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Stereoselectivity in Oxidative Dimerization of Catechins during Tea-fermentation

Research Project

Project/Area Number 16K07741
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field 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) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2018: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2017: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2016: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywords紅茶 / カテキン / DFT計算 / 分子間相互作用 / ガロイル基 / 加水分解型タンニン / エラジタンニン / 酸化的カップリング / ポリフェノール / 酸化的二量化 / テアフラビン / テアシネンシン / 酸化
Outline of Final Research Achievements

Detailed mechanism of oxidative dimerization of catechins during black tea manufacturing was investigated. Dimerization of pyrogallol-type catechins affords dehydrotheasinensins stereoselectively. DFT optimization of dehydrotheasinensin C suggested that the selectivity was accounted for intramolecular π-π stacking between two A-rings in aqueous solution.
On the other hand, oxidative coupling between pyrogallol-type and catechol-type catechins affords theaflavins with a benzotropolone chromophore. Plane structure of the chromophore is produced via a bicyclo[3.2.1]octane-type intermediate, and formation of the intermediate was non-stereoselective coupling between catechol quinone and pyrogallol.

Academic Significance and Societal Importance of the Research Achievements

紅茶製造過程におけるポリフェノール成分の化学変化機構が解明されたことは、有機化学的観点からも高い意義があるだけでなく、紅茶の食品としての生理機能性を解明する基盤となる結果であり、大きな意義を持つ。複雑な組成を有するポリフェノール含有食品の生理機能成分解明が今後さらに進むことが期待される。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (47 results)

All 2019 2018 2017 2016

All Journal Article (11 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 11 results,  Open Access: 5 results,  Acknowledgement Compliant: 1 results) Presentation (34 results) (of which Int'l Joint Research: 6 results,  Invited: 2 results) Book (2 results)

  • [Journal Article] Oligomerization mechanism of tea catechins for tea roasting2019

    • Author(s)
      Hitomi Morikawa, Keita Okuda, Yuji Kunihira, Aoi Inada, Chika Miyagi, Yosuke Matsuo, Yoshinori Saito, Takashi Tanaka
    • Journal Title

      Food Chemistry

      Volume: 285 Pages: 252-259

    • DOI

      10.1016/j.foodchem.2019.01.163

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ellagitannins and Related Compounds from Penthorum chinense2019

    • Author(s)
      Era, Manami, Matsuo, Yosuke, Saito, Yoshinori, Nishida, Kouyo, Jiang, Zhi-Hong, Tanaka, Takashi
    • Journal Title

      Journal of Natural Products

      Volume: 82 Issue: 1 Pages: 129-135

    • DOI

      10.1021/acs.jnatprod.8b00838

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Solubility of Tannins and Preparation of Oil-Soluble Derivatives2018

    • Author(s)
      Takashi Tanaka, Yosuke Matsuo, Yoshinori Saito
    • Journal Title

      Journal of Oleo Science

      Volume: 67 Issue: 10 Pages: 1179-1187

    • DOI

      10.5650/jos.ess18164

    • NAID

      130007497844

    • ISSN
      1345-8957, 1347-3352
    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Study of the Stereochemistry and Oxidation Mechanism of Plant Polyphenols, Assisted by Computational Chemistry2017

    • Author(s)
      松尾 洋介
    • Journal Title

      YAKUGAKU ZASSHI

      Volume: 137 Issue: 3 Pages: 347-354

    • DOI

      10.1248/yakushi.16-00207

    • NAID

      130005396872

    • ISSN
      0031-6903, 1347-5231
    • Year and Date
      2017-03-01
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Nonenzymatic Biomimetic Synthesis of Black Tea Pigment Theaflavins2017

    • Author(s)
      Yosuke Matsuo, Ryosuke Oowatashi, Yoshinori Saito, Takashi Tanaka
    • Journal Title

