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Ellagitannin biosynthesis via non-enzymatic quinone dimerization and redox dismutation

Research Project

Project/Area Number 26460125
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Natural medicines
Research InstitutionNagasaki University

Principal Investigator

TANAKA Takashi  長崎大学, 医歯薬学総合研究科(薬学系), 教授 (90171769)

Co-Investigator(Renkei-kenkyūsha) MATSUO Yosuke  長崎大学, 医歯薬学総合研究科(薬学系), 助教 (10432981)
SAITO Yoshinori  長崎大学, 医歯薬学総合研究科(薬学系), 准教授 (30441588)
Research Collaborator KOJIMA Daisetu  
WAKAMATSU Hatsumi  
ERA Manami  
TSUJITA Takaaki  
SHII Takuya  
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2015: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2014: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Keywordsエラジタンニン / 生合成 / 酸化還元不均化 / キノン / 紅茶 / ポリフェノール / タンニン / カテキン / ツバキ / 植物ポリフェノール / 酸化還元 / 代謝 / Carpinus / Quercus / Camellia
Outline of Final Research Achievements

Ellagitannins have hexahydroxydiphenoyl (HHDP) esters, and biogenesis of which was thought to be simple oxidative couplings between two galloyl esters. However, the HHDP esters in the leaves of Carpinus sp. were generated reductively from dehydrohexahydroxydiphenoyl (DHHDP) esters. Similar reductive metabolism were also observed in the leaves of Sapium sp. and Punica sp. Purified DHHDP esters isolated Carpinus sp. and Sapium sp. were spontaneously decomposed to give HHDP esters in aqueous solution. The reaction is non-enzymatic and probably proceed by the reduction-oxidation dismutation mechanism. The results may propose a new biosynthetic mechanisms of ellagitannins.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (43 results)

All 2017 2016 2015 2014 Other

All Int'l Joint Research (1 results) Journal Article (11 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 11 results,  Acknowledgement Compliant: 7 results,  Open Access: 5 results) Presentation (31 results) (of which Int'l Joint Research: 7 results,  Invited: 2 results)

  • [Int'l Joint Research] 澳門科技大(中国)

    • Related Report
      2015 Research-status Report
  • [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 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Three New Oxidation Products Produced from Epigallocatechin-3-O-gallate and Epicatechin-3-O-gallate.2016

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

      Natural Product Communications

      Volume: 11 Pages: 189-192

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [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 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Stereochemistry of the Black Tea Pigments, Theacitrins A and C.2016

    • Author(s)
      Matsuo, Y., Okuda, K., Morikawa, H., Oowatashi, R., Saito, Y., Tanaka, T.
    • Journal Title

      Journal of Natural Products

      Volume: 79 Issue: 1 Pages: 189-195

    • DOI

      10.1021/acs.jnatprod.5b00832

    • Related Report
      2016 Annual Research Report 2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Three New Oxidation Products Produced from Epigallocatechin-3-O-gallate and Epicatechin-3-O-gallate2016

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

      Natural Product Communications

      Volume: 11 Pages: 189-192

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Diastereomeric Ellagitannin Isomers from Penthorum chinense.2015

    • Author(s)
      Era, M., Matsuo, Y., Shii, T., Saito, Y., Tanaka, T., Jiang, Z.-H.
    • Journal Title

      Journal of Natural Products

      Volume: 78 Issue: 8 Pages: 2104-2109

    • DOI

      10.1021/acs.jnatprod.5b00439

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Oxidation mechanism of black tea pigment theaflavin by peroxidase2015

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

      Tetrahedron Letters

      Volume: 56 Issue: 36 Pages: 5099-5102

    • DOI

      10.1016/j.tetlet.2015.07.037

    • NAID

      120006986985

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [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
      2015 Research-status Report 2014 Research-status 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
      2015 Research-status Report 2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Castalagin exerts inhibitory effects on osteoclastogenesis through blocking a broad range of signaling pathways with low cytotoxicity2015

    • Author(s)
      Iwatake, M.; Sakai, E.; Okamoto, K.; Tanaka, T.; Tsukuba, T.
    • Journal Title

      Phytotherapy Research

      Volume: 29 Issue: 6 Pages: 0-0

    • DOI

      10.1002/ptr.5333

    • NAID

      120006987044

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access
  • [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
      2014 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] C-配糖体型エラジタンニンの立体配座解析ならびにcamelliatannin G および I の立体配置2017

    • Author(s)
      若松 初実, 辻田 高明, 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
      2017-03-25
    • Related Report
      2016 Annual Research Report
  • [Presentation] 薬用植物タコノアシの抗酸化ポリフェノール成分 ( 第 4 報 )2017

