Uekusa, Yoshinori



Faculty of Pharmacy, Department of Pharmacy 天然医薬資源学講座 (Shiba-Kyoritsu)


Research Associate/Assistant Professor/Instructor

External Links

Other Affiliation 【 Display / hide

  • Scripps Institution of Oceanography, University of California, San Diego , Center for Marine Biotechnology and Biomedicine, Visiting Scholar

Career 【 Display / hide

  • 2019.10

    Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego, Visiting Scholar

  • 2016.07

    Keio University, Faculty of Pharmacy, Assistant Professor

  • 2016.07

    National Institute of Health Sciences, Division of Foods, 協力研究員

  • 2013.05

    National Institute of Health Sciences, Division of Foods, technical official, Researcher

  • 2013.04

    Nagoya City University, Graduate School of Pharmaceutical Sciences, Postdoctoral Fellow

display all >>

Academic Background 【 Display / hide

  • 2005.04

    University of Shizuoka, Department of Food and Nutritional Sciences, 食品栄養科学専攻

    Graduate School, Completed, Doctoral course

  • 2005.04

    University of Shizuoka, Department of Food and Nutritional Sciences, 食品栄養科学専攻

    Graduate School, Completed, Master's course

  • 2001.04

    Tokyo University of Pharmacy and Life Science, School of Life Sciences, 分子生命科学科


Academic Degrees 【 Display / hide

  • 博士(食品栄養科学), University of Shizuoka, Coursework, 2010.03


Research Areas 【 Display / hide

  • Natural medicines (Natural Product Chemistry)

  • Analytical chemistry (Analytical Chemistry)

  • Food science (Food Chemistry)

Research Keywords 【 Display / hide

  • Analytical Chemistry

  • Natural Product Chemistry


Books 【 Display / hide

  • 試料分析講座 糖質分析

    丸善出版, 2019.07

    Scope: 6.4 NMR による糖鎖–タンパク質相互作用の解析,  Contact page: 246–252

Papers 【 Display / hide

  • Preparation of menisdaurigenin and related compounds

    Shirakawa, R., Ishikawa, S., Takahashi, M., Ueno, Y., Uekusa, Y., Narukawa, Y., Sugai, T., and Kiuchi, F.

    J. Nat. Med. (Journal of Natural Medicines)  73 ( 1 ) 236 - 243 2019

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  13403443

     View Summary

    © 2018, The Japanese Society of Pharmacognosy and Springer Japan KK, part of Springer Nature. Menisdaurin (1), a cyano glucoside, was first isolated in 1978 from Menispermum dauricum (Menispermaceae) and named after the plant. It has been also isolated from several plant sources. The stereochemistry of the aglycone part was first reported as (Z,4R,6S)-enantiomer of (4,6-dihydroxy-2-cyclohexen-1-ylidene)acetonitrile based on the CD spectrum of menisdaurilide (2), the α,β-unsaturated γ-lactone obtained by an acid hydrolysis of menisdaurin. Later, the absolute stereochemistry was revised as (Z,4S,6R) by X-ray crystal analysis of 1 isolated from Saniculiphyllum guangxiens. The aglycone part of menisdaurin (1) has not been obtained from 1, because an acid hydrolysis of 1 gave menisdaurilide (2), and enzymatic hydrolysis with emulsin did not give the aglycone. On the other hand, a compound named coculauril (3) was isolated from Cocculus lauriforius. This compound has the same planner structure corresponding to the aglycone of 1, but the stereochemistry was reported to be (E,4R,6S). Here, we confirmed the absolute stereochemistry of 1 by Mosher’s method to be (Z,4S,6R), and prepared the aglycone of 1, i.e., menisdaurigenin (4) by an enzymatic hydrolysis of 1. We also revealed that 4 is a different compound from 3 and unstable in water and MeOH.

