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2006 Fiscal Year Final Research Report Summary

Search for compounds active, against fish diseases from marine invertebrates

Research Project

Project/Area Number 16380142
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Fisheries chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

MATSUNAGA Shigeki  The University of Tokyo, Graduate School of Agricultural and Life Sciences, Professor, 大学院農学生命科学研究科, 教授 (60183951)

Co-Investigator(Kenkyū-buntansha) OGAWA Kazuo  The University of Tokyo, Graduate School of Agricultural and Life Sciences, Professor, 大学院農学生命科学研究科, 教授 (20092174)
Project Period (FY) 2004 – 2006
Keywordstunicate / Didemnidae / Vibrio anguillarum / fish pathogenic bacteria / antimicrobial / serinolipid / structure elucidation / spectral analysis
Research Abstract

We searched for antimicrobial compounds against Vibrio anguillarum from a tunicate collected at Shishi Island. The methanol extract of the organism was subjected solvent partitioning followed by reversed phase HPLC to afford five antimicrobial compounds. The molecular formula of the major constituent shishididemniol A was shown to be C45H81N3O11 on the basis of HRFABMS. Interpretation of a variety of 2D NMR spectra showed that the compound was composed of two serinol units, a substituted octopamine, and a C28 fatty acids with six sites of oxygenation. Further analysis of the 2D NMR data in conjunction with tandem FABMS analysis allowed the assignment of the planar structure of this compound. The absolute stereochemistry of the eight stereogenic centers in the molecule was determined by application of the modified Mosher analysis to the fragments obtained by chemical degradation. Especially the stereochemistry of the isolated secondary alcohol was determined by the application of the 2-NMA method, which is a modification of the Mosher analysis. The structures of other congeners were determined in the same manner.

  • Research Products

    (6 results)

All 2007 2005

All Journal Article (6 results)

  • [Journal Article] Complete Structure Elucidation of Shishididemniols, Complex Lipids with Tyramine-derived Tether and Two Serinol Units, from a Marine Tunicate of the Family Didemnidae.2007

    • Author(s)
      H.Kobayashi
    • Journal Title

      Journal of Organic Chemistry 72卷

      Pages: 1218-1225

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] The Structures of Three New Shishididemniols from a Tunicate of the Family Didemnidae2007

    • Author(s)
      H.Kobayashi
    • Journal Title

      Tetrahedron (印刷中)

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Complete Structure Elucidation of Shishididemniols, Complex Lipids with Tyramine-derived Tether and Two Serinol Units, from a Marine Tunicate of the Family Didemnidae.2007

    • Author(s)
      Kobayashi, H.
    • Journal Title

      Journal of Organic Chemistry 72

      Pages: 1218-1225

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] The Structures of Three New Shishididemniols from a Tunicate of the Family Didemnidae2007

    • Author(s)
      Kobayashi, H.
    • Journal Title

      Tetrahedron (in press)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Novel bromotyrosine derivatives that inhibit growth of the fish pathogenic bacterium Aeromonas hydrophila, from a marine sponge Hexadella sp.2005

    • Author(s)
      S.Matsunaga
    • Journal Title

      Journal of Organic Chemistry 70卷

      Pages: 1893-1896

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Novel bromotyrosine derivatives that inhibit growth of the fish pathogenic bacterium Aeromonas hydrophila, from a marine sponge Hexadella sp.2005

    • Author(s)
      Matsunaga, S.
    • Journal Title

      Journal of Organic Chemistry 70

      Pages: 1893-1896

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2008-05-27  

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