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New Marine Prostanoids from the Okinawan Soft Coral

Research Project

Project/Area Number 09680575
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionTokyo University of Pharmacy and Life Science

Principal Investigator

IGUCHI Kazuo  Tokyo Univ.of Pharm.& Life Sci., School of Life Sci., Professor, 生命科学部, 教授 (50057345)

Co-Investigator(Kenkyū-buntansha) IWASHIMA Makoto  Tokyo Univ.of Pharm.& Life Sci., School of Life Sci., Assistant, 生命科学部, 助手 (20266901)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 1998: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1997: ¥1,300,000 (Direct Cost: ¥1,300,000)
KeywordsMarine Natural Product / Prostanoid / Soft Coral / Clavularia viridis / Clavulone / Structure Determination / Biological Activity / Symbiotic Micro Organism
Research Abstract

During the course of our investigation to find new marine prostanoids from the Okinawan soft coral, eight new prostanoids and six new steroids were isolated from the methanol extract of Clavularia viridis. Their structures were determined based on the results of spectroscopic analysis. The absolute configurations of the compound 1 (clavulolactone I), 2 (4-epiclavulone II), and 3 (4-epiclavulone Ill) were confirmed by chemical conversions from the corresponding clavulones. The novel prostanoid-related compounds 4 and 5 (clavirin A and B) consist of 17 carbons, containing the terminal aldehyde on the shorter alpha-side chain. The chiral center on C-7 in both compounds were independently determined by the stereoselective total syntheses from 4-hydroxy-2-cyclopentenone. The prostanoid-related compound 6 (clavucyclin) also posseses a novel unique structure, such as tricycic 5-5-4 ring systems. The total synthesis of 6 is currently carried out in our laboratory using the same synthetic intermediate of 4 and 5. We are investigating not only the bioactivities of all new compounds, particularly cytotoxic, antitumor, and enzyme-inhibition activities, but the interaction betwen the host C.viridis and symbiotic algae (zooxanthella).

Report

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

    (6 results)

All Other

All Publications (6 results)

  • [Publications] M.Iwashima, K.Okamoto, F.Konno, and K.Iguchi: "New Marine Prostanoids from the Okinawan Soft Coral, Clavularia viridis" Journal of Natural Products. 62・2. 352-354 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Iwashima, K.Okamoto, Y.Miyai, and K.Iguchi: "4-Epiclavulones, New Marine Prostanoids from the Okinawan Soft Coral, Clavularia viridis" Chemcal and Pharmaceutical Bulletin. 22・6(in press). (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Iwashima, K.Okamoto, F.Konno, and K.Iguchi: "New Marine Prostanoids from the Okinawan Soft Coral, Clavularia viridis" Journal of Natural Products. 62. 352 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Iwashima, K.Okamoto, Y.Miyai, and K.Iguchi: "4-Epiclavulones, New Marine Prostanoids from the Okinawan Soft Coral, Clavularia viridis" Chemcal and Pharmaceutical Bulletin. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Iwahima, K.Okamoto, F.Konno, and K.Iguchi: "New Marine Prostanoids from the Okinawan Soft Coral Clavularia viridis" Journal of Natural Products. 62・2. 352-354 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Iwashima, K.Okamoto, Y.Miyai, and K.Iguchi: "4・Epiclavulones New Marine Prostanoids from the Okinawan Soft Coral, Clavularia viridis" Chemical and Pharmaceutical Bulletin. 22・6. in press (1999)

    • Related Report
      1998 Annual Research Report

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

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