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The functional analyses of new macrolides isolated from marine cyanobacteria

Research Project

Project/Area Number 25750386
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Biomolecular chemistry
Research InstitutionKeio University

Principal Investigator

OHNO Osamu  慶應義塾大学, 理工学部, 助教 (20436992)

Research Collaborator SUENAGA Kiyotake  
Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsbiselyngbyaside / biselyngbyolide / kurahyne / シアノバクテリア / アポトーシス / 小胞体ストレス / カルシウム / biselyngbyaside類 / biselyngbyolide類 / SERCA / biselyngbyolide B / アフィニティー精製 / tomuruline / 血清飢餓
Outline of Final Research Achievements

New biselyngbyaside analogs, biselyngbyolides B and C and biselyngbyasides E and F, were isolated from the marine cyanobacterium Lyngbya sp. Their structures were determined by spectroscopic analyses. These compounds inhibited the growth of human cancer cells, and biselyngbyolides B and C showed stronger activity than other analogs. Based on the detailed analyses of their biological activities, biselyngbyolides B and C were revealed to show potent endoplasmic reticulum (ER) stress-inducing activity. A new lipopeptide, kurahyne, was isolated from a cyanobacterial assemblage of Lyngbya sp. Kurahyne also exhibited ER stress-inducing activity. By the analyses using fluorescent and biotin conjugates of kurahyne, it was likely that kurahyne localized in ER and bound to ER Ca2+ pump.

Report

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

    (36 results)

All 2015 2014 2013

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Open Access: 4 results,  Acknowledgement Compliant: 2 results) Presentation (30 results) (of which Invited: 4 results)

  • [Journal Article] Jahanyne, an apoptosis-inducing lipopeptide from the marine cyanobacterium Lyngbya sp.2015

    • Author(s)
      Arihiro Iwasaki, Osamu Ohno, Shinpei Sumimoto, Hidetoshi Ogawa, Kim Anh Nguyen, and Kiyotake Suenaga
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 3 Pages: 652-655

    • DOI

      10.1021/ol5036722

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Kurahamide, a Cyclic Depsipeptide Analog of Dolastatin 13 from a Marine Cyanobacterial Assemblage of Lyngbya sp.2014

    • Author(s)
      Arihiro Iwasaki, Shinpei Sumimoto, Osamu Ohno, Shoichiro Suda, Kiyotake Suenaga:
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 87 Issue: 5 Pages: 609-613

    • DOI

      10.1246/bcsj.20140008

    • NAID

      130004153298

    • Related Report
      2014 Annual Research Report 2013 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Maedamide, a novel chymotrypsin inhibitor from a marine cyanobacterial assemblage of Lyngbya sp.2014

    • Author(s)
      Arihiro Iwasaki, Osamu Ohno, Shinpei Sumimoto, Shoichiro Suda, and Kiyotake Suenaga
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 30 Pages: 4126-4128

    • DOI

      10.1016/j.tetlet.2014.05.099

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Mebamamides A and B, Cyclic Lipopeptides Isolated from the Green Alga Derbesia marina2014

    • Author(s)
      Arihiro Iwasaki, Osamu Ohno, Shinpei Sumimoto, Teruhiko Matsubara, Satoshi Shimada, Sato Toshinori, Kiyotake Suenaga
    • Journal Title

      Journal of Natural Products

      Volume: -

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Biselyngbyolide B, a Novel ER Stress-inducer Isolated from the Marine Cyanobacterium Lyngbya sp.2014

    • Author(s)
      Osamu Ohno, Ayane Watanabe, Maho Morita, and Kiyotake Suenaga
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 3 Pages: 287-289

    • DOI

      10.1246/cl.130960

    • NAID

      130004868007

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Kurahyne, an acetylene-containing lipopeptide from a marine cyanobacterial assemblage of Lyngbya sp.2014

    • Author(s)
      Arihiro Iwasaki, Osamu Ohno, Shinpei Sumimoto, Shoichiro Suda, Kiyotake Suenaga
    • Journal Title

      RSC Advances

      Volume: 4 Issue: 25 Pages: 12840-12843

    • DOI

      10.1039/c4ra00132j

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 海洋生物からの新物質探索研究―構造解明と機能解明の2種類の謎解きへの取り組み―2015

    • Author(s)
      大野修
    • Organizer
      第一回 工学院大学生命化学科シンポジウム
    • Place of Presentation
      工学院大学八王子キャンパス(東京都・八王子市)
    • Year and Date
      2015-04-25
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 海洋微細藻類由来新規リポペプチドの構造および生物活性2015

    • Author(s)
      岩﨑有紘、大野修、澄本慎平、末永聖武
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス/薬学部(千葉県・船橋市)
    • Year and Date
      2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Isolation and functional analysis of a novel thiazole containing polyketide with selective cytotoxicity under nutrient starvation conditions.2015

