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Development of cancer preventing agent using conjugated trienoic fatty acids

Research Project

Project/Area Number 13556016
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionTohoku University

Principal Investigator

MIYAZAWA Teruo  Tohoku Universty, Graduate School of Life Science and Agriculture, Professor, 大学院・農学研究科, 教授 (20157639)

Co-Investigator(Kenkyū-buntansha) HADA Takahiko  Bizen Chemical Co.LTD Acting head of a section, 開発研究部, 課長代理
INOUE Yoshinori  Bizen Chemical Co.LTD Manager, 開発研究部, 部長
TSUDA Hroyuki  National cancer center, Experimental Pathology and Chemotherapy Division, Chief, 化学療法部, 部長
Project Period (FY) 2001 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥6,800,000 (Direct Cost: ¥6,800,000)
Fiscal Year 2002: ¥2,400,000 (Direct Cost: ¥2,400,000)
Fiscal Year 2001: ¥4,400,000 (Direct Cost: ¥4,400,000)
KeywordsConjugated fatty acid / Conjugated triene / Colon cancer / Apoptosis / Lipid peroxidation / Anticarcinogenesis / Lipid metabolism / ヌードマウス / 酸化ストレス / 大量調製法
Research Abstract

We found out that conjugated eicosapentaenoic acid (CEPA) and conjugated docosahexaenoic acid (CDHA) with conjugated trienoic structure, have the strongest cytotoxic effect selectively on human tumor cell lines. The incorporation of these conjugated fatty acids is sufficient to increase the sensitivity to oxidative damage that is indicative for apoptotic cell death. The CEPA with triene structure, prepared by aikaline treatment, showed intensive toxicity with DLD-1 cell (colorectal adenocarcinoma) -transplanted tumor in male athymic nude mice. The anticarcinogenic activity involved membrane phospholipid peroxidation. CEPA induced DNA fragmentation in DLD-1 cell-transplanted tumor in nude mice, indicating the involvement of apoptosis in the anticarcinogenic mechanism.
The occurrence of a significant amount of 9, 11-conjugated linoleic acid (CLA, 9, 11-18:2) was confirmed in the liver and plasma lipids of rats fed a 1% (w/w % of diet) eleostearic acid (ESA, 9, 11, 13-18:3) diet. The chemical structure of 9, 11-CLA was identified by gas chromatography-electron impact mass spectrometry after its conversion to a 4, 4-dimethyloxazoline derivative. The concentration of CLA in the total fatty acids of the liver and plasma lipids reached to 1% for each in the CLA-supplemented rats, while reaching 3.2% and 2.5%, respectively, in the ESA-supplemented rats. The α-ESA was shown to be metabolized partially to CLA via a delta 13-saturation reaction in the rat. Some biological activities observed in α-ESA-fed animals may be ascribed also to CLA that is formed from ESA in the body.

Report

(3 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • Research Products

    (25 results)

All Other

All Publications (25 results)

