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Chemical structure analysis of lignin using reductive treatment

Research Project

Project/Area Number 15K14767
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Wood science
Research InstitutionThe University of Tokyo

Principal Investigator

Akiyama Takuya  東京大学, 大学院農学生命科学研究科(農学部), 助教 (50553723)

Project Period (FY) 2015-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2015: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Keywordsリグニン / 還元 / 木質細胞壁 / 圧縮あて材 / 縮合型構造 / ビフェニル / 5-ホルミルバニリン / ダイバニリン / 5-フォルミルバニリン / 立体化学 / メチレン / 還元処理 / 還元型リグニン
Outline of Final Research Achievements

We tried to develop a new chemical analytical method of lignin to detect microstructural differences between compression wood of softwood and the opposite wood. It was investigated to convert the benzyl hydroxy group at the α position to a methylene group, thereby reducing the number of asymmetric carbons by half and eliminating the structural complexity caused by stereoisomerism. Although the experiments using model compounds showed the effectiveness of this method, it did not lead to the establishment of a new analysis method for a lignin sample. Therefore, as a result of changing the analysis method to the existing nitrobenzene oxidation method and re-examining the experimental scheme, the scope of analysis was broadened, and it became possible to analyze not only non-condensed-type but also condensed-type structures. New findings were obtained regarding the frequency of condensed-type structures in compression wood lignins.

Academic Significance and Societal Importance of the Research Achievements

木質材料の特性や木質化現象を理解するために、ニトロベンゼン酸化法はリグニンの基本構造や化学的特徴を調べる手法として広く用いられ、その再現性の高さから最も信頼性の高い分析手法の一つとみなされている。通常、非縮合型構造の含有量や芳香核型(H、G、S核型)の構成比など基本構造の比較に利用されるが、これに加えて縮合型構造に関する情報を引き出すことが可能であると1950年代から指摘されてきた。本研究成果により縮合型分解生成物の定量的評価が可能となり、非縮合型/β-5型/ビフェニル型の構成比に関して、リグニン試料間における微細な違いをニトロベンゼン酸化法で比較することが可能になった。

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

    (24 results)

All 2019 2018 2017 2016 Other

All Int'l Joint Research (1 results) Journal Article (8 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 8 results,  Open Access: 1 results) Presentation (8 results) (of which Int'l Joint Research: 2 results) Book (5 results) Remarks (2 results)

  • [Int'l Joint Research] Bogor Agricultural University(インドネシア)

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Influence of the p-hydroxyphenyl/guaiacyl ratio on the biphenyl and β-5 contents in compression wood lignins.2019

    • Author(s)
      Haruka Hirayama, Takuya Akiyama, Satoshi Kimura, Deded S. Nawawi, Wasrin Syafii, Tomoya Yokoyama, Yuji Matsumoto.
    • Journal Title

      Holzforschung (論文受理 2019年4月2日)

      Volume: 未定 Issue: 10 Pages: 923-935

    • DOI

      10.1515/hf-2019-0012

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Variation of the contents of biphenyl structures in lignins among wood species.2019

    • Author(s)
      Haruka Hirayama, Takuya Akiyama, Akari Tamai, Deded S. Nawawi, Wasrin Syafii, Tomoya Yokoyama, Yuji Matsumoto.
    • Journal Title

      Holzforschung (論文受理 2018年12月6日)

      Volume: 未定 Issue: 6 Pages: 569-578

    • DOI

      10.1515/hf-2018-0196

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Lignin-biosynthetic study: Reactivity of quinone methides in the diastereopreferential formation of p-hydroxyphenyl- and guaiacyl-type β-O-4 structures.2019

    • Author(s)
      Xuhai Zhu, Takuya Akiyama, Tomoya Yokoyama, Yuji Matsumoto.
    • Journal Title

      Journal of Agricultural and Food Chemistry

      Volume: 67 Issue: 8 Pages: 2139-2147

    • DOI

      10.1021/acs.jafc.8b06465

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Characteristic of β-O-4 structures in different reaction wood lignins of Eusideroxylon zwageri T. et B. and four other woody species.2017

    • Author(s)
      Deded Sarip Nawawi, Takuya Akiyama, Wasrin Syafii, and Yuji Matsumoto
    • Journal Title

      Holzforschung

      Volume: 71 Issue: 1 Pages: 11-20

    • DOI

      10.1515/hf-2016-0100

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] リグニンのβ-O-4構造の化学構造的特徴とその樹種間における多様性について2016

    • Author(s)
      秋山拓也
    • Journal Title

      触媒

      Volume: 58 Pages: 61-66

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] NMR assignment for diaryl ether structures (4-O-5 structures) in pine wood lignin.2016

    • Author(s)
      Yanding Li, Takuya Akiyama, Tomoya Yokoyama, Yuji Matsumoto
    • Journal Title

      Biomacromolecules

      Volume: 17 Issue: 6 Pages: 1921-1929

    • DOI

      10.1021/acs.biomac.6b00257

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Characteristics of guaiacyl-syringyl lignin in reaction wood in the gymnosperm Gnetum gnemon L.2016