    • Author(s)
      Osamu Ohno
    • Organizer
      日本化学会第95春季年会アジア国際シンポジウム
    • Place of Presentation
      日本大学理工学部船橋キャンパス/薬学部(千葉県・船橋市)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 新規チアゾール含有ポリケチドtomurulineの合成研究2015

    • Author(s)
      工藤千尋、大野修、佐名恭平、末永聖武
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス/薬学部(千葉県・船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] 特異な脂肪酸鎖をもつ海産シアノバクテリア由来新規鎖状リポペプチドの単離と構造決定2015

    • Author(s)
      澄本慎平、岩﨑有紘、大野修、犬塚俊康、照屋俊明、末永聖武
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス/薬学部(千葉県・船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] t-Bu 基を有する海洋シアノバクテリア由来新規環状リポペプチドの単離と構造決定2015

    • Author(s)
      小川英俊、岩﨑有紘、澄本慎平、大野修、末永聖武
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス/薬学部(千葉県・船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] 鎖状デプシペプチドMaedamideの単離、構造決定および合成研究2015

    • Author(s)
      高柳綾乃、岩﨑有紘、大野修、末永聖武
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス/薬学部(千葉県・船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] 海洋シアノバクテリア由来の新規biselyngbyaside類縁体の構造と生物活性2015

    • Author(s)
      渡邊絢音、大野修、森田真布、末永聖武
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス/薬学部(千葉県・船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] X-線結晶構造解析が明かすビセリングビアサイド類のCa2+ポンプ阻害機構2015

    • Author(s)
      森田真布、小川治夫、杖田淳子、大野修、矢守隆夫、豊島近、末永聖武
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス/薬学部(千葉県・船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] bisebromoamideのビオチン導入プローブの合成と標的生体分子の解析2015

    • Author(s)
      藤倉俊介、大野修、末永聖武
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス/薬学部(千葉県・船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] 海洋シアノバクテリア由来のマクロリドBiselyngbyaside 類の単離と生物活性2014

    • Author(s)
      森田真布、大野修、渡邊絢音、杖田淳子、小川治夫、矢守隆夫、豊島近、末永聖武
    • Organizer
      第56回天然物有機化合物討論会
    • Place of Presentation
      高知県立県民文化ホール(高知県・高知市)
    • Year and Date
      2014-10-17
    • Related Report
      2014 Annual Research Report
  • [Presentation] Kurahyne, a novel ER Stress-inducer Isolated from Marine Cyanobacterial Assemblages of Lyngbya sp.2014

    • Author(s)
      Arihiro Iwasaki, Osamu Ohno, Kiyotake Suenaga
    • Organizer
      2nd National Tsing Hua University / Keio University Bilateral Symposium of Advanced Chemistry
    • Place of Presentation
      Yokohama (Japan)
    • Year and Date
      2014-07-10
    • Related Report
      2014 Annual Research Report
  • [Presentation] 海洋シアノバクテリア由来新規小胞体ストレス誘導剤kurahyneの単離と機能解析2014

    • Author(s)
      大野修、岩崎有紘、旦慎吾、矢守隆夫、末永聖武
    • Organizer
      第18回日本がん分子標的治療学会学術集会
    • Place of Presentation
      仙台市情報・産業プラザ(AER)(宮城県・仙台市)
    • Year and Date
      2014-06-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] 海洋シアノバクテリア由来新規小胞体ストレス誘導剤 kurahyne の単離と機能解析2014

    • Author(s)
      岩崎有紘、大野修、旦慎吾、矢守隆夫、末永聖武
    • Organizer
      日本ケミカルバイオロジー学会第9回年会
    • Place of Presentation
      大阪大学豊中キャンパス(大阪府・豊中市)
    • Year and Date
      2014-06-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] 新規チアゾール含有ポリケチドtomurulineの合成研究2014

    • Author(s)
      工藤千尋、大野修、佐名恭平、末永聖武
    • Organizer
      平成26年度新規素材探索研究会
    • Place of Presentation
      新横浜フジビューホテル(神奈川県・横浜市)
    • Year and Date
      2014-06-06
    • Related Report
      2014 Annual Research Report
  • [Presentation] 海洋シアノバクテリア由来新規小胞体ストレス誘導剤 kurahyne の単離と機能解析2014

    • Author(s)
      岩崎有紘、大野修、旦慎吾、矢守隆夫、末永聖武
    • Organizer
      平成26年度新規素材探索研究会
    • Place of Presentation
      新横浜フジビューホテル(神奈川県・横浜市)
    • Year and Date
      2014-06-06
    • Related Report
      2014 Annual Research Report
  • [Presentation] Bisebromoamideビオチン導入プローブの合成とその標的生体分子の探索研究2014

