Development of a new probe of a flavonoid metabolite, DOPAC, for understanding the biomolecule modification

2012 Fiscal Year Final Research Report

• Project/Area Number: 22580129
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Food science
• Research Institution: Okayama University
• Principal Investigator: NAKAMURA Yoshimasa 岡山大学, 大学院・環境生命科学研究科, 准教授 (60324381)
• Co-Investigator(Kenkyū-buntansha): KATO Yoji 兵庫県立大学, 環境人間学部, 教授 (30305693)
• Project Period (FY): 2010 – 2012
• Keywords: ポリフェノール / ケルセチン / 生体内代謝物 / 分子標的 / DOPAC / クリックケミストリー

Research Abstract

The interest in fermented products in the large intestine such as a quercetin glucoside metabolite, 3,4-dihydroxyphenylacetic acid (DOPAC), has started to grow rapidly. In this study, we identified several plausible target molecules for polyphenols by understanding the molecular mechanisms underlying biological activities related to their chemical characteristics. We also revealed that DOPAC exhibited radical scavenging and phase II drug metabolizing enzyme-inducing activities more potently than other quercetin metabolites. Furthermore, we developed a new probe (DOPAC propargyl ester) to detect target proteins and confirmed its applicability to “click chemistry”.

Research Products

• [Journal Article] Cytotoxicity of benzyl isothiocyanate in normal renal proximal tubular cells and its modulation by glutathione. (2012)
  • Author(s): Abe, N., Okuhira, M., Tsutsui, C., Shimoishi, Y., Murata, Y., Nakamura, Y
  • Journal Title: J. Agric. Food Chem Volume: 60(7) Pages: 1887-1892
  • DOI: DOI: 10.1021/jf2052042
  • Peer Reviewed
• [Journal Article] α-Tocopherol sensitizes human leukemia HL-60 cells to apoptosis induced by benzyl isothiocyanate (2012)
  • Author(s): Abe, N., Shimizu, T., Miyoshi, N., Murata, Y., Nakamura, Y
  • Journal Title: Biosci. Biotechnol. Biochem Volume: 76(2) Pages: 381-383
  • DOI: DOI: 10.1271/bbb.110665
  • Peer Reviewed
• [Journal Article] Increased halogenated tyrosine levels are useful markers of human skin ageing, reflecting proteins denatured by past skin inflammation. (2012)
  • Author(s): Ishitsuka, Y., Maniwa, F., Koide, C., Kato, Y., Nakamura, Y., Osawa, T., Tanioka, M., Miyachi, Y
  • Journal Title: Clin. Exp. Dermatol Volume: 37(3) Pages: 252-258
  • DOI: DOI:10.1111/j.1365-2230.2011.04215.x.
  • Peer Reviewed
• [Journal Article] Luteolin overcomes resistance to benzyl isothiocyanate-induced apoptosis in human colorectal cancer HCT-116 cells (2012)
  • Author(s): Sakai, R., Yokobe, S., Abe, N., Miyoshi, N., Murata, Y., Nakamura, Y
  • Journal Title: J. Food Drug Anal Volume: 20(Suppl.) Pages: 389-393
  • DOI: DOI:10.6227/jfda
  • Peer Reviewed
• [Journal Article] Involvement of intracellular oxidative stress-sensitive pathway in phloxine B-induced photocytotoxicity in human T lymphocytic leukemia cells. (2012)
  • Author(s): Qi, H., Zhu, B., Abe, N., Shin, Y., Murata, Y., Nakamura, Y
  • Journal Title: Food Chem. Toxicol Volume: 50(6) Pages: 1841-1847
  • DOI: DOI:10.1016/j.fct.2012.03.011
  • Peer Reviewed
• [Journal Article] Development and application of a method for identification of isothiocyanate-targeted molecules in colon cancer cells (2012)
  • Author(s): Miyoshi, N., Yonemochi, T., Tomono, S., Fukutomi, R., Nakamura, Y., Ohshima, H.
  • Journal Title: Anal. Biochem. Volume: 429(2) Pages: 124-131
  • DOI: DOI:10.1016/j.ab.2012.07.018
  • Peer Reviewed
