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Chemical change of tea polyphenol in the production process of black tea and roasted green tea

Research Project

Project/Area Number 25870532
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Eating habits
Food science
Research InstitutionNagasaki University

Principal Investigator

MATSUO Yosuke  長崎大学, 医歯薬学総合研究科(薬学系), 助教 (10432981)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2013: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Keywordsポリフェノール / 紅茶 / ほうじ茶 / エピガロカテキン / テアフラビン / DFT / ECD / DFT計算
Outline of Final Research Achievements

Enzymatic oxidation of theaflavins in the presence of epicatechin was examined. Benzotropolone moiety of theaflavins with a free hydroxyl group at C-3' easily reacted with epicatechin; however, benzotropolone moiety of theaflavins having galloyl group at C-3' could not react with epicatechin. The charge-transfer interaction between benzotropolone ring and o-quinone ring of epicatechin-quinone is important in benzotropolone oxidation.
The structure of a new enzymatic oxidation product of epigallocatechin was determined. In addition, we assigned the stereostructure of known oxidation products of pyrogallol-type catechins, such as quinone dimers, theacitrins, and proepitheaflagallins, by using theoretical calculations of ECD spectra and NMR chemical shifts.
In the course of roasted green tea production, high molecular weight polyphenols are produced. We found that they are generated by condensation reaction between tea catechins and caramelized sugars.

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • Research Products

    (23 results)

All 2015 2014 2013

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Open Access: 2 results,  Acknowledgement Compliant: 1 results) Presentation (18 results) (of which Invited: 1 results)

  • [Journal Article] Selective oxidation of pyrogallol-type catechins with unripe fruit homogenate of Citrus unshiu and structural revision of oolongtheanins2015

    • Author(s)
      Matsuo, Y.; Tadakuma, F.; Shii, T.; Saito, Y.; Tanaka, T.
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 17 Pages: 2540-2548

    • DOI

      10.1016/j.tet.2015.03.016

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Reinvestigation of the Stereochemistry of the C-Glycosidic Ellagitannins, Vescalagin and Castalagin2015

    • Author(s)
      Yosuke Matsuo, Hatsumi Wakamatsu, Mohamed Omar, Takashi Tanaka
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 1 Pages: 46-49

    • DOI

      10.1021/ol503212v

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Polyphenols in lahpet-so and two new catechin metabolites produced by anaerobic microbial fermentation of green tea2014

    • Author(s)
      Takuya Shii, Chiori Asada, Yosuke Matsuo, Yoshinori Saito, Takashi Tanaka
    • Journal Title

      Journal of Natural Medicines

      Volume: 68 Issue: 2 Pages: 459-464

    • DOI

      10.1007/s11418-014-0816-1

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] New Metabolites of C-Glycosidic Ellagitannin from Japanese Oak Sapwood2014

    • Author(s)
      Mohamed Omar, Yosuke Matsuo, Hajime Maeda, Yoshinori Saito, Takashi Tanaka
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 5 Pages: 1378-1381

    • DOI

      10.1021/ol500146a

    • Related Report
      2013 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Structures of enzymatic oxidation products of epigallocatechin2013

    • Author(s)
      Y. Matsuo, T. Hayashi, Y. Saito, I. Kouno, T. Tanaka
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 42 Pages: 8952-8958

    • DOI

      10.1016/j.tet.2013.07.045

    • NAID

      120006986098

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 茶製品中のカテキン重合生成物に関する化学的研究(第一報)2015

    • Author(s)
      寺本世生、稲田 葵、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本農芸化学会2015年度大会
    • Place of Presentation
      岡山大学(岡山県岡山市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Epigallocatechin gallateのacrolein誘導体とアルコール類との縮合反応2015

    • Author(s)
      四位拓也、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院大学(兵庫県神戸市)
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 茶カテキン二量体プロエピテアフラガリン類の立体構造および生成機構の再検討2015

    • Author(s)
      松尾洋介、大渡遼介、齋藤義紀、田中 隆
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院大学(兵庫県神戸市)
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 中性条件下における紅茶色素テアフラビン類の酸化機構2014

    • Author(s)
      大渡遼介、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      第31回日本薬学会九州支部大会
    • Place of Presentation
      第一薬科大学(福岡県福岡市)
    • Year and Date
      2014-12-06 – 2014-12-07
    • Related Report
      2014 Annual Research Report
  • [Presentation] 紅茶色素テアフラビン類の酵素的酸化機構とテアシトリン類の立体構造2014

    • Author(s)
      松尾洋介、大渡遼介、齋藤義紀、田中 隆
    • Organizer
      第11回日本カテキン学会年次学術学会
    • Place of Presentation
      昭和大学(東京都品川区)
    • Year and Date
      2014-11-21 – 2014-11-22
    • Related Report
      2014 Annual Research Report
  • [Presentation] 中国産Zijuan teaのポリフェノール成分2014

    • Author(s)
      稲田 葵、松尾洋介、齋藤義紀、田中 隆、野中源一郎
    • Organizer
      日本生薬学会第61回年会
    • Place of Presentation
      福岡大学(福岡県福岡市)
    • Year and Date
      2014-09-13 – 2014-09-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] 茶ツバキ混合発酵茶のポリフェノール成分2014

