Updated on 2025/06/26

写真a

 
KUBOTA Takaaki
 
Organization
Faculty of Medicine, Dentistry and Pharmaceutical Sciences Professor
Position
Professor
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Degree

  • 2002, Ph. D. (Pharmaceutical Sciences), Hokkaido University ( 2002.3   Hokkaido University )

Research Interests

  • 立体化学

  • アルカロイド

  • 海洋由来真菌

  • アクチン

  • チューブリン

  • 分子標的

  • リード化合物

  • Natural Products Chemistry

  • 天然物有機化学

  • がん分子標的

  • がん治療

  • バイオプローブ

  • 殺細胞活性

  • 医薬リード

  • 海洋天然物

  • イエジマリド

  • 天然薬物

  • 天然物ライブラリー

  • 機能性天然分子

  • 海洋生物

  • ポリケチド合成酵素

  • 生物・生体工学

  • 天然資源

Research Areas

  • Life Science / Bioorganic chemistry

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

  • Nanotechnology/Materials / Chemistry and chemical methodology of biomolecules

  • Life Science / Pharmaceutical chemistry and drug development sciences

Education

  • Hokkaido University   大学院薬学研究科   博士後期課程

    1999.4 - 2002.3

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    Country： Japan

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  • Hokkaido University   大学院薬学研究科   修士課程

    1997.4 - 1999.3

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    Country： Japan

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  • Tokyo University of Science   薬学部   製薬学科

    1992.4 - 1996.3

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    Country： Japan

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Research History

  • Okayama University   Faculty of Medicine , Dentistry, and Pharmaceutical Sciences   Professor

    2021.4

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  • Okayama University   Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences   Professor

    2020.11 - 2021.3

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  • Showa Pharmaceutical University   薬学部   Professor

    2015.4 - 2020.10

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  • Hokkaido University   大学院薬学研究院   Associate Professor

    2010.4 - 2015.3

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  • Hokkaido University   大学院先端生命科学研究院   Associate Professor

    2009.2 - 2010.3

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  • Hokkaido University   大学院薬学研究院   Associate Professor

    2008.9 - 2009.1

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  • Hokkaido University   大学院薬学研究院   Lecturer

    2006.4 - 2008.8

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  • Hokkaido University   大学院薬学研究科   Lecturer

    2005.4 - 2006.3

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  • Hokkaido University   大学院薬学研究科   Research Associate

    2005.2 - 2005.3

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  • University of Washington   Department of Chemistry   Research Associate

    2003.4 - 2005.1

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  • Japan Society for Promotion of Science   Postdoctoral Fellowships of Japan Society for the Promotion of Science

    2002.4 - 2003.3

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  • Japan Society for Promotion of Science   Postdoctoral Fellowships of Japan Society for the Promotion of Science

    2001.4 - 2002.3

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Professional Memberships

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Committee Memberships

  • 日本農芸化学会   中四国支部参与  

    2024.12   

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    Committee type：Academic society

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  • 日本薬学会   代議員  

    2023.2   

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    Committee type：Academic society

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  • 日本薬学会   中国四国支部大学選出幹事  

    2023.2   

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    Committee type：Academic society

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  • 日本薬学会   生薬天然物部会常任世話人  

    2021.4   

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  • 日本生薬学会   関西支部委員  

    2021.4   

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  • 日本薬学会   関東支部執行部  

    2020.3 - 2021.2   

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  • 日本生薬学会   財務理事  

    2018.4 - 2022.3   

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    Committee type：Academic society

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  • 日本生薬学会   学会誌編集委員会編集副委員長  

    2018   

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  • 日本生薬学会   財務理事補佐  

    2017   

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  • 日本生薬学会   学会誌編集委員会委員  

    2016 - 2017   

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    Committee type：Academic society

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  • 日本生薬学会   代議員  

    2016 - 2017   

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  • 日本生薬学会   北海道支部庶務  

    2014   

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  • 日本生薬学会   北海道支部監事  

    2012 - 2013   

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  • 日本生薬学会   北海道支部委員  

    2010 - 2011   

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  • 日本生薬学会   北海道支部監事  

    2008 - 2009   

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    Committee type：Academic society

    日本生薬学会

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  • 日本薬学会   代議員  

    2008 - 2009   

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  • 日本薬学会   北海道支部庶務幹事  

    2008   

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    日本薬学会

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  • 日本薬学会   トピックス専門小委員  

    2007 - 2008   

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    Committee type：Academic society

    日本薬学会

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  • 日本薬学会   北海道支部幹事  

    2007   

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    Committee type：Academic society

    日本薬学会

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  • 日本生薬学会   北海道支部庶務  

    2006 - 2007   

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    日本生薬学会

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Papers

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Books

  • パートナー天然物化学（改訂第4版増補）

    森田, 博史, 阿部, 郁朗（ Role： Contributor）

    南江堂  2023.12  （ ISBN:9784524404513 ）

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    Total pages：xvi, 315p   Language：Japanese

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  • パートナー天然物化学（改訂第4版）

    森田, 博史, 阿部, 郁朗（ Role： Contributor）

    南江堂  2021.8  （ ISBN:9784524403776 ）

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    Total pages：xvi, 315p   Language：Japanese

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  • パートナー天然物化学（改訂第3版）

    海老塚, 豊, 森田, 博史, 阿部, 郁朗（ Role： Contributor）

    南江堂  2016.9  （ ISBN:9784524403325 ）

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    Total pages：xv, 299p   Language：Japanese

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  • パートナー天然物化学（改訂第2版）

    海老塚, 豊, 森田, 博史（ Role： Contributor）

    南江堂  2012.1  （ ISBN:9784524402793 ）

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    Total pages：xvi, 299p   Language：Japanese

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  • Comprehensive Natural Products II: Chemistry and Biology

    Elsevier Science  2010 

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  • パートナー天然物化学

    海老塚, 豊, 森田, 博史（ Role： Contributor）

    南江堂  2007.4  （ ISBN:9784524402250 ）

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    Total pages：xv, 330p   Language：Japanese

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  • Cooperation of Bio and Nano Sciences, II. Application to New Life Sciences

    Hokkaido University Publisher  2007 

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MISC

  • 沖縄産Amphimedon属海綿から単離した新規マンザミン関連アルカロイドZamamiphidin BおよびCの構造

    栗本慎一郎, 鈴木祥一, 上野真由美, 小林淳一, 久保田高明

    第６５回天然有機化合物討論会   2023.9

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  • 五環性トリテルペンursolic acidの抗歯周病原細菌活性および細胞毒性の評価

    佐藤 祐太郎, 石原 和幸, 久保田 高明

    Journal of Oral Biosciences Supplement   2023   [O3 - 03]   2023.9

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    Language：Japanese   Publisher：(一社)歯科基礎医学会  

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  • Search for inhibitors of advanced glycation end products formation from brown algae, Sargassum macrocarpum and Ecklonia stolonifera

    Seiya Shinoda, Arisa Uno, Tomoya Masaki, Tetsuya Sasaki, Haruaki Ishiyama, Shin-ichiro Kurimoto, Takaaki Kubota, Mitsuhiro Sekiguch

    22nd IUNS-ICN International Congress of Nutrition in Tokyo, Japan   2022.12

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  • ビルベリー由来抗歯周病原細菌活性物質の精製と同定(Purification and identification of an anti-periodontal pathogenic-bacterial active substance derived from bilberry)

    佐藤 祐太郎, 石原 和幸, 久保田 高明

    Journal of Oral Biosciences Supplement   2022   115 - 115   2022.9

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    Language：Japanese   Publisher：(一社)歯科基礎医学会  

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  • New bromotyrosine alkaloids from an Okinawan marine sponge Suberea sp.

    栗本慎一郎, 栗本慎一郎, 岡本彩乃, 清野皐月, 小林淳一, 久保田高明, 久保田高明

    日本薬学会年会要旨集(Web)   142nd   2022

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  • Structure and bioactivity of new meroterpenoid from Sargassum macrocarpum

    篠田清哉, 栗本慎一郎, 久保田高明, 関口光広

    食品薬学シンポジウム講演要旨集   9th (CD-ROM)   2022

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  • 能登産海藻Sargassum macrocarpumより単離した新規メロテルペノイド化合物の構造とAGEs生成阻害活性評価

    篠田清哉, 丹羽裕美, 栗本慎一郎, 久保田高明, 関口光広, 関口光広

    日本生薬学会年会講演要旨集   67th   2021

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  • Structure and bioactivity of polyhydroxy sterols from an Okinawan marine sponge Dysidea sp.

    栗本慎一郎, 石塚芽衣菜, 武田郁恵, 矢口貴志, 小林淳一, 久保田高明, 久保田高明

    日本薬学会年会要旨集(Web)   141st   2021

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  • Sesquiterpenoid quinone from an Okinawan marine sponge of the family Spongiidae

    猪俣実加, 小川実華, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   140th (Web)   2020

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  • New diterpene alkaloid from an Okinawan marine sponge Agelas sp.

    近藤和幸, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   140th (Web)   2020

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  • New manzamine-related alkaloid from an Okinawan marine sponge Amphimedon sp.

    栗本慎一郎, 鈴木祥一, 上野真由美, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   140th (Web)   2020

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  • New steroid from an Okinawan marine sponge Halichondria sp.

    森光希, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   140th (Web)   2020

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  • Preparation of sesquiterpenoid quinone derivatives for structure activity relationship study

    島田祐莉奈, 小川実華, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   140th (Web)   2020

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  • Search for anti-glycation agents from “Abokyu“, a cultivar of edible Chrysanthemum

    水野実穂, 栗本慎一郎, 中村隆典, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   140th   2020

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  • Ceratinadins and Ma’edamines, New Bromotyrosine Alkaloids from Okinawa Verongid Sponges

    久保田高明, 栗本慎一郎, 大野泰斗, 清野皐月, 穗苅玲, 石山亜紀, 岩月正人, 大村智, 小林淳一

    天然有機化合物討論会講演要旨集(Web)   62nd   2020

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  • 渦鞭毛藻Symbiodinium sp.から単離した新規マクロリドの構造

    石田理紗, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   139th   2019

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  • 沖縄産Suberea属海綿から単離した新規ブロモチロシンアルカロイドの構造

    清野皐月, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   139th   2019

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  • 沖縄産Stylissa属海綿から単離した新規環状ペプチドの構造

    大山英将, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   139th   2019

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  • 渦鞭毛藻Amphidinium sp.から単離した新規ポリケチドの構造

    坂根美和子, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   139th   2019

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  • 沖縄産Plakortis属海綿から単離した新規ポリケチドの構造

    木村悠登, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   139th   2019

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  • 沖縄産Hyrtios属海綿から単離した新規β-カルボリンアルカロイドの構造

    高橋秀彰, 栗本慎一郎, 小林淳一, 久保田高明

    天然薬物の開発と応用シンポジウム講演要旨集   22nd   2018

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  • 沖縄産Hyrtios属海綿から単離した新規Canthin-6-oneアルカロイドの構造

    高橋秀彰, 栗本慎一郎, 小林淳一, 久保田高明

    日本生薬学会年会講演要旨集   65th   2018

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  • 沖縄産Dysidea属海綿から単離した新規ポリヒドロキシステロールの構造

    武田郁恵, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   138th   2018

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  • 沖縄産Hyrtios属海綿から単離した新規インドールアルカロイドの構造

    高橋秀彰, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   138th   2018

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  • 沖縄産Pseudoceratina属海綿から単離した新規ブロモチロシンアルカロイドの構造

    大野泰斗, 栗本慎一郎, 小林淳一, 久保田高明

    日本薬学会年会要旨集(CD-ROM)   138th   2018

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  • Zamamiphidin A and Zamamidine D, New Manzamine Alkaloids from Okinawan Marine Sponge Amphimedon sp.

    久保田高明, 栗本慎一郎, 上條優樹, 中村健太, 酒井香奈江, 高橋梓, 穗苅玲, 石山亜紀, 岩月正人, 乙黒一彦, 五ノ井透, 大村智, 小林淳一

    天然有機化合物討論会講演要旨集(Web)   59th   2017

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  • 沖縄産Hyrtios属海綿由来新規アゼピノインドールアルカロイドhyrtinadine CおよびDの構造

    栗本慎一郎, 中村健太, 酒井香奈江, 五ノ井透, 久保田高明, 小林淳一

    日本薬学会年会要旨集(CD-ROM)   137th   2017

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  • New polyketides from dinoflagellate Amphidinium sp.

    T. Kubota, T. Iwai, H. Sato, J. Kobayashi

    PLANTA MEDICA   82   2016.12

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    Language：English   Publishing type：Research paper, summary (international conference)  

    DOI： 10.1055/s-0036-1596659

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  • 沖縄産Stylissa属海綿から単離した新規環状ペプチドの構造

    栗本慎一郎, 中村健太, 久保田高明, 小林淳一

    天然薬物の開発と応用シンポジウム講演要旨集   21st   2016

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  • 3P-272 Functional analysis of the cpaM in cyclopiazonic acid biosynthesis

    Kikuchi Tomoki, Koyama Akifumi, Iio shinichiro, Shinohara Yasutomo, Kubota Takaaki, Kobayashi Jyunichi, Koyama Yasuji, Tokuoka Masafumi, Shindo Hitoshi, Hosaka Masaru

    67   338 - 338   2015

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  • New polyketides from marine dinoflagellate Amphidinium sp.

    T. Kubota, T. Iwai, J. Kobayashi

    PLANTA MEDICA   80 ( 10 )   765 - 765   2014.7

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  • 沖縄産Agelas属海綿から単離した新規ジテルペンアルカロイドagelasine O‐Uの構造

    IWAI TAKAHIRO, KUBOTA TAKAAKI, KATAKURA KEN, KOBAYASHI JUN'ICHI

    天然薬物の開発と応用シンポジウム講演要旨集   19th   110 - 112   2012.10

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  • 沖縄産ホヤEudistoma glaucus由来の新規β‐カルボリンアルカロイドEudistomidn H‐Kの構造

    久保田高明, 鈴木哲平, 小林淳一

    日本薬学会年会要旨集   132nd ( 2 )   194   2012.3

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  • 嫌われ者の藍藻に期待!(バイオミディア)

    久保田 高明

    生物工学会誌 : seibutsu-kogaku kaishi   89 ( 10 )   617 - 617   2011.10

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    Language：Japanese   Publisher：公益社団法人日本生物工学会  

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  • 嫌われ者の藍藻に期待!

    久保田高明

    生物工学会誌   89 ( 10 )   617 - 617   2011.10

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  • 沖縄産Plakortis属海綿由来の新規ポリケタイドUntenolide Aの構造

    久保田高明, 石黒悠一朗, 城始勇, 小林淳一

    日本薬学会年会要旨集   131st ( 2 )   230   2011.3

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  • 沖縄産海綿由来新規アルカロイドnakijinamine類の構造

    高橋洋平, 久保田高明, 小林淳一

    天然有機化合物討論会講演要旨集   52nd ( 52 )   661-666 - 666   2010.9

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    Language：Japanese   Publisher：Symposium on the chemistry of natural products  

    Aaptamine (6) was a characteristeic marine natural product possessing 1H^benzo[de][1,6]-naphthyridine ring, which was isolated from the Okinawan marine sponge Aaptos aaptos. Approximately 20 related alkaloids have been isolated from several species of marine sponges so far. A lot of interstint researches have been performed since the isolation of 6 in 1982 due to its unique structures and various biological activities. During our continuous search for structurally interesting metabolites from marine sponges, a new bromoindole alkaloid, 6-bromoconicamin (1), a hybrid compound of 1 and bisdemethylaaptamne (5), nakijinamine A (2), and its derivatives, nakijinamines B (3) and C (4), have been isolated from two collections of Suberites sp. (SS-1083 and SS-1084). Their structuers were elucidated from spectroscopic data and chemical conversions. 6-Bromoconicamin (1) is an indole alkaloid having bromine atom at C-6 in conicamin, which was isolated from the Mediterranean marine tunicate Aplidium conicum. Nakijinamine A (2) is the hybrid compound of 1 and bisdemethylaaptamine (5), while nakijinamines B (3) and C (4) are related alkaloids of 2. Although the elucidatio of the gross structure of 2 from its spectroscopic data was very difficult due to broadening signals in ^1H NMR spectrum of 2, the structure of 2 was able to be a ssigned from chemical conversions of 2. The structure of 3 was assigned as the debromo analog of 2 by the comparison of NMR data with 2. Although 4 had a lot of quaternary carbons and hetero atoms in its structure, its gross structure was elucidated from careful analysis of spectroscopic data and comparison of NMR data with known compounds. The confirmation of the structure of 4 and biological activities of 1-4 are in progress.

    DOI： 10.24496/tennenyuki.52.0_661

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  • アスヒカズラより単離した新規アルカロイドの構造

    石内勘一郎, 久保田高明, 林茂樹, 柴田敏郎, 小林淳一

    日本薬学会年会要旨集   130th ( 2 )   239   2010.3

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  • ナガサキオトギリより単離した新規benzophenone rhamnosideの構造

    田中直伸, 久保田高明, 柏田良樹, 高石喜久, 小林淳一

    日本薬学会年会要旨集   130th ( 2 )   233   2010.3

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  • 沖縄産海綿由来の新規ピリジニウムアルカロイドPlatisidine A〜Cの構造

    久保田高明, 石黒悠一朗, 山本淳, 小林淳一

    日本薬学会年会要旨集   130th ( 2 )   221   2010.3

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  • スギカズラ(Lycoposiumannotinum)より単離した新規アルカロイドの構造

    石内勘一郎, 児玉志保美, 久保田高明, 小林淳一, 林茂樹, 柴田敏郎

    日本生薬学会年会講演要旨集   56th   141   2009.9

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  • エゾオトギリHypericum yezoenseより単離したyezo’otogirin A‐Cの構造

    田中直伸, 格口ゆか, 石山玄明, 久保田高明, 小林淳一

    日本生薬学会年会講演要旨集   56th   256   2009.9

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  • 海綿由来の新規マンザミンアルカロイドzamamidine A〜Cの構造と生物活性

    高橋洋平, 山田美香, 久保田高明, 石山亜紀, 乙黒一彦, 山田陽城, 大村智, 小林淳一

    天然有機化合物討論会講演要旨集   51st ( 51 )   581-586 - 586   2009.9

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    Manzamine alkdloids are well known to be a group of marine natural products, which have a β-carboline moiety and a unique heterocyclic ring system. Since manzamine A had been isolated from a marine sponge Haliclona sp. in 1986, approximately 100 manzamine alkdloids containing biogenetic precursors have been idolated so far. A great number of studies on them, such as isolation and structural analysis, biosynthesis, and total synthesis, have been actively performed due to their intriguing structures and intersting biological activities. We have also isolated s seris of manzamine alkaloids from several genera and their structures have been elucidated by means of NMR spectra, chemical correlations, X-ray crystallography, and CD spectra. During our continuous search for structurally interesting metabolites from marine sponges, new manzamine alkdloids, zamamidines A-C (1-3), have been isolated, and their structures were elucidated by spectroscopic data. 1-3 are new manzamine alkdloids possessing a second β-carboline ring via an ethylene chain at N-2 of manzamine H, 1,2,3,4-tetrahydromanzamine B, and manzamine D, respectively. Since no manzamine alkdloids possessing any side chain at N-2 other than a methyl group have been reported to date, 1〜3 are the first examples of it. Zamamidines A-C (1-3) showed inhibitory activities against Plasmodium falciparum (Kl strain) and Tripanosoma brucei brucei (GUTat 3.1) in vitro.

    DOI： 10.24496/tennenyuki.51.0_581

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  • アスヒカズラ(Lycopodium complanatum)由来新規アルカロイドの構造

    石内勘一郎, 久保田高明, 林茂樹, 柴田敏郎, 小林淳一

    天然有機化合物討論会講演要旨集   51st ( 51 )   19-24 - 24   2009.9

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    Club moss (Lycopodiaceae) is known to be a rich source of Lycopodium alkaloids possessing unique heterocyclic ring systems such as C_<16>N, C_<16>N_2, and C_<27>N_3, which have attracted great interest from biogenetic, synthetic, and biological points of view. In our continuing efforts to find new Lycopodium alkaloids, lycopladine H (1), lyconadins C-E (2-4), lycoplaidines F-G (5-6), and complanadine E (7) were isolated from Lycopodium domplanatum. The structures for 1-7 were elucidated on the basis of spectral data. Lycopladine H (1) is an unprecedented C_<16>N-type Lycopodium alkaloid possessing a novel fused-tetracyclic ring system consisting of an azocane ring fused to a [2,2,2,]-bicyclooctane ring and 3-piperidinone ring, Lyconadin C (2) is a new tetracyclic Lycopodium alkaloid consisting of cyclohexane, cycloheptane, pyperidine, and pyridone rings. Lyconadin C (2) might be a biosynthetic precursor of lyconadin A. Lyconadins D (3) and E (4) are the first fastigiatine-type alkaloids isolated from Lycopodium complanatum. Lycopladine F (5) is a rare C_<16>N_2-type Lycopodium alkaloid possessing an amino acid residue (C_4N), while lycopladine G (6) is a 17-keto and 20-methylester form of lycopladine F (5). Complanadine E (7) is a new dimeric Lycopodium alkaloid consisting of two C_<16>N_2-type skeletons, which corresponds to 1,2,3,4,5,N-1-hexahydro complanadine A.

