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Production of Anti-tumor Compounds and Degradation of Carcinogenic Compounds

Research Project

Project/Area Number 04557099
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKYOTO UNIVERSITY

Principal Investigator

UEDA Shinichi  Kyoto University, Faculty of Pharm.Sci.Associate Professor, 薬学部, 助教授 (20025688)

Co-Investigator(Kenkyū-buntansha) TOKUDA Harukuni  Kyoto Prefectural University of Medicine Medical Faculty, Instructor, 医学部, 助手 (60111960)
NAGAOKA Yasuo  Kyoto University, Faculty of Pharm.Sci.Instructor, 薬学部, 助手 (90243039)
IIDA Akira  Kyoto University, Faculty of Pharm.Sci.Instructor, 薬学部, 助手 (40202816)
藤多 哲朗  京都大学, 薬学部, 教授 (40027024)
Project Period (FY) 1992 – 1994
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥13,400,000 (Direct Cost: ¥13,400,000)
Fiscal Year 1994: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 1993: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 1992: ¥7,400,000 (Direct Cost: ¥7,400,000)
Keywordsanti-tumor-promoting substance / plant cultured cell / Rubiaceae / Moraceae / Bignoniaceae / Terpenoid / naphthoquinone / prenylchalcone / 抗発癌プロモーション物質 / 芳香族化合物 / ダイベンゾパラダイオキシン / イリドイド / 生合成
Research Abstract

Iridoid type monoterpene glucosides, prenylchalcones, and furanonaphthoquinones indicating promissing anti-tumor-promoting activities were obtained from the cell cultures of the plants of the families Rubiaceae, Moraceae, and Bignoniaceae, respectively. The biosynthetic mechanism as well as in vitro and in vivo anti-tumor-promoting activity of these secondary metabolites were examined. [1] Genipin, the aglucone of geniposide, a main iridoid glucoside of Gardenia and Genipa fruits as well as Gardenia jasminoides cell cultures remarkably inhibits tumor-promotion caused by TPA on Raji cells. It also inhibits mouse pulmonary tumorigenesis promoted by glycerol and papilloma formation promoted by TPA.[2] Mulberry cell prenylchalcones, chalcomoracin and kuwanon J completely inhibit tumor-promotion on Raji cells at 1000 times concentration relative to TPA.The viability of Raji cells was 30%. Equimolar mixture of both compounds inhibitory activity. The prenyl moieties of both compounds were found to be biosynthesized as follows : starter acetate unit for mevalonate synthesis is of glycolytic origin, while the second and third acetate units originate from the pentose phosphate cycle. [3] Administration of [^<13>C] labeled phenylalanine and tyrosine to Morus alba cell cultures revealed that both amino acids participate in parallel in the biosynthesis of the phenylpropanoid moieties of chalcomoracin and kuwanon J.[4] 5-Hydroxy-2- (1-hydroxyethyl) -naphtho [2,3-b] furan-4,9-dione and related naphthoquinones produced by a South American bignoniaceous plant Tabebuia avellanedae were found to have promissing anti-tumor-promoting activity.

Report

(4 results)
  • 1994 Annual Research Report   Final Research Report Summary
  • 1993 Annual Research Report
  • 1992 Annual Research Report
  • Research Products

    (37 results)

All Other

All Publications (37 results)

