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Synthetic studies on bioprobes designed based on the strcutures of natural products

Research Project

Project/Area Number 24580168
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionThe Institute of Physical and Chemical Research

Principal Investigator

TAKAHASHI Shunya  独立行政法人理化学研究所, 連携支援ユニット, 専任研究員 (00202151)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords有機合成 / 分子プローブ / 有機合成化学 / バイオプローブ / バイナリンB / ビオチニル化アナログ / ヨウ化サマリウム / バンレイシアセトゲニン / 機能性分子プローブ
Outline of Final Research Achievements

This research project aims to synthesize multifunctional bioprobes for the elucidation of fundamental biofunctions, and is composed of three themes as follows. 1) Vialinin B is a strong inhibitor of TNF-α production, but its target molecule was unknown. In order to clarify the target, a biotinylated phenylbenzofuran was synthesized. 2) Although the annonaceous acetogenins inhibit mitochondrial complex I, the detailed mechanism was unclear. A new synthetic method for preparation of cyclic ethers included in the acetogenins was developed, and was successfully applied to construct the probe core mimicking acetogenins. 3) Total synthesis of a couple of N-acetylglucosaminidase inhibitors, TMG-chitotriomycin and pochonicine, was accomplished, and the proposed structure of pochonicine was revised. These compounds synthesized in this project would be quite useful tools for clarification of the target molecule and for detailed understanding of the functions of the corresponding enzymes.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (26 results)

All 2014 2013 2012 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results,  Acknowledgement Compliant: 2 results,  Open Access: 1 results) Presentation (14 results)

  • [Journal Article] Synthesis and Structural Revision of a Brominated Sesquiterpenoid, Aldingenin C2014

    • Author(s)
      Takahashi S., Yasuda M., Nakamura T., Hatano K., Matsuoka K., Koshino H.
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 79 Pages: 9373-9380

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Structural Revision of Kynapcin-12 by Total Synthesis, and Inhibitory Activities against Prolyl Oligopeptidase and Cancer Cells2014

    • Author(s)
      Takahashi S., Yoshida A., Uesugi S., Hongo Y., Kimura K., Matsuoka K. and Koshino H.
    • Journal Title

      Bioorganic and Medicinal Chemistry Letters

      Volume: 24 Issue: 15 Pages: 3373-3376

    • DOI

      10.1016/j.bmcl.2014.05.091

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Structural elucidation and synthesis of vialinin C, a new inhibitor of TNF-α production2014

    • Author(s)
      Ye Y-Q, Negishi C, Hongo Y, Koshino H, Onose J, Abe N, Takahashi S.
    • Journal Title

      Bioorg. Med. Chem.

      Volume: 22 Issue: 8 Pages: 2442-2446

    • DOI

      10.1016/j.bmc.2014.02.058

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Detection of oxygen addition peaks for terpendole E and related indole-diterpene alkaloids in a positive mode ESI-MS2014

    • Author(s)
      Hongo Y., Nakamura T., Takahashi S., Motoyama T., Hayashi T., Hirota H., Osada H., Koshino H.
    • Journal Title

      J. Mass Spectrom.

      Volume: 49 Issue: 6 Pages: 537-542

    • DOI

      10.1002/jms.3360

    • Related Report
      2013 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Inhibition of tumor necrosis factor-α production by suppression of the activation of ubiquitin-specific peptidase 5, a target molecule of vialinin A2013

    • Author(s)
      Yoshioka Y., Ye Y-Q., Okada K., Taniguchi K., Yoshida A., Sugaya K., Onose J., Koshino H., Takahashi S., Yajima A., Yajima S., Abe N.
    • Journal Title

      PLOS ONE

      Volume: 8 Issue: 12 Pages: e80931-e80931

    • DOI

      10.1371/journal.pone.0080931

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Vialinin A is a ubiquitin-specific peptidase inhibitor2013

    • Author(s)
      Okada K., Ye Y-Q., Taniguchi K., Yoshida A., Akiyama T., Yoshioka Y., Onose J., Koshino H., Takahashi S., Yajima A., Abe N., Yajima S.
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 23 Issue: 15 Pages: 4328-4331

    • DOI

      10.1016/j.bmcl.2013.05.093

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of the Proposed Structure for Pochonicine and Determination of its Absolute Configuration2013

    • Author(s)
      Kitamura Y., Koshino H., Nakamura T., Tsuchida A., Nitoda T., Kanzaki H., Matsuoka K., and Takahashi S.
    • Journal Title

      Tetrahedron Lett.

