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Preparation/production and Utilization Researches of Terpenoidal Plant-growth Stimulants and Other Bioactive Substances with High Bioactivity.

Research Project

Project/Area Number 12556015
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 InstitutionYamagata University

Principal Investigator

SASSA Takeshi  Yamagata University, Dept.of Bioresource Engineering, Professor, 農学部, 教授 (80023456)

Co-Investigator(Kenkyū-buntansha) IKEDA Michimasa  Yamagata University, Dept.of Bioresource Engineering, Professor, 農学部, 教授 (20007074)
YONEYAMA Koichi  Utsunomiya University, Weed Science Center, Professor, 野生植物科学研究センター, 教授 (00114174)
KATO Nobuo  Osaka University, The Institute of Scientific and Industrial Research, Professor, 産業科学研究所, 教授 (50150537)
NUKINA Manabu  Yamagata University, Dept.of Bioresource Engineering, Professor, 農学部, 教授 (20113970)
Project Period (FY) 2000 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥13,100,000 (Direct Cost: ¥13,100,000)
Fiscal Year 2003: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 2002: ¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 2001: ¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2000: ¥4,900,000 (Direct Cost: ¥4,900,000)
Keywordsfluorofusicoccin / semi-synthesis / Phomopsis amygdali / fusicoccin / cotylenin / seed-germination promotion / cell differentiation / antitumor / 発酵生産 / 白血病細胞 / 分化誘導 / 植物成長調節 / アブシジン酸 / 3-エピフシコクシン / ガン細胞 / ABA / Phomopsis amygdali / フロロフシコクシン / コチレノール / フシコクシン・Q / コチレニンA / 3-エピフシコクシンQ / フッ素化テルペノイド / 代謝変換 / モモ枝折病菌 / 発芽促進活性 / 半合成テルペノイド
Research Abstract

1.Preparation of Highly Bioactive Fusicoccin Derivatives by Reverse-order Semi-synthesis
We have succeeded in obtaining 19/20-fluorofusicoccins quite efficiently by synthesizing 19/20-fluoro derivatives of fusicocca-2,10(14)-diene, a genuine biosynthetic intermediate of fusicoccins, and then feeding them into the fusicoccin-producing fungus for metabolic transformations. We named this novel process a "Reverse-order Semi-synthesis", as the approach deviates reversely from typical semi-synthesis insofar as purely chemical steps are followed by biochemical transformations.
2.Finding of New Fusicoccin-producing Fungi in Japan and Gram-scale Production of Fusicossins
We found peach Fusicoccum canker fungi (Phomopsis amygdali Niigata) as the first fusicoccin-producing fungi in Japan, and selected its Niigata 74 strain as one of the highest fusicoccin-productive strains. This strain in a commercial sugar-soybean meal medium produced fusicoccin A and 3'-deacetylfusicoccin A (each 0.4 g/L) for its one-week cultivation or only 3'-deacetylfusicoccin A (0.9g/L) for its 2-week cultivation.
3.Isolation of New Fusicoccins and Their Seed Germination-stimulating Activity
From the strain Niigata 74 new fusicoccins P, Q, R, and S, and 3-epifusicoccins H and Q were isolated as polar fusicoccins, and their structures were elucidated by chemical and spectroscopic evidence. Fusicoccins P and R being 16-O-methylfusicoccins showed the high activity in the seed germination-stimulating test in the presence of abscisic acid.
4.Mammal Cell Differentiation-inducing Activity of Cotylenin A and Its Tumor Cell-Growth Suppressive Activity
Cotylenin A induced the differentiation of human acute myeloid leukaemia cells in primaiy culture, and showed neurite genaration (outgrowth) promoting activity toward PC12 nerve cells at low concentrations. Cotylenin A and interferon-α cooperatively induced apoptosis and have an antitumor effect on human non-small cell lung carcinoma cells in nude mice.