  • [Publications] Tsuyoshi Tsuzuki: "The Metabolic Conversion of 9,11,13-eleostearic acid (18:3) to 9,11-conjugated Linoleic Acid (18:2) in the Rat"Journal of Nutritional Science and Vitaminology. 49・3(発表予定). (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 宮澤陽夫: "共役脂肪酸の抗癌作用"食品工業. 3・30. 23-30 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tatsuya Sugawara: "Apoptosis induction by wheat-flour sphingcid bases in DLD-1 human cancer cells"Bioscience, Biotechnoligy, and Biochemistry. 66・10. 2228-2231 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 宮澤陽夫: "過酸化脂質の分離・分析"生物薬科学実験講座-脂質-(井上、中川編)廣川書店. 3. 318-335 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Miki Igarashi: "The growth inhibitory effect of conjugated linoleic acid on a human hepatoma cell line, HepG2, is induced by a change in fatty acid metabolism, but not the facilitation of lipid peroxidation in the cells"Biochimica et Biophysica Acta. 1530. 162-171 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Moriya: "Oxidative stress in the absence of inflamation in a mouse model for hepatitis C virus-associated hepatocarcinogenesis"Cancer Research. 61. 4365-4370 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] J.-H.Song: "Enhanced levelof n-3 fatty acid in member phospholipids induces lipid peroxidation in rats fed dietary docosahexaenoic acid oil"Atherosclerosis. 155. 4365-4370 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 宮澤陽夫: "食品の機能化学"弘学出版. 191 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tsuyoshi Tsuzuki: "The Metabolic Conversion of 9, 11, 13-eleosteanc acid (18:3) to 9, 11-conjugated Linoleic Acid (18:2) in the Rat"Journal of Nutritional Science and Vitaminology. 49 ・ 3, In press. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Teruo Miyazawa: "The anticancer effect of conjugated fatty acid"Syokuhinn-kougyou. 3-30. 23-31 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tatsuya Sugawara: "Apoptosis induction by wheat-flour sphingcid bases in DLD-1 human cancer cells"Bioscience, Biotechnoligy, and Biochemistry. 66 ・ 10. 2228-2231 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Teruo Miyazawa: "The Analysis of lipid peroxidation"Seibutu-yakugaku-jikkennkouza -sisitu-. 3. 318-335 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Miki Igarashi: "The growth inhibitory effect of ccnjugated linoleic acid on a human hepatoma cell line, HepG2, is induced by a change in fatty acid metabolism, but not the facilitation of lipid peroxidation in the cells."Biochimica et Biophysica Acta. 1530. 162-171 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K. Moriya: "Oxidative stress in the absence of inflamation in a mouse model for hepatits C virus-associated hepatocarcinogenesis"Cancer Research. 61. 4365-4370 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] J.-H. Song: "Enhanced level of n-3 fatty acid in member phospholipids induces lipid peroxidation in rats fed dietary docosahexaenoic acid oil"Atherosclerosis. 155. 4365-4370 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Teruo Miyazawa: "The biodynamic of food chemistry"Hirosaki-syuppan. 191 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 宮澤陽夫: "共役脂肪酸の抗癌作用"食品工業. 3・30. 23-30 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Tsuyashi Tsuzuki: "A metabolic conversion from 9,11,13-eleostearic acid(18:3,n-5)to 9,11-conjugated linoleis acid(18:12,n-7) in the rat"Journal of Nutritional Science and Vitaminology. 49・1(発売予定). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Tatsuya Sugawara: "Apoptosis induction by wheat-flour sphingeid bases in DLD-1 human cancer cells"Bioscience, Biotechn-logy, and Biochemistry. 66・10. 2228-2231 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Miki Igarashi: "Recommended methylester-preparation methods for the conjugated dienoic and trienoic fatty acids in foods and biologies samplcal"Journal of Nutritional Science and Vitamiology. 49(発売予定). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] 宮澤陽夫: "食品の機能化学"弘学出版. 191 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Miyazawa他1名: "The growth inhibitory effect of conjugated linoleic acid on a human hepatomacell line, Hep G2, induced by a change in fatty acid metabolism, but not the facilitation of lipid peroxidation in the cells"Biochimica et Biophysica Acta. 1530・2-3. 162-171 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Miyazawa他1名: "Do conjugated eicosapentaenoic acid conjugated docosahexaenoic acid induce apoptosis via lipid peroxidation in cultured human tumor cells?"Biochemistry and Biophysics Research Communications. 270・2. 649-656 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Miyazawa他1名: "Newly recognized cytotoxic effect of conjugated trienoic fatty acids on cultured human tumor cells"Cancer Letters. 148. 173-179 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Miyazawa他3名: "Significant occurrence of 9,11-conjugated linoleic acid (18 : 2, n-7) in the liver and plasma lipids of rats fed 9, 11, 13-eleostearic acid (18 : 3, n-5)-supplemented diet"Biochimica et Biophysica Acta. (発表予定). (2002)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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