    DOI： 10.24496/tennenyuki.51.0_19

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  • Corrigendum to "Zamamidine C, 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A, and 3,4-dihydromanzamine J N-oxide, new manzamine alkaloids from sponge Amphimedon sp." [Tetrahedron 65 (2009) 2313-2317] (DOI:10.1016/j.tet.2009.01.032)

    Mika Yamada, Yohei Takahashi, Takaaki Kubota, Jane Fromont, Aki Ishiyama, Kazuhiko Otoguro, Haruki Yamada, Satoshi Omura, Jun'ichi Kobayashi

    Tetrahedron   65 ( 31 )   6263 - 6263   2009.8

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  • 渦鞭毛藻由来マクロリド・Amphidinolactone Aの全合成による立体化学の解明

    萩行正博, 石山玄明, 高橋洋平, 久保田高明, 小林淳一

    次世代を担う有機化学シンポジウム講演要旨集   7th   38-39   2009.5

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  • 沖縄産海綿由来の新規ブロモチロシンアルカロイドTyrokeradine AおよびBの構造

    久保田高明, 向井裕也, 小林淳一

    日本薬学会年会要旨集   129th ( 2 )   179   2009.3

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  • 渦鞭毛藻由来マクロリド・Amphidinolactone Aの全合成と立体化学の解明

    萩行正博, 石山玄明, 高橋洋平, 久保田高明, 小林淳一

    日本薬学会年会要旨集   129th ( 2 )   95   2009.3

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  • アスヒカズラより単離した新規リコポジウムアルカロイドの構造

    石内勘一郎, 久保田高明, 柴田敏郎, 小林淳一

    日本薬学会年会要旨集   129th ( 2 )   97   2009.3

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  • ビヨウヤナキより単離した新規xanthone誘導体の構造

    田中直伸, 大豆村拓自, 久保田高明, 今林潔, 柏田良樹, 高石喜久, 小林淳一

    日本薬学会年会要旨集   129th ( 2 )   172   2009.3

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  • アカネ科植物由来の新規モノテルペンインドールアルカロイド・Naucleamide Fの構造

    石山玄明, 格口ゆか, 高橋洋平, 久保田高明, 小林淳一

    日本薬学会年会要旨集   129th ( 2 )   179   2009.3

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  • 沖縄産Agelas属海綿より単離した新規ブロモピロールアルカロイドの構造

    荒木敦, 久保田高明, 三上襄, 小林淳一

    天然薬物の開発と応用シンポジウム講演要旨集   17th   79-80   2008.11

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  • 沖縄産海綿より単離したnakijiquinone/metachromin類の構造と生物活性

    高橋洋平, 久保田高明, 三上襄, 小林淳一

    天然有機化合物討論会講演要旨集   50th   59-64   2008.9

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  • 6 Nakijiquinones and Metachromins, New Sesquiterpenoid Quinones from Okinawan Marine Sponges : Isolation, Structure Elucidation, and Biological Activities(Oral Presentation)

    Takahashi Yohei, Kubota Takaaki, Mikami Yuzuru, Kobayashi Jun'ichi

    Symposium on the Chemistry of Natural Products, symposium papers   0 ( 50 )   59 - 64   2008.9

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    Sesquiterpenoid quinines and hydroquinones are representative marine natural products with unique structures and interesting biological activities. In our continuous search for bioactive compounds having unique structures from Okinawan marine sponges, we have isolated new sesquiterpenoid quinones, nakijiquinones E〜I (1〜5) and metachromins L-Q (6〜11), from three collections of Okinawan marine sponges. The structures of 1〜5 were elucidated on the basis of 2D NMR data, while those of 6〜11 were established by chemical correlations. Furthermore, biological activities for 1〜11 and synthetic metac...

    DOI： 10.24496/tennenyuki.50.0_59

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  • P-33 Nagelamides K, M, and N, Novel Bromopyrrole Alkaloids from Okinawan Marine Sponge Agelas sp(Poster Presentation)

    Araki Atsushi, Yasuda Tetsuro, Kubota Takaaki, Mikami Yuzuru, Kobayashi Jun'ichi

    Symposium on the Chemistry of Natural Products, symposium papers   0 ( 50 )   361 - 366   2008.9

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    Bromopyrrole alkaloids are known to be one of the most common metabolites contained in marine sponges. During our search for bioactive substances from marine organisms, we have isolated bromopyrrole alkaloids with unique cyclic skeletons from sponges of the genus Agelas or Hymeniacidon. Recently, three new bromopyrrole alkaloids, nagelamides K, M, and N (1-3), have been isolated from an Okinawan marine sponge Agelas sp. (SS-1134). The structures and relative stereochemistry of 1〜3 were elucidated on the basis of spectroscopic data. Nagelamide K (1) is a new dimeric bromopyrrole alkaloid pos...

    DOI： 10.24496/tennenyuki.50.0_361

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  • ナガサキオトギリ由来の新規フロログルシノール誘導体petiolin Dの構造

    田中直伸, 久保田高明, 石山玄明, 小林淳一, 柏田良樹, 高石喜久, 伊藤淳二, 三上襄, 城始勇

    日本生薬学会年会講演要旨集   55th   188   2008.9

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  • 沖縄産海綿由来の新規ブロモピロールアルカロイドの構造

    荒木敦, 安田鉄郎, 久保田高明, 三上襄, 小林淳一

    天然有機化合物討論会講演要旨集   50th ( 50 )   361-366 - 366   2008.9

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    Bromopyrrole alkaloids are known to be one of the most common metabolites contained in marine sponges. During our search for bioactive substances from marine organisms, we have isolated bromopyrrole alkaloids with unique cyclic skeletons from sponges of the genus Agelas or Hymeniacidon. Recently, three new bromopyrrole alkaloids, nagelamides K, M, and N (1-3), have been isolated from an Okinawan marine sponge Agelas sp. (SS-1134). The structures and relative stereochemistry of 1〜3 were elucidated on the basis of spectroscopic data. Nagelamide K (1) is a new dimeric bromopyrrole alkaloid possessing a rare piperidinoiminoimidazolone ring with an aminoimidazole ring and a taurine unit. Nagelamide M (2) is a novel bromopyrrole alkaloid possessing an 2-amino-octahydropyrrolo[2,3-d]imidazol ring with a taurine unit, while nagelamide N (3) is a new bromopyrrole alkaloid consisting of an 2-amino-tetrahydroimidazol-4-one ring with a taurine unit and 3-(dibromopyrrole-2-carboxamido)propanoic acid moiety. Nagelamides K, M, and N (1-3) showed modest antimicrobial activity.

    DOI： 10.24496/tennenyuki.50.0_361

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  • シマサルスベリより単離した新規Lythraceaeアルカロイドの構造

    久保田高明, 渡辺梢, 小林淳一, 新里孝和, 伊藤淳二, 三上襄

    日本生薬学会年会講演要旨集   55th   219   2008.9

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  • ナガサキオトギリより単離した新規フロログルシノール誘導体petiolin A‐Cの構造

    田中直伸, 久保田高明, 荒木敦, 柏田良樹, 高石喜久, 三上襄, 小林淳一

    日本薬学会年会要旨集   128th ( 2 )   11   2008.3

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  • 沖縄産海綿Spongia sp.由来の新規テルペノイドMetachromin R〜Tの構造

    山田美香, 高橋洋平, 久保田高明, 小林淳一

    日本薬学会年会要旨集   128th ( 2 )   11   2008.3

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  • ユズリハ科植物由来の新規アルカロイドCalyciphylline H〜Mの構造

    八幡弘子, 齊藤静夏, 久保田高明, 小原祐太郎, 中畑則道, 小林淳一

    日本薬学会年会要旨集   128th ( 2 )   12   2008.3

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  • 沖縄産海綿Amphimedon sp.由来の新規アルカロイドNakinadine Aの構造

    久保田高明, 西貴美, 佐々木琢磨, 小林淳一

    日本薬学会年会要旨集   128th ( 2 )   12   2008.3

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  • Multi Phenotypic Screeningによる生理活性物質の作用解析

    風見紗弥香, 風見紗弥香, 臼井健郎, 臼井健郎, 久保田高明, 小林淳一, 長田裕之, 長田裕之

    日本農芸化学会大会講演要旨集   2008   9   2008.3

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  • アスヒカズラより単離した新規アルカロイドの構造

    久保田高明, 八幡弘子, 石内勘一郎, 小林淳一

    日本生薬学会年会講演要旨集   54th   226   2007.9

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  • P-11 Calyciphyllines C〜G, Novel Daphniphyllum Alkaloids from Daphniphyllum calycinum

    Saito Shizuka, Kubota Takaaki, Fukushi Eri, Kawabata Jun, Zhang Huiping, Kobayashi Jun'ichi

    Symposium on the Chemistry of Natural Products, symposium papers   0 ( 49 )   271 - 276   2007.8

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    Daphniphyllum alkaloids are a structually diverse group of natural products with unique fused-heterocyclic skeletons, which are elaborated by trees of the genus Daphniphyllum (Daphniphyllaceae). These unusual ring systems have been challenging targets for total synthesis as well as biosynthetic studies. We have isolated novel types of Daphniphyllum alkaloids from Daphniphyllum macropodum, D. humile, D. teijsmanni, and D. glaucescense. In our continuing search for structually unique and biogenetically interesting new alkaloids, calyciphyllines C-G (1-5) have been isolated from D. calycinum, ...

    DOI： 10.24496/tennenyuki.49.0_271

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  • ユズリハ科植物由来の新規アルカロイドcalyciphylline C〜Gの構造と生物活性

    齊藤静夏, 久保田高明, 福士江里, 川端潤, ZHANG Huiping, 小林淳一

    天然有機化合物討論会講演要旨集   49th ( 49 )   271-276 - 276   2007.8

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    Daphniphyllum alkaloids are a structually diverse group of natural products with unique fused-heterocyclic skeletons, which are elaborated by trees of the genus Daphniphyllum (Daphniphyllaceae). These unusual ring systems have been challenging targets for total synthesis as well as biosynthetic studies. We have isolated novel types of Daphniphyllum alkaloids from Daphniphyllum macropodum, D. humile, D. teijsmanni, and D. glaucescense. In our continuing search for structually unique and biogenetically interesting new alkaloids, calyciphyllines C-G (1-5) have been isolated from D. calycinum, and their structures and relative stereochemistry were elucidated on the basis of spectroscopic data. Calyciphylline C (1) is a novel Daphniphyllum alkaloid with an unprecedented fused-hexacyclic skeleton having an azetidine ring. Calyciphyllines D (2) and F (4) are novel alkaloids containing a unique fused-pentacyclic skeleton with a 8-azatricyclo[4.2.1.0.^<4,8>]nonane ring system. Calyciphylline E (3) is a new alkaloid with a fused-heptacyclic ring system, while calyciphylline G (5) is a novel alkaloid possessing an unprecedented fused-hexacyclic skeleton containg 5-azatricyclo[6.2.1.0]undecane ring system. Effects of these alkaloids on neurotrophic factor biosynthesis in 1321N1 human astrocytoma cells were examined by a semiquantitative RT-PCR method to find that the mRNA expressions for NGF were enhanced.

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  • ケミカルバイオロジー研究のフロンティア 創薬リードとしての分子標的天然薬物の探索

    小林淳一, 久保田高明

    現代化学   ( 436 )   21-26 - 26   2007.7

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  • 創薬リードとしての分子標的天然薬物の探索

    小林 淳一, 久保田 高明

    現代化学   0 ( 436 )   21 - 26   2007.7

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  • 渦鞭毛藻由来の新規amphidinolide関連化合物の構造

    高橋洋平, 久保田高明, 小林淳一

    次世代を担う有機化学シンポジウム講演要旨集   5th   6-7   2007.5

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  • 免疫抑制物質brasilicardin Aの標的分子同定

    臼井健郎, 臼井健郎, 南雲陽子, 南雲陽子, 渡邉愛, 久保田高明, 小林淳一, 長田裕之

    日本農芸化学会大会講演要旨集   2007   98   2007.3

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  • 1 Agesamides and Nagelamides, Novel Bromopyrrole Alkaloids from Sponge Agelas spp.

    Yasuda Tetsuro, Araki Atsushi, Tsuda Masashi, Kubota Takaaki, Fukushi Eri, Kawabata Jun, Kobayashi Jun'ichi

    Symposium on the Chemistry of Natural Products, symposium papers   49 ( 0 )   1 - 6   2007

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    Diffusion-ordered NMR spectroscopy (DOSY) is a versatile and powerful NMR technique and a noninvasive analytical method for mixture analysis that does not require prior physical separation of the analysis. In our search for new metabolites from natural resources, DOSY was applied for constituent analysis of crude bromopyrrole fractions separated from an Okinawan marine sponge Agelas sp. (SS-1056) so that two new bromopyrrole alkaloids, agesamides A (1) and B (2), have been isolated. The structures and relative stereochemistry of 1 and 2 were elucidated fromspectroscopic data. Furthermore, two new bromopyrrole alkaloids, nagelamides J (3) and K (4), have been isolated from another Okinawan marine sponge Agelas sp. (SS-1077), and the structures and relative stereochemistries were elucidated from spectroscopic data. Nagelamide J (3) is the first bromopyrrole alkaloid possessing a cyclopentane ring fused to an amino imidazole ring and nagelamide K (4) is a unique dimeric bromopyrrole alkaloid containing an ester linkage. Nagelamide J (3) exhibited antimicrobial activity against Staphylococcus aureus (MIC, 8.35μg/ml) and antifungal activity against Cryptococcus neoformans (MIC, 16.7μg/ml), while nagelamide K (4) exhibited antimicrobial activity against Micrococcus luteus (MIC, 16.7μg/ml).

