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1987 Fiscal Year Final Research Report Summary

Bio-organic Research on Hatching Stimuli of Cyst Nematodes

Research Project

Project/Area Number 60430009
Research Category

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

Allocation TypeSingle-year Grants
Research Field 天然物有機化学
Research InstitutionHokkaido University

Principal Investigator

MASAMUNE Tadashi  Professor, Faculty of Science, Hokkaido University, 理学部, 教授 (60000717)

Co-Investigator(Kenkyū-buntansha) FUKUZAWA Akio  Instructor, Faculty of Science, Hokkaido University, 理学部, 講師 (60094843)
Project Period (FY) 1985 – 1987
KeywordsCyst nematodes / Hatch-stimulating substances / Potato cyst nematode / Nortriterpenoids / ダイズシスト線虫
Research Abstract

Natural hatching stimuli of potato cyst nematode. a) The bioassay, required for purification,was improved by pretreatment of the nematode cysts and eggs as well as by control of the pH (3-4)of the test solution. b) Active starting material was prepared by extraction of dried roots of tomato with dry ice-acidified water and absorption of the aqueous extracts on Amberlite XAD-2 followed by desorption with acetone. The resulting powdered raw material (active at 10^<-5> g/ml) was easily soluble in water and stable in an aqueous solution only with pH 2-8. c) The active raw material (34.6 g), obtained from the dried roots (24 kg), was purified by repeated chromatography (column, solvent; Amberlite XAD-2, water; Sephadex G-15, water; Sephadex-10, water; Toyopearl HW-40c, water; Toyopearl HW-40s, water) and by HPLC over -Bondapak C_<18> (water-methanol) to give an active fraction (0.1 mg) with activity of 10^<-9 -10> g/ml. Further purification will be required. d) The active substance is presumed to be neither polypeptides nor polysaccharides (by dialysiswith Cellophane) but triterpene-like substance(s) (by measurement of the ^1H NMR spectrum) with molecular weight below 1000 (by gel chromatography over Sephadex G-10) and with double bond(s) and hydrophilic functions.
Hatching stimuli of soybean cyst nematode. a) The total synthesis of the natural hatching stimulus, glycinoeclepin A (GEA), of the nematode has been achieved, indicating that GEA is indeed the active substance itself. b) The prtial synthesis will be completed in the near future: cycloastragalol, obtained easily from Chinese drug "Tragacantha", was transformed into two compounds, one having the same C and D rings as GEA and another the same A and B rings as GEA. Hatching acivity of most of these synthetic intermediates will be examined in the coming spring to elucidate what moieties are required for the biological activity.

  • Research Products

    (14 results)

All Other

All Publications (14 results)

  • [Publications] A.Fukuzawa ら: Tetrahedron Letters. 26. 5539-5542 (1985)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Masamune ら: Publisher: Naito Fandation. 25-32 (1986)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Masamune ら: The Fifth Synthetic Organic Chemistry Symposium(SOCS-5). 5. 9-12 (1986)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Masamune ら: Bullletin of the Chemical Society of Japan. 60. 981-999 (1987)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Masamume ら: Bulletin of the Chemical Society of Japan. 60. 1001-1014 (1987)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 高杉 光雄,福沢 晃夫,正宗 直: 有機合成協会誌. 5. (1988)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 正宗 直,福沢 晃夫: "(続)生物活性天然物質" 医歯薬出版株式会社, 3(96-98) (1988)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] A. Fukuzawa, H. Matsue, M. Ikura, and T. Masamune: "Glycinoeclepins B and C, Nortriterpens Related to Glycinoeclepin A" Tetrahedron Letters. 26. 5539-5542 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Masamune: "Natural Products and Biological Activities" Publisher: Naito Fandation. 25-32 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. masamune: "Synthetic Studies on Glycinoeclepin A" The Fifth Synthetic Organic Chemistry Symposium (SOCS-5). 5. 9-12 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Masamune, M. Anetai, A. Fukuzawa, M. Takasugi, H. Matsue, K. Kobayashi, S. Ueno, and N. Katsui: "Glycinoeclepins, Natural Hatching Stimuli for the Soybean Cyst Nematode,Heterodra Glyoines. I. Isolation" Bulletin of the Chemical Society of Japan. 60. 981-999 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Masamune, A. Fukuzawa, A. Furusaki, M. Ikura, H. Matsue, T. Kanedo, A. Abiko, N. Sakamoto, N. Tanimoto, A. Murai: "Glycinoeclepins, Natural Hatching Stimuli for the Soybean Cyst Nematode,Heterodera Glycines. II. Structural Elucidation" Bulletin of the Chemical Society of Japan. 60. 1001-1014 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mitsuo Takasugi, Akio Fukuzawa, and Tadashi Masamune: "Our Journey to Glycinoeclepin A, a Natural Hatching Stimulus for Soybean Cyst Nematode (Heterodera Glycines)" Journal of Synthetic Organic Chemistry, Japan,. in press. (1988)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. masamune and A. Fukuzawa: Seibutsu-Kassei-Tennenbushitsu(New Bioactive Natural Substances). Ishi-Yaku Shuppan, 96-98 (1988)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1989-03-30  

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