• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Ichthyotoxic Active Compounds from Red Tides and Mechanism of Ichthyotoxicity

Research Project

Project/Area Number 04640528
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 天然物有機化学
Research InstitutionHIROSHIMA UNIVERSITY

Principal Investigator

SUGA Takayuki  Hiroshima University, Faculty of Science, Professor, 理学部, 教授 (00033811)

Co-Investigator(Kenkyū-buntansha) HIRAGA Yoshikazu  Hiroshima University, Faculty of Science, Research Associate, 理学部, 助手 (10238347)
EGUTI Shizuko  Hiroshima University, Instrument Center for Chemical Analysis, Technical Officia, 機器分析センター, 教務員 (60090552)
OHTA Shinji  Hiroshima University, Instrument Center for Chemical Analysis, Associate Profess, 機器分析センター, 助教授 (60185270)
Project Period (FY) 1992 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1993: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1992: ¥1,500,000 (Direct Cost: ¥1,500,000)
KeywordsRed Tides / Chattonella antiqua / Ichthyotoxicity / Fatty Acid / Ichthyotoxic Active / Autoxidation / Anti-oxidizing Reagent / Hydrophobic Interaction / ステアリドン酸 / パルミチン酸 / 含窒素化合物 / 培養条件
Research Abstract

Saturated and unsaturated fatty acids present in the red tides alga Chattonella antiqua showed an ichthyotoxic activity when assayd against killifish. Among the unsaturated fatty acids, stearidonic acid (C_<18 : 4>) had the strongest activity (LC_<100> = 7 ppm). Other C_<18->unsaturated fatty acids assayd were less active, although their ichthyotoxic activities increased with increase of the unsaturation degree. However, the activity of these unsaturated fatty acids disappeared by addition of anti-oxidizing reagents (alpha-tocopherol and sodium ascorbate) at pH 8.1. These facts indicate that the ichthyotoxicity is due to damage caused to the biomembrane by radical species generated form the autoxidation of the unsaturated fatty acids.
Among the saturated fatty acids, myristic acid (C_<14 : 0>) and palmitic acid (C_<16 : 0>) had the strongest activity (LC_<100> = 10 ppm) at pH 8.1. The activities of myristic acid and palmitic acid decreased at pH 4.5 due to a diminished solubility in water. However, the activities of decanoic acid (C_<10 : 0>) and lauric acid (C_<12 : 0>) were stronger at pH 4.5 rather than at pH 8.1. At pH 4.5, decanoic acid and lauric acid are ionized to an extent of less than 30%. These facts indicate that the ichthyotoxicity ascribes to the hydrophobic interaction with the biomembrane by the non-ionic form of the saturated fatty acid.

Report

(3 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • Research Products

    (20 results)

All Other

All Publications (20 results)

  • [Publications] T.Suga: "Ichthyotoxic Active Compounds from Red Tides and Mechanism of Ichthyotoxicity" Biosci.Biotech.Biochem.in preparation.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Suga, S.Ohta, S.Eguti, Y.Hiraga, and J.Shimada: "Ichthyotoxic Active Compounds from Red Tides and Mechanism of Ichthyotoxicity" Biosci.Biotech.Biochem.(in preparation).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Suga: "Selective Hydrogenation of the C-C Double Bond of α,β-Unsaturated Carbonyl Compounds by the Immobilized Cells of Nicotiana tabacum" J.Nat.Prod.56. 1406-1409 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Suga: "Endogenous Pine Wood Nematicidal Substances in Pines,Pinus massoniana,P.strobus,and P.palustris" Phytochemistry. 33. 1395-1401 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Y.Hiraga: "^<13>C NMR Detection of Delocalized C_<10>-Allylic Cation in the Biosynthesis of Farnesyl Diphosphate" J.Chem.Soc.,Chem.Commun.1994(in press). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Y.-X.Tang: "Evidence for the Involvement of a Cytochrome P-450 Dependent Monooxygenase in the Hydroxylation at Allylic Position by Nicotiana tabacum Cell Cultures" Phytochemistry. 34(in press). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] D.I.Ito: "Facilitation of Diphosphate Group Elimination from Geranyl Diphosphate by Magnesium Ion Chelation in Cyclic Monoterpenoid Biosynthesis" J.Chem.Soc.,Perkin Trans.1,. 1992. 37-39 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Tang: "Biotransformation of(4R)‐(‐)‐Carvone by the Immobilized Cells of Nicotiana tabacum" J.Sci.Hiroshima Univ.Ser.A. 56. 53-58 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Munesada: "Biologically Active Labdane‐type Diterpene Glycosides from the Root‐stalks of Gleichenia japonica" Phytochemistry. 31. 1533-1536 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Endo: "Stereochemistry in the biosynthesis of Geranyl Diphosphate with Geranyl Diphosphate Synthase from Pelargonium roseum" Phytochemistry. 31. 1565-1568 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] S.Ohta: "An Efficient Method for Following the Enzymic Reactions Involved in Camphor Biosynthesis in Cinnamomun camphora by Use of GC‐MS and Regiospecifically Deuteriated Substrate" J.Labelled Compds.Radiopharm.30. 397-402 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] H.L.Siddiqui: "Biologically Activi Clerodane‐type Diterpene Alcohol and Its Glycosides from the Root‐stalks of Ferns" J.Chem.Soc.,Perkin Trans.1. 1992. 781-785 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Endo: "Demonstration of Geranyl Diphosphate Synthase in Several Higher Plants" Phytochemistry. 31. 2273-2275 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.‐X.Tang: "Characterization of Two Enone Reductases from Nicotiana tabacum Cell Cultures" Phytochemistry. 31. 2599-2603 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Suga: "Regioselective Hydrogen Elimination from the 10‐Methyl Group of Geranyl Diphosphate in the Biological Formation of the 8(9)‐Double Bond of Limonene" J.Chem.Soc.,Chem.Commun.1992. 1556-1558 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Suga: "Endogenous Pine‐Wood Nematicidal Substances in Pines,Pinus massoniana,P.strobus,and P,palustris" Phytochemistry. 32. (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Suga: "Selective Hydrogenation of the C‐C Double Bond of α,β‐Unsaturated Carbonyl compounds by the Immobilized Cells of Nicotiana tabacum" J.Nat.Prod.56. (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Hiraga: "Facile Synthesis of (4S)‐(‐)‐[9‐^3H] Limonene" J.Labelled Compds.Radiopharm.31. (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Hiraga: "Biosynthetic Generation of Species‐specific Chiralty of Limonene by Face‐defined Elimination of Diphosphate from Geranyl Diphosphate" J.Chem.Soc.,Chem.Commun.1993. (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Suga: "Stereocontrol in the Biosynthesis of Limonene" Proceedings of the VII Asian Symposium on Medicinal Plants,Spices,and Other Natural Products, 129-134 (1992)

    • Related Report
      1992 Annual Research Report

URL: 

Published: 1992-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi