Analysis of interaction between flavonoids and proteins for elucidating their physiological expression mechanisms.

• Project/Area Number: 22780122
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Food science
• Research Institution: University of Shizuoka
• Principal Investigator: ISHII Takeshi 静岡県立大学, 食品栄養科学部, 助教 (50448700)
• Project Period (FY): 2010 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000); Fiscal Year 2011: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2010: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
• Keywords: フラボノイド類 / カテキン類 / 標的蛋白質 / 相互作用 / 結合親和性 / フラボノイド / テアフラビン類 / 蛋白質 / 標的分子 / 共有結合 / 親和性 / 血清アルブミン / プロテオミクス

Research Abstract

Previous research has indicated that several flavonoids form complexes with target molecule such as protein in blood and organs, and differences in binding affinity toward the target molecule are believed to determine their biological activity. In this study, the interaction of catechins and their analogs to proteins were evaluated and the relationship between the chemical structure of each catechin and its binding affinity were investigated. The study indicates the galloyl group, the number of hydroxyl groups on the B-ring, and the configuration at C-2 of each catechin influence binding affinity for the serum proteins and the several cellular proteins.

Research Products

• [Journal Article] Epigallocatechin-3-gallate induces growth inhibition of human gastric cancer cell line AZ521 cells by targeting the DEAD box RNA helicase p68 (2011)
  • 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
  • Peer Reviewed
• [Journal Article] Human Serum Albumin as an Antioxidant in the Oxidation of (-)-Epigallocatechin Gallate: Participation of Reversible Covalent Binding for Interaction and Stabilization (2011)
  • 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
  • Peer Reviewed
• [Journal Article] Interaction of tea catechins with serum proteins : Development and application of a new probe for understanding the action of catechins (2011)
  • Author(s): Katsumata, T., Ishii, T., and Nakayama, T
  • Journal Title: Proceedings of the 4th International Conference on O-CHA(Tea) Culture and Science
• [Journal Article] Structural characteristics of tea catechins that affect their binding affinity with cyclodextrins (2011)
  • Author(s): Kusaka, K., Ishii, T., and Nakayama, T
  • Journal Title: Proceedings of the 4th International Conference on O-CHA(Tea) Culture and Science
• [Journal Article] Stability of(-)-epigallocatechin gallate in aqueous solutions containing food constituents : Effect of synergy between antioxidant property and binding capacity (2011)
  • Author(s): Kusaka, K., Ishii, T., Hiramatsu, M., and Nakayama, T
  • Journal Title: Proceedings of the 4th International Conference on O-CHA(Tea) Culture and Science
• [Journal Article] Electrophilic reactivity of tea catechins toward protein sulfhydryls (2011)
  • Author(s): Mori, T., Ishii, T., Katsumata, T., Akagawa, M., Nakamura, Y., and Nakayama, T
  • Journal Title: Proceedings of the 4th International Conference on O-CHA(Tea) Culture and Science
• [Journal Article] A search for the high-affinity proteins of tea catechins in human cell lysates (2011)
