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Studies on Structural Analysis of Molecular Association of Flower Pigments, Anthocyanins

Research Project

Project/Area Number 04640525
Research Category

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

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

Principal Investigator

KONDO Tadao  Nagoya University, Associate Professor Chemical Instrument Center, 化学測定機器センター, 助教授 (70093028)

Project Period (FY) 1992 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1993: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1992: ¥1,500,000 (Direct Cost: ¥1,500,000)
Keywordsanthocyanin / molecular association / strucutral analysis / color variation / stability / commelinin / protocyanin / X-ray crystallography / 金属錯体 / 構造決定 / 再合成 / 発色発現
Research Abstract

Commelinin is a real pigment of blue petals of Commelina communis and a metal-complex involving self-association and copigmentation. We obtained it as a pure pigment by reconstruction from the components, malonylawobanin (M), flavocommelin (F) and magnesium ion. By reconstruction experiments of the commelinin-like pigments by replacement of the components the metal-coordination position was determined. The exact structural analysis was succeeded by ^1H NMR,CD and atomic analyzes followed by X-ray crystallographic analysis using synchrotoron radiation. M and M,and F and F are stacking each other in face-to-face in left-handed screw and M and F is in right-handed manner. The gross strucutre is cyclo-MMFFMMFFMMFF.The association is due to hydrophobic interaction of the aromatic nuclei. The blue color development is due to the 4'-keto anhydrobase anion of the anthocyanidin nucleus arising from metal chelation.
Protocyanin is a real pigment from blue corn flower, Centaurea cyanus. We first detrmined the exact molecular weight by ESI-mass, and established the composition by reconstruction from components, succinylcyanin (Sc), malonylflavone (Mf), Fe^<3+> and Mg^<2+> tobe [Sc_6Mf_6Fe^<3+>Mg^<2+>].
We first succeeded in exact structural elucidation of real flower pigment and put a period of controversy of metal-complex theory during 70 years.

Report

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

    (19 results)

All Other

All Publications (19 results)

  • [Publications] Kumi Yoshida: "Intramolecular Stacking Conformation of Gentiodelphin,a Diacylated Anthocyanin from Gentiana Makinoi" Tetrahedron. 48. 4313-4326 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tadao Kondo: "Structural Basis of Blue-Color Development in Flower Petals from Commelina communis" Nature. 358. 515-518 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kumi Yoshida: "Diglucuronoflavones from Purple Leaves of Perilla ocimodes" Phytochemistry. 33. 917-919 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kumi Yoshida: "Stabilization of Color Variation of Anthocyanins with Inorganic Salts" Seventh Symposium on Salts. 2. 623-630 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tsukasa Mori: "Fromation of Anthocyanins from Cells Cultured from Different Parts of Strawberry Plants" Journal of Food Science. 58. 788-792 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tadao Kondo: "Mechanism for Blue Flower-Colour Development:Structural Determination of commelinin from Blue Petals of Commerina communis" Polyphenols Actualites. 10. 20-21 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kumi Yoshida, Tadao Kondo, Toshio Goto: Tetrahedron. 48. 4313-4326 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tadao Kondo, Kumi Yoshida, Atsushi Nakagawa Takatoshi Kawai, Hirotoshi Tamura, Toshio Goto: "Structural Basis of Blue-Color Development in Flower Petals from Commelina communis" Nature. 358. 515-518 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kumi Yoshida, Kiyoshi Kameda, Tadao Kondo: "Diglucuronoflavones from Purple Leaves of Perilla ocimodes" Phytochemistry. 33. 917-919 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kumi Yoshida, Tadao Kondo, Toshio Goto: "Stabilization of Color Variation of Anthocyanins with Inorganic Salts" Seventh Symposium on Salts. 2. 623-630 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tsukasa Mori, Miei Sakurai, Jun-ichi Shigeta, Kumi Yoshida, Tadao Kondo: "Formation of Anthocyanins from Cells Cultured from Different Parts of Strawberry Plants" Journal of Food Science. 58. 788-792 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tadao Kondo, Kumi Yoshida: "Mechanism for Blue Flower-Color Development : Structural Determination of commelinin from Blue Petals of Commerina communis" Polyphenols Actualites. 10. 2-21 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tadao Kondo, Kumi Yoshida: "Mechanism for Blue Flower-Color Development : Structural Determination of commelinin from Blue Petals of Commerina communis" Polyphenols Actualites. 10. 2-21 (1994)"Intramolecular Stacking Conformation of Gentiodelphin, a Diacylated Anthocyanin from Gentiana Makinoi"

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kumi Yoshida: "Diglucuronoflavones from Purple Leaves of Perilla ocimodes" Phytochemistry. 33. 917-919 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Kumi Yoshida: "Stabilization of Color Variation of Anthocyanins with Inorganic Salts" Seventh Symposium on Salts. 2. 623-630 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Tsukasa Mori: "Formation of Anthocyanins from Cells Cultured from Different Parts of Strawberry Plants" Journal of Food Science. 58. 788-792 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Tadao Kondo: "Mechanism for Blue Flower-Colour Development:Structural Determination of commelinin from Blue Petals of Commerina communis" Polyphenols Actualites. 10. 20-21 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] 吉田 久美,近藤 忠雄,後藤 俊夫: "Intramolecular Stacking Conformation of Gentiodelphin,a Diacylated Anthocyanin from Gentiana Makioi" Tetrahedron. 48. 4313-4326 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] 近藤 忠雄,吉田 久美,中川 敦史,河合 隆利,田村 啓敏,後藤 俊夫: "Structural Basis of Blue-Colour Development in Flower Petals from Commelina communis" Nature. 358. 515-518 (1992)

    • Related Report
      1992 Annual Research Report

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

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