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Chemical biology of molecular interaction between tea catechins with biological substances

Research Project

Project/Area Number 21580148
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Food science
Research InstitutionUniversity of Shizuoka

Principal Investigator

NAKAYAMA Tsutomu  静岡県立大学, 食品栄養科学部, 教授 (50150199)

Co-Investigator(Kenkyū-buntansha) KUMAZAWA Shigenori  静岡県立大学, 食品栄養科学部, 教授 (10295561)
ISHII Takeshi  静岡県立大学, 食品栄養科学部, 助教 (50448700)
NAITO Akira  横浜国立大学, 工学研究院, 教授 (80172245)
Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2010: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords食品化学 / カテキン / 化学生物学 / タンパク質 / リン脂質 / REDOR / NMR / ECg / DOSY / ケミカルバイオロジー
Research Abstract

1.The association constants obtained from the frequency changes of quartz-crystal microbalance(QCM) revealed interactions of ECg and EGCg with HSA that are 100 times stronger than those of EC and EGC.
2.The most important structural element contributing to the formation of protein carbonyl in HSA by tea catechins is the pyrogallol structural motif in the B-ring, followed by the galloyl group. By both mass spectrometry and electrophoresis/blotting with redox-cycling staining, we revealed that pyrogallol-type catechins had higher reactivity with protein thiols than catechol-type catechins.
3.We synthesized[^<13> C]-ECg, in which the carbonyl carbon of the galloyl moiety was labeled by^<13> C isotope, and analyzed it by solid-state NMR spectroscopy. Solid-state^<31> P NMR analysis indicated that ECg changes the gel-to-liquid-crystalline phase transition temperature of DMPC bilayers as well as the dynamics and mobility of the phospholipids. The accurate intermolecular. interatomic distance between the labeled carbonyl carbon of[^<13> C]-ECg and the phosphorus of the phospholipid was determined to be 5.3±0.1 A by^<13> C.^<31> P rotational echo double resonance(REDOR) measurements.
4.The DEAD-box RNA helicase p68, which is overexpressed in a variety of tumor cells and plays an important role in cancer development and progression, was identified as a novel EGCG-binding target.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (19 results)

All 2011 2010 2009 Other

All Journal Article (11 results) (of which Peer Reviewed: 8 results) Presentation (3 results) Remarks (3 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Human Serum Albumin as an Antioxidant in the Oxidation of (-)-Epigallocatechin Gallate: Participation of Reversible Covalent Binding for Interaction and Stabilization2011

    • Author(s)
      Takeshi Ishii, Tatsuya Ichikawa, Kanako Minoda, Koji Kusaka, Sohei Ito, Yukiko Suzuki, Mitsugu Akagawa, Kazuki Mochizuki, Toshinao Goda, and Tsutomu Nakayama
    • Journal Title

      Bioscience, Biotechnology, and Biochemistry

      Volume: 75 Issue: 1 Pages: 100-106

    • DOI

      10.1271/bbb.100600

    • NAID

      10027896843

    • ISSN
      0916-8451, 1347-6947
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Interaction of epicatechin gallate with phospholipid membranes as revealed by solid-state NMR spectroscopy2011

    • Author(s)
      Yoshinori Uekusa, Miya Kamihira-Ishijima, Osamu Sugimoto, Takeshi Ishii, Shigenori Kumazawa, Kozo Nakamura, Ken-ichi Tanji, Akira Naito, and Tsutomu Nakayama
    • Journal Title

      Biochim. Biophys. Acta

      Volume: 1808 Issue: 6 Pages: 1654-1660

    • DOI

      10.1016/j.bbamem.2011.02.014

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Journal Article] Epigallocatechin-3-gallate induces growth inhibition of human gastric cancer cell line AZ521 cells by targeting the DEAD box RNA helicase p682011

    • Author(s)
      Tomoko Tanaka, Takeshi Ishii, Daisuke Mizuno, Taiki Mori, Ryoichi Yamaji, Yoshimasa Nakamura, Shigenori Kumazawa, Tsutomu Nakayama, and Mitsugu Akagawa
    • Journal Title

      Free Radic. Biol. Med

      Volume: 50 Issue: 10 Pages: 1324-1335

    • DOI

      10.1016/j.freeradbiomed.2011.01.024

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] 茶カテキン類と脂質膜との相互作用2011

    • Author(s)
      熊澤茂則、中山勉
    • Journal Title

      化学と生物

      Volume: 49 Pages: 243-249

    • NAID

      10028117213

    • Related Report
      2011 Final Research Report
  • [Journal Article] Influence of the galloyl moiety in tea catechins on binding affinity for human serum albumin2010

    • Author(s)
      Kanako Minoda, Tatsuya Ichikawa, Tomoharu Katsumata, Ken-ichi Onobori, Taiki Mori, Yukiko Suzuki, Nakayama
    • Journal Title

