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New browning reaction of tea polyphenols during the roasting process of green tea leaves

Research Project

Project/Area Number 22700734
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Eating habits, studies on eating habits
Research InstitutionNagasaki University

Principal Investigator

MATSUO Yosuke  長崎大学, 大学院・医・歯薬学総合研究科, 助教 (10432981)

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2011: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2010: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Keywordsポリフェノール / 褐変反応 / アミノ・カルボニル反応 / アクリルアミド / 食品 / ほうじ茶
Research Abstract

Green tea is produced from the leaves of Camellia sinensis. Some green tea products are further roasted to add a characteristic flavor. By roasting, color of the tea leaves changes from green to reddish brown, and the amount of catechins, amino acids, and free sugars decreased. However, details of the chemical reactions of catechins on roasting still are not clarified. In this study, we demonstrated that epigallocatechin-3-O-gallate reacted with theanine and glucose to afford condensation products. Epigallocatechin-3-O-gallate was heated at 150℃in the presence of theanine to yield six new compounds. Two products are red pigments having p-quinone structure, and the production of these pigments may explain the color change of tea leaves by roast treatment. On the other hand, heating of mixtures of epigallocatechin-3-O-gallate, theanine, and glucose at 150℃afforded two products. These products are considered to be produced by condensation of 1-ethyl-5-hydroxy-2-pyrrolidinone, which is produced by Strecker degradation of theanine, with epigallocatechin-3-O-gallate at the A-ring 8 and 6 positions.

Report

(3 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • Research Products

    (9 results)

All 2011 2010

All Journal Article (3 results) (of which Peer Reviewed: 3 results) Presentation (6 results)

  • [Journal Article] Production and degradation mechanism of theacitrin C, a black tea pigment derived from epigallocatechin-3-O-gallate via a bicyclo[ 3. 2. 1] octane-type intermediate2011

    • Author(s)
      Yosuke Matsuo, Yan Li, Sayaka Watarumi, Takashi Tanaka, Isao Kouno
    • Journal Title

      Tetrahedron

      Volume: 67巻 Pages: 2051-2059

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Biomimetic one-pot preparation of a black tea polyphenol theasinensin A from epigallocatechin gallate by treatment with copper(II) chloride and ascorbic acid2011

    • Author(s)
      Takuya Shii, Makoto Miyamoto, Yosuke Matsuo, Takashi Tanaka, Isao Kouno
    • Journal Title

      Chemical & Pharmaceutical Bulletin

      Volume: 59巻 Pages: 1183-1185

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Production and degradation mechanism of theacitrin C, a black tea pigment derived from epigallocatechin-3-O-gallate via a bicyclo[3.2.1]octane-type intermediate2011

    • Author(s)
      Yosuke Matsuo, Yan Li, Sayaka Watarumi, Takashi Tanaka, Isao Kouno
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 2051-2059

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] エピガロカテキンガレートによるアクリルアミド生成抑制機構2011

    • Author(s)
      國平雄士、松尾洋介、田中隆、河野功
    • Organizer
      日本生薬学会第58回年会
    • Place of Presentation
      東京
    • Related Report
      2011 Final Research Report
  • [Presentation] エピガロカテキンガレートによるアクリルアミド生成抑制機構2011

    • Author(s)
      國平雄士、松尾洋介、田中隆、河野功
    • Organizer
      日本生薬学会第58回年会
    • Place of Presentation
      東京・昭和大学
    • Related Report
      2011 Annual Research Report
  • [Presentation] 茶葉の焙煎加工におけるエピガロカテキンガレートとグルコースとの縮合反応2010

    • Author(s)
      國平雄士、松尾洋介、田中隆、河野功
    • Organizer
      日本生薬学会第57回年会
    • Place of Presentation
      徳島
    • Year and Date
      2010-09-25
    • Related Report
      2011 Final Research Report
  • [Presentation] 茶葉の焙煎加工におけるエピガロカテキンガレートとグルコースとの縮合反応2010

    • Author(s)
      國平雄士、松尾洋介、田中隆、河野功
    • Organizer
      日本生薬学会第57回年会
    • Place of Presentation
      徳島県徳島文理大学
    • Year and Date
      2010-09-25
    • Related Report
      2010 Annual Research Report
  • [Presentation] Condensation reaction of epigallocatechin-3-O-gallate with theanine during the roasting process of green tea leaves2010

    • Author(s)
      Yuji Kunihira, Yosuke Matsuo, Takashi Tanaka, Isao Kouno
    • Organizer
      7th Tannin Conference (In 58th International Congress and Annual Meeting of Society for Medicinal Plant and Natural Product Research)
    • Place of Presentation
      ドイツベルリン自由大学
    • Year and Date
      2010-08-30
    • Related Report
      2010 Annual Research Report
  • [Presentation] Condensation reaction of epigallocatechin-3-O-gallate with theanine during the roasting process of green tea leaves2010

    • Author(s)
      Yuji Kunihira, Yosuke Matsuo, Takashi Tanaka, Isao Kouno
    • Organizer
      7th Tannin Conference(In 58th International Congress and Annual Meeting of Society for Medicinal Plant and Natural Product Research)
    • Place of Presentation
      ドイツ
    • Related Report
      2011 Final Research Report

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Published: 2010-08-23   Modified: 2016-04-21  

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