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Approach to Black Tea Pigments based on Bioorganic Chemistry of Catechin Oxidation

Research Project

Project/Area Number 12680594
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionNagasaki University

Principal Investigator

TANAKA Takashi  Nagasaki University, Graduate School of Biomedical Sciences, Associate Professor, 大学院・医歯薬学総合研究科, 助教授 (90171769)

Co-Investigator(Kenkyū-buntansha) KOUNO Isao  Nagasaki University, Graduate School of Biomedical Sciences, Professor, 大学院・医歯薬学総合研究科, 教授 (20038607)
Project Period (FY) 2000 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 2002: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 2001: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 2000: ¥1,900,000 (Direct Cost: ¥1,900,000)
Keywordspolyphenol / Black tea / tannin / catechin / oxidation / proanthocyanidin / theaflavin / thearubigin
Research Abstract

Black tea accounts for almost 80 % of the world's tea production and is the most important source of polyphenol in the world. However, little has been known about the chemistry of black tea polyphenols due to their complexity. Since most of the black tea polyphenols are produced by enzymatic oxidation of green tea catechins, first, we developed new in large-scale model fermentation system using pure green tea catechins and various plant homogenates.
In this research, structures of four novel oxidation products of theaflavin and two new dimers of epigallocatechin and its gallate have been elucidated. In addition, accumulation of unstable dimer quinones of epigallocatechin and its gallate during tea fermentation has been firstly demonstrated. When the fermented leaves were heated briefly, the dimer quinones were converted to theasinensins, which are another major polyphenol characteristic of black tea. Formation and degradation of theaflavins and epigallocatechin dimer quinones are major pathways in catechin oxidation during tea fermentation and understanding the chemical mechanism is important in clarifying black tea polyphenols.
We also found that the dimer quinone of epigallocatechin gallate was generated on autoxidation in aqueous solution. In addition, a new oxidation product generated by oxidative cleavage of the catechin B-ring was isolated. The latter was also found in commercial black tea products. The result showed that enzymatic and non-enzymatic oxidation on catechins are closely related to each other.
Furthermore, a new pigment named theafladione was isolated from commercial black tea, which is produced by oxidation of one of the precursor of theaflavin.
In order to apply black tea pigment theaflavin as functional food ingredients, we devdoped a method to produce a theaflavin-rich tea extract by treatment of green tea with unripe loquat fruit. The extract showed strong inhibition activity against amylase, which related to increase of blood sugar level.

Report

(4 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • Research Products

    (26 results)

All Other

All Publications (26 results)

