Uekusa, Yoshinori



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


Research Associate/Assistant Professor/Instructor

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Career 【 Display / hide

  • 2016.07

    Keio University, Faculty of Pharmacy, Assistant Professor

  • 2016.07

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

  • 2019.10

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

  • 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

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Academic Background 【 Display / hide

  • 2007.04

    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

  • Solubility enhancement of berberine–baicalin complex by the constituents of Gardenia Fruit

    Okoshi, K., Uekusa, Y., Narukawa, Y., Kiuchi, F.

    Journal of Natural Medicines (Journal of Natural Medicines)   2020.08

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

     View Summary

    © 2020, The Japanese Society of Pharmacognosy. A Kampo prescription usually consists of several crude drugs and contains many kinds of compounds. Physicochemical interactions between the compounds may occur in the process of decoction, by which Kampo prescriptions are usually prepared for ingestion, and the interactions may change the extraction yields of the constituents. Berberine and baicalin have been reported to form precipitates. Orengedokuto, which consist of Coptis Rhizome, Gardenia Fruit, Phellodendron Bark and Scutellaria Root, has been a representative Kampo prescription used to treat inflammatory diseases. In our previous papers, we revealed that the precipitates formed in the decoction of orengedokuto without Gardenia Fruit mainly consists of berberine–baicalin complex and that Gardenia Fruit reduced the amount of the precipitates in orengedokuto decoction. In this report, through solubility-enhancement assay based on HPLC, we identified crocins as the constituents of Gardenia Fruits, which enhanced the solubility of berberine–baicalin complex. All-trans crocin-1 (1) and 13-cis crocin-1 (5) showed high activities among the isolated crocins, and the number of glucosyl groups in the molecule seemed correlated with the activity. As berberine and baicalin were reported as the anti-inflammatory constituents of Coptis Rhizome and Phellodendron Bark, and Scutellaria Root, respectively, Gardenia Fruit contributes anti-inflammatory activity of orengedokuto by increasing solubilities of anti-inflammatory constituents of the other component crude drugs in the prescription. Our result will add a scientific basis to the understanding of the effectiveness of orengedokuto as a whole.

  • Solid-state 17O NMR analysis of synthetically 17O-enriched D-glucosamine

    Yamada, K., Yamaguchi, Y., Uekusa, Y., Aoki, K., Shimada, I., Yamaguchi, T., Kato, K.

    Chemical Physics Letters (Chemical Physics Letters)  749   137455 2020.06

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  00092614

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    © 2020 Elsevier B.V. The hydroxyl groups of carbohydrates are critical determinants of their conformational dynamics and intermolecular interactions but are difficult to characterize by conventional 1H nuclear magnetic resonance (NMR) approaches in solution. Here, we report a solid-state 17O NMR analysis of synthetic glucosamine with 17O enrichment at position 6. Based on magic-angle spinning and stationary spectral data obtained at varying magnetic fields in conjunction with quantum chemical calculations, we successfully estimated 17O chemical shift and electric field gradient tensors, providing benchmark for 17O NMR analyses of oligosaccharide structures.

  • Synthesis of methylophiopogonanone A

    Katagiri, R., Uekusa, Y., Narukawa, Y., and Kiuchi, F.

    Heterocycles 100   803 - 808 2020

    Research paper (scientific journal), Joint Work, Accepted

  • Five new 2-(2-phenylethyl)chromone derivatives from agarwood

    Shibata, S., Sugiyama, T., Uekusa, Y., Masui, R., Narukawa, Y., Kiuchi, F.

    Journal of Natural Medicines (Journal of Natural Medicines)  749 ( 3 ) 561 - 570 2020

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

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    © 2020, The Japanese Society of Pharmacognosy. Agarwood has been used as an incense and in traditional medicines as aphrodisiac, sedative, cardiotonic, and carminative. In this study, five new 2-(2-phenylethyl)chromones (2, 13–16) and eleven known compounds (1, 3–12) were isolated from the agarwood. The structures of the new compounds were determined by 1H-, 13C-, and two-dimensional NMR together with electronic circular dichroism (ECD) spectroscopy. All isolated compounds were evaluated for the phosphodiesterase (PDE) 3A and 5A1 inhibitory activity by the fluorescence polarization method. Dimeric 2-(2-phenylehyl)chromones (13, 14, 16) had potent inhibitory activity to PDE 5A1 with IC50 values of micro molar range (13: 4.2 μM, 14: 7.9 μM, 16: 4.3 μM), whereas they had weak activity to PDE 3A. In contrast, compound (15), which has a phenylpropionic acid moiety instead of the 2-(2-phenylethyl)chromone moiety in the dimers, showed moderate inhibition of both PDE 3A (IC50: 42.6 μM) and PDE 5A1 (IC50: 15.1 μM).

  • 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.

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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

  • Investigation of the interaction between theaflavins and phospholipid membranes as revealed by NMR spectroscopy

    日本薬学会第 140 回年会, 2020.03, Poster (general)

  • チャ由来 Benzotropolone 骨格を有する化合物のキサンチンオキシダーゼ阻害活性評価

    日本薬学会第 140 回年会, 2020.03, Poster (general)

  • 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)

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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

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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











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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

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Memberships in Academic Societies 【 Display / hide

  • The Pharmaceutical Society of Japan

  • The Japanese Society of Pharmacognosy

  • Japanese Society of Food Chemistry

  • Japanese Society for Food Hygiene and Safety