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  • 1 Agesamides and Nagelamides, Novel Bromopyrrole Alkaloids from Sponge Agelas spp.

    Yasuda Tetsuro, Araki Atsushi, Tsuda Masashi, Kubota Takaaki, Fukushi Eri, Kawabata Jun, Kobayashi Jun'ichi

    Symposium on the Chemistry of Natural Products, symposium papers   49 ( 0 )   1 - 6   2007

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    Diffusion-ordered NMR spectroscopy (DOSY) is a versatile and powerful NMR technique and a noninvasive analytical method for mixture analysis that does not require prior physical separation of the analysis. In our search for new metabolites from natural resources, DOSY was applied for constituent analysis of crude bromopyrrole fractions separated from an Okinawan marine sponge Agelas sp. (SS-1056) so that two new bromopyrrole alkaloids, agesamides A (1) and B (2), have been isolated. The structures and relative stereochemistry of 1 and 2 were elucidated fromspectroscopic data. Furthermore, two new bromopyrrole alkaloids, nagelamides J (3) and K (4), have been isolated from another Okinawan marine sponge Agelas sp. (SS-1077), and the structures and relative stereochemistries were elucidated from spectroscopic data. Nagelamide J (3) is the first bromopyrrole alkaloid possessing a cyclopentane ring fused to an amino imidazole ring and nagelamide K (4) is a unique dimeric bromopyrrole alkaloid containing an ester linkage. Nagelamide J (3) exhibited antimicrobial activity against Staphylococcus aureus (MIC, 8.35μg/ml) and antifungal activity against Cryptococcus neoformans (MIC, 16.7μg/ml), while nagelamide K (4) exhibited antimicrobial activity against Micrococcus luteus (MIC, 16.7μg/ml).

    DOI： 10.24496/tennenyuki.49.0_1

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  • STRUCTURES AND PLAUSIBLE BIOGENETIC PATHWAY FOR NOVEL ALKALOIDS FROM DAPHNIPHYLLUM SPECIES

    MATSUNO YOSUKE, OKAMOTO MARIKO, ZAIMA KAZUMASA, KUBOTA TAKAAKI, KOBAYASHI JUN'ICHI, SHINZATO TAKAKAZU, MORITA HIROSHI

    薬学雑誌   126 ( Suppl.5 )   100-103 - 103   2006.11

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  • ABSOLUTE STEREOCHEMISTRY AND MOLECULAR TARGET OF ANTITUMOR MACROLIDES, IEJIMALIDES

    KUBOTA TAKAAKI, NOZAWA KOHEI, TSUDA MASASHI, ISHIYAMA HARUAKI, KAZAMI SAYAKA, USUI TAKEO, OSADA HIROYUKI, KOBAYASHI JUN'ICHI

    薬学雑誌   126 ( Suppl.5 )   222-225   2006.11

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  • アスヒカズラLycopodium complanatum由来の新規アルカロイドの構造と生物活性

    石内勘一郎, 久保田高明, 森田博史, 星野智洋, 小原祐太郎, 中畑則道, 小林淳一

    天然有機化合物討論会講演要旨集   48th ( 48 )   493-498 - 498   2006.9

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    Club moss (Lycopodiaceae) is known to be a rich source of Lycopodium alkaloids posessing unique heterocyclic ring systems such as C_<16>N, C_<16>N_2, and C_<27>N_3, which have attracted great interest from biogenetic, synthetic, and biological points of view. In our continuing efforts to find new Lycopodium alkaloids, lycopladines A-D (1-4), lyconadin B (5), and complanadines C (6), D (7) were isolated from the club moss Lycopodium complanatum. The structures for 1-7 were elucidated on the basis of spectral data. Lycopladine A (1) obtained as colorless amourphous solid, showed the pseudomolecular ion peak at m/z 260 (M+H)^+ in the ESIMS, and the molecular formula, C_<16>H_<21>NO_2, was established by HRESIMS [m/z 260.1653, (M+H)^+, △+0.2mmu]. The gross structure of 1 was elucidated on the basis of 2D NMR data. The relative stereochemistry of 1 was elucidated from NOESY data. Lycopladine A (1) possesses an unprecedented skeleton different from known C_<16>N-type Lycopodium alkaloids. The stuructures of lycopladines B-D (2-4) were elucidated on the basis of spectroscopic data and modified Mosher's method. Lycopladine B (2) was 5-hydroxyl, △_<8,15>, △_<13,14>, and 17-methyl ester form of fawcettidane skeleton. Lycopladine C (3) was assigned as 5-O-acetyl form of 2. Lycopladine D (4) had fawcettidane skeleton with hydroxyl group at C-5 and lactone ring (C-13〜C-16). The absolute stereochemistry of 2 and 4 were elucidated by modified Mosher's method. The absolute configuration at C-5 of 2 and 4 were assigned to be S and R, respectively. Lyconadin B (5) was assigned as dihydro form of lyconadin A. Complanadines C (6) and D (7) were obtained as colorless amorphous solids. The structures and relative stereochmistry of 6 and 7 were elucidated on the basis of spectroscopic data. Complanadine C (6) was assigned as the dimer of 9-keto, △_<10,11> form of lycopodine and △_<9,10> form of lycopodine. The dimer of lycopodane skeleton has not been reported previously. Complanadine D (7) was tetrahydro form of complanadine A. A plausible biogenetic path of lyconadin A (8) was proposed on the basis of structure of lycopladine A (1). Biogenetically, lyconadines A (8) and B (5) might be derived from L-lysine via pelletierine, phlegmarane skeleton, and an intermediate X from which lycopladine A (1) might be provided. Effects of lycopladines A-D (1-4), and lyconadins A (8) and B (5) on neurotrophic factor biosynthesis in 1321N1 human astrocytoma cells were examined. The mRNA expressions of NGF in 1321N1 cells were examined by a semiquantitative RT-PCR method. The mRNA expressions for NGF were enhanced by lyconadins A (8) and B (5).

    DOI： 10.24496/tennenyuki.48.0_493

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  • P-16 Structures and Biological Activity of New Lycopodium Alkaloids from Lycopodium complanatum

    Ishiuchi Kan'ichiro, Kubota Takaaki, Morita Hiroshi, Hoshino Tomohiro, Obara Yutaro, Nakahata Norimichi, Kobayashi Jun'ichi

    Symposium on the Chemistry of Natural Products, symposium papers   0 ( 48 )   493 - 498   2006.9

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    Club moss (Lycopodiaceae) is known to be a rich source of Lycopodium alkaloids posessing unique heterocyclic ring systems such as C_&lt;16&gt;N, C_&lt;16&gt;N_2, and C_&lt;27&gt;N_3, which have attracted great interest from biogenetic, synthetic, and biological points of view. In our continuing efforts to find new Lycopodium alkaloids, lycopladines A-D (1-4), lyconadin B (5), and complanadines C (6), D (7) were isolated from the club moss Lycopodium complanatum. The structures for 1-7 were elucidated on the basis of spectral data. Lycopladine A (1) obtained as colorless amourphous solid, showed the pseudomol...

    DOI： 10.24496/tennenyuki.48.0_493

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  • ヒメユズリハ(Daphniphyllum teijsmannii)より単離した新規アルカロイドDaphtenidine A‐Dの構造

    松野陽介, 松野陽介, 久保田高明, 森田博史, 新里孝和, 関口光広, 小林淳一

    日本生薬学会年会講演要旨集   53rd   152 - 152   2006.9

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  • アスヒカズラLycopodium complanatum由来の新規アルカロイドの構造と生物活性

    石内勘一郎, 久保田高明, 小林淳一, 森田博史, 星野智洋, 小原祐太郎, 中畑則道

    日本生薬学会年会講演要旨集   53rd   157   2006.9

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  • 放線菌由来細胞毒性物質・ブラシリカルジン類の構造と活性

    小林淳一, 久保田高明

    日本癌学会学術総会記事   65th   466-467   2006.8

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  • リコポジウムアルカロイドの構造の多様性と生物活性

    石内勘一郎, 久保田高明, 小林淳一, 森田博史

    万有生命科学振興国際交流財団札幌シンポジウム   18th   42   2006.7

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  • Promising V-ATPase Inhibitors as Drugs for Treatment of Osteoporosis and Tumor.

    KOBAYASHI JUN'ICHI, KUBOTA TAKAAKI

    化学   61 ( 6 )   68-69   2006.6

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  • 沖縄産海綿Cribrochalina sp.より単離した新規ピリジンアルカロイドPyrinadine Aの構造

    久保田高明, 仮屋佑子, 小林淳一

    日本薬学会年会要旨集   126th ( 4 )   86   2006.3

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  • Iejimalidesの標的分子の同定

    風見紗弥香, 臼井健郎, 室井誠, 久保田高明, 小林淳一, 長田裕之

    日本農芸化学会大会講演要旨集   2006   11   2006.3

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  • 沖縄産ホヤ由来マクロリド・イエジマリド類の構造と生物活性 (第16回 天然薬物の開発と応用シンポジウム講演要旨集)

    久保田 高明, 野沢 耕平, 津田 正史

    薬学雑誌   126 ( 0 )   222 - 225   2006

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  • 海洋渦鞭毛藻由来の新規ポリケチドの探索

    久保田高明, 佐久間裕介, 新保和高, 津田正史, 小林淳一

    マリンバイオテクノロジー学会大会講演要旨集   8th   109   2005.5

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  • 27 Structure Elucidation and Biosynthetic Studies of Amphezonol A, a Novel Polyhydroxyl Metabolite from Symbiotic Marine Microalga

    Kubota Takaaki, Sakuma Yusuke, Shimbo Kazutaka, Tsuda Masashi, Uozumi Yasuhiro, Kobayashi Jun'ichi

    Symposium on the Chemistry of Natural Products, symposium papers   47 ( 0 )   151 - 156   2005

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    Amphezonol A (1), a novel polyhydroxyl compound, was isolated from a marine dinoflagellate Amphidinium sp. (Y-72), and the structure was elucidated on the basis of 2D NMR data including HSQC-TOCSY and INADEQUATE spectra (920MHz) using the ^<13>C-enriched sample. Amphezonol A (1), C_<62>H_<114>O_<24>, was the first member of a new class of polyketide natural products consisting of a C_<60>-linear aliphatic chain with twenty-one hydroxyl groups, and two tetrahydropyran and a tetrahydrofuran rings. Cloning of polyketide synthase (PKS) gene from a dinoflagellate Amphidinium sp. was attempted and PKS gene fragments were obtained by PCR amplification from degenerated primer sets designed on the basis of the conserved amino acid sequences in known type I PKSs. The PCR analysis, using primer sets designed from these PKS gene fragments, revealed that these DNA sequences exist only in the dinoflagellates producing polyketides.