      Volume: 54 Issue: 11 Pages: 1456-1459

    • DOI

      10.1016/j.tetlet.2013.01.015

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total synthesis of curvulone B and a proposed structure for dothiorelone B; determination of the configuration of curvulone B and structural revision of phomopsin A2012

    • Author(s)
      Takahashi S., Akita Y., Nakamura T., and Koshino H.
    • Journal Title

      Tetrahedron Asymmetry

      Volume: 23 Issue: 13 Pages: 952-958

    • DOI

      10.1016/j.tetasy.2012.06.009

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and biological activity of both enantiomers of kujigamberol isolated from 85-million-years-old Kuji amber2012

    • Author(s)
      Ye Y-Q., Koshino H., Hashizume D., Minamikawa Y., Kimura K., Takahashi S.
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 22 Issue: 13 Pages: 4529-4262

    • DOI

      10.1016/j.bmcl.2012.05.022

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Inhibitory effects of vialinin A and its advanced analog on TNF-α release and production from RBL-2H3 cells2012

    • Author(s)
      Onose J., Yoshioka Y., Ye Y-Q., Sugaya K., Yajima A., Taniguchi K., Okada K., Yajima S., Takahashi S., Koshino H., Abe N.
    • Journal Title

      Cell. Immunol.

      Volume: 279 Issue: 2 Pages: 140-144

    • DOI

      10.1016/j.cellimm.2012.10.008

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Kujigamberol, a new dinorlabdane diterpenoid isolated from 85 million years old Kuji amber using a biotechnological assay2012

    • Author(s)
      Kimura K., Minamikawa Y., Ogasawara Y., Yoshida J., Saitoh K., Shinden H., Ye Y-Q., Takahashi S., Miyakawa T., Koshino H.
    • Journal Title

      Fitoterapia

      Volume: 83 Issue: 5 Pages: 907-912

    • DOI

      10.1016/j.fitote.2012.03.024

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Design and synthesis of a vialinin A analog with a potent inhibitory activity of TNF-α production and its transformation into a couple of bioprobes2012

    • Author(s)
      Ye Y-Q., Onose J., Abe N., Koshino H., and Takahashi S.
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 22 Issue: 7 Pages: 2385-2387

    • DOI

      10.1016/j.bmcl.2012.02.034

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] トリメチルアミノ基を有する擬似糖の合成研究2014

    • Author(s)
      松本倫太朗、松岡浩司、越野広雪、高橋俊哉
    • Organizer
      Glyco東京
    • Place of Presentation
      千葉大学園芸学部(松戸)
    • Year and Date
      2014-11-08
    • Related Report
      2014 Annual Research Report
  • [Presentation] Formation of isomeric ions in collision-induced dissociation process probed by energy-resolved ion mobility tandem mass spectrometry (ER-IMS/MS2)2014

    • Author(s)
      Takemichi Nakamura, Asuka Yamashita, Yayoi Hongo, Shunya Takahashi, Takae Takeuchi
    • Organizer
      20th International Mass Spectrometry Conference
    • Place of Presentation
      Geneva, Switzerland
    • Year and Date
      2014-08-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] Structure and energy dependent ion isomerizations of folates detected using ER-IMS/MSn2014

    • Author(s)
      Yayoi Hongo, Hiroyuki Koshino, Shunya Takahashi, Takemichi Nakamura, Takae Takeuchi
    • Organizer
      20th International Mass Spectrometry Conference
    • Place of Presentation
      Geneva, Switzerland
    • Year and Date
      2014-08-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] Study of small neutral losses and ion rearrangements on protonated bunodosine 391 and IAA(indole-3-acetic acid)-amino acid conjugates2014

    • Author(s)
      Hiroyuki Koshino, Yayoi Hongo, Naomi Muto, Shunya Takahashi, Kohei Kazuma, Katsuhiro Konno, Andre, J. Zaharenko
    • Organizer
      20th International Mass Spectrometry Conference
    • Place of Presentation
      Geneva, Switzerland
    • Year and Date
      2014-08-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] 合成化学的手法を用いた天然物の構造訂正研究

