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Structural and Biogenic Analysis of Bioactive Marine Natural Products

Research Project

Project/Area Number 12640527
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionAOYAMA GAKUIN UNIVERSITY

Principal Investigator

KIMURA Junji  College of Science and Engineering, Aoyama Gakuin University, Professor, 理工学部, 教授 (40082854)

Project Period (FY) 2000 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 2002: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2001: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2000: ¥1,500,000 (Direct Cost: ¥1,500,000)
Keywordshalogenated terpenes / oxylipin / kulokekahilide / Calytogena soyoae / Ifremeria nautilei / Rimicaris kairei / Data-mining / デプシペプチド / ハロゲン化モノテルペン / ロリオライド / オクトデン / カイレイツノナシオハラエビ / Ifremeria nautilei / Calyptogena soyoae / 4-フェニルバリン / 3-アミノ-2-メチルヘキサン酸
Research Abstract

I divided the theme into five next items and studied it.
1. From the red alga genus Laurencia nidifica, two new halogenated sesqiterpenes, chamigrane derivatives were obtained together with ten known compounds and two artifacts. Also, three halogenated monoterpenes, octodene derivatives were isolated from the red alga, Scinecia okamurae. The structures of these compounds were elucidated by NMR and mass spectroscopy, and plausible reaction pathways were proposed.
2. Nine novel oxylipin metabolites together with several known ones were isolated from the brown alga, Eisenia bicyclis. Though bioactive investigation against B. subtilis and S. aureus, was done, unfortunately these compounds have poorer inhibition against their bacteria than a standard sample of vancomycin.
3. Two new cyclic depsipeptides (kulokekahilide-1, -2) which showed cytotoxity against P388 murine lymphocytic leukemia cells with IC_<50> values of 2.1 μg/mL and 3.5 ng/mL were isolated from a marine mollusk Pilinopsis speciosa in Hawaii. The absolute stereochemistry of amino acids and hydroxy acids composed with depsipeptides were determined by Marfey analysis and chiral HPLC analysis. In order to examine the relationship between activity and structure, the total synthesis of kulokekahilide-2 was attempted.
4. The analysis of components contained in deep-sea organisms, Calytogena soyoae, Ifremeria nautilei, and Rimicaris kairei was studied. No novel compounds were obtained but many known compounds were isolated from their materials. It was clear that fatty acids composition in deep-sea organisms was different from that in shallow-sea organisms.
5. Data-mining method applied for the active compounds against E.coli, B.subtilis, and S.aureus. Thus, it was found that the classification rules of the activity were extracted from flavonoid and terpene derivatives

Report

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

    (15 results)

All Other

All Publications (15 results)

  • [Publications] 鎌田昇, 木村純二: "Chamigrane誘導体の酸による変換反応"日本化学会誌. 571-575 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Hyosu, J.Kimura: "Two New Spongian Diterpene from Coscinoderma mathewsi"J. Nat. Prod.,. 63・3. 422-423 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] J.Kimura, N.Maki: "New Loliolide Derivatives from the Brown Alga Undaria pinnatifida"J. Nat. Prod.,. 65・1. 57-58 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] J.Kimura, Y.Takada, T.Inayoshi, G.Geoettz, Y.Nakao, P.J.Scheuer: "Kulokekahilide-1,Cytotoxic Depsipeptide from a Cephalaspiedean Mollusk, Philinopsis speciosa"J. Org. Chem.,. 67・6. 1760-1767 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Kousaka, N.Ogi, Y.Akazawa, M.Fujieda, Y.Yamamoto, Y.Takada, J.Kimura: "Novel Oxlipin Metabolites from the Brown Alga, Eisenia bicyclis"J. Nat. Prod.,. 66. (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Hyosu and J.Kimura: "Two New Songian Diterpenes from Coscinoderma mathewsi"J.Nat.Prod.. 63. 422-423 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Noboru Kamada and Junji Kimura: "Acid Catalyzed Transformation of Chamigrane Derivatives"Nippon Kagaku Kaishi. 571-575 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] J.Kimura and N.Maki: "New Loliolide Derivatives from the Brown Alga, Undaria pinnatifida"J.Nat.Prod.. 65. 57-58 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] J.Kimura, Y.Takada, T.Inayoshi, G.Geoetz, Y.Nakao, and P.J.Scheuer: "Kulokekahilide-1, a Cytotoxic Depsipeptide from a Cephalaspidean Mollusk Phillinopsis speciosa"J.Org.Chem.. 67. 1760-1767 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Kousaka, N.Ogi, Y.Akazawa, M.Fujieda, Y.Yamamoto, Y.Takada, and J.Kimura: "Novel Oxylipin Metabolites from the Brown Alga, Eisenia bicyclisis"J.Nat.Prod.. 66. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] J.Kimura et al.: "Kulokekahilide-1, Cytotoxic Depsipeptide from a Cephalaspiedean Mollusk, Philinopsis speciosa"J. Org. Chem.. 67・6. 1760-1767 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] J.Kimura et al.: "New Loliolide Derivatives from the Brown Alga Undaria pinnatifida"J. Nat. Prod.. 65・1. 57-58 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Junji Kimura: "New Loliolide Derivatives from the Brown Alga Undaria Pinnatifida"J. Nat. Prod.. 65. 57-58 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Junji Kimura: "Kulokekahilide-1, A Cytotoxic Depsipeptide from a Cephalaspiedean Mollusk Philinopsis speciosa"J. Org. Chem. (in print). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Junji Kimura,: "Kulokekahikide-1, a Cytotoxic Depsipeptide from a Cephalaspidean Mollusk Philinopsis speciosa,"J.Org.Chem.,. (accepted).

    • Related Report
      2000 Annual Research Report

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

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