    • Author(s)
      森川仁美、松尾洋介、齋藤義紀、宮田裕次、田嶋幸一、田丸静香、田中一成、田中 隆
    • Organizer
      日本生薬学会第61回年会
    • Place of Presentation
      福岡大学(福岡県福岡市)
    • Year and Date
      2014-09-13 – 2014-09-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] 紅茶ポリフェノール生成における茶カテキン類の二量化機構2014

    • Author(s)
      松尾洋介
    • Organizer
      日本生薬学会第61回年会
    • Place of Presentation
      福岡大学(福岡県福岡市)
    • Year and Date
      2014-09-13 – 2014-09-14
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Stereochemistry of black tea pigment theacitrins2014

    • Author(s)
      Yosuke Matsuo, Ryosuke Oowatashi, Yoshinori Saito, Takashi Tanaka
    • Organizer
      The 8th JSP-CCTCNM-KSP Joint Symposium on Pharmacognosy
    • Place of Presentation
      福岡大学(福岡県福岡市)
    • Year and Date
      2014-09-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] Stereoselective Biphenyl Bond Formation of Black Tea Polyphenol in Tea Leaf2014

    • Author(s)
      Masaaki Yamasaki, Takuya Shii, Yosuke Matsuo, Yoshinori Saito, Takashi Tanaka
    • Organizer
      The XXVIIth International Conference on Polyphenols & The 8th Tannin Conference
    • Place of Presentation
      名古屋大学(愛知県名古屋市)
    • Year and Date
      2014-09-02 – 2014-09-06
    • Related Report
      2014 Annual Research Report
  • [Presentation] Enzymatic Oxidation of Black Tea Pigment Theaflavins in the Presence of Epicatechin by Polyphenol Oxidase2014

    • Author(s)
      Yosuke Matsuo, Ryosuke Oowatashi, Rie Kusano, Yoshinori Saito, Takashi Tanaka
    • Organizer
      The XXVIIth International Conference on Polyphenols & The 8th Tannin Conference
    • Place of Presentation
      名古屋大学(愛知県名古屋市)
    • Year and Date
      2014-09-02 – 2014-09-06
    • Related Report
      2014 Annual Research Report
  • [Presentation] ポリフェノール酸化酵素によるepigallocatechinとgallic acidとの酸化的縮合反応2013

    • Author(s)
      只熊郁也、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      第30回日本薬学会九州支部大会
    • Place of Presentation
      長崎国際大学(長崎県佐世保市)
    • Related Report
      2013 Research-status Report
  • [Presentation] Chemical change of tea catechins in roasting and suppression mechanism against the formation of toxic Maillard reaction products2013

    • Author(s)
      Aoi Inada, Yuji Kunihira, Yosuke Matsuo, Yoshinori Saito, Isao Kouno, Takashi Tanaka
    • Organizer
      The 5th International Conference on O-CHA (Tea) Culture and Science
    • Place of Presentation
      グランシップ(静岡県静岡市)
    • Related Report
      2013 Research-status Report
  • [Presentation] Minor constituents of green tea and their inhibitory activity against advanced glycation end products formation2013

    • Author(s)
      Takahiro Uchijima, Ken Shiraiwa, Yosuke Matsuo, Yoshinori Saito, Takashi Tanaka
    • Organizer
      The 5th International Conference on O-CHA (Tea) Culture and Science
    • Place of Presentation
      グランシップ(静岡県静岡市)
    • Related Report
      2013 Research-status Report
  • [Presentation] エピガロカテキンの新規酵素酸化生成物及びラジカル酸化反応2013

    • Author(s)
      只熊郁也、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本生薬学会第60回年会
    • Place of Presentation
      北海道医療大学(北海道石狩郡)
    • Related Report
      2013 Research-status Report
  • [Presentation] 緑茶カテキンによるAGEs生成抑制機構2013

    • Author(s)
      稲田 葵、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本生薬学会第60回年会
    • Place of Presentation
      北海道医療大学(北海道石狩郡)
    • Related Report
      2013 Research-status Report
  • [Presentation] 紅茶色素テアフラビンの酸化におけるエピカテキンキノンとの分子間相互作用2013

    • Author(s)
      松尾洋介、内島崇裕、齋藤義紀、田中 隆
    • Organizer
      日本生薬学会第60回年会
    • Place of Presentation
      北海道医療大学(北海道石狩郡)
    • Related Report
      2013 Research-status Report
  • [Presentation] Oxidative Conversion of Tea Polyphenols during Post-fermented Tea Production by Aerobic Microbial Fermentation2013

    • Author(s)
      Yosuke Matsuo, Keisuke Sugihara, Tomoko Matsuda, Takahiro Uchijima, Yoshinori Saito, Kanji Ishimaru, Takashi Tanaka
    • Organizer
      13th International Conference of FFC - First International Symposium of ASFFBC: Functional and Medical Foods with Bioactive Compounds: Science and Practical Application
    • Place of Presentation
      京都府立医科大学(京都府京都市)
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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