    • Author(s)
      江良 真名美, 松尾 洋介, 齋藤 義紀, 姜 志宏, 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
      2017-03-25
    • Related Report
      2016 Annual Research 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
      仙台国際センター(宮城県仙台市)
    • Year and Date
      2017-03-25
    • Related Report
      2016 Annual Research 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
      2017-03-25
    • Related Report
      2016 Annual Research 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 Annual Research 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 Annual Research Report
  • [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会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 Annual Research Report
  • [Presentation] Ellagitannin Metabolism in the Leaves of Camellia japonica2016

    • Author(s)
      Takaaki Tsujita, Yosuke Matsuo, Yoshinori Saito, Takashi Tanaka
    • Organizer
      The International Symposium on Natural Products for the Future 2016
    • Place of Presentation
      Tokushima Bunri University(徳島県徳島市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] A New Epigallocatechin Dimer Produced by Enzymatic Oxidationand Production Mechanism of Black Tea Polyphenols, Theasinensins2016

    • Author(s)
      Yosuke Matsuo, Ayane Yoshida, Keisuke Sugihara, Toshimi Hayashi, Chie Mine, Yoshinori Saito, Takashi Tanaka
    • Organizer
      The International Symposium on Natural Products for the Future 2016
    • Place of Presentation
      Tokushima Bunri University(徳島県徳島市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [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
      The International Symposium on Natural Products for the Future 2016
    • Place of Presentation
      Tokushima Bunri University(徳島県徳島市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research 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
      The XXVIIIth International Conference on Polyphenols
    • Place of Presentation
      Vienna (Austria)
    • Year and Date
      2016-07-11
    • Related Report
      2016 Annual Research 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
      The XXVIIIth International Conference on Polyphenols
    • Place of Presentation
      Vienna (Austria)
    • Year and Date
      2016-07-11
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 食品加工時におけるカテキン類と糖との反応2016

    • Author(s)
      森川仁美、稲田 葵、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      日本食品化学学会第22回学術大会
    • Place of Presentation
      高知市文化プラザカルポート(高知県高知市)
    • Year and Date
      2016-06-02
    • Related Report
      2016 Annual Research Report
  • [Presentation] Epigallocatechin-3-O-gallate の酸化反応初期に生成する不安定二量体の構造2016

    • Author(s)
      奥田 慶太, 松尾 洋介, 齋藤 義紀, 田中 隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県・横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] エラジタンニン生合成における還元的代謝について2016

    • Author(s)
      江良 真名美, 松尾 洋介, 齋藤 義紀, 田中 隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県・横浜市
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] スダジイ葉におけるエラジタンニンの季節変化2016

    • Author(s)
      若松 初実, 松尾 洋介, 齋藤 義紀, 田中 隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県・横浜市
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] エピガロカテキンの酵素酸化によって生成する新規二量体の構造2016

    • Author(s)
      吉田 綾音, 杉原 啓介, 林 利美, 三根 千枝, 松尾 洋介, 齋藤 義紀, 田中 隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県・横浜市
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 紅茶黄色色素theacitrin Aの立体構造2015

    • Author(s)
      奥田慶太、森川仁美、松尾洋介、齋藤義紀、田中 隆
    • Organizer
      第32回日本薬学会九州支部大会
    • Place of Presentation
      九州保健福祉大学(宮崎県・延岡市)
    • Year and Date
      2015-11-28
    • Related Report
      2015 Research-status Report
  • [Presentation] Oxidation, reduction, and polymerization of tea polyphenols and ellagitannins2015

    • Author(s)
      Takashi Tanaka, Takaaki Tsujita, Manami Era, Daisuke Kojima, Takuya Shii, Yoshinori Saito, Yosuke Matsuo
    • Organizer
      International Conference on Conservation of Biodiversity and Sustainable Use of Tropical and Subtropical Plants
    • Place of Presentation
      Guilin, China
    • Year and Date
      2015-11-02
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] 紅茶ポリフェノール生成時におけるカテキンA 環の反応2015

    • Author(s)
      寺本世生,松尾洋介,四位拓也,齊藤義紀,田中 隆
    • Organizer
      第6回食品薬学シンポジウム
    • Place of Presentation
      岡山大学(岡山県・岡山市)
    • Year and Date
      2015-10-30
    • Related Report
      2015 Research-status Report
  • [Presentation] 紅茶ポリフェノール成分テアシネンシン類の立体体配座解析と生成機構2015

