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Chemical Studies toward Development of Nerve Cell Degeneration Repairing or Protecting Agent

Research Project

Project/Area Number 09680582
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionTokushima Bunri University

Principal Investigator

FUKUYAMA Yoshiyasu  Faculty of Pharmaceutical Sciences, Tokushima Bunri University Professor, 薬学部, 教授 (70208990)

Co-Investigator(Kenkyū-buntansha) OKAZAKI Hiroshi  Research Institute of Biotechnology, Otsuka Pharmaceutical Co.Ltd., Researcher, 細胞工学研究所, 研究員
MINAMI Hiroyuki  Faculty of Pharmaceutical Sciences, Assistant, 薬学部, 助手 (20229769)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 1998: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1997: ¥2,600,000 (Direct Cost: ¥2,600,000)
Keywordsneurotrophic substance / culture of fetat rat neuron / limonoid / terpene / aromatic compound / palladium / plant tissue culture / HRP / 神経栄養因子 / フロログルシン
Research Abstract

This research project has been performed toward development of nerve cell degeneration repairing and/or protecting agent from novel neurotrophic natural products. The following results have been obtained.
(1) An unprecedented macrocyclic vibsane-type diterpene bearing an endo-peroxide in the molecule and novel limonoids were isolated as new neurotrophic active substances from the leaves of Viburnum awabuki and the roots of Melia azedarach Linn ver. Japonica, respectively.
(2) The first synthesis of plagiochin A, a 16-membered bis(bibenzyl) which is one of the potent neurotrophic natural products has been accomplished by an intramolecular Pd(O)-catalyzed Still-Kelly reaction. Another neurotrophic sesquiterpenes dimers, mastigophorenes A and B have been obtained by oxidative phenol coupling of (+)-herebertendiol, which was already synthesized by applying an intramolecular Heck reaction to the construction of the quaternary carbon center linked to the benzene ring. The extremely simple syntheses of neurotrophic active substnaces, americanol A and isoamericanol A which were isolated from Phytolacca americana have been performed by HRP-catalyzed oxidative dimerization of caffeic acid.
(3) Plant tissue culture has been applied to produce americanol A and isoamericanol A in the callus of Phytolacca americana, but their formation has not been so far realized. The callus successfully induced from the seeds of Belamcanda chinensis is now subjected to study on the condition of liquid culture. We will continue working on the production and biotransformation of neurotrophic active substances by using the plant tissue culture.
(4) Apotosis system in the cell culture of fetal rat cerebral hemisphere has been modified, and thereby we will be able to screen natural products which inhibit the apotosis of the nerve cell induced by beta-amyloid protein.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (38 results)

All Other

All Publications (38 results)

