Saikawa, Yoko

写真a

Affiliation

Faculty of Science and Technology, Department of Applied Chemistry （Yagami）

Position

Associate Professor

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Career 【 Display / hide 】

  • 2002.04
    -
    Present

    慶應義塾大学理工学部, 応用化学科, 助手

  • 2008.04
    -
    Present

    慶應義塾大学理工学部, 応用化学科, 専任講師

  • 2014.04
    -
    Present

    慶應義塾大学理工学部, 応用化学科, 准教授

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Academic Background 【 Display / hide 】

  • 1998.03

    Keio University, Faculty of Science and Engineering, 応用化学科

    University, Graduated

  • 2000.03

    Keio University, Graduate School, Division of Science and Engineeri, 基礎理工学専攻

    Graduate School, Completed, Master's course

  • 2003.03

    Keio University, 理工学研究科, 基礎理工学専攻

    Graduate School, Withdrawal after completion of doctoral course requirements, Doctoral course

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Academic Degrees 【 Display / hide 】

  • 博士(理学), Keio University, Coursework, 2004.07

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Research Areas 【 Display / hide 】

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry (Organic Chemistry)

  • Life Science / Bioorganic chemistry (Organic Chemistry)

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Research Keywords 【 Display / hide 】

  • 天然物化学

  • natural product synthesis

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Papers 【 Display / hide 】

  • Biological evaluation for anti-inflammatory effect of africane-type sesquiterpenoids

    Kawano S., Matagawa T., Matsuda Y., Koyama T., Miura K., Nakata M., Saikawa Y., Simizu S.

    Bioorganic and Medicinal Chemistry （Bioorganic and Medicinal Chemistry)  68 2022.08

    ISSN  09680896

    　View Summary

    Africane-type sesquiterpenoids are a unique tricyclic carbon architecture sesquiterpenoid isolated as natural products. Δ9(15) -africanene has been reported to exhibit anti-inflammatory activity for carrageenan-induced rat foot edema. In this study, we reported structure–activity relationship study of africane-type sesquiterpenoids and found that some africane-type sesquiterpenoid analogs and their synthetic intermediate showed potent anti-inflammatory activity. To identify the mode of action of africane-type sesquiterpenoids and their synthetic intermediate, we evaluated the anti-inflammatory activity using lipopolysaccharide (LPS)-stimulated mouse macrophage RAW264.7 cells. Treatment with the africane-type compounds and their synthetic intermediate suppressed LPS-induced expressions of Cox-2 protein and mRNAs of the inflammatory cytokines IL-1β and IL-6 at the concentrations that did not affect cell viability. Interestingly, although these africane-type compounds and their synthetic intermediate suppressed the pro-inflammatory cytokines’ expressions, the compounds did not modulate NF-κB activation. These results suggest that the africane-type compounds and their synthetic intermediate are anti-inflammatory compounds that suppress the expression of LPS-induced inflammatory mediators independently of NF-κB activation.

  • Scalable Syntheses and Biological Evaluation of Africane-Type Sesquiterpenoids

    Matsuda Y., Koyama T., Kawano S., Miura K., Simizu S., Saikawa Y., Nakata M.

    Chemistry and Biodiversity （Chemistry and Biodiversity)  19 （ 3 ）  2022.03

    ISSN  16121872

    　View Summary

    Practical total syntheses of africane-type sesquiterpenoids were realized by reexamination of a divergent strategy employing optimized three-component coupling followed by ring-closing metathesis and substrate-controlled cyclopropanation. This sequential eight-step conversion provided Δ9(15)-africanene, a common bicyclo[5.3.0]decane intermediate for the syntheses of africane derivatives, in more than twice the yield as in the previous approach. The scalability and robustness of this improved synthetic route were confirmed by gram-scale preparation of Δ9(15)-africanene. In vitro cell-based assays of the synthesized africane-type sesquiterpenoids disclosed that ester-incorporating derivatives showed cytotoxic activity against HeLa cells. The effect of relative and absolute configuration of africane-9,15-diol monoacetates on the cytotoxicity against HeLa cells was also investigated.

  • Histological and quantitative image analyses of rice gall formed by orange leafhopper Cicadulina bipunctata (Hemiptera: Cicadellidae)

    Miyazaki S., Endo A., Matsui S., Tokuda M., Saikawa Y.

    Applied Entomology and Zoology （Applied Entomology and Zoology)  56 （ 3 ） 419 - 425 2021.08

    ISSN  00036862

    　View Summary

    The orange leafhopper, Cicadulina bipunctata (Melichar) (Hemiptera: Cicadellidae), is an insect pest of various Poaceae plants. Feeding by this leafhopper species induces growth suppression and gall formation, which is characterized by severe swelling of leaf veins, named wallaby ear symptoms. In this study, we performed histological analysis of the cell differentiation in the galled leaves of rice seedlings and devised a new method to quantify the degree of gall formation. In the histological study, abnormal vascular cell patterning and differentiation were observed in the galled leaves. Morphological changes during gall formation were quantitatively evaluated through image analysis.