    • Author(s)
      杉原啓介,山崎雅亮,松尾洋介、齋藤義紀,田中隆
    • Organizer
      日本生薬学会第62回年会
    • Place of Presentation
      長良川国際会議場(岐阜県・岐阜市)
    • Year and Date
      2015-09-11
    • Related Report
      2015 Research-status Report
  • [Presentation] 紅茶色素テアフラビン類の酸化機構2015

    • Author(s)
      松尾 洋介、大渡 遼介、草野 リエ、齋藤 義紀、田中 隆
    • Organizer
      第57回天然有機化合物討論会
    • Place of Presentation
      神奈川県民ホール(神奈川県・横浜市)
    • Year and Date
      2015-09-09
    • Related Report
      2015 Research-status Report
  • [Presentation] Ellagitannin Metabolism in the Leaves of Quercus glauca and Addition of Catechin to a Vescalagin Oxidation Product2015

    • Author(s)
      H. Wakamatsu, Y. Matsuo, Y. Saito, T. Tanaka
    • Organizer
      The Inaugural Symposium of the Phytochemical Society of Asia 2015,
    • Place of Presentation
      徳島文理大学(徳島県・徳島市)
    • Year and Date
      2015-08-30
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Diastereomeric Isomers of Ellagitannins and Its Oxidative Metabolites from Penthorum chinense2015

    • Author(s)
      M. Era, Y. Matsuo, Y. Saito, Z-H. Jiang, T. Tanaka
    • Organizer
      The Inaugural Symposium of the Phytochemical Society of Asia 2015
    • Place of Presentation
      徳島文理大学(徳島県・徳島市)
    • Year and Date
      2015-08-30
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] アラカシ葉におけるエラジタンニン類の代謝機構の解明2015

    • Author(s)
      若松 初実, 松尾 洋介, 齋藤 義紀, 田中 隆
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸サンボーホール(兵庫県神戸市)
    • Year and Date
      2015-03-26 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] シデ類のエラジタンニン季節変化と還元的代謝について2014

    • Author(s)
      兒島大雪、江良真名美、親富祖翔太郎、四位拓也、松尾洋介、齋藤義紀、野中源一郎、田中隆
    • Organizer
      第56回天然有機化合物討論会
    • Place of Presentation
      高知県立県民文化ホール(高知県高知市)
    • Year and Date
      2014-10-15 – 2014-10-17
    • Related Report
      2014 Research-status Report
  • [Presentation] ツバキ葉エラジタンニンの酸化的分解に関する研究2014

    • Author(s)
      辻田高明,松尾洋介,齋藤義紀,宮田裕次,田嶋幸一,久林高市,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
      福岡大学薬学部(福岡県福岡市)
    • Year and Date
      2014-09-13 – 2014-09-14
    • Related Report
      2014 Research-status Report
  • [Presentation] Oxidation Mechanism of Polyphenols and Chemistry of Black Tea2014

    • Author(s)
      Takashi Tanaka
    • Organizer
      ICP2014 & 8th Tannin Conference
    • Place of Presentation
      名古屋大学豊田講堂(愛知県名古屋市)
    • Year and Date
      2014-09-02 – 2014-09-06
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Reinvestigation of Stereochemistry and Enzymatic Oxidation of Castalagin and Vescalagin2014

    • Author(s)
      H. Wakamatsu, M. Omar, Y. Matsuo, Y. Saito, T. Tanaka
    • Organizer
      ICP2014 & 8th Tannin Conference
    • Place of Presentation
      名古屋大学豊田講堂(愛知県名古屋市)
    • Year and Date
      2014-09-02 – 2014-09-06
    • Related Report
      2014 Research-status Report
  • [Presentation] Reductive Metabolism of Ellagitannins in the Leaves of Carpinus japonica2014

    • Author(s)
      D. Kojima, K. Aritake, Y. Matsuo, Y. Saito, Takashi Tanaka, Gen-ichiro Nonaka
    • Organizer
      ICP2014 & 8th Tannin Conference
    • Place of Presentation
      名古屋大学豊田講堂(愛知県名古屋市)
    • Year and Date
      2014-09-02 – 2014-09-06
    • Related Report
      2014 Research-status Report
  • [Presentation] Microbial Degradation Products of Oak Wood Ellagitannin Vescalagin2014

    • Author(s)
      M. Omar, Y. Matsuo, H. Maeda, Y. Saito, T. Tanaka
    • Organizer
      ICP2014 & 8th Tannin Conference
    • Place of Presentation
      名古屋大学豊田講堂(愛知県名古屋市)
    • Year and Date
      2014-09-02 – 2014-09-06
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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