  • [Publications] Yoshiyasu Fukuyama: "Garsubellins, Polyisoprenylated Phlorogulcin Derivatives from Garcinia subelliptica." z z Phytochemistry. 49.3. 853-857 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama: "Naturally Occurring 5-Lipoxygenase Inhibitors. VII. Practical Syntheses of Ardisiaquinones D. E and F." Chem.Pharm.Bull.46.11. 1770-1775 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama: "Total Synthesis of Plagiochin D, a Macrocyclic Bis (bibenzyl) from the Liverwort by Intramolecular Still-Kelly Reaction." Tetrahedron Letters. 40.1. 105-108 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama: "Total Synthesis of (-)-Laurequinone." Chem.Lett.6. 485-486 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama: "Neovibsanins H and I, Novel Diterpenens from the leaves of Vibumum awabuki." Chem.Pharm.Bull.46.3. 545-547 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama: "Structures of New 7-Membered Ring Vibsane-type Diterepenes Isolated from Leaves of Viburnum awabuki." Chem.Pharm.Bull.46.3. 1194-1198 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama: "Oleanane-type Triterpenes from Viburnum awabuki." Phytochemistry. 47.6. 1101-1105 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama: "Antimicrobial Indoloquinones from the Mid-Intestinal Gland of the Muricid gastropod Drupella fragum." Tetrahedron. 54.34. 10007-10016 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama: "Antioxidative Indol Derivatives from the Mid-Intestinal Gland of the Muricid gastropod Drupella fragum." J.Nat.Prod.61.8. 1034-1045 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama: "Xanthones and Benzophenone from Garcinia subelliptica." Phytochmistry. 49.6. 1783-1785 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama et al.: "Neovibsanins H and I,Novel Diterpenens from the leaves of Viburnum awabuki." Chem.Pharm.Bull.46, (3). 545-547 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama et al.: "Oleanane-type Triterpenes from Viburnum awabuki." Phytochemistry. 47, (6). 1101-1105 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama et al.: "Total Synthesis of (-)-Laurequinone." Chem.Lett.(6). 485-486 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama et al.: "Antimicrobial Indoloquinones from the Mid-Intestinal Gland of the Muricid gastropod Drupella fragum." Tetrahedron. 54, (34). 10007-10016 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama et al.: "Structures of New 7-Membered Ring Vibsane-type Diterepenes Isolated from Leaves of Viburnum awabuki." Chem.Pharm.Bull.46, (8). 1194-1198 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama et al.: "Antioxidative Indol Derivatives from the Mid-Intestinal." J.Nat.Prod., 61. (8). 1043-1045 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama et al.: "Garsubellins, Polyisoprenylated Phlorogulcin Derivatives from Garcinia subelliptica." Phytochemistry. 49, (3). 853-857 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama et al.: "Xanthones and Benzophenone from Garcinia subelliptica." Phytochemistry. 49, (6). 1783-1785 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama et al.: "Naturally Occurring 5-Lipoxygenase Inhibitors. VII.Practical Syntheses of Ardisiaquinones D,E and F." Chem.Pharm.Bull.46, (11). 1770-1775 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama et al.: "Total Synthesis of Plagiochin D,Macrocyclic Bis (bibenzyl) from the Liverwort by Intramolecular Still-Kelly Reaction." Tetrahedron Lettes. 40, (1). 105-108a (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama et al.: "Chemical Conversion of Vibsanin C to Vibsanin E and Structure of 3-Hydroxyvibsanin E." J.Nat.Prod. 62. 337-339 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama et al.: "Aldovibsanins, Enol Ester Free Vibsane-type Diterpenes from Viburnum odoratissimum" Chem.Pharm.Bull.47. 295-296(2) (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiyasu Fukuyama: "Garsubellins,Polyisoprenyl Phloroglucin Derivatives" Phytochemistry. 49.3. 853-857 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshiyasu Fukuyama: "Naturally Occurring 5-Lipoxygenase Inhibitors.VII.Practical Syntheses of Aridisiaquinones D,E and F" Chem.Pharm.Bull.46.11. 1770-1775 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshiyasu Fukuyama: "Total Synthesis of Plagiochin D,a Macrocyclic Bis(bibenzyl)from the Liverwort by Intramolecular Still-Kelly Reaction" Tetrahedron Letters. 40.1. 105-108 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshiyasu Fukuyama: "Total Synthesis of(-)-Laurequinone" Chem.Lett.6. 485-486 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshiyasu Fukuyama: "Neovibsanins H and I,Novel Diterpenes form V.awabuki" Chem.Pharm.Bull.46.3. 545-547 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshiyasu Fukuyama: "Structures of New 7-Membered Ring Vibsane-type Diterpenes Isolated from the Leaves of Viburnum awabuki" Chem.Pharm.Bull.46.8. 1194-1198 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Masami Kagawa: "Oleanane-type Triterpenes from Viburnum awabuki." Phytochemistry. 47.6. 1101-1105 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshiyasu Fukuyama: "Antimicrobial Indoloquinones from the Mid-Intestinal Gland of the Muricid gastropod Drupella fragum." Tetrahedron. 54.34. 10007-10016 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Masamitsu Ochi: "Antioxidative Indol Derivatives from the Mid-Intestinal Gland of the Muricid gastropod Drupella fragum." J.Nat.Prod.61.8. 1034-1045 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hiroyuki Minami: "Xanthones and Benzophenone from Garcinia subelliptica." Phytochemistry. 49.6. 1783-1785 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshiyasu Fukuyama: "Enatioselective Synthesis of Octalactin A" Chem.Lett.2. 117-118 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Yoshiyasu Fukuyama: "Absolute Structure of Vibsanins B and C, and Their Chemical Correlation" Tetrahedron Letters. 38・8. 1435-1438 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Yoshiyasu Fukuyama: "Garsubellin A, a Novel Polyprenylated Phloroglucin Derivative Increasing Choline Acetyltransferase (ChAT) Activity in Culture of PIO Rat Spetal Neurons" Chem. Pharm. Bull.45・5. 947-949 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Yoshiyasu Fukuyama: "Bicycloillicinone Asarone Acetal, A Novel Prenylated C6-C3 Compound Increcasing Choline Acetyltransferase (ChAT) Activity Irom Illicium tashiroi" Planta Medica. 63・3. 275-277 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Yoshiyasu Fukuyama: "Synthetic Studies on Neurotrophic Isocuparane- Type Dimers, Mastigophorenes, Isolated from the Liverwort Mastigophora diclados" Phytomedcine. 3・Suppl.1. 250-252 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Yoshiyasu Fukuyama: "Synthesis of Cytotoxic Maesaquinone Bearing a 2,5- Dihydroxy-6-Methyl-1,4- Benzoquinone Nucleus" Tetrahedron. 53・50. 16969-16976 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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