      Synlett

      Volume: 28 Issue: 18 Pages: 2505-2508

    • DOI

      10.1055/s-0036-1588529

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Structural Revision and Biomimetic Synthesis of Goupiolone B2017

    • Author(s)
      Yosuke Matsuo, Ayane Yoshida, Yoshinori Saito, Takashi Tanaka
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 56 Issue: 39 Pages: 11855-11859

    • DOI

      10.1002/anie.201706532

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Characterization of Proanthocyanidin Oligomers of Ephedra sinica2017

    • Author(s)
      Joanna Orejola, Yosuke Matsuo, Yoshinori Saito, Takashi Tanaka
    • Journal Title

      Molecules

      Volume: 22 Issue: 8 Pages: 1308-1308

    • DOI

      10.3390/molecules22081308

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Conjugation of Vescalagin with Glucose and Phenylpropanoid: Reactions Related to the Insolubilization of Oak Wood Ellagitannins2017

    • Author(s)
      Yuki Koga, Yosuke Matsuo, Takashi Tanaka
    • Journal Title

      Natural Product Communications

      Volume: 12 Pages: 1291-1294

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Enzymatic oxidation of ellagitannin and a new ellagitannin metabolite from Camellia japonica leaves2017

    • Author(s)
      T. Tsujita, Y. Matsuo, Y. Saito, T. Tanaka
    • Journal Title

      Tetrahedron

      Volume: 73 Issue: 5 Pages: 500-507

    • DOI

      10.1016/j.tet.2016.12.027

    • NAID

      120006987564

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Theagalloflavic Acid, a New Pigment Derived from Hexahydroxydiphenoyl Group, and Lignan Oxidation Products Produced by Aerobic Microbial Fermentation of Green Tea2016

    • Author(s)
      MATSUO, Y.; MATSUDA, T.; SUGIHARA, K.; ZHANG, Y.-J.; YANG, C.-R.; TANAKA, T.
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 7 Pages: 918-923

    • DOI

      10.1248/cpb.c16-00098

    • NAID

      130005160058

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Characterization of the α-Amylase Inhibitory Activity of Oligomeric Proanthocyanidins from Acacia mearnsii Bark Extract2016

    • Author(s)
      Yosuke Matsuo, Rie Kusano, Sosuke Ogawa, Yoshikazu Yazaki, Takashi Tanaka
    • Journal Title

      Natural Product Communications

      Volume: 11 Pages: 1851-1854

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Presentation] エラジタンニン生合成に関わるガロイル基の酸化的カップリング機構2019

    • Author(s)
      山下貴子、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] フラボアルカロイドの構造および合成に関する研究2019

    • Author(s)
      川副里菜、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 茶成分の逆相 HPLC 分析における試料溶媒の影響2019

    • Author(s)
      田中 隆、松尾洋介
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] エラジタンニン生合成に関わるガロイルエステルのバイオミメティック酸化2018

    • Author(s)
      山下貴子、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      第35回日本薬学会九州支部大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 茶カテキン自動酸化の反応機構に関する研究2018

    • Author(s)
      片山滉平、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本生薬学会第65回年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 茶発酵におけるカテキン重合機構に関する研究2018

    • Author(s)
      廣谷真優、齋藤義紀、松尾洋介、田中 隆
    • Organizer
      日本生薬学会第65回年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 茶カテキンとグルコースとの加熱によるスピロケタールの生成2018

    • Author(s)
      奥田慶太、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本生薬学会第65回年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] OLIGOMERIZATION OF CATECHINS WITH SUGARS ON TEA ROASTING2018

    • Author(s)
      Hitomi Morikawa, Chika Miyagi, Keita Okuda, Yosuke Matsuo, Yoshinori Saito, Takashi Tanaka
    • Organizer
      XXIX International Conference on Polyphenols and the 9th Tannin Conference
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] STEREOSELECTIVITY IN OXIDATIVE DIMERIZATION OF CATECHINS DURING TEA-FERMENTATION2018