      J. Nutr. Sci. Vitaminol

      Volume: 56 Pages: 331-334

    • NAID

      10026966230

    • URL

      https://www.jstage.jst.go.jp/article/jnsv/56/5/56_5_331/_article

    • Related Report
      2011 Final Research Report
  • [Journal Article] Structural characteristics of green tea catechins for formation of protein carbonyl in human serum albumin2010

    • Author(s)
      Takeshi Ishii, Taiki Mori, Tatsuya Ichikawa, Maiko Kaku, Koji Kusaka, Yoshinori Uekusa, Mitsugu Akagawa, Yoshiyuki Aihara, Takumi Furuta, Toshiyuki Wakimoto, Toshiyuki Kan, and Tsutomu Nakayama
    • Journal Title

      Bioorg. Med. Chem

      Volume: 18 Issue: 14 Pages: 4892-4896

    • DOI

      10.1016/j.bmc.2010.06.021

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Covalent Binding of Tea Catechins to Protein Thiols: The Relationship between Stability and Electrophilic Reactivity2010

    • Author(s)
      Taiki Mori, Takeshi Ishii, Mitsugu Akagawa, Yoshimasa Nakamura, and Tsutomu Nakayama
    • Journal Title

      Bioscience, Biotechnology, and Biochemistry

      Volume: 74 Issue: 12 Pages: 2451-2456

    • DOI

      10.1271/bbb.100509

    • NAID

      10027728118

    • ISSN
      0916-8451, 1347-6947
    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Influence of the galloyl moiety in tea catechins on binding affinity for human serum albumin2010

    • Author(s)
      K.Minoda, T.Ichikawa, T.Katsumata, K.Onobori, T.Mori, Y Suzuki, T.Ishii, T.Nakayama
    • Journal Title

      J.Nutri.Sci.Vitaminol.

      Volume: 56 Pages: 331-334

    • NAID

      10026966230

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Covalent binding of tea catechins to protein thiols : The relationship between stability and electrophilic reactivity2010

    • Author(s)
      T.Mori, T.Ishii, M.Akagawa, Y.Nakamura, T.Nakayama
    • Journal Title

      Biosci.Biotechnol.Biochem.

      Volume: 74 Pages: 2451-2456

    • NAID

      10027728118

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Human serum albumin as an antioxidant in the oxidation of(-)-epicatechin gallate : Participation of reversible covalent binding for interaction and stabilization2010

    • Author(s)
      T.Ishii, T.Ichikawa, K.Minoda, K.Kusaka, S.Ito, Y. Suzuki, M.Akagawa., K.Mochizuki, T.Goda, T.Nakayama
    • Journal Title

      Biosci.Biotechnol.Biochem.

      Volume: 75 Pages: 100-106

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Albumin stabilizes(-)-epigallocatechin gallate in human serum : binding capacity and antioxidant property2009

    • Author(s)
      M.-J.Bae, et al.
    • Journal Title

      Mol.Nutr.Food Res. 53

      Pages: 709-715

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] Interaction of tea catechins with phospholipids-Roles in their tastes and biological activities2011

    • Author(s)
      Tsutomu Nakayama
    • Organizer
      2011 International Conference of Food Factors
    • Place of Presentation
      Taipei, Taiwan
    • Year and Date
      2011-11-22
    • Related Report
      2011 Annual Research Report
  • [Presentation] Interaction of epicatechin gallate with model phospholipid membranes as revealed by solid-state NMR spectroscopy.2010

    • Author(s)
      Y.Uekusa, M.Kamihira-Ishijima, O.Sugimoto, T.Ishii, S.Kumazawa, K.Nakamura, K.Tanji, K.Kato, A.Naito, T.Nakayama
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Hawaii, U.S.A.
    • Year and Date
      2010-12-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] Solid-state NMR study of the interaction between epicatechin gallate and phospholipid membranes2009

    • Author(s)
      Y.Uekusa, et al.
    • Organizer
      4^<th> International Conference on Polyphenols and Health
    • Place of Presentation
      Yorkshire, UK
    • Year and Date
      2009-12-08
    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://sfns.u-shizuoka-ken.ac.jp/foodbioc/index.html

    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://sfns.u-shizuoka-ken.ac.jp/foodbioc/index.html

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://sfns.u-shizuoka-ken.ac.jp/foodbioc/index.html

    • Related Report
      2010 Annual Research Report
  • [Patent(Industrial Property Rights)] 特許2011

    • Inventor(s)
      中山勉、石井剛志、山田智
    • Industrial Property Rights Holder
      静岡県公立大学法人、日油株式会社
    • Filing Date
      2011-11-21
    • Related Report
      2011 Final Research Report
  • [Patent(Industrial Property Rights)] 特許2011

    • Inventor(s)
      中山勉、石井剛志、山田智
    • Industrial Property Rights Holder
      静岡県公立大学法人、日油株式会社
    • Industrial Property Number
      2011-253607
    • Filing Date
      2011-11-21
    • Related Report
      2011 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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