Narukawa, Yuji



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


Assistant Professor/Senior Assistant Professor


Research Areas 【 Display / hide

  • Natural medicines


Books 【 Display / hide

  • 薬用食品の開発.

    竹田忠紘*、成川佑次、浅野 孝., 東京/シーエムシー出版, 2007.02

    Scope: 267-277

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)  75 ( 1 ) 76 - 83 2021.01

    ISSN  13403443

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    © 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.

  • 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)  74 ( 3 ) 561 - 570 2020.06

    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).

  • LC–MS analysis of saponins of Achyranthes root in the Japanese market

    Kuwada K., Kawase S., Nakata K., Shinya N., Narukawa Y., Fuchino H., Kawahara N., Kiuchi F.

    Journal of Natural Medicines (Journal of Natural Medicines)  74 ( 1 ) 135 - 141 2020.01

    ISSN  13403443

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    © 2019, The Japanese Society of Pharmacognosy. LC–MS analyses of saponin fractions of Achyranthes roots in the Japanese market revealed that there were three patterns for the saponin fraction of their water extracts, i.e., the saponins with a sugar moiety at position 28 [achyranthosides B (3), C (4) and D (5)] were the major constituents, the saponins without sugar moiety at position 28 [betavulgarosides II (10) and IV (11)] were the major constituents, and mixtures of these saponins. In a decoction prepared from the sample which contained 10 and 11 as the major saponins, their amounts were largely decreased compared with those of the water extract. As large amounts of these saponins were found in the precipitates formed by heating of the water extract, these saponins were seemed to precipitate out under heating. When hot water was used for the extraction, 3, 4 and 5 were detected even from the samples whose water extract did not contain these saponins. This was attributed to inhibition of endogenous esterase which hydrolyzes the ester linkage at position 28. When saponins were extracted with reagent grade 1-butanol, in addition to the decrease of the amounts of highly polar saponins, oxidative decarboxylation of 3 and 10 occurred resulting in formation of achyranthoside E (6) and spinacoside D (12), respectively. As these changes were not observed with HPLC grade 1-butanol, which contain not more than 5 ppm of peroxide impurities, the change was attributable to the peroxide impurities contained in the reagent grade 1-butanol.

  • Synthesis of methylophiopogonanone a

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

    Heterocycles (Heterocycles)  100 ( 5 ) 803 - 808 2020

    ISSN  03855414

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    © 2020 The Japan Institute of Heterocyclic Chemistry. Ophiopogon Root (root of Ophiopogon japonicus Ker-Gawler, Liliaceae) is a crude drug used as expectorant, anti-cough and tonic in Kampo medicine (traditional Japanese medicine) as well as other traditional medicines of Asian countries. It contains characteristic homoisoflavonoids with methylated ring A. We synthesized methylophiopogonanone A (1), which is a candidate marker compound for identification test of Ophiopogon Root, from phloroglucinol in 9 steps with overall yield of 11.1%.

  • Preparation of menisdaurigenin and related compounds

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

    Journal of Natural Medicines (Journal of Natural Medicines)  73 ( 1 ) 236 - 243 2019.01

    ISSN  13403443

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    © 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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Papers, etc., Registered in KOARA 【 Display / hide

Reviews, Commentaries, etc. 【 Display / hide

  • ジンコウ(沈香)の品質評価は何を指標とすればいいか?


    ファルマシア (日本薬学会)  56 ( 3 ) 266 2020.03

    Introduction and explanation (others)

Presentations 【 Display / hide

  • シソ科植物由来ジテルペンの抗トリパノソーマ活性評価

    加々美 茉那、中村 美青、植草 義徳、成川 佑次、嶋田 淳子、木内 文之

    日本薬学会第141年会, 2021.03, Poster (general)

  • ジンコウ(沈香)由来2-(2-phenylethyl)chromoneのPDE阻害活性

    成川 佑次、柴田 峻佑、杉山 拓司、増井 涼、木内 文之

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

  • Salvia属植物由来の抗トリパノソーマ活性成分の探索

    中村 美青、新島 万稀、成川 佑次、嶋田 淳子、木内 文之

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

  • マンケイシの女性ホルモン代謝に対する影響

    森 有紗、馬場 久子、丸山 瑞、成川 佑次、木内 文之

    日本薬学会第140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

    工藤 隼、植草 義徳、成川 佑次、木内 文之

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

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

  • 漢方処方における生薬間相互作用の解析


    MEXT,JSPS, Grant-in-Aid for Scientific Research, 成川 佑次, Grant-in-Aid for Scientific Research (C), Principal Investigator


Courses Taught 【 Display / hide











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