  • [Publications] Y. Hano: "A novel way of determining the structure of artonin I,an optically active Diels-Alder type adduct,with the aid of enzyme system of Morus alba cell cultures" J. Chem. Soc. Chem. Commun. 1177-1178 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] S. Ueda: "Genipa americana L. (Marmalade Box):In vitro production of inidoid glucosides" Biotechnology in Agriculture and Furestry ( Medicinal and Aromatic Plants). 21. 162-171 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Y. Hano: "Direct NMR evidence for the equivalent purticipation of L-phenylalanine and L-tyrosine in the biosynthesis of the intermolecular Diels-Aider type adducts of prenylchalcune and prenylated 2-arylben2ofuaun in Morus alba cell cultures" Canadian J. Chem.72. 12-14 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Y. Hano: "A chimeric hemiterpene biosynthesis in Morus alba cell cultures" Naturwissenschaften. 81. 260-262 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] S. Ueda: "Production of antitumar-promoting furano naphthoquinones in Tabebuia avellanedal cell cultures" Phytochemistry. 36. 323-325 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Y. Hano: "Origin of the acetate units composing the hemiterpene moieties of chaicomoracin in Morus alba cell cultures" J. Am. Chem. Soc.116. 4189-4193 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] S. Ueda: "Tabebuia avellanedae Lorentz ex Griseb. (Taheebo):In vitro production of naphthoquinonoes" Biotechnology in Agriculture and Forestry(Medicinal and Aromatic Plants Vll). 28. 445-456 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Y. Hano: "Parallel contribution of L-phenylalanine and L-tyrosine to the biosynthesis of prenylchalcones in Mosus alba cell cultures" Naturwissenschaften. 81. 507-509 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] S.Ueda: "Morus alba L.( whitemulbetty) : In Vitro culture and the production of intermolecular Diels-Alder type adducts of prenyl-chalcone and prenylated 2-arylhenzofuran" Biotechnology in Agriculture and Forestry( Medicinal and Aromatic Plants). (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Y.Hano: "A novel way of determining the structure of artonin I,an optically active Diels-Alder type adduct with the aid of enzyme system of Morus alba cell cultures" J.Chem.Soc.Chem.Commun.1177-1178 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] S.Ueda: "Genipa americana L.(Marmalade Box) : In vitro production of iridoid glucosides" Biotechnology in Agriculture and Forestry (Medicinal and Aromatic Plants). 21. 162-171 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Y.Hano: "Direct NMR evidence for the equivalent participation of L-phenylalanine and L-tyrosine in the biosynthesis of the intermolecular Diels-Alder type adducts of prenylchalcone and prenylated 2-arylbenzofuran in Morus alba cell cultures" Canadian J.Chem.72-1. 12-14 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Y.Hano: "A chimeric hemiterpene biosynthesis in Morus alba cell cultures" Naturwissenschaften. 81-6. 260-262 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] S.Ueda: "Production of antitumor-promoting furanonaphthoquinones in Tabebuia avellanedae cell culturees" Phytochemistry. 36-2. 323-325 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Y.Hano: "Origin of the acetate units composing the hemiterpene moieties of chalcomoracin in Morus alba cell cultures" J.Am.Chem Soc.116-10. 4189-4193 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] S.Ueda: "Tabebuia avellanedae Lorentz ex Griseb. (Taheebo) : In vitro production of naphthoquinones" Biotechnology in Agriculture and Forestry (Medicinal and Aromatic Plants). 28. 445-456 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Y.Hano: "Parallel contribution of L-phenylalanine and L-tyrosine to the biosynthesis of prenylchalcones in Morus alba cell cultures" Naturwissenschaften. 81-11. 507-509 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] S.Ueda: "Morus alba L.(white mulberry)In vitro cultures and the production of intermolecular Diels-Alder type adducts of prenylchalcone and prenylated 2-arylbenzofuran" Biotechnology in Agriculture and Forestry (Medicinal and Aromatic Plants). (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] S.Ueda,et al.: "A novel way of dellrmining the structure of artoninI,on optically active Diels Alder type adduct,with the aidot enzyme system of Morus Alba cell cultures" J.Chem.Soc.Chem.Commun.1177-1178 (1992)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ueda: "Genipa amlricana L.(Marmalade Box):In vitre procluchon of isidoid glecosides" Biotechnology in Agriculture and Forestay(Medicanal and Aromidic Plants). 21. 162-171 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ueda,et al.: "Direct NMR evidence for the age Valent participation of L-phenylalanine and L-tyrosine in the biosynthesis of the intermoiecuiar Diels-Alder type adducts of prenyl-chalcore and prenylated 2-arylhenzofuran in Morus alba cell cultures" Canadian J.Chem.72. 12-14 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ueda,et al.: "Achimenic hemiterpene biosynthesis in Morus alba cell culfures" Natur wissens chaften. 81. 260-262 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ueda,et al.: "Production of anti-tumor promoting furanonaphthoguinones in Tabeluia or ellanedal cell cultures" Phytochemistry. 36. 323-325 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ueda,et al.: "Origin of the acetate units composing the hemiterpene moieties of Chalcomoracin in Morus alba cell cultures" J.Am.Chem.Soc.116. 4189-4193 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ueda: "Tabeluia avellanedal Lorentz ex Griseb,(Tahebo):In vitro production of naphthoguinones" Biotechnology in Agriculturl and Forestry(Medicinal and aronatic plants VII. 28. 445-456 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ueda,et al.: "Parellel contribution of L-phenylalanine and L-tyrosine to the biosynthesis of prenylchakores in Morus alba cell cultures" Naturwissenschaften. 81. 507-509 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ueda: "Morus alba L.(White mulberry):In vitro calture and the production of intermolecular Diels Alder type adducts of prenylchalcone and prenylaled 2-arylbenzofuran" Biotechnology in Agricu Hare and Forlstry(Medicinal and Aromatic Plants). (印刷中).

    • Related Report
      1994 Annual Research Report
  • [Publications] Shinichi Ueda: "Genipa americana 2.:In vitro Production of Iridoid Glucosides" Biotechnology in Agriculture and Forestry. 21. 162-171 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Yoshio Hano: "A direct NMR evidence for the equivalent participation of L-phenylalanine and L-tyrosine in the biosynthesis of the intermolecular Diels-Alder type adducts of prenylchalcone and prenylated 2-arylbenzoturan in Morus alba cell cultures" Canadian Journal of Chemistry. 72(印刷中). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Shinichi Ueda: "Production of anti-tumor-promoting turanonaphthoquinones in Tabebuia avellanedae cell cultures" Phytochemistry. 35(印刷中). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Yoshio Hano: "Chimeric hemiterpene biosynthesis in Morus alba cell cultures" Naturwissenschaften. 81(印刷中). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Yoshio Hano: "Origin of the acetate units composing the hemiterpene moieties of chalcomoracin in Morus alba cell cultures" Journal of the American Chemical Society. 116(印刷中). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Shinichi Ueda: "Tabebuia avellanedae Lorentz ex Griseb.(TAHEEBO):In vitro Production of Naphthoquinones" Biotechnology in Agriculture and Forestry. 28(印刷中). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Taro Nomura: "Chemistry and Biosynthesis of Natural Diels-Alder Type Adducts from Moraceous Plants" Elsevier Science Publishers-Amsterdam(印刷中), (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Yoshio Hano: "Dynamic Participation of Primasy Metabdites in the Biosynthesis of Chalcomoracin and β-sitosterol in Morus alba Cell Cultures" Naturwissenschaften. 79. 180-182 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Yoshio Hano: "A Novel Way of defermining the Structure of Astonin I,an optically Active Diels-Alder Type Adduct,with the Aid of an Enzyme System of Morus alba Cell Cultures" J.Chem.Soc.,Chemical Communications. 1177-1178 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Shinichi Ueda: "Genipa americanaL.:In vitro Production of Iridoid Glucosides" Biotechnology in Agriculture and Forestry. 21. (1993)

    • Related Report
      1992 Annual Research Report

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Published: 1992-04-01   Modified: 2016-04-21  

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