  • Author(s): Katsumata, T., Ishii, T., and Nakayama, T
  • Journal Title: Proceedings of the 4th International Conference on O-CHA(Tea) Culture and Science
• [Journal Article] (-)-Epigallocatechin-3-gallate inhibits EGF signaling via covalent binding to EGF receptor (2011)
  • Author(s): Maeda, T., Kubo, Y., Kimura, K., Tanaka, T., Ishii, T., and Akagawa, M
  • Journal Title: Proceedings of the 4th International Conference on O-CHA(Tea) Culture and Science
• [Journal Article] Human serum albumin as an antioxidant in the oxidation of (-)-epigallocatechin gallate : participation of reversible covalent binding for interaction and stabilization. (2011)
  • Author(s): Ishii, T., et al.
  • Journal Title: Bioscience, Biotechnology,and Biochemistry Volume: 75 Pages: 100-106
  • NAID: 10027896843
  • Peer Reviewed
• [Journal Article] Covalent Binding of Tea Catechins to Protein Thiols: The Relationship between Stability and Electrophilic Reactivity (2010)
  • 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
  • Peer Reviewed
• [Journal Article] Influence of the galloyl moiety in tea catechins on binding affinity for human serum albumin (2010)
  • Author(s): Minoda, K., Ichikawa, T., Katsumata, T., Onobori, K., Mori, T., Suzuki, Y., Ishii, T., and Nakayama, T
  • 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
  • Peer Reviewed
• [Journal Article] Structural characteristics of green tea catechins for formation of protein carbonyl in human serum albumin (2010)
  • 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
  • Peer Reviewed
• [Journal Article] Binding affinity of tea catechins for HSA : characterization by high-performance affinity chromatography with immobilized albumin column (2010)
  • Author(s): Ishii, T., Minoda, K., Bae, M.-J., Mori, T., Uekusa, Y., Ichikawa, T., Aihara, Y., Furuta, T., Wakimoto, T., Kan, T., and Nakayama, T
  • Journal Title: Mol. Nutr. Food Res Volume: 54 Issue: 6 Pages: 816-822
  • DOI: 10.1002/mnfr.200900071
  • Peer Reviewed
• [Journal Article] お茶の効能を分子レベルで解明する (2010)
  • Author(s): 石井剛志、菅敏幸
  • Journal Title: ファルマシア Volume: 46 Pages: 1143-1148
  • NAID: 110009867673
• [Journal Article] Binding affinity of tea catechins for HSA : characterization by high-performance affinity chromatography with immobilized albumin column. (2010)
  • Author(s): Ishii, T., et al.
  • Journal Title: Molecular Nutrition and Food Research Volume: 54 Pages: 816-822
  • Peer Reviewed
• [Journal Article] Structural characteristics of green tea catechins for formation of protein carbonyl in human serum albumin. (2010)
  • Author(s): Ishii, T., et al.
  • Journal Title: Bioorganic and Medicinal Chemistry Volume: 18 Pages: 4892-4896
  • Peer Reviewed
• [Journal Article] Influence of the galloyl moiety in tea catechins on binding affinity for human serum albumin. (2010)
  • Author(s): Minoda, K., et al.
  • Journal Title: Journal of Nutritional Science and Vitaminology Volume: 56 Pages: 331-334
  • Peer Reviewed
• [Journal Article] Covalent binding of tea catechins to protein thiols : Relationship between stability and electrophilic reactivity. (2010)
  • Author(s): Mori, T., et al.
  • Journal Title: Bioscience, Biotechnology, and Biochemistry Volume: 74 Pages: 2451-2456