Report

(5 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • Research Products

    (16 results)

All Other

All Publications (16 results)

  • [Publications] K.Yamada: "Differentiation of human acute myeloid leukaemia cells in response to cotylenin A, a plant growth regulator."J.Haematology. 114. 814-821 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Tajima: "Chemical identification of fusicoccins from a Japanese isolate Niigata 2 of peach Fusicoccum canker fungus (Phomopsis amygdoli) and production of 3'-deacetylfusicoccinA by the fungus."J.Pesticides Sci.. 27(1). 64-67 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Sassa: "Fusicoccins P and Q, and 3-epifusicoccins H and Q, new polar fusicoccins from isolate Niigata 2-A of a peach Fusicoccum canker fungus."Biosci.Biotechnol.Biochem.. 66(11). 2356-2361 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Honma: "Cotylenin A, a differentiation-inducing agent, and IFN-α cooperatively induce apoptosis and have an antitumor effect on human non-small cell lung carcinoma cells in nude mice."Cancer Res.. 63. 3659-3666 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Tajima: "Novel fusicoccins R and S, and fusicoccin S aglycon (phomopsiol) from Phomopsis amygdali Niigata 2-A, and their seed germination-stimulating activity in the presence of abscisic acid."Biosci.Biotechnol.Biochem.. 66(5)(in press). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Yamada: "Differentiation of human acute myeloid leukaemia cells in response to cotylenin A, a plant growth regulator."J.Haematilogy. 114. 814-821 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Tajima: "Chemical identification of fusicoccins from a Japanese isolate Niigata 2 of peach Fusicoccum canker fungus (Phomopsis amygdali) and production of 3'-deacetylfusicoccin A by the fungus."Pesticide Chem.. 27(1). 64-67 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Sassa.: "Fusicoccins P and Q, and 3-epifusicoccins H and Q, new polar fusicoccins from isolate Niigata 2-A of a peach Fusicoccum canker fungus."Biosci.Biotechnol.Biochem. 66(11). 2356-2361 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Honma: "Cotylenin A, a differentiation-inducing agent, and IFN-α cooperatively induce apoptosis and have an antitumor effect on human non-small cell lung carcinoma cells in nude mice."Cancer Res.. 63. 3659-3666 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Tajima: "Novel fusicoccins R and S, and fusicoccin S aglycon (phmopsiol) from Phomopsis amygdali Niigata 2-A, and their seed germination-stimulating activity in the presence of abscisic acid."Biosci Biotechnol Biochem.. 66(5)(in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Naoto Tajima: "Novel fusicoccins R and S, and the fusicoccin S aglycon (phomopsiol) from Phomopsis amygdali Niigata 2-A, and their seed germination-stimulating activity_in_the_presence_of abscisic acid"Biosci.Biotechnol.Biochem.. 68(5)(In press). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Takeshi Sassa: "Fusicoccins P and Q, and 3-epifusicoccins H and Q, new polar fusicoccins from isolate Niigata 2-A of a peach Fusicoccum canker fungus"Biosci. Biotechnol. Biochem. 66・11. 2356-2361 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 加藤 修雄: "特異な生理活性菌頚ジテルペン配糖体-フシコクシン、エリナシン-における初期生合成経路の解明と応用"日本農芸化学会誌. 76・12. 1202-1205 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] N.Tajima: "Chemical identification of fusicoccins from the isolate Niigata 2 of a peach Fusicoccum canker fumgus and production of 3'-deacetyl-fusicoccin A by the fumgus"J.Pesticide Chem.. 27・1. 64-67 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Yamada: "Differentiation of human acute myelsid leukaemia cells in primary culture in response to cotylenin A,plant growth regulator"British J.Haematology. 114. 814-821 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] M.Omoto: "Revisit to the reduction of allylic chlorides to less substituted olefins by alow-valent chromium species in the presence of a proton source"Tetrahedron Lett.. 42・5. 939-941 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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