    • Author(s)
      髙橋俊哉
    • Organizer
      理研シンポジウム(化学と情報学の融合:13C-NMR化学シフト・分子構造予測システムCAST/CNMRの開発と展開)
    • Place of Presentation
      理化学研究所(埼玉県和光市)
    • Related Report
      2013 Research-status Report
  • [Presentation] Total synthesis and structural revision ofpochonicine, a polyhydroxylated pyrrolizidine alkaloid as a potent GlcNAcase inhibitor

    • Author(s)
      Y. Kitamura, H. Koshino, T. Nakamura, A. Tsuchida, T. Nitoda, H. Kanzaki, K. Matsuoka, and S. Takahashi
    • Organizer
      第2回マックスプランクシンポジウム
    • Place of Presentation
      理化学研究所(埼玉県和光市)
    • Related Report
      2013 Research-status Report
  • [Presentation] ピロリジジンアルカロイドPochonicineの合成研究

    • Author(s)
      北村裕二郎,越野広雪,土田彩,仁戸田照彦,神崎浩,松岡浩司,高橋俊哉
    • Organizer
      日本化学会第93春期年会
    • Place of Presentation
      立命館大学(滋賀県草津市)
    • Related Report
      2013 Research-status Report
  • [Presentation] キナプシン-12の合成と構造訂正

    • Author(s)
      吉田彩香,叶躍奇,越野広雪,松岡浩司,高橋俊哉
    • Organizer
      日本化学会第93春期年会
    • Place of Presentation
      立命館大学(滋賀県草津市)
    • Related Report
      2013 Research-status Report
  • [Presentation] 紅藻由来含臭素セスキテルペノイドAldingenin C の合成研究

    • Author(s)
      安田将之,越野広雪,幡野健,松岡浩司,高橋俊哉
    • Organizer
      日本化学会第93春期年会
    • Place of Presentation
      立命館大学(滋賀県草津市)
    • Related Report
      2013 Research-status Report
  • [Presentation] ESI-MS分析で観測されるTerpendoleイオンの酸化とその制御

    • Author(s)
      本郷やよい,中村健道,高橋俊哉,本山高幸,林敏明,廣田洋,長田裕之, 越野広雪
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      東北大学(宮城県仙台市)
    • Related Report
      2013 Research-status Report
  • [Presentation] TNF-α放出阻害物質vialinin AのRBL-2H3細胞における標的分子の同定

    • Author(s)
      岡田潔、叶躍奇、吉岡泰淳、谷口佳代子、本橋寛子、菅谷紘一、小野瀬淳一、高橋俊哉、越野広雪、矢島新、矢嶋俊介、阿部尚樹
    • Organizer
      日本農芸化学会
    • Place of Presentation
      東北大学川内キャンパス(仙台)
    • Related Report
      2012 Research-status Report
  • [Presentation] Vialinin A標的分子USP5の活性化抑制がTNF-α放出に与える影響

    • Author(s)
      吉岡泰淳、岡田潔、叶躍奇、谷口佳代子、菅谷紘一、小野瀬淳一、高橋俊哉、越野広雪、矢島新、矢嶋俊介、阿部尚樹
    • Organizer
      日本農芸化学会
    • Place of Presentation
      東北大学川内キャンパス(仙台)
    • Related Report
      2012 Research-status Report
  • [Presentation] Vialinin Aアナログ誘導体を分子プローブとして用いた細胞内標的 タンパク質の同定とTNF-α放出阻害作用の解析

    • Author(s)
      阿部尚樹、吉岡泰淳、叶躍奇、岡田潔、谷口佳代子、菅谷紘一、小野瀬淳一、高橋俊哉、越野広雪、矢島新、矢嶋俊介
    • Organizer
      第54回天然有機化合物討論会
    • Place of Presentation
      東京農業大学(東京)
    • Related Report
      2012 Research-status Report
  • [Presentation] ビオチン標識化Vialinin Aアナログによる細胞内標的分子の同定と TNF-α放出阻害作用の解析

    • Author(s)
      吉岡泰淳、叶躍奇、岡田潔、谷口佳代子、菅谷紘一、小野瀬淳一、高橋俊哉、越野広雪、矢島新、矢嶋俊介、阿部尚樹
    • Organizer
      2012年 日本ハーブ療法研究会 設立記念学術集会
    • Place of Presentation
      光の家会館(東京)
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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