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Studies on search of protease inhibitors in blue-green algae and biosynthetic pathways

Research Project

Project/Area Number 05453172
Research Category

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

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

Principal Investigator

MURAKAMI Masahiro  The University of Tokyo, Faculty of Agriculture, Associate Professor, 農学部, 助教授 (70134517)

Project Period (FY) 1993 – 1994
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥7,400,000 (Direct Cost: ¥7,400,000)
Fiscal Year 1994: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1993: ¥5,300,000 (Direct Cost: ¥5,300,000)
KeywordsProtease / Protease inhibitor / Trypsin / Trypsin inhibitor / Blue-green algae / Microcystis / Cytotoxicity / - / エラスターゼ / キモトリプシン / Nostoc / ペプチド
Research Abstract

Microcystis aeruginosa (NIES-98) was obtained from the NIES-collection (Microbial Culture Collection, the National Institute for Environmental Studies, Japan) . The 80% methanol extract of freeze-dried alga was partitioned between water and diethyl ether. The aqueous layr that showed potent trypsin inhibitory activity was further extracted with n-butanol and subjected to ODS column chromatography, followed by ODS HPLC to yield aeruginosin 98-A (1), B (2) and C (3) and aeruginoguanidine 98-A(4) , B (5) and C (6).
Molecular formula of 1 was decides as C_<29>H_<45>N_6O_9ClS from HRFABMS and NMR data.Amino acid analysis of the acid hydrolyzate gave allo-Ile and an unknown imino acid. ^1H-^1H COSY,HMQC and HMBC date showed the presence of Choloro Hpla (3-chloro-4-hydroxyphenyllactic acid), allo-Ile, Choi sulfate (2-carboxy-6-hydroxyoctahydroindole sulfate) andagmatin. Interpretation of HMBC spectra revealed the structure of 1. The stereochemistryof allo-Ile was determined to be D-form by the chiral GC analysis. The relative stereochemistry of Choi sulfare was elucidated by NOESY spectra. The structures of 2 and 3 only differ from 1 in the substitution of the benzene ring of Chloro Hpla. The IC_<50> of 1,2 and 3 against trypsin was 0.55,0.6 and 3.93 mg/mL,respectively.
Molecular formula of 5 was decided as C_<34>H_<59>N_9O_<14>S_3 from HRFABMS and NMR data. ^1H-^1HCOSY,HOHAHA,HMQC and HMBC data showed the presence of Hphpa trisulfate (1- (4-hydroxy-3-hydroxymethyl) phenyl-1-hydroxy-2-propylamine 4', 3', 1-tri-O-sulfate) , N-MeArg and NmgArg (N^a-methyl-N^W-geranylarginine). Interpretation of HMBC and NOESY spectra revealed the structure of 5. The structures of 4 and 6 were elucidated asanalogs of 5, having the different side chains of N-MeArg. These compounds showed weak cytotoxicity against P388 leukemia cells.

Report

(3 results)
  • 1994 Annual Research Report   Final Research Report Summary
  • 1993 Annual Research Report
  • Research Products

    (3 results)

All Other

All Publications (3 results)

  • [Publications] Masahiro Murakami: "Aeruginosin 98-A and B,Trypsin Inhibitors from the Blue-Green Alga Microcystis aeruginosa(NIES-98)" Tetrahedron Letters. (in press.).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Murakami: "Aeruginosin 98-A and B,Trypsin Inhibitors from the Blue-Green Alga Microcystis aeruginosa (NIES-98)" Tetrahedron Lett.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masahiro Murakami: "Aeruginosin 98-A and B,Trypsin Inhibitors from theBlue-Green Alga Microcystis aeruginosa(NIES-98)" Tetrahedron Letters. (in press).

    • Related Report
      1994 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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