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Toxic substance in red tides, Heterocapsa circularisquama, appeared in Seto inland sea

Research Project

Project/Area Number 11558077
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field 環境保全
Research InstitutionHiroshima University

Principal Investigator

HIRAGA Yoshikazu  Hiroshima Univ., Graduate School of Science, Assistant, 大学院・理学研究科, 助手 (10238347)

Co-Investigator(Kenkyū-buntansha) OHKATA Katsuo  Hiroshima Univ., Graduate School of Science, Professor, 大学院・理学研究科, 教授 (50033882)
Project Period (FY) 1999 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥6,800,000 (Direct Cost: ¥6,800,000)
Fiscal Year 2001: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 2000: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 1999: ¥3,900,000 (Direct Cost: ¥3,900,000)
KeywordsRed Tide Plankton / Dinoflagellate / Heterocapsa circularisquama / Bivalves / Fatty Acids / Sterols / Galactolipids / Cytolytic Activity / ガラクトース / 遊離脂肪酸 / トリアシルグリセライド / ディノステロール / 7-デヒドロコレステロール / 培養 / 殺二枚貝活性 / 魚毒活性
Research Abstract

The compositions of fatty acids and sterols were determined in laboratory cultures of the marine dinoflagellate Heterocapsa circularisquama. In the free fatty acids, C_<22 : 6>,C_<16 : 0> and C_<18 : 4> were major components. Polyunsaturated fatty acids account for a substantial portion of the total free fatty acids (63.6 %) and include C_<18>, C_<20> and C_<22> acids. The fraction containig the free fatty acid exhibited potent cytotoxicity towards primary cultured gill cells of oyster. The major components in the fatty acids consisted of triacylglycerols were C_<18 : 2>, C_<16 : 0> and C_<14 : 0>.
Ten kinds of the sterol in H. circularisquama were identified by capillary gas chromatography-mass spectrometry. The major sterol was a 4-methyl sterol, 4α, 23, 24-trimethyl-5α-cholest-22E-en-3β-ol (dinosterol) which is the common sterol in many dinoflagellates. On the other hand, 5, 8α-epidioxy-5α-cholest-6-en-3β-ol was isolated as potent cytotoxic substance.
A novel digalactosyl diacylglycerol has been isolated from H. circularisquama together with two known monogalactosyl diacylglycerols, and their structures were elucidated by spectroscopic methods. The isolated monogalactosyl and digalactosyl diacylglycerols showed potent cytolytic activity towards heart cells of oyster.

Report

(4 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • Research Products

    (34 results)

All Other

All Publications (34 results)