    • Author(s)
      Deded Sarip Nawawi, Wasrin Syafii, Takuya Akiyama, and Yuji Matsumoto
    • Journal Title

      Holzforschung

      Volume: 70 Issue: 7 Pages: 593-602

    • DOI

      10.1515/hf-2015-0107

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Analysis of Lignin Aromatic Structure in Wood Fractions Based on IR Spectroscopy.2016

    • Author(s)
      Yu Huang, Zhiguo Wang, Linshan Wang, Yuesheng Chao, Takuya Akiyama, Tomoya Yokoyama, Yuji Matsumoto
    • Journal Title

      Journal of Wood Chemistry and Technology

      Volume: 36 Issue: 5 Pages: 377-382

    • DOI

      10.1080/02773813.2016.1179325

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] 針葉樹あて材のリグニンにおけるH/G比とビフェニル型構造量との関係性2019

    • Author(s)
      平山晴加、秋山拓也、木村聡、Deded S. Nawawi、Wasrin Syafii、横山朝哉、松本雄二
    • Organizer
      第69回日本木材学会大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 針葉樹単離リグニンの分子量分画とビフェニル型構造の分布2018

    • Author(s)
      羽田尚希、秋山拓也、横山朝哉、松本雄二
    • Organizer
      第63回リグニン討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Difference in the content of biphenyl structures between the compression and the opposite wood lignins of Japanese cedar.2018

    • Author(s)
      Haruka Hirayama, Takuya Akiyama, Tomoya Yokoyama and Yuji Matsumoto.
    • Organizer
      International Convention of Society of Wood Science and Technology and Japan Wood Research Society
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Stereo-preferential formation of p-hydroxyphenyl-type β-O-4 structures from the quinone methides: Part 2. Water addition to a quinone methide β-etherified with a biphenyl unit.2018

    • Author(s)
      Xuhai Zhu, Takuya Akiyama, Tomoya Yokoyama and Yuji Matsumoto.
    • Organizer
      第68回木材学会大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] スギあて材のリグニンにおけるH/G比とビフェニル型構造量との関係性2018

    • Author(s)
      平山晴加、秋山拓也、松本雄二
    • Organizer
      第68回日本木材学会大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] NMR assignment for diaryl ether structures (4-O-5 structures) in pine wood lignin.2016

    • Author(s)
      Yanding Li, Takuya Akiyama, Tomoya Yokoyama, Yuji Matsumoto
    • Organizer
      5th International Symposium on Emerging Technologies of Pulping and Papermaking & 3rd International Papermaking and Environment Conference
    • Place of Presentation
      University Town International Hotel (中国、広州)
    • Year and Date
      2016-11-06
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 解析法の概要と樹木リグニンの化学構造的特徴2016

    • Author(s)
      秋山拓也
    • Organizer
      第61回リグニン討論会
    • Place of Presentation
      京都大学宇治キャンパス(京都、宇治)
    • Year and Date
      2016-10-27
    • Related Report
      2016 Research-status Report
  • [Presentation] β-1型構造に関する研究:3量体モデル化合物のNMRデータに基づく広葉樹リグニン中のスピロジエノン構造の同定2016

    • Author(s)
      秋山拓也、横山朝哉、松本雄二
    • Organizer
      第61回リグニン討論会
    • Place of Presentation
      京都大学宇治キャンパス(京都、宇治)
    • Year and Date
      2016-10-27
    • Related Report
      2016 Research-status Report
  • [Book] 植物細胞壁実験法(分担2.1.2項 NMRによるリグニンの化学構造解析)2016

    • Author(s)
      秋山拓也
    • Total Pages
      7
    • Publisher
      弘前大学出版会
    • Related Report
      2016 Research-status Report
  • [Book] 植物細胞壁実験法(分担3.5.1項 ニトロベンゼン酸化)2016

    • Author(s)
      秋山拓也
    • Total Pages
      4
    • Publisher
      弘前大学出版会
    • Related Report
      2016 Research-status Report
  • [Book] 植物細胞壁実験法(分担3.5.7項 オゾン分解法)2016

    • Author(s)
      秋山拓也
    • Total Pages
      4
    • Publisher
      弘前大学出版会
    • Related Report
      2016 Research-status Report
  • [Book] 植物細胞壁実験法(分担3.5.10項 メトキシ基定量)2016

    • Author(s)
      秋山拓也
    • Total Pages
      3
    • Publisher
      弘前大学出版会
    • Related Report
      2016 Research-status Report
  • [Book] 植物細胞壁実験法(分担9.4項 リグニンNMRデータベース)2016

    • Author(s)
      秋山拓也
    • Total Pages
      2
    • Publisher
      弘前大学出版会
    • Related Report
      2016 Research-status Report
  • [Remarks] 東京大学 木材化学研究室

    • Related Report
      2018 Annual Research Report
  • [Remarks] 東京大学木材化学研究室 業績 秋山拓也

    • URL

      http://www.woodchemistry.fp.a.u-tokyo.ac.jp/member003001.pdf

    • Related Report
      2016 Research-status Report

URL: 

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

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