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1994 Fiscal Year Final Research Report Summary

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)
Project Period (FY) 1992 – 1994
Keywordsanti-tumor-promoting substance / plant cultured cell / Rubiaceae / Moraceae / Bignoniaceae / Terpenoid / naphthoquinone / prenylchalcone
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.

  • Research Products

    (18 results)

All Other

All Publications (18 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 1996-04-15  

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