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Elucidation of formation mechanism of oolong tea polyphenol: Oolongtheanins

Research Project

Project/Area Number 24780123
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Food science
Research InstitutionGifu University

Principal Investigator

YANASE Emiko  岐阜大学, 応用生物科学部, 准教授 (60313912)

Research Collaborator NAGAOKA Satoshi  岐阜大学, 応用生物科学部, 教授 (50202221)
Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2014: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2012: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsウーロン茶ポリフェノール / ウーロンテアニン / カテキン / 酸化反応 / 反応機構 / コレステロール吸収阻害 / コレステロール吸収抑制 / ウーロン茶 / Oolongtheanin / Catechin / Dehydrotheasinensin / Prooolongtheanin
Outline of Final Research Achievements

Oolongtheanins are the catechin dimers found in oolong tea leaves. To clarify the formation mechanism, the oxidation of EGC was investigated. As a result, the formation mechanism was proposed on the basis of isolated three intermediates. 1) After one pyrogallol type catechin was oxidized to form o-quinone, another pyrogallol type catechin attacked on o-quinone. 2) Resulting dimer is oxidative cyclized, then hydrated, generating bicyclo type intermediate I (dehydrotheasinensins). 3) Transformation of I to lactone type intermediate II (pro-oolongtheanins) by dehydration and rearrangement reaction. 4) Generation of intermediate III by hydrolysis of lactone moiety and recyclization. 5) Oolongtheanins are formed by decarboxylation and oxidation. Effective synthetic method of oolongtheanins was investigated based on this mechanism. In addition, the micellar solubility of cholesterol with them were measured in vitro, and Oolongtheanin-3’-O-gallate showed a strong inhibitory ability.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (15 results)

All 2015 2014 2013 Other

All Journal Article (4 results) (of which Peer Reviewed: 2 results,  Open Access: 1 results,  Acknowledgement Compliant: 2 results) Presentation (8 results) Remarks (3 results)

  • [Journal Article] Synthesis of oolongtheanins and their inhibitory activity on micellar cholesterol solubility in vitro.2015

    • Author(s)
      Ogawa, K., Hirose, S., Yamamoto, H., Shimada, M., Nagaoka, S. and Yanase, E.
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 25 Issue: 4 Pages: 749-752

    • DOI

      10.1016/j.bmcl.2015.01.002

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Formation mechanism of oolongtheanins2014

    • Author(s)
      Hirose, S., Yanase, E.
    • Journal Title

      The XXVIIth International Conference on Polyphenols & The 8th Tannin Conference

      Volume: 1 Pages: 167-168

    • Related Report
      2014 Annual Research Report
    • Acknowledgement Compliant
  • [Journal Article] Isolation of key intermediates during formation of oolongtheanins.2013

    • Author(s)
      Hirose, S., Tomatsu, K., Yanase, E.
    • Journal Title

      Tetrahedron Lett.

      Volume: 54(51) Issue: 51 Pages: 7040-7043

    • DOI

      10.1016/j.tetlet.2013.10.069

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Formation Mechanism of Oolong Tea Polyphenol: Oolongtheanins2013

    • Author(s)
      Hirose, S., Tomatsu, K., Yanase, E.
    • Journal Title

      Proceedings of the 5th international conference on O-CHA culture and science

      Volume: 1

    • Related Report
      2013 Research-status Report
  • [Presentation] ウーロンテアニン類の化学的合成2015

    • Author(s)
      小川和樹 廣瀬紗弓 柳瀬笑子
    • Organizer
      日本農芸化学会2015年度大会(岡山)
    • Place of Presentation
      岡山大学
    • Year and Date
      2015-03-27 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] テアフラビン類の合成収率の改善2015

    • Author(s)
      内田和宏 小川和樹 柳瀬笑子
    • Organizer
      日本農芸化学会2015年度大会(岡山)
    • Place of Presentation
      岡山大学
    • Year and Date
      2015-03-27 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Formation mechanism of oolongtheanins2014

    • Author(s)
      Hirose, S., Yanase, E.
    • Organizer
      The XXVIIth International Conference on Polyphenols & The 8th Tannin Conference
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-09-02 – 2014-09-06
    • Related Report
      2014 Annual Research Report
  • [Presentation] ウーロンテアニン類の生成機構の証明2014

    • Author(s)
      廣瀬 紗弓,柳瀬 笑子
    • Organizer
      日本農芸化学会2014年度大会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] Formation Mechanism of Oolong Tea Polyphenol: Oolongtheanins2013

    • Author(s)
      Hirose, S., Tomatsu, K., Yanase, E.
    • Organizer
      The 5th international conference on O-CHA culture and science
    • Place of Presentation
      静岡
    • Related Report
      2013 Research-status Report
  • [Presentation] ウーロン茶ポリフェノールの生成機構に関する研究2013

    • Author(s)
      廣瀬 紗弓,戸松 薫,柳瀬 笑子
    • Organizer
      第55回天然有機化合物討論会
    • Place of Presentation
      京都
    • Related Report
      2013 Research-status Report
  • [Presentation] カテキン類の酸化縮合反応に関する研究

    • Author(s)
      戸松薫、柳瀬笑子
    • Organizer
      日本農芸化学会中部支部会165回例会
    • Place of Presentation
      名古屋大学
    • Related Report
      2012 Research-status Report
  • [Presentation] 茶カテキンB環部の酸化生成物に関する研究

    • Author(s)
      廣瀬紗弓、柳瀬笑子
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学
    • Related Report
      2012 Research-status Report
  • [Remarks] 岐阜大学応用生物科学部生物有機化学研究室ホームページ

    • URL

      http://www1.gifu-u.ac.jp/~biochem/

    • Related Report
      2014 Annual Research Report
  • [Remarks] 岐阜大学応用生物科学部生物有機化学研究室ホームページ

    • URL

      http://www1.gifu-u.ac.jp/~biochem/

    • Related Report
      2013 Research-status Report
  • [Remarks] 岐阜大学応用生物科学部生物有機化学研究室ホームページ

    • URL

      http://www1.gifu-u.ac.jp/~biochem/

    • Related Report
      2012 Research-status Report

URL: 

Published: 2013-05-31   Modified: 2019-07-29  

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