    • Author(s)
      Yosuke Matsuo, Keita Okuda, Ryosuke Oowatashi, Ayane Yoshida, Yoshinori Saito, Takashi Tanaka
    • Organizer
      XXIX International Conference on Polyphenols and the 9th Tannin Conference
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ポリフェノール酸化酵素によるテアシネンシン類の酸化機構2018

    • Author(s)
      木下遼祐、奥田慶太、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 茶カテキン類の酵素酸化におけるβ-シクロデキストリンならびにA環置換基の影響2018

    • Author(s)
      奥田慶太、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Presentation] デヒドロテアシネンシン類の立体選択的生成におけるπ-π相互作用の影響2017

    • Author(s)
      奥田慶太、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学川内北キャンパス(宮城県・仙台市)
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] 茶焙煎時におけるカテキン重合メカニズム2017

    • Author(s)
      森川仁美, 稲田 葵, 松尾洋介, 齋藤義紀, 田中 隆
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台国際センター(宮城県・仙台市)
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] Goupiolone B の構造訂正ならびに合成2017

    • Author(s)
      吉田綾音, 松尾洋介, 齋藤義紀, 田中 隆
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台国際センター(宮城県・仙台市)
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] 茶カテキン類の酸化的二量化におけるA環の役割2017

    • Author(s)
      奥田慶太、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      第34回日本薬学会九州支部大会
    • Related Report
      2017 Research-status Report
  • [Presentation] 紅茶成分テアシネンシン類の酵素酸化反応2017

    • Author(s)
      木下遼祐、奥田慶太、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      第34回日本薬学会九州支部大会
    • Related Report
      2017 Research-status Report
  • [Presentation] 茶焙煎時におけるカテキンと糖類との重合反応2017

    • Author(s)
      森川仁美、宮城知佳、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      第7回食品薬学シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] DFT計算を利用したC-配糖体型エラジタンニン類の立体配座解析2017

    • Author(s)
      若松初実、木下遼祐、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      第7回食品薬学シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] 紅茶色素テアフラビン類の自動酸化ならびにペルオキシダーゼ酸化機構2017

    • Author(s)
      大渡遼介、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      第7回食品薬学シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] 植物ポリフェノールの酸化的二量化機構に関する研究2017

    • Author(s)
      松尾洋介
    • Organizer
      第7回食品薬学シンポジウム
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] 紅茶製造過程におけるカテキン類の酸化的二量化反応の立体選択性2017

    • Author(s)
      奥田慶太、大渡遼介、吉田綾音、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      第59回天然有機化合物討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 紅茶色素テアフラビン類生成におけるビシクロ[3.2.1]オクタン型前駆体の立体構造2017

    • Author(s)
      大渡遼介、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本生薬学会第64回年会
    • Related Report
      2017 Research-status Report
  • [Presentation] エラジタンニン生合成における還元的代謝 (2)2017

    • Author(s)
      江良真名美、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本生薬学会第64回年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 不安定二量体を経由したピロガロール型カテキンの酸化反応機構2017

    • Author(s)
      奥田慶太、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本生薬学会第64回年会
    • Related Report
      2017 Research-status Report
  • [Presentation] DNA傷害物質 goupiolone B のラセミ化2017

    • Author(s)
      松尾洋介、吉田綾音、齋藤義紀、田中 隆
    • Organizer
      日本生薬学会第64回年会
    • Related Report
      2017 Research-status Report
  • [Presentation] Goupiolone B の構造訂正2016

    • Author(s)
      吉田綾音、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      第33回日本薬学会九州支部大会
    • Place of Presentation
      鹿児島大学郡元キャンパス(鹿児島県・鹿児島市)
    • Year and Date
      2016-12-03
    • Related Report
      2016 Research-status Report
  • [Presentation] ビシクロ[3.2.1]オクタン型中間体を経由したピロガロール型カテキン二量化機構の解明2016

