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Isolation, structure, and glucose uptake activity of compounds produced by marine organisms.

Research Project

Project/Area Number 18K05337
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 37020:Chemistry and chemical methodology of biomolecules-related
Research InstitutionUniversity of the Ryukyus

Principal Investigator

Teruya Toshiaki  琉球大学, 教育学部, 教授 (90375428)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2020: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2019: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2018: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords海洋ラン藻 / 筋管細胞 / mabuniamide / komesuamide / odopenicillatamide / 海洋シアノバクテリア / L6筋管細胞 / リポペプチド / AMP活性化プロテインキナーゼ / L6筋芽細胞 / グルコーストランスポータータイプ4
Outline of Final Research Achievements

Mabuniamide was isolated from an Okeania sp. marine cyanobacterium collected in Okinawa. The gross structure of mabuniamide was determined by spectroscopic analyses, and its absolute configuration was determined using Marfey’s analysis of the acid hydrolysate of mabuniamide. The absolute configuration of mabuniamide was confirmed by total synthesis. Mabuniamide stimulated glucose uptake in cultured rat L6 myotubes. In addition, mabuniamide and its stereoisomer exhibited moderate antimalarial activity. The linear lipopeptides komesuamide and odopenicillatamide were isolated from Caldora penicillata a marine cyanobacterium collected in Okinawa. The structures of these compounds were established by spectroscopic analyses, and the absolute configurations were determined by HPLC analyses of the acid hydrolysates. Both compounds showed glucose uptake activity in cultured L6 myotubes.

Academic Significance and Societal Importance of the Research Achievements

糖尿病治療薬の代表的なものとしては、スルフォニル尿酸薬やα‐グルコシダーゼ阻害剤などがあるが、低血糖や腹部膨満感などの副作用が問題となっており、新しいタイプの血糖値を調節する化合物が求められている。このような背景から、琉球列島沿岸で採集した海洋生物に含まれる血糖値を調節する化合物を探索したところ、筋管細胞への糖取り込みを促進する化合物を3種類得ることが出来た。この成果は糖尿病に関する学術的基礎研究に有用な新知見が得られるだけでなく、糖尿病予防、治療薬標的となりえる分子に関する情報が得られ、新たな糖尿病予防、治療薬の探索手段を提供すると考えられる。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (26 results)

All 2021 2020 2019 2018

All Journal Article (14 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 14 results) Presentation (12 results)

  • [Journal Article] Komesuamide and odopenicillatamide, two linear lipopeptides from the marine cyanobacterium Caldora penicillata2021

    • Author(s)
      Kaori Ozaki, Atsuhide Jinno, Noriyuki Natsume, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya
    • Journal Title

      Tetrahedron

      Volume: 85 Pages: 131969-131969

    • DOI

      10.1016/j.tet.2021.131969

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Irijimasides A-E, Macrolide Glycosides from an Okeania sp. Marine Cyanobacterium2020

    • Author(s)
      Aki Yamano, Noriyuki Natsume, Miki Yamada, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya
    • Journal Title

      Journal of Natural Products

      Volume: 83 Issue: 5 Pages: 1585-1591

    • DOI

      10.1021/acs.jnatprod.0c00042

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Schumannione, a new butenolide derivative isolated from Schumannianthus dichotomus as a potential phytotoxic agent2020

    • Author(s)
      Md Mahfuzur Rob, Kaori Ozaki, Toshiaki Teruya, Hisashi Kato-Noguchi
    • Journal Title

      Tetrahedron Letters

      Volume: 61 Issue: 30 Pages: 152168-152168

    • DOI

      10.1016/j.tetlet.2020.152168

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structure-Activity Relationship Study of Majusculamides A and B and Their Analogues on Osteogenic Activity2020

    • Author(s)
      Noriyuki Natsume, Kaori Ozaki, Daisuke Nakajima, Satoshi Yokoshima, Toshiaki Teruya
    • Journal Title

      Journal of Natural Products

      Volume: 83 Issue: 8 Pages: 2477-2482

    • DOI

      10.1021/acs.jnatprod.0c00441

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Potential use of Schumannianthus dichotomus waste: the phytotoxic activity of the waste and its identified compounds2020