  • Efficient Synthesis of Theaflavin 3-Gallate by a Tyrosinase-Catalyzed Reaction with (-)-Epicatechin and (-)-Epigallocatechin Gallate in a 1-Octanol/Buffer Biphasic System

    Narai-Kanayama A., Uekusa Y., Kiuchi F., Nakayama T.

    Journal of Agricultural and Food Chemistry (Journal of Agricultural and Food Chemistry)  66 ( 51 ) 13464 - 13472 2018.12

    ISSN  00218561

     View Summary

    © 2018 American Chemical Society. Theaflavins, the orange-red pigments contained in black tea, have attracted attention as a result of their health-promoting effects. However, their synthetic preparation, in which the enzymatic oxidation of catechol-type catechin is followed by the quinone-induced oxidative dimerization of selectively combined catechol- and pyrogallol-type catechins, provides only a low yield. In the present study, we found that a 1-octanol/buffer biphasic system improved the yield of theaflavin 3-gallate in a tyrosinase-catalyzed synthetic reaction with (-)-epicatechin and (-)-epigallocatechin gallate. When the enzymatic reaction proceeded in a buffer solution, oxidized (-)-epigallocatechin gallate was preferentially used for self-dimerization. However, self-dimerization was suppressed in the octanol phase, allowing oxidized (-)-epigallocatechin gallate to participate in coupling with (-)-epicatechin quinone, leading to effective production of theaflavin 3-gallate. Furthermore, the preferential localization of theaflavin 3-gallate in the octanol phase prevented (-)-epicatechin-quinone-induced degradation.

  • Concentration of radioactive cesium in domestic foods collected from the Japanese market in fiscal years 2014-2016

    Imamura M., Nabeshi H., Tsutsumi T., Uekusa Y., Maisuda R., Maeda T., Soga K., Teshima R., Hachisuka A., Akiyama H.

    Journal of the Food Hygienic Society of Japan (Journal of the Food Hygienic Society of Japan)  59 ( 5 ) 239 - 247 2018.10

    ISSN  00156426

     View Summary

    © 2018 Food Hygienic Society of Japan.All right reserved. Between fiscal years 2014 and 2016, we surveyed the concentration of radioactive cesium in commercial foods produced in areas where there is a risk of radiation contamination due to the Fukushima Daiichi nuclear disaster. The number of samples with a concentration of radioactive cesium that exceeded the regulatory limit(100 Bq/kg for general foods)was 9 out of 1,516(0.6%)in fiscal 2014, 12 out of 900(1.3%)in fiscal 2015, and 10 out of 654(1.5%)in fiscal 2016. Even though some samples were expected to be contaminated with radioactive cesium, because wild mushrooms and edible wild plants were intentionally included in this survey, the percentage of samples that exceeded the regulatory limit was only around 1%. The surveillance results confirmed that the pre-shipment food monitoring conducted by local governments was properly and efficiently performed, although continuous monitoring of the concentration of radioactive cesium in cultivated and wild mushrooms, edible wild plants, and wild animal meats is still required.

  • Determination of polychlorinated biphenyls in marine fish obtained from tsunami-stricken areas of Japan

    Uekusa, Y., Takatsuki, S., Tsutsumi, T., Akiyama, H., Matsuda, R., Teshima, R., Hachisuka, A., and Watanabe, T.

    PLOS ONE 12 ( 4 ) e0174961 2017.04

    Research paper (scientific journal), Joint Work, Accepted

  • Concentration of uranium in foods after the Fukushima Daichi Nuclear Power Plant Accident

    Uekusa, Y., Nabeshi, H., Kataoka, Y., Watanabe, T., Hachisuka, A., Akiyama, H., Tsutsumi, T., Matsuda, R., and Toshiba, R.

    Japanese Journal of Food Chemistry and Safety 23   43 - 48 2016.03

    Research paper (scientific journal), Joint Work, Accepted

display all >>

Reviews, Commentaries, etc. 【 Display / hide

  • 多成分系から相乗作用に関与する化合物を探し出す

    UEKUSA Yoshinori

    ファルマシア 54 ( 10 ) 982 2018.10

    Introduction and explanation (scientific journal), Single Work

  • NMR characterization of the conformations, dynamics, and interactions of glycosphingolipids

    Yagi-Utsumi, M., Yamaguchi, Y., Uekusa, Y., and Kato, K.