    • Author(s)
      奥田慶太、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本生薬学会第63回年会
    • Place of Presentation
      富山国際会議場(富山県・富山市)
    • Year and Date
      2016-09-24
    • Related Report
      2016 Research-status Report
  • [Presentation] 生合成機構に基づく紅茶色素テアフラビン類の簡易合成2016

    • Author(s)
      大渡遼介、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本生薬学会第63回年会
    • Place of Presentation
      富山国際会議場(富山県・富山市)
    • Year and Date
      2016-09-24
    • Related Report
      2016 Research-status Report
  • [Presentation] 計算化学的手法を取り入れたポリフェノールの立体構造および酸化機構に関する研究2016

    • Author(s)
      松尾洋介
    • Organizer
      日本生薬学会第63回年会
    • Place of Presentation
      富山国際会議場(富山県・富山市)
    • Year and Date
      2016-09-24
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] 紅茶ポリフェノール生成におけるピロガロール型カテキンの酸化的二量化機構2016

    • Author(s)
      松尾洋介、奥田慶太、森川仁美、齋藤義紀、田中 隆
    • Organizer
      第58回天然有機化合物討論会
    • Place of Presentation
      東北大学百周年記念会館(宮城県・仙台市)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] Unstable Dimer of Pyrogallol-type Catechins Produced in the Early Stage of Oxidation during Tea-fermentation2016

    • Author(s)
      Keita Okuda, Yosuke Matsuo, Yoshinori Saito, Takashi Tanaka
    • Organizer
      International Symposium on Natural Products for the Future 2016 (ISNPF2016)
    • Place of Presentation
      徳島文理大学(徳島県・徳島市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] A New Epigallocatechin Dimer Produced by Enzymatic Oxidation and Production Mechanism of Black Tea Polyphenols, Theasinensins2016

    • Author(s)
      Yosuke Matsuo, Ayane Yoshida, Keisuke Sugihara, Toshimi Hayashi, Chie Mine, Yoshinori Saito, Takashi Tanaka
    • Organizer
      International Symposium on Natural Products for the Future 2016 (ISNPF2016)
    • Place of Presentation
      徳島文理大学(徳島県・徳島市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] OXIDATION MECHANISM OF EPIGALLOCATECHIN-3-O-GALLATE BY POLYPHENOL OXIDASE2016

    • Author(s)
      Yosuke Matsuo, Keita Okuda, Hitomi Morikawa, Yoshinori Saito, Takashi Tanaka
    • Organizer
      XXVIIIth International Conference on Polyphenols
    • Place of Presentation
      ウィーン(オーストリア)
    • Year and Date
      2016-07-11
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] PYROGALLOL-PHLOROGLUCINOL COUPLING:A POSSIBLE OLIGOMERIZATION MECHANISM OF TEA CATECHINS2016

    • Author(s)
      Takashi Tanaka, Yosuke Matsuo, Kohei Katayama, Sena Teramoto, Yoshinori Saito
    • Organizer
      XXVIIIth International Conference on Polyphenols
    • Place of Presentation
      ウィーン(オーストリア)
    • Year and Date
      2016-07-11
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Book] Recent Advances in Polyphenol Research, Vol. 5 (Oxidation Mechanism of Polyphenols and Chemistry of Black Tea)2017

    • Author(s)
      Yosuke Matsuo, Takashi Tanaka
    • Total Pages
      350
    • Publisher
      John Wiley & Sons
    • Related Report
      2016 Research-status Report
  • [Book] ポリフェノール:機能性成分研究開発の最新動向(計算化学を利用したポリフェノールの立体構造解析)2016

    • Author(s)
      松尾洋介
    • Total Pages
      288
    • Publisher
      シーエムシー出版
    • Related Report
      2016 Research-status Report

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Published: 2016-04-21   Modified: 2020-03-30  

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