    • Author(s)
      Md Mahfuzur Rob, Arihiro Iwasaki, Kiyotake Suenaga, Kaori Ozaki, Toshiaki Teruya, Hisashi Kato-Noguchi
    • Journal Title

      Journal of Environmental Science and Health, Part B

      Volume: 55 Issue: 12 Pages: 1099-1105

    • DOI

      10.1080/03601234.2020.1822716

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effect of methoxyflavones contained in Kaempferia parviflora on CRE-mediated transcription in PC12D cells2020

    • Author(s)
      Noriyuki Natsume, Aki Yamano, Akio Watanabe, Takayuki Yonezawa, Je-Tae Woo, Tohru Yamakuni, Toshiaki Teruya
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters

      Volume: 30 Issue: 23 Pages: 127606-127606

    • DOI

      10.1016/j.bmcl.2020.127606

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Tree Fern Cyathea lepifera May Survive by Its Phytotoxic Property2020

    • Author(s)
      Ida Noriyuki, Iwasaki Arihiro, Teruya Toshiaki, Suenaga Kiyotake, Kato-Noguchi Hisashi
    • Journal Title

      Plants

      Volume: 9 Issue: 1 Pages: 46-46

    • DOI

      10.3390/plants9010046

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Majusculamides A and B2019

    • Author(s)
      Nakajima Daisuke, Sueyoshi Kosuke, Orihara Kensuke, Teruya Toshiaki, Yokoshima Satoshi
    • Journal Title

      Synlett

      Volume: 30 Issue: 08 Pages: 924-927

    • DOI

      10.1055/s-0037-1611805

    • NAID

      120006848994

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Kyanamide, a new Ahp-containing depsipeptide from marine cyanobacterium Caldora penicillata2019

    • Author(s)
      Ozaki Kaori, Iwasaki Arihiro, Suenaga Kiyotake, Teruya Toshiaki
    • Journal Title

      Tetrahedron

      Volume: 75 Issue: 25 Pages: 3382-3386

    • DOI

      10.1016/j.tet.2019.04.046

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Isolation and Total Synthesis of Mabuniamide, a Lipopeptide from an Okeania sp. Marine Cyanobacterium2019

    • Author(s)
      Ozaki Kaori, Iwasaki Arihiro,Sezawa Dai, Fujimura Haruka, Nozaki Tomoyoshi, Saito-Nakano Yumiko, Suenaga Kiyotake, Teruya Toshiaki
    • Journal Title

      Journal of Natural Products

      Volume: 82 Issue: 10 Pages: 2907-2915

    • DOI

      10.1021/acs.jnatprod.9b00749

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Minnamide A, a Linear Lipopeptide from the Marine Cyanobacterium Okeania hirsuta2019

    • Author(s)
      Sumimoto Shimpei、Kobayashi Masayuki、Sato Rio、Shinomiya Seiichi、Iwasaki Arihiro、Suda Shoichiro、Teruya Toshiaki、Inuzuka Toshiyasu、Ohno Osamu、Suenaga Kiyotake
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 4 Pages: 1187-1190

    • DOI

      10.1021/acs.orglett.9b00135

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Ypaoamides B and C, Linear Lipopeptides from an Okeania sp. Marine Cyanobacterium2018

    • Author(s)
      Sueyoshi Kosuke、Yamada Miki、Yamano Aki、Ozaki Kaori、Sumimoto Shimpei、Iwasaki Arihiro、Suenaga Kiyotake、Teruya Toshiaki
    • Journal Title

      Journal of Natural Products

      Volume: 81 Issue: 4 Pages: 1103-1107

    • DOI

      10.1021/acs.jnatprod.8b00088

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Isolation of Jahanene and Jahanane, and Total Synthesis of the Jahanyne Family2018

    • Author(s)
      Iwasaki Arihiro、Fujimura Haruka、Okamoto Shinichiro、Kudo Takafumi、Hoshina Shizuka、Sumimoto Shimpei、Teruya Toshiaki、Suenaga Kiyotake
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Issue: 17 Pages: 9592-9603

    • DOI

      10.1021/acs.joc.8b00310

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Epimagnolin A, a tetrahydrofurofuranoid lignan from Magnolia fargesii, reverses ABCB1-mediated drug resistance2018

