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Development of Natural Product-like Library by Using Diversity-enhanced Extracts

Research Project

Project/Area Number 25350959
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

Kikuchi Haruhisa  東北大学, 薬学研究科(研究院), 准教授 (90302166)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords天然物化学 / 多様性指向型合成 / 化合物ライブラリー / 多様性拡大抽出物 / 構造決定 / セスキテルペン / メロテルペノイド
Outline of Final Research Achievements

Diversity-enhanced extracts are prepared from chemical reactions that remodel molecular scaffolds directly on extracts of natural resources. The subsequent isolation of each compound produced from such reactions affords a diverse natural product-like library. Although there have been several reports on similar methods that chemically convert natural extracts, diversity-enhanced extracts represents an unprecedented approach in terms of applying reactions to form new carbon-carbon bonds and modify molecular skeletons.
We applied this method of diversification on the medicinal plant, Curcuma zedoaria. Epoxidation and subsequent ring-opening reactions of epoxides were used to modify molecular skeletons. As a result, new and diverse sesquitepene-like compounds with some containing new molecular skeletons. Therefore, this method of diversification was efficient for producing chemically-diverse natural products.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (21 results)

All 2016 2015 2014 2013 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 2 results) Presentation (18 results) (of which Int'l Joint Research: 2 results,  Invited: 3 results)

  • [Journal Article] Isolation of a Cyclic Depsipetide, Aspergillicin F, and Synthesis of Aspergillicins with Innate Immune Modulating Activity2015

    • Author(s)
      Haruhisa Kikuchi, Tsuyoshi Hoshikawa, Shimpei Fujimura, Noriaki Sakata, Shoichiro Kurata, Yoshiteru Oshima
    • Journal Title

      Journal of Natural Products

      Volume: 78 Issue: 8 Pages: 1949-1956

    • DOI

      10.1021/acs.jnatprod.5b00286

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of prenylated quinolinecarboxylic acid derivatives and their anti-obesity activities2015

    • Author(s)
      Haruhisa Kikuchi, Toshiyuki Suzuki, Masato Ogura, Miwako K. Homma, Yoshimi Homma, Yoshiteru Oshima
    • Journal Title

      Bioorganic & Medicinal Chemistry

      Volume: 23 Issue: 1 Pages: 66-72

    • DOI

      10.1016/j.bmc.2014.11.024

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Development of Diversity-Enhanced Extracts of Curcuma zedoaria and Their New Sesquiterpene-like Compounds2014

    • Author(s)
      Haruhisa Kikuchi, Kazuyoshi Sakurai, Yoshiteru Oshima
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 7 Pages: 1916-1919

    • DOI

      10.1021/ol5004324

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 多様性拡大抽出物を活用した天然化合物類縁体ライブラリーの創出2016

    • Author(s)
      菊地 晴久
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 多様性拡大抽出物を利用したビアリール・ビアリールアミン型化合物群の創出2016

    • Author(s)
      榎大介, 中城陽太, 菊地晴久, 大島吉輝
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] 多様性拡大抽出物を利用したメロテルペノイド様化合物群の創出2016

    • Author(s)
      河合航輔, 中城陽太, 菊地晴久, 大島吉輝
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] Development of Natural Product-like Library by Using Diversity-enhanced Extracts2015

    • Author(s)
      Haruhisa Kikuchi, Yota Nakashiro, Kazuyoshi Sakurai, Keisuke Ichinohe, Daisuke Enoki, Yoshiteru Oshima
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Hilton Hawaiian Village Waikiki Beach Resort (Hawaii, USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 多様性拡大抽出物を利用した新規含窒素多環式化合物群の創出2015

    • Author(s)
      榎大介,菊地晴久,大島吉輝
    • Organizer
      第54回日本薬学会東北支部大会
    • Place of Presentation
      岩手医科大学(岩手県矢巾町)
    • Year and Date
      2015-09-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] 多様性拡大抽出物を利用した非天然型芳香族アルカロイド様化合物 ライブラリーの構築2015

    • Author(s)
      一戸佳祐,菊地晴久,大島吉輝
    • Organizer
      第54回日本薬学会東北支部大会
    • Place of Presentation
      岩手医科大学(岩手県矢巾町)
    • Year and Date
      2015-09-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] Development of Natural Product-like Library Derived from Diversity Enhanced Extracts2015