  • Characterization of Plasmodium falciparum Pantothenate Kinase and Identification of Its Inhibitors From Natural Products

    Nurkanto A., Jeelani G., Santos H.J., Rahmawati Y., Mori M., Nakamura Y., Goto K., Saikawa Y., Annoura T., Tozawa Y., Sakura T., Inaoka D.K., Shiomi K., Nozaki T.

    Frontiers in Cellular and Infection Microbiology （Frontiers in Cellular and Infection Microbiology)  11 2021.03

    　View Summary

    Coenzyme A (CoA) is a well-known cofactor that plays an essential role in many metabolic reactions in all organisms. In Plasmodium falciparum, the most deadly among Plasmodium species that cause malaria, CoA and its biosynthetic pathway have been proven to be indispensable. The first and rate-limiting reaction in the CoA biosynthetic pathway is catalyzed by two putative pantothenate kinases (PfPanK1 and 2) in this parasite. Here we produced, purified, and biochemically characterized recombinant PfPanK1 for the first time. PfPanK1 showed activity using pantetheine besides pantothenate, as the primary substrate, indicating that CoA biosynthesis in the blood stage of P. falciparum can bypass pantothenate. We further developed a robust and reliable screening system to identify inhibitors using recombinant PfPanK1 and identified four PfPanK inhibitors from natural compounds.

  • Orange leafhopper cicadulina bipunctata feeding induces gall formation nitrogen dependently and regulates gibberellin signaling

    Miyazaki S., Kasahara K., Matsui S., Tokuda M., Saikawa Y.

    Plants （Plants)  9 （ 10 ） 1 - 12 2020.10

    　View Summary

    Orange leafhopper Cicadulina bipunctata feeding induces wallaby ear symptoms, namely growth suppression and gall formation characterized by severe swelling of leaf veins, on various Poaceae, thereby leading to low crop yields. Here, we investigated the development of wallaby ear symptoms on rice seedlings due to C. bipunctata feeding. After confirming that C. bipunctata feeding induces growth suppression and gall formation on rice seedlings, we further demonstrated that gall formation score decreased with decreasing levels of nitrogen in the medium and that C. bipunctata feeding induces the expression levels of nitrogen transporter genes. These gene expression changes may participate in the nutrient accumulation observed in galled tissues and in gall formation. In addition, these expression changes should induce growth promotion but the inhibition of gibberellin signaling by C. bipunctata feeding might be the reason why growth is suppressed. Treatment with plant growth regulators did not affect gall formation, suggesting the existence of a complex gall formation mechanism by C. bipunctata feeding.

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

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Reviews, Commentaries, etc. 【 Display / hide 】

  • Identification of a cyanidin-3-O-β-galactoside in gall tissue induced by midges on Japanese beech (Fagus crenata Blume)

    Miyazaki S., Kurisu H., Nakata M., Saikawa Y.

    Bioscience, Biotechnology and Biochemistry (Bioscience, Biotechnology and Biochemistry)  84 ( 4 ) 797 - 799 2020.04

    ISSN  09168451

    　View Summary

    Insect gall structures have many characteristic forms and colors, which are distinguishable from host plants. In this study, we identified an anthocyanin from red color insect galls and revealed that the anthocyanin biosynthesis of plants was induced by the gall extracts. The galling insects presumably regulate the anthocyanin biosynthesis of host plants to protect their larvae from environmental stresses.

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Presentations 【 Display / hide 】

  • ニワトリ卵殻成分の添加による胚のカルシウム吸収効率の調査

    上村美帆・糸川肇・伊藤卓・田原豊・中田雅也・犀川陽子

    日本畜産学会第124回大会, 

    2018.03
    , 

    Oral presentation (general), 日本畜産学会

    　View Summary

    ニワトリ胚の殻外培養にて、市販の炭酸カルシウムを与えても孵化しないにもかかわらず、乳酸カルシウムでは孵化することから、卵殻内側の炭酸カルシウムは特に容易に溶解し、胚に吸収されやすいしくみがあると考えられる。卵殻に含まれる何らかの成分が、胚による炭酸カルシウムの溶解・吸収を容易にしているのかどうかを調べるため、卵殻内側から卵殻の有機成分を抽出して卵殻カルシウムの再構築を検討した。酸カルシウムをそれぞれカルシウム源として培養容器にセットし、ニワトリ胚の生育状況を比較した。

