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Synthetic Study on Chlorosulfolipids Fluorescent Probe Directed toward Elucidation of Action Mechanism

Research Project

Project/Area Number 16K01908
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Biomolecular chemistry
Research InstitutionHokkaido University

Principal Investigator

Matsuda Fuyuhiko  北海道大学, 地球環境科学研究院, 教授 (10219446)

Co-Investigator(Kenkyū-buntansha) 沖野 龍文  北海道大学, 地球環境科学研究院, 教授 (30280910)
Research Collaborator UMEZAWA Taiki  
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Keywords全合成 / クロロスルフォリピッド / 含塩素化合物 / 構造活性相関 / プローブ分子 / エポキシド / クロロスルホリピッド
Outline of Final Research Achievements

Chlorosulfolipids (CSLs), first isolated from the freshwater alga, are a unusual family of natural products includes Danicalipin A and Mytilipin C. CSLs are unique in featuring straight chain hydrocarbon skeleton densely functionalized with chlorine atoms. They have drawn considerable attention as substances of toxicological concern, because some of them display cytotoxicity and are associated with seafood poisoning. Due to the unprecedented structure and interesting biological activity, CSLs recently garnered interest as targets of total synthesis. Several groups including our group have achieved total syntheses of CSLs. In this research, synthetic study on fluorescent probes of Mytilipin C and Danicalipin A directed toward elucidation of action mechanism was carried out. We developed synthetic process to stereoselectively construct polychlorinated skeleton of Mytilipin C. We also succeeded synthesis of fluorescent probe of Danicalipin A which exhibited toxicity against brine shrimp.

Academic Significance and Societal Importance of the Research Achievements

CSLsは多彩な生物活性を示し、その特異な分子構造と相まって注目されている。特に、食中毒の原因物質として特定されていることから、生物活性発現の分子レベルでの作用機序解明が喫緊の課題で、社会的意義も大きい。分子レベルでの活性発現作用機序の解明には、CSLsの蛍光プローブの合成が必須である。しかしながら、多数のCSLsの全合成が報告されているものの、蛍光プローブの合成を指向した研究は現在までに報告例はなく、その学術的意義は大きい。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (12 results)

All 2019 2018 2017 2016

All Journal Article (7 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 7 results) Presentation (5 results)

  • [Journal Article] Synthesis and Structure?Activity Relationship of Omaezallene Derivatives2019

    • Author(s)
      Umezawa Taiki、Prakoso Nurcahyo Iman、Kannaka Miho、Nogata Yasuyuki、Yoshimura Erina、Okino Tatsufumi、Matsuda Fuyuhiko
    • Journal Title

      Chemistry & Biodiversity

      Volume: 16 Issue: 1 Pages: 1800451-1800451

    • DOI

      10.1002/cbdv.201800451

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Total synthesis and biological activity of dolastatin 162017

    • Author(s)
      1.Casalme, L. O., Yamauchi, A., Sato, A., Petitbois, J. G., Nogata, Y., Yoshimura, E., Okino, T., Umezawa, T., & Matsuda, F.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 15 Issue: 5 Pages: 1140-1150

    • DOI

      10.1039/c6ob02657e

    • NAID

      120006374983

    • Related Report
      2017 Research-status Report 2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Design, Synthesis, and Antifouling Activity of Glucosamine-Based Isocyanides2017

    • Author(s)
      T. Umezawa, Y. Hasegawa, I. S. Novita, J. Suzuki, T. Morozumi, Y. Nogata, E. Yoshimura, and F. Matsuda
    • Journal Title

      Mar. Drugs

      Volume: 15 Issue: 7 Pages: 203-203

    • DOI

      10.3390/md15070203

    • NAID

      120006346113

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (-)-Kainic Acid and (+)-allo-Kainic Acid through SmI2-Mediated Intramolecular Coupling between Allyl Chloride and an α,β-Unsaturated Ester2017

    • Author(s)
      J. Suzuki, N. Miyano, S. Yashiro, T. Umezawa, and F. Matsuda
    • Journal Title

      Org. Biomol. Chem.

      Volume: 15 Issue: 31 Pages: 6557-6566

    • DOI

      10.1039/c7ob01427a

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Columbamides D and E: Chlorinated Fatty Acid Amides from the Marine Cyanobacterium Moorea bouillonii Collected in Malaysia2017

    • Author(s)
      J. A. V. Lopez, J. G. Petitbois, C. S. Vairappan, T. Umezawa, F. Matsuda, and T. Okino
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 16 Pages: 4231-4234

    • DOI

      10.1021/acs.orglett.7b01869

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Serinolamides and Lyngbyabellins from an Okeania sp. Cyanobacterium Collected from the Red Sea2017

    • Author(s)
      J. G. Petitbois, L. O. Casalme, J. A. V. Lopez, W. M. Alarif, A. Abdel-Lateff, S. S. Al-Lihaibi, E. Yoshimura, Y. Nogata, T. Umezawa, F. Matsuda, and T. Okino
    • Journal Title

      J. Nat. Prod.

      Volume: 80 Issue: 10 Pages: 2708-2715

    • DOI

      10.1021/acs.jnatprod.7b00449

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] 着生阻害活性を有する天然有機化合物の全合成2016

    • Author(s)
      梅澤大樹,西川慶祐,沖野龍文,松田冬彦
    • Journal Title

      有機合成化学協会誌

      Volume: 74 Pages: 689-699

    • NAID

      130005253391

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Presentation] エポキシド開環反応における隣接基効果の検討2018

    • Author(s)
      玉川竜太郎、梅澤大樹、松田冬彦
    • Organizer
      北海道支部2018年夏季研究発表会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Danicalipin A 誘導体の合成研究2017

    • Author(s)
      秋山拓哉、前田武志、梅澤大樹、松田冬彦
    • Organizer
      北海道支部2017年夏季研究発表会
    • Related Report
      2017 Research-status Report
  • [Presentation] Danicalipin A 誘導体の合成研究2017

    • Author(s)
      秋山拓哉、前田武志、梅澤大樹、松田冬彦
    • Organizer
      第59回天然有機化合物討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] Mytilipin Cの合成研究2016

    • Author(s)
      小倉陽佑,梅澤大樹,松田冬彦
    • Organizer
      北海道支部2016年夏季研究発表会
    • Place of Presentation
      室蘭工業大学(室蘭市)
    • Related Report
      2016 Research-status Report
  • [Presentation] Mytilipin Cの全合成研究2016

    • Author(s)
      小倉陽佑,佐藤匠,梅澤大樹,松田冬彦
    • Organizer
      第28回万有札幌シンポジウム
    • Place of Presentation
      北海道大学(札幌市)
    • Related Report
      2016 Research-status Report

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Published: 2016-04-21   Modified: 2020-03-30  

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