  • [Publications] Tanaka, T.: "Theanaphthoquinone, a novel pigment oxidatively derived from the aflavin during tea-fermentation"Chem.Commun. 1365-1366 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.: "Oxidation and epimerization of epigallocatechin in banana fruits"Phytochemistry. 53. 311-316 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.: "Two Types of Oxidative Dimerization of the Black Tea Polyphenol Theaflavin"Journal of Agricultural and Food Chemistry. 49. 5785-5789 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.: "Structures of Two New Oxidation Products of Green Tea Polyphenols Generated by Model Tea Fermentation"Tetrahedron. 58. 8851-8856 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.: "Accumulation of Epigallocatechin Quinone Dimers during Tea Fermentation and Formation of Theasinensins"Journal of Natural Product. 65. 1582-1587 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.: "synthesis of Theaflavin from Epicatechin and Epigallocatechin by Plant Homogenates and Role of Epicatechin Quinone in the Synthesis and Degradation of Theaflavin"Journal of Agricultural and Food Chemistry. 50. 2142-2148 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Kondo, K.; Kurihara, M.; Fukuhara, K.; Tanaka, T.; Suzuki, T.; Miyata, N.; Toyoda, M.: "Conversion of procyanidin B-type (catechin dimer) to A-type : evidence for abstraction of C-2 hydrogen in catechin during radical oxidation"Tetrahedron Letters. 41. 485-488 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.; Betsumiya, Y.; Mine, C.; Kouno, I.: "Theanaphthoquinone, a novel pigment oxidatively derived from theaflavin during tea-fermentation"Chem.Commun. 1365-1366 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.; Kondou, K.; Kouno, I.: "Oxidation and epimerization of epigallocatechin in banana fruits"Phytochemistry. 53. 311-316 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka,T.; Inoue, K.; Betsumiya, Y.; Mine, C.; Kouno, I.: "Two Types of Oxidative Dimerization of the Black Tea Polyphenol Theaflavin"J.Agric.Food Chem.. 49. 5785-5789 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.; Mine, C.; Inoue, K.; Matsuda, M.; Kouno, I.: "Synthesis of Theaflavin from Epicalechin and Epigallocatechin by Plant Homogenates and Role of Epicatechin Quinone in the Synthesis and Degradation of Theaflavin"J.Agric.Food Chem.. 50. 2142-2148 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.; Mine, C.; Kouno, I.: "Structures of Two New Oxidation Products of Green Tea Polyphenols Generated by Model Tea Fermentation"Tetrahedron. 58. 8851-8856 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.; Mine, C.; Watarumi, S.; Fujioka, T.; Mihashi, K.; Zhang, Y.-J.; Kouno, I.: "Accumulation of Epigallocatechin Quinone Dimers during Tea Fermentation and Formation of Theasinensins"J.Nat.Prod.. 65. 1582-1587 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.: "Oxidation of tea catechins and production of black tea pigments"Kagaku to Seibutu. 40(8). 513-518 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.; Kouno, I.: "Oxidation of Tea Catechins : Chemical Structures and Reaction Mechanism"Food Science and Technology Research. "accepted". (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tanaka, T.: "Synthesis of Theaflavin from Epicatechin and Epigallocatechin by Plant Homogenates and Role of Epicatechin Quinone in the Synthesis and Degradation of Theaflavin"Journal of Agricultural and Food Chemistry. 50・7. 2142-2148 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Tanaka, T.: "Structures of Two New Oxidation Products of Green Tea Polyphenols Generated by Model Tea Fermentation"Tetrahedron. 58・43. 8851-8856 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Takana, T.: "Accumulation of Epigallocatechin Quinone Dimers during Tea Fermentation and Formation of Theasinensins"Journal of Natural Product. 65・11. 1582-1587 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Ahang, Y.-J.: "Two New Acyalted Flavanone Glycosides from the Leaves and Branches of Phyllanthus emblica"Chemical and Phamaceutical Bulletin. 50・6. 841-843 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 田中 隆: "緑茶カテキンの産科と紅茶ポリフェノールの生成"化学と生物. 40・8. 513-518 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Tanaka, T.: "Two Types of Oxidative Dimerization of the Black Tea Polyphenol Theaflavin"Journal of Agricultural and Food Chemistry. 49・12. 5785-5789 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] Tanaka, T.: "Theanaphthoquinone, a novel pigment oxidatively derived from theaflavin during tea-fermentation."Chem.Commun. 2000. 1365-1366 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] Tanaka, T.: "Two Types of Oxidative, Dimerization of the Black Tea Polyphenol Theaflavin"J.Agric.Food Chem.. 49. 5785-5789 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Zhang, Y.-J: "Association of Tannins and Related Polyphenols with the Cyclie Peptide Gramicidin S"Chem.Pharm.Bull. 50. 258-262 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Tanaka, T.: "Synthesis of Theaflavin from Epicatechin and Epigallocatechin by Plant Homogenates and Role of Epicatechin Quinone in the Synthesis and Degradation of Theaflavin"J.Agric.Food Chem.. 50(accepted 01/08/02). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Tanaka,Y.Betsumiya,C.Mine,Isao Kouno: "Theanaphthoquinone, a novel pigment oxidatively derived from theaflavin during tea-fermentation"Chemical Communication. 2000. 1365-1366 (2000)

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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