  • Peer Reviewed
• [Presentation] 紅茶テアフラビン類の蛋白質に対する反応性 (2012)
  • Author(s): 石井剛志, ほか
  • Organizer: 日本農芸化学会2012年度大会
  • Place of Presentation: 京都
  • Year and Date: 2012-03-23
• [Presentation] (-)-Epigallocatechin-3-gallate suppresses growth of AZ521 human gastric cancer cells by targeting the DEAD box RNA helicase p68 (2011)
  • Author(s): Akagawa, M., Tanaka, T., Mizuno, D., Mori, T., Yamaji, R., Nakamura, Y., Kumazawa, S., Nakayama, T., and Ishii, T
  • Organizer: 2011 International Conference of Food Factors
  • Place of Presentation: Taipei, Taiwan
  • Year and Date: 2011-11-21
• [Presentation] エピガロカテキンガレートと細胞膜との相互作用に血清蛋白質が及ぼす影響 (2011)
  • Author(s): 山本祥平、石井剛志、勝間田知治、中山勉
  • Organizer: 第84回日本生化学会大会
  • Place of Presentation: 京都
  • Year and Date: 2011-09-24
• [Presentation] エピガロカテキンガレートと相互作用する血清蛋白質:アルブミンとトランスサイレチンの関係 (2011)
  • Author(s): 山本祥平、勝間田知治、石井剛志、中山勉
  • Organizer: 第8回日本カテキン学会総会
  • Place of Presentation: 京都
  • Year and Date: 2011-09-22
• [Presentation] カテキン類とカフェインの生体成分に対する結合親和性評価 (2011)
  • Author(s): 北村実穂、石井剛志、中山勉
  • Organizer: 第8回日本カテキン学会総会
  • Place of Presentation: 京都
  • Year and Date: 2011-09-22
• [Presentation] テアフラビン類と生体成分との相互作用解析 (2011)
  • Author(s): 上園博美、石井剛志、中山勉
  • Organizer: 第65回日本栄養・食糧学会大会
  • Place of Presentation: 東京
  • Year and Date: 2011-05-14
• [Presentation] カテキン類結合セファロースを用いた標的蛋白質の探索 (2011)
  • Author(s): 勝間田知治、石井剛志、中山勉
  • Organizer: 日本農芸化学会2011年度大会
  • Place of Presentation: 京都
  • Year and Date: 2011-03-27
• [Presentation] 紅茶テアフラビン類の蛋白質に対する反応性 (2011)
  • Author(s): 林美香、石井剛志、平松未宇、中山勉
  • Organizer: 日本農芸化学会2011年度大会
  • Place of Presentation: 京都
  • Year and Date: 2011-03-23
• [Presentation] Interaction of tea catechins with serum and cell proteins (2010)
  • Author(s): Katsumata, T., Ishii, T., and Nakayama, T
  • Organizer: Biochemistry and Molecular Biology 2010
  • Place of Presentation: 神戸
  • Year and Date: 2010-12-07
• [Presentation] Structural characteristics of tea catechins for formation of protein carbonyl in human serum albumin (2010)
  • Author(s): Mori, T., Ishii, T., and Nakayama, T
  • Organizer: Biochemistry and Molecular Biology 2010
  • Place of Presentation: 神戸
  • Year and Date: 2010-12-07
• [Presentation] カテキン類とヒト血清アルブミンとの結合特性 (2010)
  • Author(s): 勝間田知治、石井剛志、蓑田香奈子、森大気、伊藤創平、中山勉
  • Organizer: 第15回日本フードファクター学会
  • Place of Presentation: 仙台
  • Year and Date: 2010-10-04
• [Presentation] カテキン類と親和性の高い細胞タンパク質の探索 (2010)
  • Author(s): 勝間田知治、石井剛志、森大気、中山勉
  • Organizer: 第57回日本食品科学工学会大会
  • Place of Presentation: 東京
  • Year and Date: 2010-09-03
• [Presentation] カテキン類と血清タンパク質との相互作用 (2010)
  • Author(s): 石井剛志、勝間田知治、日下耕二、市川達也、尾登賢一、蓑田香奈子、加来麻衣子、森大気、伊藤創平、中山勉
  • Organizer: 第64回日本栄養・食糧学会大会
  • Place of Presentation: 徳島
  • Year and Date: 2010-05-23
• [Presentation] カテキン類と血清タンパク質との相互作用 (2010)
  • Author(s): 石井剛志, ほか
  • Organizer: 第64回日本・栄養食糧学会大会
  • Place of Presentation: 徳島
  • Year and Date: 2010-05-23
• [Remarks]
  • URL: http://sfns.u-shizuoka-ken.ac.jp/foodbioc/index.html
• [Remarks]
  • URL: http://sfns.u-shizuoka-ken.ac.jp/foodbioc/index.html
• [Patent(Industrial Property Rights)] ポリフェノール類化合物の苦渋味の評価方法
  • Inventor(s): 中山勉、石井剛志、山田智
  • Industrial Property Rights Holder: 中山勉、石井剛志、山田智
  • Industrial Property Number: 2011-253607