    DOI： 10.24496/tennenyuki.47.0_151

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  • 27 Structure Elucidation and Biosynthetic Studies of Amphezonol A, a Novel Polyhydroxyl Metabolite from Symbiotic Marine Microalga

    Kubota Takaaki, Sakuma Yusuke, Shimbo Kazutaka, Tsuda Masashi, Uozumi Yasuhiro, Kobayashi Jun'ichi

    Symposium on the Chemistry of Natural Products, symposium papers   47 ( 0 )   151 - 156   2005

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    Amphezonol A (1), a novel polyhydroxyl compound, was isolated from a marine dinoflagellate Amphidinium sp. (Y-72), and the structure was elucidated on the basis of 2D NMR data including HSQC-TOCSY and INADEQUATE spectra (920MHz) using the ^<13>C-enriched sample. Amphezonol A (1), C_<62>H_<114>O_<24>, was the first member of a new class of polyketide natural products consisting of a C_<60>-linear aliphatic chain with twenty-one hydroxyl groups, and two tetrahydropyran and a tetrahydrofuran rings. Cloning of polyketide synthase (PKS) gene from a dinoflagellate Amphidinium sp. was attempted and PKS gene fragments were obtained by PCR amplification from degenerated primer sets designed on the basis of the conserved amino acid sequences in known type I PKSs. The PCR analysis, using primer sets designed from these PKS gene fragments, revealed that these DNA sequences exist only in the dinoflagellates producing polyketides.

    DOI： 10.24496/tennenyuki.47.0_151

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  • Absolute Stereochemistry of Amphidinolide E.

    KUBOTA TAKAAKI, TSUDA MASASHI, KOBAYASHI JUN'ICHI

    日本化学会講演予稿集   81st ( 2 )   707   2002.3

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  • Studies on biosynthesis of amphidinolides.

    TSUDA MASASHI, KUBOTA TAKAAKI, SHIMBO KAZUTAKA, HORIGUCHI TAKEO, KATSUMATA KAZUHITO, KOBAYASHI JUN'ICHI

    日本化学会講演予稿集   80th   3   2001.9

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  • 沖縄産海綿Suberea sp.より単離した新規ブロモチロシンアルカロイドMa′edamine AとBの構造

    久保田高明, 津田正史, 平野敬子, 渡部賢二, 小林淳一

    日本薬学会年会要旨集   121年会 ( 2 )   119 - 119   2001.3

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  • 17 Stereochemistry of Amphidinolides C and T1〜T5

    Kubota Takaaki, Tsuda Masashi, Endo Tetsuya, Shiro Motoo, Kobayashi Jun'ichi

    Symposium on the Chemistry of Natural Products, symposium papers   43 ( 0 )   97 - 102   2001

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    Amphidinolide C (1) is a unique 25-membered macrolide isolated from a marine dinoflagellate Amphidinium sp. (strain Y-5). The gross structure of 1 has been elucidated by 2D-NMR data, whereas the stereochemistry remains undefined. During our search for bioactive metabolites from marine dinoflagellates, relatively large amounts of 1 have been recently isolated from two strains (Y-56 and Y-71) of the genus Amphidinium, which allowed us to investigate the stereochemistry of 1 Absolute configurations at C-12, C-13, C-20, C-23, C-24, and C-29 of amphidinolide C (1) were assigned by combination of NMR analyses including J-based configuration analysis and Mosher's method, while absolute configurations at C-7 and C-8 of 1 were assigned by application of Mosher's method for erythro glycol and comparison of ^1H-NMR data of natural specimen with those of synthetic C-1-C-10 segments. Absolute configurations at C-3, C-4, C-6, and C-16 of 1 were elucidated by comparison of NMR data of degradation products of 1 with synthetic C-1-C-7 and C-16-C-18 segments. On the other hand, five new 19-membered macrolides amphidinolides T1-T5 (2-6) have been isolated from the Y-56 and Y-71 strains of the genus Amphdinium. The gross structures were elucidated by 2D-NMR analyses. Absolute configurations at C-2, C-13, C-14, and C-18 of amphidinolide T1 (2) were assigned on the basis of NMR data of the MTPA esters of 2 and those of degradation products of 2, while absolute configurations at C-7, C-8, and C-10 of 2 were elucidated by comparison of ^1H-NMR data of C-1-C-12 segment with those of synthetic model compounds for tetrahydrofuran portion. The absolute stereochemistry of amphidinolides T2-T5 (3-6) were also elucidated by similar methods. The stereostructure of 2 was also confirmed by a single crystal X-ray diffraction analysis.

    DOI： 10.24496/tennenyuki.43.0_97

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  • 17 Stereochemistry of Amphidinolides C and T1〜T5

    Kubota Takaaki, Tsuda Masashi, Endo Tetsuya, Shiro Motoo, Kobayashi Jun'ichi

    Symposium on the Chemistry of Natural Products, symposium papers   43 ( 0 )   97 - 102   2001

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    Amphidinolide C (1) is a unique 25-membered macrolide isolated from a marine dinoflagellate Amphidinium sp. (strain Y-5). The gross structure of 1 has been elucidated by 2D-NMR data, whereas the stereochemistry remains undefined. During our search for bioactive metabolites from marine dinoflagellates, relatively large amounts of 1 have been recently isolated from two strains (Y-56 and Y-71) of the genus Amphidinium, which allowed us to investigate the stereochemistry of 1 Absolute configurations at C-12, C-13, C-20, C-23, C-24, and C-29 of amphidinolide C (1) were assigned by combination of NMR analyses including J-based configuration analysis and Mosher's method, while absolute configurations at C-7 and C-8 of 1 were assigned by application of Mosher's method for erythro glycol and comparison of ^1H-NMR data of natural specimen with those of synthetic C-1-C-10 segments. Absolute configurations at C-3, C-4, C-6, and C-16 of 1 were elucidated by comparison of NMR data of degradation products of 1 with synthetic C-1-C-7 and C-16-C-18 segments. On the other hand, five new 19-membered macrolides amphidinolides T1-T5 (2-6) have been isolated from the Y-56 and Y-71 strains of the genus Amphdinium. The gross structures were elucidated by 2D-NMR analyses. Absolute configurations at C-2, C-13, C-14, and C-18 of amphidinolide T1 (2) were assigned on the basis of NMR data of the MTPA esters of 2 and those of degradation products of 2, while absolute configurations at C-7, C-8, and C-10 of 2 were elucidated by comparison of ^1H-NMR data of C-1-C-12 segment with those of synthetic model compounds for tetrahydrofuran portion. The absolute stereochemistry of amphidinolides T2-T5 (3-6) were also elucidated by similar methods. The stereostructure of 2 was also confirmed by a single crystal X-ray diffraction analysis.

    DOI： 10.24496/tennenyuki.43.0_97

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  • Two New Cyclic Depsipeptides from Okinawan Marine Sponge Theonella sp.

    SHIMBO KAZUTAKA, KUBOTA TAKAAKI, TSUDA MASASHI, KOBAYASHI JUN'ICHI

    日本化学会講演予稿集   78th ( 2 )   849   2000.3

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  • Amphidinolide V, Novel 14-Membered Macrolide from Marine Dinoflagellate Amphidinium sp.

    KUBOTA TAKAAKI, TSUDA MASASHI, KOBAYASHI JUN'ICHI

    日本化学会講演予稿集   78th ( 2 )   884   2000.3

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  • 100(P48) Colopsinols A and B, Novel Polyhydroxyl Metabolites from Marine Dinoflagellate Amphidinium sp.

    Kubota Takaaki, Tsuda Masashi, Takahashi Miho, Ishibashi Masami, Kobayashi Jun'ichi, Naoki Hideo

    Symposium on the Chemistry of Natural Products, symposium papers   41 ( 0 )   595 - 600   1999

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    Marine dinoflagellates of the genus Amphidinium have been recognized as a rich source of novel bioactive substances with unique structures. We previously isolated a series of cytotoxic macrolides, designated amphidinolides, possessing unique structural features from several strains of the dinoflagellates Amphidinium sp., among which the strain Y-5 was the richest source of the amphidinolides. Further search for metabolites from the strain Y-5, which was a symbiont of Okinawan marine acoel flatworm Amphiscolops sp., resulted in the isolation of two novel polyhydoroxyl compounds, colopsinols A (1) and B (2), belonging to a new class of polyketide metabolites. The structures of 1 and 2 were elucidated on the basis of extensive NMR techniques including a newly developed 2D NMR experiments such as CH_2-selected editing HSQC (E-HSQC) as well as FABMS/MS data. Colopsinols A (1) and B (2) are new class of polyketide natural products consisting of C_<56> and C_<53>-liner carbon chains, respectively, possessing a gentiobioside (β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside) moiety and a sulfate ester. From this strain (Y-5), 13 cytotoxic macrolides, amphidinolides A-D, J, K, and M-S, have been isolated so far. Biosynthetically it is interesting that quite different type of polyketides such as colopsinols and amphidinolides are produced from the same dinoflagellate. Colopsinol A (1) showed inhibitory activity against DNA polymerase α and β with IC_<50> values of 13 and 7μM, respectively.

    DOI： 10.24496/tennenyuki.41.0_595

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  • 100(P48) Colopsinols A and B, Novel Polyhydroxyl Metabolites from Marine Dinoflagellate Amphidinium sp.

    Kubota Takaaki, Tsuda Masashi, Takahashi Miho, Ishibashi Masami, Kobayashi Jun'ichi, Naoki Hideo

    Symposium on the Chemistry of Natural Products, symposium papers   41 ( 0 )   595 - 600   1999

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    Marine dinoflagellates of the genus Amphidinium have been recognized as a rich source of novel bioactive substances with unique structures. We previously isolated a series of cytotoxic macrolides, designated amphidinolides, possessing unique structural features from several strains of the dinoflagellates Amphidinium sp., among which the strain Y-5 was the richest source of the amphidinolides. Further search for metabolites from the strain Y-5, which was a symbiont of Okinawan marine acoel flatworm Amphiscolops sp., resulted in the isolation of two novel polyhydoroxyl compounds, colopsinols A (1) and B (2), belonging to a new class of polyketide metabolites. The structures of 1 and 2 were elucidated on the basis of extensive NMR techniques including a newly developed 2D NMR experiments such as CH_2-selected editing HSQC (E-HSQC) as well as FABMS/MS data. Colopsinols A (1) and B (2) are new class of polyketide natural products consisting of C_<56> and C_<53>-liner carbon chains, respectively, possessing a gentiobioside (β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside) moiety and a sulfate ester. From this strain (Y-5), 13 cytotoxic macrolides, amphidinolides A-D, J, K, and M-S, have been isolated so far. Biosynthetically it is interesting that quite different type of polyketides such as colopsinols and amphidinolides are produced from the same dinoflagellate. Colopsinol A (1) showed inhibitory activity against DNA polymerase α and β with IC_<50> values of 13 and 7μM, respectively.

    DOI： 10.24496/tennenyuki.41.0_595

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  • Structure of new polyol compound Luteophanol B isolated from Gonyaulax Amphidinium species.

    KUBOTA TAKAAKI, TSUDA MASAFUMI, DOI YUKIKO, NAKAMICHI HIROKO, ISHIBASHI MASAMI, KOBAYASHI JUN'ICHI

    日本薬学会年会要旨集   118th ( 2 )   108   1998.3

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  • 80(P63) Luteophanols B and C, New Polyhydroxyl Compounds from Marine Dinoflagellate

    Kubota Takaaki, Tsuda Masashi, Doi Yukiko, Takahashi Ayako, Nakamichi Hiroko, Ishibashi Masami, Fukushi Eri, Kawabata Jun, Kobayashi Jun'ichi

    Symposium on the Chemistry of Natural Products, symposium papers   40 ( 0 )   473 - 478   1998

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    During our continuing search for structurally unique secondary metabolites from marine dinoflagellates, we previously isolated a series of cytotoxic macrolides, amphidinolides, from dinoflagellates Amphidinium sp. Recently we investigated another strain of Amphidinium sp. (strain number Y-52), which was isolated from the inside cells of the Okinawan marine acoel flatworm Pseudaphanostoma luteocoloris, and isolated two new polyhydroxyl compounds, luteophanols B (1) and C (2), both consisting of a C_<64>-linear aliphatic chain. The structure elucidation of 1 and 2 were elucidated on the basis of chemical degradation and newly developed 2D NMR experiments, E-HSQC and E-HSQC-TOCSY. E-HSQC and E-HSQC-TOCSY are very useful techniques for structure elucidations of complex natural products possessing many aliphatic methine and methylene carbons such as luteophanols B (1) and C (2). CH_2-selected E-HSQC-TOCSY^6 experiments seem to be suitable to assign very closely resonated carbon signals, since this method affords the high resolution in F_1 axis by limiting the F_1 spectral width, in which sp^2 methylene carbons are resonated.

