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Biosynthesis of a Bioactive DiterpeneーDiol

Research Project

Project/Area Number 63470021
Research Category

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

Allocation TypeSingle-year Grants
Research Field 天然物有機化学
Research InstitutionTohoku University

Principal Investigator

OGURA Kyoko  Chemical Reserch Institute of NonーAqueous Solutions, Professor, 非水溶液化学研究所, 教授 (80006303)

Project Period (FY) 1988 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥7,200,000 (Direct Cost: ¥7,200,000)
Fiscal Year 1990: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1989: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1988: ¥4,800,000 (Direct Cost: ¥4,800,000)
KeywordsDiterpene / Geranylgeraniol / Plaunotol / Hydroxylase / Biosynthesis / Prenyltransferase / Geranylgeranyl Diphosphate / Isoprenoid / プラウノト-ル / ゲラニルゲラニル二リン酸 / カルス / ゲラニルゲラニオ-ル / イソペンテニル二リン酸 / プレニルトランスフェラ-ゼ / プラウノトール / 生理活性テルペノイド / プレニ ルトランスフェラーゼ / オキシゲナーゼ
Research Abstract

Biosynthesis of a diterpene-diol, plaunotol (18-hydroxy-E, E-geranylgeraniol) in Croton sublyratus was studied with attention to enzymatic hydroxylaton, and it was found that the homogenate of seeding of C. Sublyratus catalyzed the conversion of geranylgerany diphosphate into plaunotol. The enzyme activity was associated with the 100,000 X g precipitate, and it depended on molecular oxygen and NADPH. Geranylgeraniol was also hydroxylated when inclubated in the presence of Trion X-100, suggesting that the free alcohol is the direct substrate. However, it is necessary to ascertain the reproducibility, because the preparation of the hydroxylase requires very critical conditions in terms of the growing state of seedling as well as the procedure of preparation. The enzyme activities for isopentenyl diphosphate isomerase, farnesyl diphosphate synthase, and geranylgeranyl diphosphate synthase were also examined with soluble extracts from C. Sublyratus leaves of various growing states. As a result, the activity of geranylgeranyl diphosphate synthase was found to be much higher in seedlings than in young or adult leaves.

Report

(4 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • 1988 Annual Research Report
  • Research Products

    (21 results)

All Other

All Publications (21 results)

  • [Publications] 小倉 協三: "Artificially Elicited Capabilites of Enzymes and their Application in Natural Product Chemistry" Pure & Applied Chemistry. 61. 477-480 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 小倉 協三 他: "Negative Ion Fast Atom BombardmentーTandem Mass Spectrometry for Structural Analysis of Isoprenoid Diphosphates" Analitical Biochemistry. 185. 182-186 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 小倉 協三 他: "Prenyltransferase Reaction Involving Enantiomeric Discrimination ーーー Enzymatic Synthesis of (S)ー10,11ーEpoxyfarnesol from Racemic 6,7ーEpoxyfarnesyl Diphosphate and Isopentenyl Diphosphate" Tetrahedron Letters. 31. 4189-4190 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 小倉 協三 他: "Enzymatic Synthesis of Glycinoprenols" Tetrahedron Letters. 32. 241-242 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 小倉 協三 他: "Formation of Z,E,EーGeranylgeranyl Diphosphate by Rat Liver Microsomes" The Journal of Biochemistry. 266. 3458-3463 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 小倉 協三 他: "Variable Product Specificity of Microsomal Dehydrodolichyl Diphosphate Synthase from Rat Liver" The Journal of Biological Chemistry. 266. 3464-3468 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Masahiro Kitaoka, Hidemi Nagaki, Takeshi Kinoshita, Masaki Kurabayashi, Tanetoshi Koyama, and Kyozo Ogura,: "Negative Ion Fast Atom Bombardment Tandem Mass Spectrometry for Structural Analysis of Isoprenoid Diphosphates" Analytical BioChemistry. 185, No. 1. 182-186 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] T. Koyama, H. Inoue, S. Ohnuma, and K. Ogura,: "Prenyltransferase Reaction Involving Enantiomeric Discriminatin" Tetrahedron Letters,. 31-29. 4189-4190, (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] S. Ohnuma, T. Koyama, and K. Ogura,: "Enzymatic synthesis of Glycinoprenols" Tetrahedron Letters. 32-2. 241-242, (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] H. Sagami, S. Matsuoka, and K. Ogura,: "Formation of Z, E, E-Geranygeranyl Diphosphate by Rat Liver Microsomes" The Journal of Biological Chemistry. 266-6. 3458-3463 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] S. Matsuoka, H. Sagami, A Kurisaki, and K. Ogura,: "Variable Product Specificity of Microsomal Dehydrodolichyl Diphosphate Synthase from Rat liver" The Journal of Biological Chemistry,. 266-6,. 3464-3468 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 小倉 協三 他: "Negative Ion Fast Atom BombardmentーTandem Mass Spectrometry for Structural Analysis of Isoprenoid Diphosphates" Analytical Biochemistry. 185. 182-186 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] 小倉 協三 他: "Prenyltransferase Reaction Involving Enantiomeric Discrimination" Tetrahedron Letters. 31. 4189-4190 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] 小倉 協三 他: "Enzymatic Synthesis of Glycinoprenols" Tetrahedron Letters. 32. 241-242 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] 小倉 協三 他: "Formation of <Z,E,E>___ーーGeranylgeranyl Diphosphate by Rat Liver Microsomes" The Journal of Biological Chemistry. 266. 3458-3463 (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] 小倉 協三 他: "Variabale Product Specificity of Microsomal Dehydrodolichyl Diphosphate Synthase from Rat Liver" The Journal of Biological Chemistry. 266. 3464-3468 (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] 小倉協三: "Artificially elicited capabilities of enzymes and their Application in natural product chemistry" Pure and Applied Chemistry. 61. 477-480 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 佐上博: "The Biosynthesis of dehydrodolicyl phosphates by rat liver microsomes" Biochimica et Biophysica Acta. 1002. 218-224 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 吉田一郎: "Protection of hexaprenyl diphosphate synthase of Micrococcus luteus B-P 26 against inactivation by sulfhydryl reagents and arginine-specific reagents" Biochimica et Biophysica Acta. 995. 138-143 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Tanetoshi,Koyama;Yuichirou,Kokubun;Kyozo Ogura: Phytochemistry. 27. 2005-2009 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Tanetoshi,Koyama;Michio,Ito;Shin-ichi,Ohnuma;Kyozo,Ogura: Tetrahedron Letters. 29. 3807-3810 (1988)

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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