    NMR in Glycoscience and Glycotechnology (RSC Publishing (Cambridge))     161 - 178 2017.05

    Introduction and explanation (scientific journal), Joint Work

Presentations 【 Display / hide

  • かんきつ果汁中の新規 OATP2B1 阻害成分の探索とその阻害活性の定量的評価

    第13回 次世代を担う若手医療薬科学シンポジウム, 2019.10, Poster (general)

  • Solubility-enhancement of berberine-baicalin complex by crocins

    American Society of Pharmacognosy 2019 Annual Meeting, 2019.07, Poster (general)

  • Structural analysis of the complex of baicalin and berberine in aqueous solution

    American Society of Pharmacognosy 2019 Annual Meeting, 2019.07, Poster (general)

  • チェストツリー成分の女性ホルモン分泌に対する影響に関する研究

    日本薬学会第139年会, 2019.03, Poster (general)

  • 抗トリパノソーマ活性を有するラクウショウ由来成分の探索

    日本薬学会第139年会, 2019.03, Poster (general)

display all >>

Research Projects of Competitive Funds, etc. 【 Display / hide

  • 生物活性発現初期段階におけるフラボン類とリン脂質膜との相互作用解析


    MEXT,JSPS, Grant-in-Aid for Scientific Research, 植草 義徳, Grant-in-Aid for Scientific Research (C), Principal Investigator

  • フラボノイド混合物の抗炎症作用メカニズムの解析とその応用


    日本学術振興会, Grant-in-Aid for Scientific Research, Co-investigator

  • テアフラビン類とリン脂質との分子間相互作用の解析


    Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research, Research grant, Co-investigator

  • 生薬の品質評価および基原植物推の推定を目的とした多成分一斉分析法の開発


    Keio University, Keio Gijuku Fukuzawa Memorial Fund for the Advancement of Education and Research, Research grant

  • 震災に起因する食品中の放射性物質ならびに有害化学物質の実態に関する研究 震災・津波による食品の化学物質汚染実態の調査


    Ministry of Health, Labour and Welfare, Health and Labour Sciences Research Grants, Co-investigator

display all >>

Awards 【 Display / hide

  • Poster Award, The 65th Annual Meeting of the Japanese Society of Pharmacognosy

    2018.09, Structural analysis of the baicalin–berberine complex in water

  • Encouragement Award in Japanese Society of Food Chemistry

    2016.06, 日本食品化学学会, 東日本大震災に起因した食品中の有害物質等の実態に関する研究

  • Young Investigator Award

    2009.11, 日本フードファクター学会, NMR法による緑茶カテキン類のリン脂質膜中における存在位置の解明

  • 第18回フードサイエンスフォーラム 最優秀プレゼンテーション賞

    2008.11, フードサイエンスフォーラム, ECgの脂質膜中における動態挙動解析(固体NMRによる相互作用解析)

  • 第17回フードサイエンスフォーラム 最優秀プレゼンテーション賞

    2008.03, フードサイエンスフォーラム, 茶カテキン類は生体膜(脂質二重層)の表面と相互作用する(溶液NMRを用いた相互作用部位の解析)


Courses Taught 【 Display / hide











display all >>

Courses Previously Taught 【 Display / hide

  • Molecular design of medicine

    Keio University, 2017, Spring Semester

  • Structural analysis of biological molecules and bioactive compounds

    Keio University, 2017, Spring Semester

  • Advanced natural products chemistry

    Keio University, 2017, Spring Semester

  • Pharmacognosy laboratory course

    Keio University, 2017, Autumn Semester

  • Basic pharmaceutical sciences laboratory course

    Keio University, 2017, Autumn Semester

display all >>