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  • 80(P63) Luteophanols B and C, New Polyhydroxyl Compounds from Marine Dinoflagellate

    Kubota Takaaki, Tsuda Masashi, Doi Yukiko, Takahashi Ayako, Nakamichi Hiroko, Ishibashi Masami, Fukushi Eri, Kawabata Jun, Kobayashi Jun'ichi

    Symposium on the Chemistry of Natural Products, symposium papers   40 ( 0 )   473 - 478   1998

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    During our continuing search for structurally unique secondary metabolites from marine dinoflagellates, we previously isolated a series of cytotoxic macrolides, amphidinolides, from dinoflagellates Amphidinium sp. Recently we investigated another strain of Amphidinium sp. (strain number Y-52), which was isolated from the inside cells of the Okinawan marine acoel flatworm Pseudaphanostoma luteocoloris, and isolated two new polyhydroxyl compounds, luteophanols B (1) and C (2), both consisting of a C_<64>-linear aliphatic chain. The structure elucidation of 1 and 2 were elucidated on the basis of chemical degradation and newly developed 2D NMR experiments, E-HSQC and E-HSQC-TOCSY. E-HSQC and E-HSQC-TOCSY are very useful techniques for structure elucidations of complex natural products possessing many aliphatic methine and methylene carbons such as luteophanols B (1) and C (2). CH_2-selected E-HSQC-TOCSY^6 experiments seem to be suitable to assign very closely resonated carbon signals, since this method affords the high resolution in F_1 axis by limiting the F_1 spectral width, in which sp^2 methylene carbons are resonated.

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Industrial property rights

  • 渦鞭毛藻由来のポリケチド合成酵素遺伝子

    久保田 高明, 小林 淳一

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    Applicant：国立大学法人 北海道大学

    Application no：特願2005-186086  Date applied：2005.6.27

    Announcement no：特開2007-000104  Date announced：2007.1.11

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Awards

  • 学術貢献賞

    2016   日本生薬学会  

    久保田 高明

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Research Projects

  • Revealing symbiotic mechanisms from useful metabolites of microorganisms in corals

    Grant number：23H02132  2023.04 - 2026.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    將口 栄一, 濱田 麻友子, 久保田 高明, 竹内 猛

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    Grant amount：\18720000 （ Direct expense: \14400000 、 Indirect expense：\4320000 ）

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  • 海産天然物をシーズとした核内受容体PXRアンタゴニストの開発

    Grant number：20K07116  2020.04 - 2023.03

    日本学術振興会  科学研究費助成事業  基盤研究(C)

    久保田 高明

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    Grant amount：\4290000 （ Direct expense: \3300000 、 Indirect expense：\990000 ）

    薬物代謝は異物を体外に排出する重要な解毒機構であるが、一方で異物とみなした薬物の薬効を減弱させてしまう。核内受容体 Pregnane X Receptor（PXR）は、薬物代謝酵素や薬物トランスポーターの発現を誘導し、薬物代謝を亢進させることにより様々な薬物の薬効を減弱させる。PXRの機能を阻害すれば薬物の薬効減弱を防ぐことができるが、選択的な阻害剤は合成化合物のSPA70のみであるため、新しいタイプの阻害剤の開発が求められている。本研究では、PXR阻害剤の探索源として十分に研究が行われていない海洋生物を研究材料として、薬物の薬効減弱を防ぐ新たな医薬品のリード化合物の創出を目指して研究を進めている。
    本年度は、昨年度までにAmphidinium属の３種の渦鞭毛藻から単離した、２個のマクロリドおよび１個の長鎖ポリケチド、Agelas属、Dysidea属、Hippospongia属、Pseudoseratina属およびSuberea属の海綿動物から単離した、１個のジテルペノイド、１個のポリヒドロキシステロール、５個のメロテルペノイド、３個のブロモチロシンアルカロイドについて、２次元NMRスペクトルおよび計算化学により得られたデータに基づいて立体化学の解析を行い、未決定であった立体化学の一部を明らかにした。また、新たにSymbiodiniaceae科の２種の渦鞭毛藻と、Alteromonas属やVibrio属などの４種の海洋細菌の培養を行い、それらの抽出物およびStylissa属などの２種の海綿動物の抽出物を用いて、新規化合物の探索を開始した。

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  • Development of new anti-infective drugs from dinoflagellate

    Grant number：17K08345  2017.04 - 2020.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    KUBOTA Takaaki

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    Grant amount：\4810000 （ Direct expense: \3700000 、 Indirect expense：\1110000 ）

    The search for new antifungal and antiprotozoal natural products from marine organisms was performed. As a result, twenty-six new natural products were isolated from marine dinoflagellates and sponges, and the structures of six new compounds were elucidated. Among them, one macrolide from dinoflagellates and two alkaloids from a sponge exhibited cytotoxicity against murine leukemia cell line L1210 in vitro. While one alkaloid from a sponge exhibited antimalarial activities against a drug-resistant and a drug-sensitive strains of Plasmodium falciparum. The investigation about antifungal and antiprotozoal activities of other new compounds were currently in progress.

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  • Development of new antitrypanosomal drugs from marine alkaloids

    Grant number：25460115  2013.04 - 2016.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    KUBOTA Takaaki, KOBAYASHI Jun'ichi, KATAKURA Ken, GONOI Tohru

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    Grant amount：\5200000 （ Direct expense: \4000000 、 Indirect expense：\1200000 ）

    The search for new anti-trypanosomal natural products from marine organisms was performed. As a result, seventeen new natural products were isolated from marine sponges and dinoflagellates, and the structures of new compounds were elucidated. Three new compounds were analogs of anti-trypanosomal natural products previously found by us. These compounds were isolated to analyze the structure activity relationships of anti-trypanosomal natural products. The detailed investigation about anti-trypanosomal activity of new compounds were currently in progress.

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  • Development of new antitumor agents and immunosuppressive agents using brasilicardin-A as a lead compound

    Grant number：25670043  2013.04 - 2015.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Challenging Exploratory Research

    KOBAYASHI Jun'ichi, KUBOTA Takaaki, ISHIYAMA Haruaki, TANAKA Naonobu

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    Grant amount：\3900000 （ Direct expense: \3000000 、 Indirect expense：\900000 ）

    To increase the quantity of our natural products library, 60 new bioactive natural products were isolated from various biological resources and the structures were elucidated. Stereochemistry or mode of action of some known natural products, which were originally found by our group, were also elucidated. However, no System L inhibitor greater than brasilicardin A was found from our natural products library and analogs prepared by chemical conversion from brasilicardin A and its related known natural products.

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  • 渦鞭毛藻由来マクロリドの特異な生合成経路の解明

    Grant number：23108502  2011.04 - 2013.03

    日本学術振興会  科学研究費助成事業  新学術領域研究(研究領域提案型)

    久保田 高明

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    Authorship：Principal investigator  Grant type：Competitive

    Grant amount：\6760000 （ Direct expense: \5200000 、 Indirect expense：\1560000 ）

    研究代表者らが海洋渦鞭毛藻Amphidinium sp.から単離、構造決定している一連の抗腫瘍性マクロリドであるアンフィジノリド類のポリケチド鎖は、13C標識酢酸の投与実験により、通常の酢酸-マロン酸経路だけでは説明できない特異な炭素鎖伸長経路により生合成されていることが分かっている。この特異な炭素鎖伸長経路は、他の属の渦鞭毛藻が生産するポリケチドの生合成にも関与していることが示唆されている。
    植物や菌類のポリケチド生合成酵素(PKS)は、酢酸由来の2炭素を直列に2炭素ずつポリケチド鎖を伸長する事しかできないが、渦鞭毛藻のPKSはポリケチド鎖を2炭素伸長させるだけでなく、酢酸のメチル基炭素を用いて1炭素のみ伸長させることも可能と考えられる。生合成工学的手法により、渦鞭毛藻のPKSを利用することが可能になれば、菌類に比べて培養が困難な渦鞭毛藻のポリケチドを、他のホストで効率よく生産させることが可能になるだけでなく、既知のPKSでは生産することができない多彩な炭素骨格の化合物を、酵素的に合成することも可能となる。しかし、この特異な1炭素伸長のメカニズムは不明である。
    本研究では、2011年に採取したアンフィジノリド生産株について、RNA-Seq解析によるmRNAの網羅的な解析を行った結果、アンフィジノリド類の生合成に関与している可能性のある遺伝子として、既知のPKSに見られる酵素や、β-メチル化に関与する酵素と相同性を示す酵素遺伝子の他、藍藻の生産するバルバミドの生合成において特異な炭素鎖伸長に関与している酵素と相同性を示す、非リボソームペプチド合成酵素に見られるドメインとPKSの混合したモジュール型酵素の遺伝子を取得した。

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  • Research and development of bioactive marine natural products

    Grant number：20390001  2008 - 2010

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    KOBAYASHI Jun'ichi, KUBOTA Takaaki, ISHIYAMA Haruaki

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    Authorship：Collaborating Investigator(s) (not designated on Grant-in-Aid)  Grant type：Competitive

    Grant amount：\19760000 （ Direct expense: \15200000 、 Indirect expense：\4560000 ）

    Investigation of extracts of an Okinawan marine organisms (sponge, tunicate, and dinoflagellate etc.) resulted in the isolation of new manzamine alkaloids exhibiting antimalarial and antitrypanosomal activities, new pyridinium alkaloids exhibiting acetylcholine esterase inhibitory activity, and new terpenoid quinones exhibiting tyrosine kinase inhibitory activity. In addition, many new compounds that show cytotoxic activity (pyridine alkaloids, beta-carboline alkaloids, bromotyrosine alkaloids, a macrolide, and sesquiterpenoids) and anti-microbial activity (bromopyrrole alkaloids, bromotyrosine alkaloids, triterpenoids) were isolated from the marine organisms. The absolute stereochemistries of known cytotoxic macrolides, previously isolated from dinoflagellete by our group, were also elucidated.

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  • 創薬素材としての細胞骨格系機能性分子の探索

    Grant number：18032005  2006 - 2007

    日本学術振興会  科学研究費助成事業  特定領域研究

    小林 淳一, 久保田 高明, 石山 玄明, 津田 正史

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    Authorship：Collaborating Investigator(s) (not designated on Grant-in-Aid)  Grant type：Competitive

    Grant amount：\6200000 （ Direct expense: \6200000 ）

    本研究では、海洋生物、植物、微生物などの広範な天然資源を素材として、細胞骨格系において重要な役割を果たしているアクチンおよびチューブリン等を分子標的にしたスクリーニングを行うことにより、これらの蛋白質の重合・脱重合を阻害する新しい天然分子を見い出すとともに、これらの天然分子の構造活性相関を検討し、特異な重合阻害剤や脱重合阻害剤(重合促進剤)を開発する目的で研究を行った。以下に本年度の研究成果の概要を報告する。アクチンファイバーの安定化促進作用を有する渦鞭毛藻由来マクロリド化合物アンフィジノリドHの関連化合物として、渦鞭毛藻より、アンフィジノラクトンB、アンフィジノリドB6,B7およびイリオモテオリド1aを単離、構造決定した。イリオモテオリド1aについては、human Blymphocyte DG-75 cellsに対する作用を調べた結果、アンフィジノリドHと同程度の細胞毒性を示すこと見い出した。また、強力なチューブリン脱重合阻害作用と抗癌作用を示すイチイ科植物由来め化合物・タキソールの関連化合物として、日本産イチイよりタキセゾピジンOおよびPを単離、構造決定した。今回単離、構造解析した化合物については、分子標的に対する詳細な活性評価、および各種ヒト腫瘍パネルに対するin vitro、in vivoでの活性を評価し、開発した阻害剤あるいは促準剤の新しい癌治療薬等としての可能性を...

