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Development of Methods for Synthesis of Stereo-Selective Lipid Peroxides

Research Project

Project/Area Number 63850175
Research Category

Grant-in-Aid for Developmental Scientific Research

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionUNIVERSITY OF TOKYO

Principal Investigator

NIKI Etsuo  University of Tokyo, Faculty of Engineering, Professor, 工学部, 教授 (20011033)

Co-Investigator(Kenkyū-buntansha) YAMAMOTO Yorihiro  University of Tokyo, Faculty of Engineering, Assistant, 工学部, 助手 (60134475)
Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 1989: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1988: ¥3,000,000 (Direct Cost: ¥3,000,000)
KeywordsLipid Peroxides
Research Abstract

The Autoxidation of linolenic acid gave its 9- and 13-hydroperoxy derivatives. The autoxidation of fatty acids which have more than 3 double bonds gave cyclic peroxides as a by-product. But the addition of hydrogen donor in this system increased the selectivity for the formation of hydroperoxides. Four different hydroperoxides were formed from linolenic acid and six hydroperoxides from arachidonic acid. These hydroperoxides mentioned above were separated and purified by High Performance Liquid Chromatography. The autoxidation of phospholipids, triglycerides, and cholesteryl esters also gave their hydroperoxides, but the separation of their isomers were not easy.
About 3 nM of cholesteryl ester hydroperoidde was detected in human blood plasma. According to the retention times of the compounds, they were ascribed to be hydroperoxides of cholesteryl linolate and cholesteryl arachidonate. On the other hand, phospholipid hydroperoidde was not detected.
A methods for the detection of picomole level of fatty acid oxidation products was developed using monodansyl cadaverin as a fluorescent derivatizing reagent 1% method will be useful for the quantitation and qualification of lipid peroxides derived from biological samples.
It is very important know whether lipid peroxides are formed by non-enzymatic pathway or not. The methods developed in this project will be useful to answer this question.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (19 results)

All Other

All Publications (19 results)

  • [Publications] Yorihiro Yamamoto: "Presence of cholesteryl ester hydroperoxide in human blood plasma" Biochim.Biophys.Res.Comunn.165. 988-993 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Mitsunobu Matsuo: "Radical scavenging reactions of vitamin E and its model compound,2,2,5,7,8-pentamethylchroman-6-ol,in tertbutylperoxyl radical generating system" J.Am.Chem.Soc.111. 7179-7185 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Mareyuki Takahashi: "Scavenging of radicals by vitamin E in the membranes as studied by spin labelling" J.Am.Chem.Soc.111. 6350-6353 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 山本順寛(共著): "活性酸素と発光" 日本医学館,

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Etsuo Niki: "Lipid peroxidation in Biological Systems" American Oil Chemists' Society, 254 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Y.YAMAMOTO: "Presence of cholesterylester hydroperoxide in human blood plasma" Biochem. Biophys. Res. Comunn., 165, 988 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Matsuo: "Radical-scavenging reactions of vitamin E and its model compound, 2, 2, 5, 7, 8-pentamethylchroman-6-ol, in a tert-butylperoxy radical generating system" J. Am. Chem. Soc., 111, 7179 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Takahashi: "Scavenging of radicals by vitamin E in the membranes as studied by spin labeling" J. Am. Chem. Soc., 111, 6350 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] E.Niki: "Lipid peroxidation in biological systems" American Oil Chemists' Society (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yorihiro Yamamoto: "Presence of cholesteryl ester hydroperoxide in human blood plasma" Biochem.Biophys.Res.Commun. 165. 988-993 (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Matsuo: "Radical-scavenging reactions of vitamin E and its model compound,2,2,5,7,8,-pentamethylchroman-6-o1,in a tert-butylperoxyl radical generating system" J.Am.Chem.Soc.111. 7179-7185 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Takahashi: "Scavenging of radicals by vitamin E in the membranes as studied by spin labelling" J.Am.Chem.Soc.111. 6350-6353 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 山本順寛(共著): "活性酸素と発光" 日本医学館,

    • Related Report
      1989 Annual Research Report
  • [Publications] E.Niki: "Lipid Peroxidation in Biological Systems" Americal oil Chemists' Society,Champaign,IL., 254 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Mareyuki Takahashi: J.Nutr.Sci.Vitaminol.34. 25-34 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Etsuo Niki: Chem.-Biol.Interactions. 67. 81-93 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Etsuo Niki: J.Nutr.Sci.Vitaminal.34. 507-512 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Etsuo Niki: J.Biol.Chem.263. 19809-19814 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Etsuo Niki: "Free Radicals in Digestive Diseases" Elsevier,Amsterdam, 15-25 (1988)

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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