    • Author(s)
      Haruhisa Kikuchi
    • Organizer
      The 6th Japanese-Sino Symposium on Organic Chemistry for Young Scientists
    • Place of Presentation
      ホテルクレセント(仙台市)
    • Year and Date
      2015-09-06
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Humulene を基盤とした多様性指向型合成によるアルカロイド様化合物群の創出2015

    • Author(s)
      西村壮央,才川敦之,菊地晴久,大島吉輝
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院大学(神戸市)
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 多様性拡大抽出物を利用したインドールアルカロイド様化合物ライブラリーの創出2015

    • Author(s)
      一戸 佳祐, 菊地 晴久, 大島 吉輝
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      デザイン・クリエイティブセンター神戸(神戸市)
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] Development of Natural Product-like Library Derived from Diversity Enhanced Extracts2014

    • Author(s)
      Haruhisa Kikuchi, Yoshiteru Oshima
    • Organizer
      9th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Eastin Hotel Petaling Jaya, Malaysia
    • Year and Date
      2014-12-01 – 2014-12-04
    • Related Report
      2014 Research-status Report
  • [Presentation] 多様性拡大抽出物を利用した天然化合物様ライブラリーの構築2014

    • Author(s)
      菊地晴久,大島吉輝
    • Organizer
      第32回メディシナルケミストリーシンポジウム
    • Place of Presentation
      神戸国際会議場(神戸市)
    • Year and Date
      2014-11-26 – 2014-11-28
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] パラジウム触媒による結合形成反応を基盤とした多様性拡大抽出物2014

    • Author(s)
      中城陽太,菊地晴久,大島吉輝
    • Organizer
      第53回日本薬学会東北支部大会
    • Place of Presentation
      いわき明星大学(いわき市)
    • Year and Date
      2014-10-05
    • Related Report
      2014 Research-status Report
  • [Presentation] ホップ中に含まれるhumuleneの構造を基盤としたアルカロイド様化合物群の創出2014

    • Author(s)
      西村壮央,才川敦之,菊地晴久,大島吉輝
    • Organizer
      第53回日本薬学会東北支部大会
    • Place of Presentation
      いわき明星大学(いわき市)
    • Year and Date
      2014-10-05
    • Related Report
      2014 Research-status Report
  • [Presentation] Development of Natural Product-like Library Derived from Diversity Enhanced Extracts2014

    • Author(s)
      Haruhisa Kikuchi, Yoshiteru Oshima
    • Organizer
      24th French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      Faculte de medecine Lyon RTH Laennec, France
    • Year and Date
      2014-09-14 – 2014-09-17
    • Related Report
      2014 Research-status Report
  • [Presentation] パラジウム触媒反応を基盤とした多様性拡大抽出物とそれを利用した化合物ライブラリーの創出2014

    • Author(s)
      中城陽太,菊地晴久,大島吉輝
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本市青年会館(熊本市)
    • Related Report
      2013 Research-status Report
  • [Presentation] Development of Natural Product-like Library by Using Diversity-enhanced Natural Extracts2013

    • Author(s)
      Haruhisa Kikuchi, Kazuyoshi Sakurai, Tetsuri Watanabe, Yota Nakashiro, Yoshiteru Oshima
    • Organizer
      9th AFMC International Medicinal Chemistry Symposium in 2013
    • Place of Presentation
      Grand Hotel, Taipei, Taiwan
    • Related Report
      2013 Research-status Report
  • [Presentation] 多様性拡大抽出物を利用した天然化合物様ライブラリーの構築2013

    • Author(s)
      菊地晴久,櫻井和嘉,渡邉哲理,中城陽太,大島吉輝
    • Organizer
      第31回メディシナルケミストリーシンポジウム
    • Place of Presentation
      アステールプラザ(広島市)
    • Related Report
      2013 Research-status Report
  • [Presentation] 構造多様性を拡大したガジュツ抽出物より得られた新規化合物群

    • Author(s)
      櫻井和嘉,菊地晴久,大島吉輝
    • Organizer
      第52回日本薬学会東北支部大会
    • Place of Presentation
      東北大学川内北キャンパス(仙台市)
    • Related Report
      2013 Research-status Report

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

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