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  • フォトンフォース計測技術を用いた細胞系ダイナミック分析法の開発

    Grant number：17034001  2005 - 2006

    日本学術振興会  科学研究費助成事業  特定領域研究

    笹木 敬司, 久保田 高明, 山本 隆晴

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    Authorship：Collaborating Investigator(s) (not designated on Grant-in-Aid)  Grant type：Competitive

    Grant amount：\4900000 （ Direct expense: \4900000 ）

    これまでに我々は、フォトンフォース(光の放射圧)を利用して単一徴粒子やマイクロ・ナノ構造体に作用するフェムトニュートンオーダーの力を計測し、表面電荷・吸収・粘弾性特性・吸着力等の物性を非接触・非破壊的に解析する新しい手法を提案するとともに、高精度かつ汎用性の高い計測システムを開発してきた。本特定領域研究では、フォトンフォース計測技術を単一細胞や複数細胞集団の新しい分析法として応用し、細胞系のダイナミック分析を実現することを目的として、a)新しいアイデアに基づく2ビームフォトンフォース計測システムを開発、b)単一細胞の粘弾性特性や表面修飾した徴粒子との相互作用ポテンシャルを計測、c)細胞間の接着特性や徴細構造を持つ基板への付着特性の解析、を課題として研究を展開した。細胞と徴粒子あるいは細胞間の相互作用ポテンシャルの解析を実現するために、偏光の異なる2つのパルスレーザービームを個々に照射し、透過散乱光を偏光で分離して同時3次元ポジションセンシングを可能とする新しいフォトンフォース計測システムを試作し、感度、精度について検証した上で、2つの微粒子間の相互作用の解析に応用した。また、フォース計測システムにより細胞の各ポジションの表面弾性や粘性を解析して、細胞が固有の形態で運動するメカニズムの解明を試みている。さらに、細胞間の選択的接着特性を解析するために、外部環境を変えながら細胞間の...

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  • 蛋白質リン酸化を標的とした新規抗腫瘍性シーズの探索

    Grant number：17035004  2005

    日本学術振興会  科学研究費助成事業  特定領域研究

    津田 正史, 小林 淳一, 久保田 高明

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    Authorship：Collaborating Investigator(s) (not designated on Grant-in-Aid)  Grant type：Competitive

    Grant amount：\3200000 （ Direct expense: \3200000 ）

    海洋生物からの生物活性物質探索の一環として、本研究では、海洋由来真菌Penicillium citrinum N055株より、新規4環性アルカロイドPerinadin Aを単離し、絶対立体配置を含む化学構造を明らかにした。同じくP.citrinum N059株より、5環性アルカロイドCitrinadin Aとともに新規化合物Citrinadin Bを単離し、Citrinadin AとBの絶対立体配置を含む化学構造を推定した。沖縄県辺戸岬沖にて採取したアオブダイの消化管より分離した真菌P.citrinum N05株の培養液の上清より、新規アルカロイドPerinadin Aを得た。Perinadin Aは、光学活性な無色の非結晶性固体として得られ、HRESIMSより分子式がC_<28>H_<37>NO_2であることが明らかとなった。2D NMRデータの詳細な解析に基づいて、Perinadin Aの相対立体配置を含む化学構造を帰属した。CDスペクトルの解析より、絶対立体配置を1S、3R、4R、2'R、3'Sであると帰属した。C-7'はエピ体の混合物であると推定した。沖縄県辺戸岬沖にて採取した紅藻より分離した真菌P.citrinum N059株の培養液の菌体より、新規アルカロイドCitrinadin Bを、既知関連化合物Citrinadin Aとともに単離した。2D NMRデータの詳...

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  • がん分子標的に特異的に作用する天然薬物の開発

    Grant number：17016003  2005

    日本学術振興会  科学研究費助成事業  特定領域研究

    小林 淳一, 久保田 高明, 石山 玄明

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    Authorship：Collaborating Investigator(s) (not designated on Grant-in-Aid)  Grant type：Competitive

    Grant amount：\3100000 （ Direct expense: \3100000 ）

    研究代表者らはこれまでに、広範な天然資源より種々の分子標的阻害物質を数多く見い出しており、そのいくつかは新しい医薬リード化合物として開発研究が展開される一方、生体機能解明のためのバイオプローブとして利用されている。本研究では、海洋生物、植物、微生物などの広範な天然資源を素材として、チューブリン、トポイソメラーゼ、ヒストンデアセチラーゼ、チロシンキナーゼ、等の分子標的に対するスクリーニングを行うことにより、新しいがん分子標的阻害物質を見い出すことを目的とし、以下の研究を行った。放線菌Nocardia brasiliensisより単離した免疫抑制物質ブラシリカルジンAのアナログを調製し構造活性相関について研究を行った。現在、ビオチン誘導体を用いて、分子標的の特定を行っている。一方、アクチンファイバーの安定化を促進させる作用を有する海洋共生渦鞭毛藻由来マクロリド化合物・アンフィジノリドHの溶液中のコンホメーション解析を行うとともに、関連抗腫瘍性マクロリドとしてアンフィジノリドB4およびB5を単離構造決定した。また、沖縄産群体ホヤEudistoma cf.rigidaより単離した抗腫瘍性マクロリド化合物・イエジマリド類の絶対立体配置を決定した。今後、活性を示した化合物については、構造活性相関を通じて、より特異性の高い分子標的阻害物質を分子設計する予定である。さらに、得られた分子標的阻...

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  • Research and development of bioactive natural products targeting cytoskeleton.

    Grant number：16310143  2004 - 2005

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    KOBAYASHI Jun'ichi, TSUDA Masashi, KUBOTA Takaaki, ISHIYAMA Haruaki

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    Authorship：Collaborating Investigator(s) (not designated on Grant-in-Aid)  Grant type：Competitive

    Grant amount：\13500000 （ Direct expense: \13500000 ）

    1)Eight stilbenoids, 1-(p-hydroxybenzyl)-4,8-dimethoxyphenanthrene-2,7-diol (1), 2,7-dihydroxy-1,3-bis(p-hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene (2), 4,7-dihydroxy-1-(p-hydroxyberzyl)-2-methoxy-9,10-dihydrophenanthrene (3), 3,3'-dihydroxy- 2',6'-bis(p-hydroxybenzyl)-5-methoxybibenzyl (4), 3',5-dihydroxy-2-(p-hydroxybenzyl)-3-methoxybibenzyl (5), blestriarenes B (6) and C (7), and blestrianol A (8) have been isolated by the guidance of inhibitory effect of tubulin polymerization from the tubers of Bletilla striata (Orchidaceae). Among them, 4 and 5 inhibited the polymerization of t...

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  • 抗腫瘍性マクロリド・イエジマリド類の真の生産微生物の解明

    Grant number：16651104  2004 - 2005

    日本学術振興会  科学研究費助成事業  萌芽研究

    小林 淳一, 津田 正史, 久保田 高明

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    Authorship：Collaborating Investigator(s) (not designated on Grant-in-Aid)  Grant type：Competitive

    Grant amount：\2900000 （ Direct expense: \2900000 ）

    沖縄産群体ホヤEudistoma cf.rigidaより単離したイエジマリド類は、旅線菌などの二次代謝産物にみられるアミノ酸結合型ポリケチドであり、ホヤの体内に共生する微生物が生産しているものと推定される。そこで本研究では、共生微生物を含むホヤの全ゲノムDNAより、イエジマリド合成酵素遺伝子のクローニングを行い、イエジマリドの生合成経路の遺伝子レベルでの解明、および、分子マーカーと免疫学的手法を駆使してイエジマリド類の真の生産微生物の特定を目的として研究を行った。まず、これまで不確定であったイエジマリド類の立体化学について、NMRデータ解析、酸化分解生成物の立体選択的合成、化学相関実験により、全絶対立体配置を確定した。次にポリケチド合成酵素のKetosynthaseドメインに特異的な遺伝子プローブや、非リボゾーム型ペプチド合成酵素の遺伝子プローブを種々設計し、沖縄で採取したホヤについて、ゲノムDNAを分離精製するとともに、ホヤの全DNAよりコスミドライブラリーの作成を行った。作成した遺伝子プローブをプライマーとしてホヤゲノムDNAについてPCRを行い、PCR生成物よりプラスミドDNAを調製した。特異的なパターンを示す遺伝子については、DNAシークエンサーで塩基配列を決定し、その塩基配列に基づいた特異的な遺伝子プローブを設計した。今後これら特異的遺伝子プローブを用いて、コスミド...

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  • 渦鞭毛藻由来マクロリドamphidinolide Cの立体化学と生合成経路の解明

    Grant number：01J10818  2001 - 2002

    日本学術振興会  科学研究費助成事業  特別研究員奨励費

    久保田 高明

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    Grant amount：\2000000 （ Direct expense: \2000000 ）

    海洋産の渦鞭毛藻Amphidinium sp.の培養藻体から単離した抗腫瘍性25員環マクロリド・Amphidinolide Cは、テトラヒドロフラン環、共役ジエン(S-cisおよびS-trans)、水酸基、エキソメチレン、エステルカルボニル基、ケトカルボニル基、といった多彩な官能基・部分構造を持ち、12個の不斉炭素を有するユニークで複雑な構造の化合物である。しかしながらこれまで、Amphidinolide Cの立体化学については、一部の相対立体配置の推定がなされているのみであり、作用メカニズムの解明および構造活性相関についての研究が展開できない状況にある。一方、Amphidinolide Cは奇数員環のマクロリドで、隣接するメチル基-エキソメチレン基を有するなど通常のポリケチド生合成経路では説明のつかない炭素骨格を有しており、その生合成経路についても興味が持たれる。本研究では、Amphidinolide Cの絶対立体配置を解明し、合成研究とそれに続く活性評価を可能にするとともに、生合成経路の解明を目的として研究を行った。
    1)Amphidinolide CのC-1〜C-10とC-17〜C29に相当するセグメントを合成し、天然物由来の反応生成物とスペクトルデータを比較により、3位、4位、6位、7位、8位、20位、23位および24位の絶対立体配置を決定した。
    2)Amphidinolide Eについて、NMRデータの解析、分解反応、セグメントの合成により、8個の不斉炭素の絶対立体配置を明らかにした。

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  • Search for bioactive natural products and its biosynthesis

    1995

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    Grant type：Competitive

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  • 生物活性天然物質の探索と生合成

    1995

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    Grant type：Competitive

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  • Advanced Pharmaceutical Research （2024academic year） Summer concentration  - その他

  • Advanced Seminars in Drug Discovery and Drug Development (Natural Product Chemistry) （2024academic year） special  - その他

  • Experimental Organic Chemistry （2024academic year） 1st and 2nd semester  - その他5～9

  • Experimental Organic Chemistry （2024academic year） 1st and 2nd semester  - その他5～9