    • Author(s)
      Mitani Yuji、Satake Kazuhiro、Tsukamoto Megumi、Nakamura Ichiro、Kadioglu Onat、Teruya Toshiaki、Yonezawa Takayuki、Cha Byung-Yoon、Efferth Thomas、Woo Je-Tae、Nakagawa Hiroshi
    • Journal Title

      Phytomedicine

      Volume: 51 Pages: 112-119

    • DOI

      10.1016/j.phymed.2018.06.030

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] 沖縄産海洋シアノバクテリアに含まれる脂肪細胞分化促進物質の探索2021

    • Author(s)
      安里 優佳、山野 亜紀、照屋 俊明
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 沖縄県産海洋シアノバクテリア由来の鎖状ペプチド komesuamide の単離、構造決定と生物活性2021

    • Author(s)
      神野 敦秀、尾崎 香織、夏目 矩行、岩崎 有紘、末永 聖武、照屋 俊明
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 熊野市特産柑橘『新姫』果皮抽出エキスの抗肥満効果2021

    • Author(s)
      渡辺 章夫、米澤 貴之、深尾 弦貴、渡邉 晴奈、中村 太郎、山野 亜紀、照屋 俊明、禹 済泰
    • Organizer
      日本農芸化学会2021年度大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 月桃由来DK及びDDK高純度原料の製造法とその生物活性2021

    • Author(s)
      山野 亜紀、戸井田 佳子、中村 太郎、夏目 敬行、渡辺 章夫、米澤 貴之、照屋 俊明、禹 済泰
    • Organizer
      日本農芸化学会2021年度大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 微生物代謝産物からのマラリア原虫増殖阻害活性物質の探索2021

    • Author(s)
      渡邊 善洋、蜂谷 広大、池田 朱里、穗苅 玲、石山 亜紀、野口 千夏子、村松 玲子、戸澤 美帆、肥後 茉由佳、野中 健一、照屋 俊明、石井 貴広、廣瀬 友靖、砂塚 敏明、岩月 正人
    • Organizer
      日本農芸化学会2021年度大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 沖縄産海洋生物由来の骨代謝調節物質の探索2020

    • Author(s)
      尾崎 香織、夏目 矩行、山野 亜紀、中嶋 大輔、澄本 慎平、岩崎 有紘、末永 聖武、横島 聡、照屋 俊明
    • Organizer
      第62回 天然有機化合物討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ネクローシス様の細胞死を誘導するminnamide Aの絶対立体配置の決定と生物活性2020

    • Author(s)
      澄本 慎平、小林 正幸、佐藤 理央、四宮 誠一、岩崎 有紘、須田 彰一郎、照屋 俊明、犬塚 俊康、大野 修、岡田 正弘、末永 聖武
    • Organizer
      第62回 天然有機化合物討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 沖縄産海洋シアノバクテリア由来新規鎖状ペプチドの単離、構 造決定および糖取り込み活性の評価2020

    • Author(s)
      尾崎香織、澄本慎平、岩﨑有紘、末永聖武、照屋俊明
    • Organizer
      日本化学会 第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 海洋シアノバクテリア由来リポペプチド Jahanyne 類のアポ トーシス誘導活性の作用機序解明研究2020

    • Author(s)
      保科静香、岩﨑有紘、工藤隆文、田代悦、照屋俊明、井本正哉、末永聖武
    • Organizer
      日本化学会 第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 海洋リポペプチドJahanyne類の結合タンパク質の探索及び同定2019

    • Author(s)
      保科静香、岩﨑有紘、工藤隆文、照屋俊明、末永 聖武
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 海洋産リポペプチドMinnamide AにおけるC-9位メチル基の合成的手法による絶対立体配置の決定2019

    • Author(s)
      小林正幸、佐藤理央、澄本慎平、四宮誠一、照屋俊明、岩﨑有紘、末永聖武
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 沖縄県産海洋シアノバクテリアにおける新規生理活性物質の探索2019

    • Author(s)
      尾崎香織、瀬澤大、藤村 遥、岩﨑有紘、末永 聖武、照屋俊明
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2022-01-27  

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