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Molecular design of the antioxidative peptide motif by combinatorial chemistry and its application to food proteins

Research Project

Project/Area Number 11556022
Research Category

Grant-in-Aid for Scientific Research (B).

Allocation TypeSingle-year Grants
Section展開研究
Research Field 食品科学・栄養科学
Research InstitutionTohoku University

Principal Investigator

MURAMOTO Koji  Graduate School of Agricultural Science, Tohoku University, Professor, 農学研究科, 教授 (90157800)

Co-Investigator(Kenkyū-buntansha) NOKIHARA Kiyoshi  Shimadzu Scientific Research Inc, Research Manager, 主席研究員 (60137073)
NAGANUMA Takako  Graduate School of Agricultural Science, Tohoku University, Research Associate, 農学研究科, 助手 (50250733)
OGAWA Tomohisa  Graduate School of Agricultural Science, Tohoku University, Associate Professor, 農学研究科, 助教授 (80240901)
YASUHARA Tadashi  Tokyo University of Agriculture, Associate Professor, 短期大学部, 助教授 (90110444)
Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥8,200,000 (Direct Cost: ¥8,200,000)
Fiscal Year 2000: ¥2,800,000 (Direct Cost: ¥2,800,000)
Fiscal Year 1999: ¥5,400,000 (Direct Cost: ¥5,400,000)
KeywordsPeptide / Peptide library / Free radical / Antioxidant / Radical / Antioxidative peptide / Oxidation / Combichem / 大豆
Research Abstract

We investigated the antioxidative properties of 114 synthetic His- or Tyr-containing peptide libraries, and 108 synthetic peptide libraries, which were designed on basis of antioxidative peptides derived from a proteolytic digest of soybean protein, to explore the antioxidative mechanism and to design the antioxidative peptide motif. Antioxidative activity of the peptide library was screened by high throughput screening assamps on micro titerplates as well as the ferric thiocyanate method. The activity spectrum of the tripeptides obtained from theeasurement of the radical scavenging activity was different from those from the ferric thiocyanate method in the peroxidation of linoleic acid. Pro-His-His which was very potent in the peroxidation of linoleic acid, did not act as a radical scavenger. The tripeptides containing Trp residue in the middle showed higher activity than the peptides containing His residue in the radical scavenging activity. The activities of tripeptides containing Trp or Tyr at the C-terminus were very high. Tyr-His-Tyr had a strong synergistic effect by the combined use with BHA or σ-tocopherol against the peroxidation of linoleic acid. We designed new antioxidant compounds, which were hybrids of peptides and nonpeptidic antioxidants, and measured their radical scavenging activity. The abilities of food protein hydrolysates and synthetic peptides to scavenge the peroxynitrite were also investigated. The tripeptides containing CySH had stronger scavenging activities than the peptides containing Met or other amino aciresidues. The peptides of the same amino acid composition exerted sequence dependent activities. i.e., CySH-Tyr-Tyr and Tyr-Tyr-CySH were more potent than Tyr-CySH-Tyr. Reversed-phase HPLC analysis of the reaction mixture revealed the extensive modification of peptides added.

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (22 results)

All Other

All Publications (22 results)

  • [Publications] K.Muramoto: "Comparison of the amino acid sequences of acorn barnacle lectins showing different inhibitory activities toward the crystal growth of calcium carbonate"Fisheries Sci.. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] D.-H.Jin: "Inhibitory effect of protein hydrolysates on calcium carbonate crystallization"J.Agric.Food Chem.. 48. 5450-5454 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Nokihara: "Solid-phase synthesis of peptides having different sequences : Synthesis of peptides related to the HIV-V3 region for immunological studies"Peptide Science 2000. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Nokihara: "Development of biomimetic materials exhibiting DDS-effets : Novel composite material carrying immobilized functional peptides"Peptide Science 2000. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Jimbo.: "Cloning of the microcystis aeruginosa M228 lectin gene"Biochem.Biophys.Res.Commun.. 273. 499-504 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Muramoto: "Physiological functions of plant lectins contained in foodstuffs"Food and Food Ingredients Journal of Japan. No.187. 11-16 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 軒原清史: "コンビナトリアルケミストリーの最近の進歩:ライブラリーの検定のためのコンビナトリアル分析"化学と生物. 39. 56-62 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Muramoto, D.-H.Jin, Y.Niino, K.Fujiwara, S.Kabuto, T.Ogawa, M.Toda and H.Kamiya: "Comparison of the amino acid sequences of acorn barnacle lectins showing different inhibitory activities toward the crystal growth of calcium carbonate"Fisheries Sci.. (in press.).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] D.-H.Jin, Y.Zhang, Y.Suzuki, T.Naganuma, T.Ogawa, E.Hatakeyama and K.Muramoto: "Inhibitory effect of protein hydrolysates on calcium carbonte crystallization"J.Agric. Food Chem.. 48. 5450-5454 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Jimbo, M.Yamaguchi, K.Muramoto and H.Kamiya: "Cloning of the Microcystis aeruginosa M228 lectin (MAL) gene, Biochem."Biophys. Res. Commun.. 273(2). 499-504 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Nokihara, S.Shimizu, R.Pipkorn, T.Yasuhara and T.Shioda: "Solid-phase Synthesis of Peptide having Difficult Sequences : Synthesis of Peptides Related to the HIV-V3 Region for Immunological Studies"Peptide Science 2000. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Nokihara, A.Blahunka Y.Yamazaki, Y.Yoshida and M.Okazaki: "Development of Biomimetic Materials Exhibiting DDS-Effects : Novel Composite Material Carrying Immobilized Functional Peptides"Peptide Science 2000. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Muramoto: "Physiological functions of plant lectins contained in foodstuffs"Foods & Food Ingredients Journal of Japan. No187. 11-16 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Muramoto: "Modulating effects of food components on brain functions"Report of Kansei Fukushi Research Center. No.1. 118-123 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Nokihara: "Recent development of combinatorial chemistry"Chemistry and Biology. 39. 56-62 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Dong-Hao Jin: "Inhibitory effect of protein hydrolysates on calcium carbonate crystallization"J.Agric.Food Chem.. 48. S450-S454 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] C.Frost: "Purification and characterization of ostrich prothrombin"Int.J.Biochem.Cell Biol.. 32. 1151-1159 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] 村本光二: "食品素材に含まれる植物レクチンの生理機能"Food and Food Ingredients Journal of Japan. No.187. 11-16 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Shizuya Kabuto: "The amino acid sequence of pancreatic d-amylase from the ostrich"Comp.Biochem.Physiol.B. 127. 481-490 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Hiroaki Tateno: "A novel rhamnose-binding lectin family from eggs of steelhead trout with different structures and tissue distribution"Biosci.Biotechnol.Biochem.. (印刷中).

    • Related Report
      2000 Annual Research Report
  • [Publications] Leona Wagner: "Isolation and partial characterization of dipeptidyl peptidase IV from ostrich kidney"Enzyme and Microbial Technology. 25. 576-583 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] 村本 光二: "食品における脳機能調節因子"東北福祉大学感性福祉研究所年報. 1. 118-123 (2000)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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