• [Journal Article] (-)-Epigallo -catechin-3-gallate suppresses growth of AZ521 human gastric cancer cells by targeting the DEAD box RNA helicase (2011)
  • Author(s): Tanaka, T., Ishii, T., Mizuno, D., Mori, T., Yamaji, R., Nakamura, Y., Kumazawa, S., Nakayama, T., Akagawa, M
  • Journal Title: Free Radical Biol. Med Volume: 50(10) Pages: 1324-1335
  • DOI: DOI:10.1016/j.freeradbiomed.2011.01.024
  • Peer Reviewed
• [Journal Article] Hydrogen peroxide-dependent photocyto -toxicity by phloxine B, a xanthene food colorant (2011)
  • Author(s): Qi, H., Takano, H., Kato, Y., Wu, Q., Ogata, C., Zhu, B., Murata, Y., Nakamura, Y
  • Journal Title: Biochim. Biophys. Acta Gen. Sub Volume: 1810(7) Pages: 704-712
  • DOI: DOI:10.1016/j.bbagen.2011.04.010
  • Peer Reviewed
• [Journal Article] Localized cysteine sulfenic acid formation by vascular endothelial growth factor: Role in endothelial cell migration and angiogenesis (2011)
  • Author(s): Kaplan, N., Urao, N., Furuta, E., Kim, S.J., Razvi, M., Nakamura, Y., McKinney, R.D., Poole, L.B., Fukai, T., Ushio-Fukai, M
  • Journal Title: Free Radical Res Volume: 45(10) Pages: 1124-1135
  • DOI: DOI:10.3109/10715762.2011.602073
  • Peer Reviewed
• [Journal Article] バイオメディア: 3週間前に摂取した野菜の履歴が血中に (2011)
  • Author(s): 中村宜督
  • Journal Title: 生物工学. Volume: 89(4) Pages: 206
  • URL: https://www.sbj.or.jp/wp-content/uploads/file/sbj/8904/8904_biomedia_3.pdf
• [Journal Article] イソチオシアネートとがん予防 (2011)
  • Author(s): 中村宜督
  • Journal Title: Functional Food. Volume: 4(4) Pages: 321-327
  • URL: http://ci.nii.ac.jp/naid/40018846306
• [Journal Article] Artificial food colorants inhibit superoxide production in differentiated HL-60 cells (2010)
  • Author(s): Qi, H., Kawagishi, M., Yoshimoto, M., Takano, H., Zhu, B., Shimoishi, Y., Tada, M., Murata, Y., Nakamura, Y
  • Journal Title: Biosci. Biotechnol. Biochem Volume: 74(8) Pages: 1725-1728
  • DOI: DOI:10.1271/bbb.100314
  • Peer Reviewed
• [Journal Article] Covalent binding of tea catechins to protein thiols: Relationship between oxidation stability and electrophilic reactivity (2010)
  • Author(s): Mori, T., Ishii, T., Akagawa, M., Nakamura, Y., Nakayama, T
  • Journal Title: Biosci. Biotechnol. Biochem Volume: 74(12) Pages: 2451-2456
  • DOI: DOI:10.1271/bbb.100509
  • Peer Reviewed
• [Presentation] ケルセチン配糖体体内代謝物の分子プローブ合成 (2012)
  • Author(s): 齋木俊也、山口佑也、村田芳行、中村宜督
  • Organizer: 第17回日本フードファクター学会(JSoFF)学術集会・第9回日本カテキン学会総会 合同大会
  • Place of Presentation: 静岡
  • Year and Date: 2012-11-10
• [Presentation] ケルセチン配糖体体内代謝産物分子プローブの合成 (2012)
  • Author(s): 山口佑也、齋木俊也、村田芳行、中村宜督
  • Organizer: 第32回日本農芸化学会中四国支部講演会
  • Place of Presentation: 鳥取
  • Year and Date: 2012-01-21
• [Presentation] アブラナ科野菜の機能性:イソチオシアネートの化学:福山大学グリーンサイエンス研究センター「環境健康科学の研究拠点の形成」 (2012)
  • Author(s): 中村宜督
  • Organizer: 第2回公開講演会
  • Place of Presentation: 福山
  • Year and Date: 2012-01-06
• [Presentation] Overcoming resistance to isothiocyanate in colon cancer cells (2011)
  • Author(s): Yoshimasa Nakamura
  • Organizer: 2011 International Conference on Food Factors: ICoFF 2011
  • Place of Presentation: Taipei
  • Year and Date: 2011-11-22
• [Presentation] 食品に含まれる求電子性物-イソチオシアネートの機能性とその化学- (2011)
  • Author(s): 中村宜督
  • Organizer: 日本農芸化学会関西支部第465回講演会ミニシンポジウム『食品成分と健康:生体応答の分子メカニズム』
  • Place of Presentation: 堺
  • Year and Date: 2011-07-03
• [Presentation] ベンジルイソチオシアネート代謝物のアポトーシス誘導作用 (2011)
  • Author(s): 中村宜督、筒井千春、村田芳行、加藤陽二
  • Organizer: 日本農芸化学会大会
  • Place of Presentation: 京都
  • Year and Date: 2011-03-27