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1993 Fiscal Year Final Research Report Summary

STUDIES ON BIOACTIVE SUBSTANCES FROM MARINE MICROORGANISMS

Research Project

Project/Area Number 04453030
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 天然物有機化学
Research InstitutionHOKKAIDO UNIVERSITY

Principal Investigator

NAKAMURA Hideshi  HOKKAIDO UNIVERSITY, DEPARTMENT OF CHEMISTRY, ASSOCIATE PROFESSOR, 理学部, 助教授 (90217878)

Project Period (FY) 1992 – 1993
KeywordsSYMBIOTIC ALGAE / ZOOXANTHELLA / ZOOXANTHELLATOXIN / STRUCTURE DETERMINATION
Research Abstract

Vasoconstrictive compounds, zooxanhtellatoxin-A (ZT-A) and ZT-B were isolated from a symbiotic marine dinoflagellate Symbiodinium sp. Sodium periodate oxidation of Zt-A followied by sodium borohydride reduction gave fragments containing characteristic functionalities including an exomethyoene, a diexpoxide, a sulfate, a conjugated diene, a spiroacetal, and an amide. The structures correspond to about 80% of the full structure of ZT-A.TOCSY spectra of ZT-A under various conditions enable us to connect the partial structures deduced from the degradation products. The unveiled structures were obtained by detailed analyes of HMBC, HMQC and 13-C NMR spectra. The structure of ZT-A was determined on the basis of the spectral data and chemical degradation experiments to be a novel 62-membered lactonewith and amide linkage.
Model compounds of tumor-promorting sabstance, aplysiatoxin were designed on the basis of the structure-activity relationship. Synthesis of a model containing functionalities essential for biological activity was finally achieved.

  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] Nakamura,H.,Asari,T.,Ohizumi,Y.,Kobayashi,J.,Yamasu,T.,and Murai,A.: "Isolation of zooxanthellatoxins,novel vasconstrictive subsances from the zooxanthella Symbiodinium sp." Toxicon. 31. 371-376 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nakamura,H.,Asari,T.,Murai,A.,Kondo,T.,Yoshida,K.,and Ohizumi,Y.: "Structure of periodate oxidation products with characteristic partial structures of zooxanthellatoxin-A,a potent vasoconstrictive polyol from a symbiotic dinoflagellate." J.Org.Chem.58. 313-314 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Asari,T.,Nakamura,H.,and Murai,A.: "Structures of periodate oxidation products with a conjugated diene or an exomethylene from zooxanthellatoxin-A" Tetrahedron Lett.34. 4059-4062 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nakamura,H.,Oba,Y.,and Murai,A.: "Synthesis and Absolute Configuration of the Ozonolysis Product of Krill Fluorescent Compound F" Tetrahedron Lett.34. 2779-2782 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nakamura,H.,Fujimaki,K.,Sampei,O.,and Murai,A.: "Gonyol:Methionine-induced Sufonium Accumulation in a Dinoflagellate Gonyaulax polyedra." Tetrahedron Lett.34. 8481-8484 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nakamura, H., Asari, T., Ohizumi, Y., Kobayashi, J., Yamasu, T., and Murai, A.: "Isonation of zooxanthellatoxins, novel vasoconstrictive subsances from the zooxanthella Symbiodinium sp." Toxicon. 31. 371-376 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Nakamura, H., Asari, T., Murai, A., Kondo, T., Yoshida, K., and Ohizumi, Y.: "Structure of periodate oxidation products with characteristic partial structures of zooxanthellatoxin-A, a potent vasoconstrictive polyol from a symboiotic dinoflagellate." J.Org. Chem.58. 313-314 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Asari, T., Nakamura, H., and Murai, A.: "Structures of periodate oxidation products with a conjugated diene or an exomethylene from zooxanthellatoxin-A" Tetrahedron lett.34. 4059-4062 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Nakamura, H., Oba, Y., and Murai, A.: "Synthesis and Absolute Configuration of the Ozonolysis Product of Krill Fluorescent Compound F" Tetrahedron lett.34. 2779-2782 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Nakamura, H., Fujimaki, K., Sampei, O., and Murai A.: "Gonyol : Methionine-induced Sufonium Accumulation in a Dinoflagellate Gonyaulax polyedra." Tetrahedron lett.34. 8481-8484 (1993)

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

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Published: 1995-03-27   Modified: 2022-02-14  

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