  • Synthesis of a fluorescent probe using sneeze inducing grayanotoxin I

    ISHIKAWA SHUN, UBUKATA YUSUKE, ITO TAKU, NAKATA MASAYA, SAIKAWA YOKO

    日本化学会第98春季年会, 

    2018.03
    , 

    Oral presentation (general), 日本化学会

    　View Summary

    くしゃみ誘発物質として知られるグラヤノトキシン類を用いて、蛍光プローブを合成し、生体内でのイメージングを行うことで、くしゃみ誘発物質受容体の探索を行うことにした。最もくしゃみ誘発活性の強いグラヤノトキシンＩから誘導化することによって得たアルコールの水酸基を足掛かりとして、蛍光分子を導入する検討を行った。その結果、強固なアミド結合で連結したクマリン誘導体の合成に成功した。

  • ynthetic Studies of Oxazoline-Tetrahydrofuran Moiety of Leupyrrin A1

    TAKEDA KAZUTAKA, MAEDA CHIHIRO, TAKAYAMA TOMOKO, JIKAN TETSUHIKO, TEI JINPEI, SAIKAWA YOKO, NAKATA MASAYA

    日本化学会第98春季年会, 

    2018.03
    , 

    Oral presentation (general), 日本化学会

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    ルーピリンA1のオキサゾリン－テトラヒドロフラン部分の合成研究を行った。ペント-4-イン-1-オールから得た四置換ヨードアルケンと、ロイシン酸のワインレブアミドをエーテル化した。これのリチオ化、続くワインレブアミドの分子内付加により、テトラヒドロフラン部分相当のフラノンを合成した。また、(R)-グリシドールから合成したアリルカーバメートの分子内アミノヒドロキシ化により、オキサゾリン部分相当のオキサゾリジノンを合成した。

  • Synthesis and Properties of Butterfly-shaped Non-substituted Biphenothiazine with an Embedded Hydrazine Structure

    Yuri Shindo, Yoko Saikawa, Masaya Nakata, Kengo Hanaya, Takeshi Sugai, Shuhei Higashibayashi

    日本化学会第98春季年会, 

    2018.03
    , 

    Oral presentation (general), 日本化学会

    　View Summary

    ヒドラジン構造を含有し、バタフライ型構造を有するビフェノチアジンの無置換体を、1,9-ジブロモフェノチアジンの二量化により合成した。また、S原子の酸化により、ビフェノチアジンのスルホキシド体を合成した。合成したこれらの分子の構造、光物性を分光測定により明らかにしたので、報告する。

  • 芳香環作って壊して天然物合成

    SAIKAWA YOKO

    第15回有機合成化学談話会, 

    2017.09
    , 

    Oral presentation (invited, special), 有機合成化学協会

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Awards 【 Display / hide 】

  • CSJ Award for Outstanding Young Women Chemists

    Yoko Saikawa, 2015.03, The Chemical Society of Japan, Efficient Synthesis of Valuable Polyketides Featuring Late-stage Skeleton Construction

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Courses Taught 【 Display / hide 】

  • SEMINAR IN APPLIED CHEMISTRY

    2024

  • ORGANIC STRUCTURE ANALYSIS

    2024

  • ORGANIC CHEMISTRY

    2024

  • OFF-CAMPUS WORK-STUDY PROGRAM

    2024

  • LABORATORIES IN BASIC CHEMISTRY

    2024

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Courses Previously Taught 【 Display / hide 】

  • 化学B

    Keio University

    2018.04
    -
    2019.03
    , 

    Autumn Semester, Lecture, Lecturer outside of Keio

  • 基礎化学実験

    Keio University

    2018.04
    -
    2019.03
    , 

    Autumn Semester, Other, Laboratory work/practical work/exercise, Lecturer outside of Keio

  • 有機構造解析

    Keio University

    2018.04
    -
    2019.03
    , 

    Autumn Semester, Lecture, Lecturer outside of Keio

  • 応用化学実験B

    Keio University

    2018.04
    -
    2019.03
    , 

    Spring Semester, Other, Laboratory work/practical work/exercise, Lecturer outside of Keio

  • 自然化学実験

    Keio University

    2018.04
    -
    2019.03
    , 

    Spring Semester, Other, Laboratory work/practical work/exercise, Lecturer outside of Keio

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Social Activities 【 Display / hide 】

  • 有機合成化学協会

    1998.07
    -
    Present
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Memberships in Academic Societies 【 Display / hide 】

  • The Society of Synthetic Organic Chemistry, Japan, 

    1998.07
    -
    Present

  • The Chemical Society of Japan, 

    1998
    -
    Present
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Committee Experiences 【 Display / hide 】

  • 2018.04
    -
    Present

    事業委員, 有機合成化学協会

  • 1998.07
    -
    Present

    会員, 有機合成化学協会

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