approach to carbocyclic systems with a reactive exo-alkylidene moiety, which is advantageous for further transformations.

Chemical and Free Radical-scavenging Activity Changes of Ginsenoside Re by Maillard Reaction and Its Possible Use as a Renoprotective Agent

  • Yamabe, Noriko;Song, Kyung-Il;Lee, Woo-Jung;Han, Im-Ho;Lee, Ji-Hwan;Ham, Jung-Yeob;Kim, Su-Nam;Park, Jeong-Hill;Kang, Ki-Sung
    • Journal of Ginseng Research
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    • 제36권3호
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    • pp.256-262
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    • 2012
  • Reactive oxygen species play critical role in kidney damage. Free radical-scavenging activities of Panax ginseng are known to be increased by heat-processing. The structural change of ginsenoside and the generation of Maillard reaction products (MRPs) are closely related to the increased free radical-scavenging activities. In the present study, we have demonstrated the Maillard reaction model experiment using ginsenoside Re and glycine mixture to identify the renoprotective effect of MRPs from ginseng or ginsenosides. Ginsenoside Re was transformed into less-polar ginsenosides, namely Rg2, Rg6 and F4 by heat-processing. The free radical-scavenging activity of ginsenoside Re-glycine mixture was increased in a temperature-dependant manner by heatprocessing. The improved free radical-scavenging activity by heat-processing was mediated by the generation of antioxidant MRPs which led to the protection of LLC-PK1 renal epithelial cells from oxidative stress. Although the free radical scavenging activities of less-polar ginsenosides were weak, they could protect LLC-PK1 cells from oxidative stress. Therefore, MRPs and less-polar ginsenosides contributed to the combined renoprotective effects against oxidative renal damage.

Azotobacter vinelandii Shethna Flavoprotein 의 Free Radical 생성(生成)을 위(爲)한 전자전달물질(電子傳達物質)- (Electron Transport Carrier for the Free Radical Shethna Flavoprotein in Azotobacter vinelandii)

  • 전재근;골드 토-린
    • Applied Biological Chemistry
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    • 제16권1호
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    • pp.31-40
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    • 1973
  • Azotobacter vinelandi의 세포추출물(細胞抽出物)들이 Shethna flavoprotein의 free radical 형(型)으로의 전자전달기구(電子傳達機構)에 관하여 연구(硏究)하였다. 전자전달(電子傳達)에 관여도(關與度)가 높은 단백질(蛋白質)로 황색형광성단백질(黃色榮光性蛋白質)(protein I)과 갈색단백질(褐色蛋白質)(protein II)을 정제(精製)하였고 이들은 $N_2$ 기압하(氣壓下) 또는 aceton-dry ice 동결(凍結)저장하에서도 쉽게 실활(失活)되었고 반응속도(反應速度) 역시 너무 완만하여 생체내반응(生體內反應)이기에는 의문점을 보였다. 한편 세포추출물중(細胞抽出物中)의 FMN은 NADH에 의(依)하여 환원이 쉽게 이루어졌으며, 환원형 $FMNH_2$는 비효소적(非酵素的)으로 Shethna flavoprotein 의 free radical 을 형성(形成)시켰으며 , 효소적반응속도(酵素的反應速度)보다 15배(倍)의 높은 반응속도(反應速度)를 보였다. 비록 FMN이 생체내(生體內)에서 타(他)단백질과 비결합형(非結合型)으로 존재(存在)하지 않는다해도 FMN의 전자전달체(電子電達體)의 가능성(可能性)을 제시(提示)하였다.

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DNA Cleavage Induced by the Reaction of Salsolinol with Cu,Zn-Superoxide Dismutase

  • Kang, Jung-Hoon
    • Bulletin of the Korean Chemical Society
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    • 제28권12호
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    • pp.2329-2332
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    • 2007
  • Salsolinol, endogenous neurotoxin, is known to be involved in the pathogenesis of Parkinson's disease (PD). In the present study, we have investigated the oxidative damage of DNA induced by the reaction of salsolinol with Cu,Zn-SOD. When plasmid DNA incubated with salsolinol and Cu,Zn-SOD, DNA cleavage was proportional to the concentrations of salsolinol and Cu,Zn-SOD. The salsolinol/Cu,Zn-SOD system-mediated DNA cleavage was significantly inhibited by radical scavengers such as mannitol, ethanol and thiourea. These results indicated that free radicals might participate in DNA cleavage by the salsolinol/Cu,Zn-SOD system. Spectrophotometric study using a thiobarbituric acid showed that hydroxyl radical formation was proportional to the concentration of salsolinol and was inhibited by radical scavengers. These results indicated that hydroxyl radical generated in the reaction of salsolinol with Cu,Zn-SOD was implicated in the DNA cleavage. Catalase and copper chelators inhibited DNA cleavage and the production of hydroxyl radicals. These results suggest that DNA cleavage is mediated in the reaction of salsolinol with Cu,Zn-SOD via the generation of hydroxyl radical by a combination of the oxidation reaction of salsolinol and Fenton-like reaction of free copper ions released from oxidatively damaged SOD.