  • Natural Products Chemistry （2024academic year） 1st and 2nd semester  - 木5～6

  • Natural Products Chemistry （2024academic year） 1st and 2nd semester  - 木5～6

  • Introduction to Natural Product Chemistry （2024academic year） special  - その他

  • Introduction to Natural Product Chemistry （2024academic year） special  - その他

  • Seminar on Natural Product Chemistry （2024academic year） special  - その他

  • Advanced Lectures: Natural Products Chemistry （2024academic year） special  - その他

  • Natural Products Chemistry 1 （2024academic year） 1st semester  - 木5～6

  • Natural Products Chemistry 1 （2024academic year） 1st semester  - 木5～6

  • Natural Products Chemistry 2 （2024academic year） Second semester  - 木5～6

  • Natural Products Chemistry 2 （2024academic year） Second semester  - 木5～6

  • Organic Chemistry and Natural Products Chemistry （2024academic year） special  - その他

  • Organic Chemistry and Natural Products Chemistry （2024academic year） special  - その他

  • Introduction to Kampo Medicine 1 （2024academic year） Third semester  - 金5～6

  • Introduction to Kampo Medicine 1 （2024academic year） Third semester  - 金5～6

  • Introduction to Kampo Medicine A （2024academic year） Third semester  - 金5～6

  • Introduction to Kampo Medicine A （2024academic year） Third semester  - 金5～6

  • Pharmacognosy （2024academic year） 3rd and 4th semester  - 金1～2

  • Pharmacognosy （2024academic year） 3rd and 4th semester  - 金1～2

  • Pharmacognosy 1 （2024academic year） Third semester  - 金1～2

  • Pharmacognosy 1 （2024academic year） Third semester  - 金1～2

  • Pharmacognosy 2 （2024academic year） Fourth semester  - 金1～2

  • Pharmacognosy 2 （2024academic year） Fourth semester  - 金1～2

  • Guidance for Pharmaceutical Sciences （2024academic year） 1st and 2nd semester  - [第１学期]水4, [第２学期]月1

  • Guidance for Pharmaceutical Sciences （2024academic year） 1st and 2nd semester  - [第１学期]水4, [第２学期]月1

  • Practice in Fundamental Pharmaceutical Sciences II （2024academic year） 1st and 2nd semester  - その他5～9

  • Practice in Fundamental Pharmaceutical Sciences II （2024academic year） 1st and 2nd semester  - その他5～9

  • Chemistry of medicinal natural products I （2024academic year） special  - その他

  • Chemistry of medicinal natural products II （2024academic year） special  - その他

  • Familiar medicinal herbs and poisonous plants （2024academic year） 1st semester  - 木7～8

  • Advanced Seminars in Drug Discovery and Drug Development (Natural Product Chemistry) （2023academic year） special  - その他

  • Experimental Organic Chemistry （2023academic year） 1st and 2nd semester  - その他5～9

  • Experimental Organic Chemistry （2023academic year） 1st and 2nd semester  - その他5～9

  • Natural Products Chemistry （2023academic year） 1st and 2nd semester  - 木5～6

  • Natural Products Chemistry （2023academic year） 1st and 2nd semester  - 木5～6

  • Introduction to Natural Product Chemistry （2023academic year） special  - その他

  • Introduction to Natural Product Chemistry （2023academic year） special  - その他

  • Seminar on Natural Product Chemistry （2023academic year） special  - その他

  • Advanced Lectures: Natural Products Chemistry （2023academic year） special  - その他

  • Natural Products Chemistry 1 （2023academic year） 1st semester  - 木5～6

  • Natural Products Chemistry 1 （2023academic year） 1st semester  - 木5～6

  • Natural Products Chemistry 2 （2023academic year） Second semester  - 木5～6

  • Natural Products Chemistry 2 （2023academic year） Second semester  - 木5～6

  • Organic Chemistry and Natural Products Chemistry （2023academic year） special  - その他

  • Organic Chemistry and Natural Products Chemistry （2023academic year） special  - その他

  • Introduction to Kampo Medicine 1 （2023academic year） Third semester  - 金5～6

  • Introduction to Kampo Medicine 1 （2023academic year） Third semester  - 金5～6

  • Introduction to Kampo Medicine A （2023academic year） Third semester  - 金5～6

  • Introduction to Kampo Medicine A （2023academic year） Third semester  - 金5～6

  • International Collaborative Pharmaceutical Education(Field Studies Overseas) （2023academic year） special  - その他

  • International Collaborative Pharmaceutical Education(Field Studies Overseas) （2023academic year） special  - その他

  • International Collaborative Pharmaceutical Education(Field Studies Overseas) （2023academic year） special  - その他

  • International Collaborative Pharmaceutical Education(Field Studies Overseas) （2023academic year） special  - その他

  • Pharmacognosy （2023academic year） 3rd and 4th semester  - 金1～2

  • Pharmacognosy （2023academic year） 3rd and 4th semester  - 金1～2

  • Pharmacognosy 1 （2023academic year） Third semester  - 金1～2

  • Pharmacognosy 1 （2023academic year） Third semester  - 金1～2

  • Pharmacognosy 2 （2023academic year） Fourth semester  - 金1～2

  • Pharmacognosy 2 （2023academic year） Fourth semester  - 金1～2

  • Guidance for Pharmaceutical Sciences （2023academic year） 1st and 2nd semester  - [第１学期]水4, [第２学期]月1

  • Guidance for Pharmaceutical Sciences （2023academic year） 1st and 2nd semester  - [第１学期]水4, [第２学期]月1

  • Practice in Fundamental Pharmaceutical Sciences II （2023academic year） 1st and 2nd semester  - その他5～9

  • Practice in Fundamental Pharmaceutical Sciences II （2023academic year） 1st and 2nd semester  - その他5～9

  • Chemistry of medicinal natural products I （2023academic year） special  - その他

  • Chemistry of medicinal natural products II （2023academic year） special  - その他

  • Familiar medicinal herbs and poisonous plants （2023academic year） 1st semester  - 木7～8

  • Natural Products Chemistry （2022academic year） 1st and 2nd semester  - 木5～6

  • Natural Products Chemistry （2022academic year） 1st and 2nd semester  - 木5～6

  • Introduction to Natural Product Chemistry （2022academic year） special  - その他

  • Seminar on Natural Product Chemistry （2022academic year） special  - その他

  • Natural Products Chemistry 1 （2022academic year） 1st semester  - 木5～6

  • Natural Products Chemistry 1 （2022academic year） 1st semester  - 木5～6

  • Natural Products Chemistry 2 （2022academic year） Second semester  - 木5～6

  • Natural Products Chemistry 2 （2022academic year） Second semester  - 木5～6

  • Organic Chemistry and Natural Products Chemistry （2022academic year） special  - その他

  • Introduction to Kampo Medicine 1 （2022academic year） Third semester  - 金5～6

  • Introduction to Kampo Medicine 1 （2022academic year） Third semester  - 金5～6

  • Introduction to Kampo Medicine 2 （2022academic year） Fourth semester  - 金5～6

  • Introduction to Kampo Medicine 2 （2022academic year） Fourth semester  - 金5～6

  • Introduction to Kampo Medicine A （2022academic year） Third semester  - 金5～6

  • Introduction to Kampo Medicine A （2022academic year） Third semester  - 金5～6

  • Introduction to Kampo Medicine B （2022academic year） Fourth semester  - 金5～6

  • Introduction to Kampo Medicine B （2022academic year） Fourth semester  - 金5～6

  • Pharmacognosy （2022academic year） 3rd and 4th semester  - 金1～2

  • Pharmacognosy （2022academic year） 3rd and 4th semester  - 金1～2

  • Pharmacognosy 1 （2022academic year） Third semester  - 金1～2

  • Pharmacognosy 1 （2022academic year） Third semester  - 金1～2

  • Pharmacognosy 2 （2022academic year） Fourth semester  - 金1～2

  • Pharmacognosy 2 （2022academic year） Fourth semester  - 金1～2

  • Guidance for Pharmaceutical Sciences （2022academic year） 1st and 2nd semester  - [第１学期]水4, [第２学期]月7

  • Guidance for Pharmaceutical Sciences （2022academic year） 1st and 2nd semester  - [第１学期]水4, [第２学期]月7

  • Guidance for Pharmaceutical Sciences （2022academic year） 1st and 2nd semester  - [第１学期]水4, [第２学期]月7

  • Guidance for Pharmaceutical Sciences （2022academic year） 1st and 2nd semester  - [第１学期]水4, [第２学期]月7

  • Practice in Fundamental Pharmaceutical Sciences II （2022academic year） 1st and 2nd semester  - その他5～9

  • Practice in Fundamental Pharmaceutical Sciences II （2022academic year） 1st and 2nd semester  - その他5～9

  • Chemistry of medicinal natural products I （2022academic year） special  - その他

  • Chemistry of medicinal natural products II （2022academic year） special  - その他

  • Familiar medicinal herbs and poisonous plants （2022academic year） 1st semester  - 木7～8

  • Medicinal Sciences （2021academic year） Second semester  - 金5～6

  • Medicinal Sciences （2021academic year） Third semester  - 金5～6

  • Introduction to Natural Product Chemistry （2021academic year） special  - その他

  • Seminar on Natural Product Chemistry （2021academic year） special  - その他

  • Natural Products Chemistry 1 （2021academic year） 1st semester  - 木7,木8

  • Natural Products Chemistry 1 （2021academic year） 1st semester  - 木7,木8

  • Natural Products Chemistry 2 （2021academic year） Second semester  - 木7,木8

  • Natural Products Chemistry 2 （2021academic year） Second semester  - 木7,木8

  • Organic Chemistry and Natural Products Chemistry （2021academic year） Late  - その他

  • Introduction to Kampo Medicine 1 （2021academic year） Third semester  - 金5,金6

  • Introduction to Kampo Medicine 1 （2021academic year） Third semester  - 金5,金6

  • Introduction to Kampo Medicine 2 （2021academic year） Fourth semester  - 金5,金6

  • Introduction to Kampo Medicine 2 （2021academic year） Fourth semester  - 金5,金6

  • Pharmacognosy （2021academic year） 3rd and 4th semester  - 金1,金2

  • Pharmacognosy （2021academic year） 3rd and 4th semester  - 金1,金2

  • Pharmacognosy 1 （2021academic year） Third semester  - 金1,金2

  • Pharmacognosy 1 （2021academic year） Third semester  - 金1,金2

  • Pharmacognosy 2 （2021academic year） Fourth semester  - 金1,金2

  • Pharmacognosy 2 （2021academic year） Fourth semester  - 金1,金2

  • Guidance for Pharmaceutical Sciences （2021academic year） 1st and 2nd semester  - [第１学期]水4, [第２学期]月1

  • Guidance for Pharmaceutical Sciences （2021academic year） 1st and 2nd semester  - [第１学期]水4, [第２学期]月1

  • Guidance for Pharmaceutical Sciences （2021academic year） 1st and 2nd semester  - [第１学期]水4, [第２学期]月1

  • Guidance for Pharmaceutical Sciences （2021academic year） 1st and 2nd semester  - [第１学期]水4, [第２学期]月1

  • Practice in Fundamental Pharmaceutical Sciences II （2021academic year） 1st and 2nd semester  - その他6～9

  • Practice in Fundamental Pharmaceutical Sciences II （2021academic year） 1st and 2nd semester  - その他6～9

  • Chemistry of medicinal natural products I （2021academic year） special  - その他

  • Chemistry of medicinal natural products II （2021academic year） special  - その他

  • Chemistry of Functional Natural Products 1 （2020academic year） Fourth semester  - その他

  • Chemistry of Functional Natural Products 1 （2020academic year） Fourth semester  - その他

  • Chemistry of Functional Natural Products 2 （2020academic year） Fourth semester  - その他

  • Chemistry of Functional Natural Products 2 （2020academic year） Fourth semester  - その他

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