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Simple evaluation of authenticity of foods by using NMR method

Research Project

Project/Area Number 15K05533
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Analytical chemistry
Research InstitutionUniversity of Toyama

Principal Investigator

Aizawa Sen-ichi  富山大学, 大学院理工学研究部(工学), 教授 (60231099)

Project Period (FY) 2015-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
KeywordsNMRキラルシフト試薬 / ランタノイド錯体 / 食品の真正証明 / NMRキラルシグナル分離機構 / NMRシフト試薬
Outline of Final Research Achievements

Since addition of food adulterants makes a difference in enantiomer distribution from natural products, determination of the enantiomer compositions of organic compounds can become an evaluation of authenticity of natural foods. In this study, the NMR chiral shift reagents with high resolution performance have been developed to take advantage of NMR method, which can identify the compounds simpler than chromatographic or electrophoretic methods. Furthermore, prediction of the chiral signal separation behaviors have become possible by obtaining the parameters that determine the signal separation.

Academic Significance and Societal Importance of the Research Achievements

容易に入手できるL-アミノ酸等を連結させて不斉中心を増やしたことにより、ランタノイド錯体のキラルシグナル分離能を向上させた。さらに、付加体の生成定数と結合した基質の化学シフトを実験的に求めたため、測定しなくてもキラルシグナルの分離挙動が予想できるようになった点は学術的に注目に値する。また、開発途上にある可動式の低磁場NMRを利用することによって、食品の汎用的なその場分析にNMRが有効利用でき、新規な食品の真正証明システムを構築できると期待される。キラル化合物が含まれる農薬もあり、光学活性体間で分解・代謝過程や環境に対する影響も異なる場合があるため、農薬の動態分析にも有効な方法となりえる。

Report

(5 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (30 results)

All 2019 2018 2017 2016 2015

All Journal Article (10 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 10 results,  Acknowledgement Compliant: 2 results) Presentation (20 results) (of which Int'l Joint Research: 1 results)

  • [Journal Article] Separation of Synephrine Enantiomers in Citrus Fruits by a Reversed Phase HPLC after Chiral Precolumn Derivatization2019

    • Author(s)
      TANAKA Sohei、SEKIGUCHI Misaki、YAMAMOTO Atsushi、AIZAWA Sen-ichi、SATO Kanta、TAGA Atsushi、TERASHIMA Hiroyuki、ISHIHARA Yoshimi、KODAMA Shuji
    • Journal Title

      Analytical Sciences

      Volume: 35 Issue: 4 Pages: 407-412

    • DOI

      10.2116/analsci.18P441

    • NAID

      130007629974

    • ISSN
      0910-6340, 1348-2246
    • Year and Date
      2019-04-10
    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chiral separation of isoxanthohumol and 8-prenylnaringenin in beer, hop pellets and hops by HPLC with chiral columns2018

    • Author(s)
      Moriya Hyuga、Tanaka Sohei、Iida Yukari、Kitagawa Satomi、Aizawa Sen-ichi、Taga Atsushi、Terashima Hiroyuki、Yamamoto Atsushi、Kodama Shuji
    • Journal Title

      Biomedical Chromatography

      Volume: 32 Issue: 10

    • DOI

      10.1002/bmc.4289

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] HPLC Separation of Sulforaphane Enantiomers in Broccoli and Its Sprouts by Transformation into Diastereoisomers Using Derivatization with (S)-Leucine2017

    • Author(s)
      Okada Makiko、Yamamoto Atsushi、Aizawa Sen-ichi、Taga Atsushi、Terashima Hiroyuki、Kodama Shuji
    • Journal Title

      Journal of Agricultural and Food Chemistry

      Volume: 65 Issue: 1 Pages: 244-250

    • DOI

      10.1021/acs.jafc.6b04966

    • Related Report
      2017 Research-status Report 2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Enantiomeric NMR signal separation behavior and mechanism of samarium(III) and neodymium(III) complexes with (S,S)-ethylenediamine-N,N'-disuccinate2017

    • Author(s)
      Aizawa Sen-ichi、Okano Masaru、Kidani Takahiro
    • Journal Title

