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2004 Fiscal Year Final Research Report Summary

Medicinal chemistry on marine alkaloid as a seed of the development for a new anticancer drug in Malaya area

Research Project

Project/Area Number 14370725
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionFaculty of Pharmaceutical Sciences, Meiji Pharmaceutical University

Principal Investigator

KUBO Akinori  Meiji Pharmaceutical University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (60097201)

Co-Investigator(Kenkyū-buntansha) SAITO Naoki  Meiji Pharmaceutical University, Faculty of Pharmaceutical Sciences, Assistant Professor, 薬学部, 助教授 (80142545)
MIKAMI Yuzuru  Chiba University, Research center for Pathbenic Fungi and Microbiol Toxicoses, Professor, 真菌医学研究センター, 教授 (40092100)
Project Period (FY) 2002 – 2004
KeywordsNatural Marine Product / Alkaloid / Isoquinoline / Ecteinascidin / Renieramy / Anticancer Drug / Structure Elucidation / Large amount Supply
Research Abstract

Ecteinascidin 743 is a natural product isolated from the marine tunicate Ecteinascida turbinata, which has been demonstrated to be a highly promising, exceeding potent antitumor agent currently in phase II/III clinical trials in USA and EU. As a part of our search for new anticancer metabolites in the isolation and characterization of biologically active compounds from Thai marine animals, we have succeeded to find a Thai tunicate, Ecteinascida thurstoni Herdman 1891, which is the first example of the Asian tunicate containing this class of molecules, growing around Phuket Island. We report the isolation and structural elucidation of ecietnascidins 770 and 786 from the KCN pretreated Thai tunicate. Isolation of natural marine products using this procedure has the advantage of increasing the yield of labile Ecteinascidin-type compounds. Furthermore, we found a blue sponge, Xestospongia sp., growing around Sichang Island in the Gulf of Thailand, and by the same strategy, we are succeeded the gram-scale isolation of renieramycins M, which has also potent amtitumor activity.
By the way, one of the most intriguing problems, which is how to maintain a consistent supply of ecteinascidins for drug development : by isolation from marine sources or by total synthesis still remains. In connection with the development of a short-step synthesis of this series of natural product, we have previous reported the preparation of the tricyclic lactam intermediate, and the partial synthesis of the ABC ring model compound. Encourage by the results of our studies, we apply these strategies for preparation of the ABCDE ring system of ecteinascidins, having characteristic substituents in both benzene rings.

  • Research Products

    (10 results)

All 2004 2003 2002 2001 2000

All Journal Article (9 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Synthesis of a Simple Natural Marine Product, 6-Hydroxy-7-methoxyisoquino linemethanol2004

    • Author(s)
      Naoki Saito et al.
    • Journal Title

      Chem.Pharm.Bull. 52

      Pages: 282-286

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of a Simple Natural Marine Product, 6-Hydroxy-7-methoxyisoquinolinemethanol2004

    • Author(s)
      Naoki Saito et al.
    • Journal Title

      Chem.Pharm.Bull. 52

      Pages: 282-286

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthetic Approaches toward Ecteinascidins. Part 2. Preparation of the ABCDE Ring System of Ecieinascidins having Characteristic Substituents in Both Benzene Rings2003

    • Author(s)
      Naoki Saito et al.
    • Journal Title

      Chem.Pharm.Bull. 51

      Pages: 821-831

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Chemistry of Renieramycins. Part 3. Isolation and Structure of Stabilized Renieramycin Type Derivatives Possessing Antitumor Activity from Thai Sponge, Xestospongia Species, Pretreated with Potassium Cyanide2003

    • Author(s)
      Khanit Suwanborirux et al.
    • Journal Title

      J.Nat.Prod. 66

      Pages: 1441-1446

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthetic Approaches toward Ecteinascidins. Part 2. Preparation of the ABCDE Ring System of Ecteinascidins having Characteristic Substituents in Both Benzene Rings2003

    • Author(s)
      Naoki Saito et al.
    • Journal Title

      Chem.Pharm.Bull. 51

      Pages: 821-831

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Chemistry of Renieramycins. Part 3. Isolation and Structure of Stabilized Renieramycin Type Derivatives Possessing Antitumor Activity from Thai Sponge, Xestospongia Species, Pretreated Pottasium Cyanide2003

    • Author(s)
      Khanit Suwanborirux et al.
    • Journal Title

      J.Nat.Prod. 66

      Pages: 1441-1446

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Ecteinascidins 770 and 786 from Thai Tunicate Ecteinascidia thurstoni2002

    • Author(s)
      Khanit Suwanborirux et al.
    • Journal Title

      J.Nat.Prod. 65

      Pages: 935-937

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A Practical Synthesis of the ABC Ring Model of Ecteinascidins2000

    • Author(s)
      Naoki Saito et al.
    • Journal Title

      Chem.Pharm.Bull. 48

      Pages: 1549-1557

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A Practical Synthesis of the ABC Ring of Ecteinascidins2000

    • Author(s)
      Naoki Saito et al.
    • Journal Title

      Chem.Pharm.Bull. 48

      Pages: 1549-1557

    • Description
      「研究成果報告書概要(欧文)」より
  • [Patent(Industrial Property Rights)] エクチナサイジン786、その所得方法およびその用途2001

    • Inventor(s)
      久保陽徳ら
    • Industrial Property Rights Holder
      久保陽徳ら
    • Industrial Property Number
      特許出願2001-264762
    • Filing Date
      2001-08-31
    • Acquisition Date
      2002-08-29
    • Description
      「研究成果報告書概要(和文)」より

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Published: 2006-07-11  

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