    • Author(s)
      藤倉俊介、大野修、末永聖武
    • Organizer
      平成26年度新規素材探索研究会
    • Place of Presentation
      新横浜フジビューホテル(神奈川県・横浜市)
    • Year and Date
      2014-06-06
    • Related Report
      2014 Annual Research Report
  • [Presentation] 海洋シアノバクテリア由来新規チアゾール含有ポリケチドtomurulineの単離と機能解析2014

    • Author(s)
      大野修、佐名恭平、工藤千尋、照屋俊明、清水史郎、末永聖武
    • Organizer
      化学療法基盤支援活動第3回シンポジウム
    • Place of Presentation
      万国津梁館(沖縄県・名護市)
    • Year and Date
      2014-05-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] 海洋シアノバクテリア由来新規小胞体ストレス誘導剤 kurahyne の単離と機能解析2014

    • Author(s)
      岩崎有紘、大野修、旦慎吾、矢守隆夫、末永聖武
    • Organizer
      化学療法基盤支援活動第3回シンポジウム
    • Place of Presentation
      万国津梁館(沖縄県・名護市)
    • Year and Date
      2014-05-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] 海洋シアノバクテリア由来細胞応答制御物質の探索研究2014

    • Author(s)
      大野修
    • Organizer
      第2回慶應有機化学若手シンポジウム
    • Place of Presentation
      慶應義塾大学矢上キャンパス(神奈川県・横浜市)
    • Year and Date
      2014-05-10
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Tomurulineの合成研究2014

    • Author(s)
      工藤千尋、佐名恭平、大野修、末永聖武
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] 海洋シアノバクテリアが形成するバイオマット由来の新規生物活性物質の単離と構造2014

    • Author(s)
      岩崎有紘、大野修、澄本慎平、須田彰一郎、末永聖武
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] 海洋産マクロリド,ビセリングビアサイド類の作用機構解析2013

    • Author(s)
      大野修、森田真布、渡邊絢音、照屋俊明、矢守隆夫、末永聖武
    • Organizer
      第27回海洋生物活性談話会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] 海洋産マクロリドbiselyngbyaside類の構造と生物活性2013

    • Author(s)
      末永聖武、森田真布、渡邊絢音、大野修、照屋俊明
    • Organizer
      第15回マリンバイオテクノロジー学会大会
    • Place of Presentation
      那覇
    • Related Report
      2013 Research-status Report
  • [Presentation] 海洋シアノバクテリア由来のマクロリド biselyngbyolide B の構造と生物活性2013

    • Author(s)
      渡邊絢音、大野修、森田真布、末永聖武
    • Organizer
      平成25年度新規素材探索研究会
    • Place of Presentation
      横浜
    • Related Report
      2013 Research-status Report
  • [Presentation] 海洋産マクロリドBiselyngbyaside類の構造とアポトーシス誘導機構2013

    • Author(s)
      森田真布、大野修、矢守隆夫、末永聖武
    • Organizer
      平成25年度新規素材探索研究会
    • Place of Presentation
      横浜
    • Related Report
      2013 Research-status Report
  • [Presentation] 海洋産マクロリドbiselyngbyaside類によるアポトーシス誘導機構の解析2013

    • Author(s)
      大野修、森田真布、矢守隆夫、末永聖武
    • Organizer
      第17回日本がん分子標的治療学会学術集会
    • Place of Presentation
      京都
    • Related Report
      2013 Research-status Report
  • [Presentation] Isolation and Structures of Bioactive Substances from Marine Cyanobacteria2013

    • Author(s)
      Arihiro Iwasaki, Osamu Ohno, Toshiaki Teruya, Kiyotake Suenaga
    • Organizer
      The first Mini‐Symposiumfor Junior Chemists between Keio University and National Tsing Hua University
    • Place of Presentation
      Hsinchu, Taiwan
    • Related Report
      2013 Research-status Report
  • [Presentation] Biselyngbyasides, Novel Macrolides from the Marine Cyanobacterium, Induce Endoplasmic Reticulum Stress and Apoptosis2013

    • Author(s)
      Maho Morita, Osamu Ohno, Ayane Watanabe, Yuki Niwa, Siro Simizu, Kiyotake Suenaga
    • Organizer
      2013 ISACS11
    • Place of Presentation
      Boston
    • Related Report
      2013 Research-status Report
  • [Presentation] 海洋生物由来新規二次代謝産物の探索と機能解析2013

    • Author(s)
      大野修
    • Organizer
      第37回星薬科大学大学院研究科助手会・大学院自治会合同公開セミナー
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
    • Invited

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Published: 2014-07-25   Modified: 2019-07-29  

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