      Chirality

      Volume: 29 Issue: 6 Pages: 273-281

    • DOI

      10.1002/chir.22681

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Simultaneous determination of alcohols including diols and triols by HPLC with ultraviolet detection based on the formation of a copper(II) complex2017

    • Author(s)
      Tanaka Sohei、Dohi Takumi、Aizawa Sen-ichi、Kemmei Tomoko、Terashima Hiroyuki、Taga Atsushi、Yamamoto Atsushi、Kodama Shuji
    • Journal Title

      Journal of Separation Science

      Volume: 40 Issue: 21 Pages: 4168-4175

    • DOI

      10.1002/jssc.201700635

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Enantiomeric NMR Signal Separation Behavior and Mechanism of Samarium(III) and Neodymium(III) Complexes with (S,S)-Ethylenediamine-N,N’-Disuccinate2017

    • Author(s)
      S. Aizawa, M. Okano, T. Kidani,
    • Journal Title

      Chirality

      Volume: 印刷中

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Simple Resolution of Enantiomeric NMR Signals of Alpha-Amino Acids by Using Samarium(III) Nitrate with L-Tartarate2015

    • Author(s)
      S. Aizawa, T. Kidani, S. Takada, Y. Ofusa
    • Journal Title

      Chirality

      Volume: 27 Issue: 5 Pages: 353-357

    • DOI

      10.1002/chir.22443

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Simultaneous Enantioseparation of Aldohexoses and Aldopentoses Derivatized with L-Tryptophanamide by Reversed Phase HPLC Using Butylboronic Acid as a Complexation Reagent of Monosaccharides2015

    • Author(s)
      M. Shou, H. Terashima, S. Aizawa, A. Taga, A. Yamamoto, S. Kodama
    • Journal Title

      Chirality

      Volume: 27 Issue: 7 Pages: 417-421

    • DOI

      10.1002/chir.22456

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Simultaneous Determination of Trigonelline, Caffeine, Chlorogenic Acid and Their Related Compounds in Instant Coffee Samples by HPLC Using an Acidic Mobile Phase Containing Octanesulfonate2015

    • Author(s)
      K. Arai, H. Terashima, S. Aizawa, A. Taga, A. Yamamoto, K. Tsutsumiuchi, S. Kodama
    • Journal Title

      Analytical Sciences

      Volume: 31 Issue: 8 Pages: 831-835

    • DOI

      10.2116/analsci.31.831

    • NAID

      130005092123

    • ISSN
      0910-6340, 1348-2246
    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Polymer-Supported Optically Active fac(S)-Tris(thiotato)rhodium(III) Complex for Sulfur-Bridging Reaction with Precious Metal Ions2015

    • Author(s)
      S. Aizawa, S. Tsubosaka
    • Journal Title

      Chirality

      Volume: 27 Issue: 1 Pages: 1200-1206

    • DOI

      10.1002/chir.22546

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 不斉小分子を有するCo(III)Cl(TPPS)錯体の不斉会合体形成2019

    • Author(s)
      太田直希、會澤宣一
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] オルト置換ジフェニルトリアゼニド配位子を有するPd(I)-Pd(I)二核錯体の触媒活性2018

    • Author(s)
      中橋有太、會澤宣一
    • Organizer
      錯体化学会第68回討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Speciation of Ru(II)(p-cymene) with Amino Acids and Reaction Mechanism of Their Formation2018

    • Author(s)
      Sen-ichi Aizawa, Kouhei Takizawa
    • Organizer
      43rd International Conference on Coordination Chemistry
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] プレカラム誘導体化法による柑橘類中シネフリンのキラルHPLC分析2018

    • Author(s)
      田中壮平、山本敦、會澤宣一、多賀淳、寺島弘之、小玉修嗣
    • Organizer
      日本分析化学会第67回年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 日本酒中フェルラ酸のHPLC分析2018

    • Author(s)
      小玉修嗣、石下雄介、後藤宏章、田中壮平、佐野博之、山本敦、會澤宣一、多賀 淳、寺島 弘之
    • Organizer
      日本分析化学会第67回年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] アブシシン酸の光学異性体分析2018

    • Author(s)
      田中壮平、山本敦、會澤宣一、多賀 淳、小玉修嗣
    • Organizer
      第35回イオンクロマトグラフィー討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 柑橘類中シネフリンの光学異性体分析2018