Mechanism of Lipid Peroxidation in Meat and Meat Products -A Review

  • Min, B.;Ahn, D.U.
    • Food Science and Biotechnology
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    • 제14권1호
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    • pp.152-163
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    • 2005
  • Lipid peroxidation is a primary cause of quality deterioration in meat and meat products. Free radical chain reaction is the mechanism of lipid peroxidation and reactive oxygen species (ROS) such as hydroxyl radical and hydroperoxyl radical are the major initiators of the chain reaction. Lipid peroxyl radical and alkoxyl radical formed from the initial reactions are also capable of abstracting a hydrogen atom from lipid molecules to initiate the chain reaction and propagating the chain reaction. Much attention has been paid to the role of iron as a primary catalyst of lipid peroxidation. Especially, heme proteins such as myoglobin and hemoglobin and "free" iron have been regarded as major catalysts for initiation, and iron-oxygen complexes (ferryl and perferryl radical) are even considered as initiators of lipid peroxidation in meat and meat products. Yet, which iron type and how iron is involved in lipid peroxidation in meat are still debatable. This review is focused on the potential roles of ROS and iron as primary initiators and a major catalyst, respectively, on the development of lipid peroxidation in meat and meat products. Effects of various other factors such as meat species, muscle type, fat content, oxygen availability, cooking, storage temperature, the presence of salt that affect lipid peroxidation in meat and meat products are also discussed.

Reactions of Two Isomeric Thiols with Thianthrene Cation Radical

  • Park, Hyun-Ju;Lee, Wang-Keun
    • Bulletin of the Korean Chemical Society
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    • 제26권9호
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    • pp.1335-1338
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    • 2005
  • Thianthrene cation radical perchlorate ($Th^{+{{\cdot}}}{ClO_4}^-$) reacted readily with two isomeric thiols, benzylthiol (1) and 4-methylbenzenethiol (7) in an acetonitrile solution at room temperature. From the reaction of 1, the major products, N-benzylacetamide (4) and benzyl sulfide (5), are characteristic of benzyl carbocations while the minor one, benzyl disulfide (6) implies free radical component of the reaction. It is unprecedented that the formation of a benzyl carbocation was caused by the extrusion of sulfur atoms from benzyl sulfur cations (3). In contrast, from the reaction of 7, only p-tolyl disulfide (10) was obtained from both sulfur radicals and cations. In the reaction of 7 the thio-extrusion was not observed from the p-tolyl sulfur cation (9). A thianthrene cation radical ($Th^{+{{\cdot}}}$) was reduced quantitatively to thianthrene (Th) in both reactions.

Lipid Peroxidation Induced by the Reaction of Cytochrome c with Hydrogen Peroxide

  • Kang, Jung-Hoon
    • Bulletin of the Korean Chemical Society
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    • 제27권6호
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    • pp.830-834
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    • 2006
  • Lipid peroxidation induced by the reaction of cytochrome c with $H_2O_2$ was investigated. When linoleic acid micelles or phosphatidyl choline liposomes were incubated with cytochrome c and $H_2O_2$, lipid peroxidation was increased in cytochrome c and $H_2O_2$ concentrations-dependent manner. Radical scavengers, azide, formate and ethanol prevented lipid peroxidation induced by the cytochrome c/$H_2O_2$ system. Iron specific chelator, desferoxamine also prevented the cytochrome c/$H_2O_2$ system-mediated lipid peroxidation. These results suggest that lipid peroxidation may be induced by the cytochrome c/$H_2O_2$ system via the generation of free radicals. Carnosine, homocarnosine and anserine are present in the muscle and brain of many animals and human. Previous studies show that these compounds have an antioxidant function. In the present study, carnosine, homocarnosine and anserine significantly prevented the cytochrome c/$H_2O_2$ system-mediated lipid peroxidation. Carnosine and related compounds also inhibited the free radical-generating activity of cytochrome c. The results suggest that carnosine, homocarnosine and anserine may prevent lipid peroxidation induced by the cytochrome c/$H_2O_2$ system through a free radical scavenging.

Reaction of ferritin with hydrogen peroxide induces lipid peroxidation

  • Yoon, Hung-Hwan;Lee, Myeong-Seon;Kang, Jung-Hoon
    • BMB Reports
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    • 제43권3호
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    • pp.219-224
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    • 2010
  • Lipid peroxidation is known to be an important factor in the pathologies of many diseases associated with oxidative stress. We assessed the lipid peroxidation induced by the reaction of ferritin with $H_2O_2$. When linoleic acid micelles or phosphatidyl choline liposomes were incubated with ferritin and $H_2O_2$, lipid peroxidation increased in the presence of ferritin and $H_2O_2$ in a concentration-dependent manner. The hydroxyl radical scavengers, azide and thiourea, prevented lipid peroxidation induced by the ferritin/$H_2O_2$ system. The iron specific chelator desferoxamine also prevented ferritin/$H_2O_2$ systemmediated lipid peroxidation. These results demonstrate the possible role of iron in ferritin/$H_2O_2$ system-mediated lipid peroxidation. Carnosine is involved in many cellular defense processes, including free radical detoxification. In this study, carnosine, homocarnosine, and anserine were shown to significantly prevent ferritin/$H_2O_2$ system-mediated lipid peroxidation and also inhibited the free radical-generation activity of ferritin. These results indicated that carnosine and related compounds may prevent ferritin/$H_2O_2$ system-mediated lipid peroxidation via free radical scavenging.