  • [Publications] M.Tokumasu: "Synthesis of rac-Hippospongic acid A and Revision of the Structure"Journal of the Chemical Society, Perkin Transactions 1. 1999. 489-496 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y.Hiraga: "Ion-transport Activity of Phenylpentanoic Acids Occurring in the Roots of Athyrimu yokoscens"Bioscience, Biotechnology, and Biochemistry. 63. 958-960 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] R.Takagi: "The Julia-Colonna Asymmetric Epoxidation Reaction of Charcone Catalyzed by length Defined Oligo-L-leucine ; Importance of the N-Terminal Functional Group and Helical Structure of the Catalyst in the Asymmetric Induction"Bulletin of the Chemical Society of Japan. 73. 2115-2121 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y.Hiraga: "Synthesis of Hippospongic Acid A Analogues Designed to Investigate the Structure-Activity Relationship of the Biological Activity"Australian Journal of Chemistry. 53. 909-912 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Kanchanapoom: "Lignan glucosides from Acanthus ilicifolius"Phytochemistry. 56. 369-372 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Kanchanapoom: "Canthin-6-one and beta-carboline alkaloids from Eurycoma harmandiana"Phytochemistry. 56. 383-386 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y.Kanosue: "Kinetic Evidence for Hydrophobic Atmosphere of Catalytic Cavity in Carboxypeptidase Y on the Basis of linear Free Energy Relationship between Michaelis-Menten Constant Km and Hydrophobicity of the Substrates"Chemistry Letters. 2001. 418-419 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Kanchanapoom: "Megastigmane and Iridoid Glucosides from Clerodendrum inerme"Phytochemistry. 58. 333-336 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Kanchanapoom: "Benzoxazinoid Glucosides from Acanthus ilifolius"Phytochemistry. 58. 637-640 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Tokumasu, H. Ando, Y. Hiraga, S. Kojima, and K. Ohkata: "Synthesis of rac-Hippospongic acid A and Revision of the Structure"J. Chem. Soc. Perkin Trans.. 1. 489-496 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y. Hiraga, M. Kurokawa, J.-R. Guo, and T. Suga: "Ion-transport Activity of Phenylpentanoic Acids Occurring in the Roots of Athyrium yokoscense"Biosci. Biotechnol. Biochem.. 63. 958-960 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] R. Takagi, T. Manabe, A. Shiraki, A. Yoneshige, Y. Hiraga, S. Kojima, and K. Ohkata: "The Julia-Colonna Asymmetric Epoxidation Reaction of Charcone Catalyzed by Length Defined Oligo-L leucine ; Importance of the N-Terminal Functional Group and Helical Structure of the Catalyst in the Asymmetric Induction"Bull. Chem. Soc. Jpn.. 73. 2115-2121 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y. Hiraga, M. Ago, M. Tokumasu, K. Kaku, and K. Ohkata: "Synthesis of Hippospongic Acid A Analogues Designed to Investigate the Structure-Activity Relationship of the Biological Activity"Aust. J. Chem.. 53. 909-912 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Kanchanapoom, M. S. Kamel, R. Kasai, K. Yamasaki, C. Picheansoonthon, and Y. Hiraga: "Lignan glucosides from Acanthus ilicifolius"Phytochemistry. 56. 369-372 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Kanchanapoom, R. Kasai, P. Chumsri, Y. Hiraga, and K. Yamasaki: "Canthin-6-one and beta-carboline alkaloids from Eurycoma harmandiana"Phytochemistry. 56. 383-386 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y. Kanosue, Y. Hiraga, S. Kojima, and K. Ohkata: "Kinetic Evidence for Hydrophobic Atmosphere of Catalytic Cavity in Carboxypeptidase Y on the Basis of Linear Free Energy Relationship between Michaelis-Menten Constant Km and Hydrophobicity of the Substrates"Chem. Lett.. 418-419 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Kanchanapoom, R. Kasai, P. Chumsri, Y. Hiraga, and K. Yamasaki: "Megastigmane and Iridoid Glucosides from Clerodendrum inerme"Phytochemistry. 58. 333-336 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Kanchanapoom, M. S. Kamel, R. Kasai, C. Picheansoonthon, Y. Hiraga, and K. Yamasaki: "Benzoxazinoid Glucosides from Acanthus ilifolius"Phytochemistry. 58. 637-640 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Kanchanapoom et al.: "Canthin-6-one and beta-carboline alkaloids from Eurycoma harmandiana"Phytochemistry. 56. 383-386 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Kanchanapoom et al.: "Lignan glucosides from Acanthus ilicifolius"Phytochemistry. 56. 369-372 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Y.Kanosue et al.: "Kinetic Evidence for Hydrophobic Atmosphere of Catalytic Cavity in Carboxypeptidase Y on the Basis of Linear Free Energy Relationship between Michaelis-Menten Constant Km and Hydrophobicity of the Substrates"Chemistry Letters. 2001. 418-419 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Kanchanapoom et al.: "Megastigmane and Iridoid Glucosides from Clerodendrum inerme"Phytochemistry. 58. 333-336 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Kanchanapoom et al.: "Benzoxazinoid Glucosides from Acanthus ilifolius"Phytochemistry. 58. 637-640 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Hashizume et al.: "Purification and Characterization of a O-Methyltransferase Capable of Methylating 2-Hydroxy-3-alkylpyrane from Vitis vinifera L. (cv. Cabernet Sauvignon)"Bioscience, Biotechnolgy, and Biochemistry. 65. 2213-2219 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] R.Takagi et al.: "The Julia-Colonna Asymmetric Epoxidation Reaction by Soluble Oligo-L-leucine Containing an α-Aminobutylic Acid Residue : Importance of Helical Structure of the Catalyst on the Asymmetric Induction"Chemistry Letters. 2000(4). 366-367 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Kojima et al.: "Highly Z-Selective Synthesis of α,β-Unsaturated Amides with the Peterson Reaction"Chemical Comunications. 2000(20). 1795-1796 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] R.Takagi et al.: "The Julia-Colonna Asymmetric Epoxidation Reaction Catalyzed by Length Defined Oligo-L-leucine : Importance of the N-Terminal Functional Group and Helical Structure of Catalyst in the Asymmetric Induction"Bulletin of the Chemical Society of Japan. 73(9). 2115-2121 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Kojima et al.: "Stereoselective Formation of Activated Cyclopropanes with Pyridinium Ylides bearing a(-)-8-Phenylmenthyl Group as the Chiral Auxiliary"Tetrahedron Letters. 41(50). 9847-9851 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Y.Shinohara et al.: "Stereoselectivity in the Darzens Condensation of Substituted Cyclohexanones with α-Chloroacetate"Heterocycles. 55(1). 9-12 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] Y.Hiraga et al.: "Synthesis of Hippospongic Acid Analogues toward to investigate the Expression of the Biological Activity"Australian Journal of Chemistry. 54(in press). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] H. Nishitani et al.: "Asymmetric Synthesis of Rhopaloic Acid A Analogues and Their Biological Propaties"Heterocycles. 50(1). 35-38 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] M. Tokumasu et al: "Synthesis of rac-Hippospongic acid A and Revision of Structural Assignment"J. Chem. Soc., Perkin Trans. I. 1999(4). 489-496 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Y. Hiraga et al: "Ion-transport Activity of Phenylpentanoic Acids Occurring in the Roots of Athyrium yokoscense"Biosci. Biotechnol. Biochem.. 63(5). 958-960 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] R. Takagi et al: "The Julia-Colonna Type Asymmetric Epoxidation Reaction by Soluble Oligo-Oligo-L-leucine Containing an α-Aminobutilic Acid Residue: Importance of Helical Structure of the Catalyst in the Asymmetric Induction"Chem. Lett.. (in press). (2000)

    • Related Report
      1999 Annual Research Report

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

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