    • Author(s)
      田中壮平、山本敦、多賀淳、會澤宣一、寺島弘之、小玉修嗣
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Presentation] ビール中のイソキサントフモール及び8-プレニルナリンゲニンの光学異性体分析2018

    • Author(s)
      小玉修嗣、田中壮平、守屋日向、飯田結香莉、北川 仁美、會澤宣一、山本敦、多賀淳、寺島弘之
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 銅錯体形成を利用したアルコール類のHPLC分析2017

    • Author(s)
      田中壮平、土肥巧、會澤宣一、山本敦、多賀淳、寺島弘之、小玉修嗣
    • Organizer
      第77回分析化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] スルフォラファンの光学異性体分析 ~ブロッコリーの花蕾と茎中の光学異性体比の検討~2017

    • Author(s)
      岡田眞希子、山本敦、會澤宣一、多賀淳、寺島弘之、小玉修嗣
    • Organizer
      第77回分析化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] Pd(OAc)2を用いたI2によるフェニル基のオルトヨウ素化反応の機構論的研究2017

    • Author(s)
      竹内陽一、會澤宣一
    • Organizer
      錯体化学会第67回討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] L-アスパラギン酸架橋配位子を有するランタノイド(Ⅲ)錯体のキラル分子に対するNMRシグナル分離機構2017

    • Author(s)
      高木一樹、岡野優、會澤宣一
    • Organizer
      錯体化学会第67回討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 不斉アミンおよびアミノ酸を有するポルフィリン錯体のCD特性2017

    • Author(s)
      太田直希、會澤宣一
    • Organizer
      平成29年度北陸地区講演会と研究発表会
    • Related Report
      2017 Research-status Report
  • [Presentation] ブロッコリー中のスルフォラファンの光学異性体分析2016

    • Author(s)
      岡田眞希子、寺島博之、會澤宣一、多賀淳、山本敦、小玉修嗣
    • Organizer
      日本分析化学会第65回年会
    • Place of Presentation
      札幌
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] 単糖類の光学異性体分析2016

    • Author(s)
      岡田眞希子、寺島博之、山本敦、會澤宣一、多賀淳、小玉修嗣
    • Organizer
      日本分析化学会第65回年会
    • Place of Presentation
      札幌
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] ジフェニルホスフィンから三級ホスフィンとジホスフィンを生成するCuおよびNi触媒の反応2016

    • Author(s)
      仁井大志、會澤宣一
    • Organizer
      錯体化学会第66回討論会
    • Place of Presentation
      福岡
    • Year and Date
      2016-09-10
    • Related Report
      2016 Research-status Report
  • [Presentation] L-アスパラギン酸エチレン架橋配位子を持つランタノイド(III)錯体の不斉分子に対するNMR特性2016

    • Author(s)
      岡野優、高木一樹、會澤宣一
    • Organizer
      錯体化学会第66回討論会
    • Place of Presentation
      福岡
    • Year and Date
      2016-09-10
    • Related Report
      2016 Research-status Report
  • [Presentation] Ni(II)、Co(II)、Cu(I)触媒を用いたヨウ化アリールと二硫化ジフェニル、チオフェノール、ベンジルアミンのカップリング反応2015

    • Author(s)
      岡本哲哉、邑井裕一、山田裕也、會澤宣一
    • Organizer
      錯体化学会第65回討論会
    • Place of Presentation
      奈良
    • Year and Date
      2015-09-21
    • Related Report
      2015 Research-status Report
  • [Presentation] L-グルタミン酸及びL-アスパラギン酸エチレン架橋配位子を有するランタノイド錯体のNMRキラルシフト試薬としての特性2015

    • Author(s)
      岡野優、木谷崇宏、會澤宣一
    • Organizer
      錯体化学会第65回討論会
    • Place of Presentation
      奈良
    • Year and Date
      2015-09-21
    • Related Report
      2015 Research-status Report
  • [Presentation] L-アミノ酸誘導体化単糖の光学異性体分離2015

    • Author(s)
      翔美玲、寺島博之、會澤宣一、多賀淳、山本敦、小玉修嗣
    • Organizer
      日本分析化学会第64回年会
    • Place of Presentation
      福岡
    • Year and Date
      2015-09-09
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2020-03-30  

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