第1章
Adler E, Lignin chemistry-past, present and future, Wood Science and Technology, 11, 169 (1977)
Akiyama T and Ralph J, Characteristics in 1H- and 13C-NMR chemical shifts of non-phenolic dibenzodioxocin model compounds as branch-points in lignin, 第52回リグニン討論会要旨集, 東京, 84 (2008)
Akiyama T, Dixon RA, Kim H and Ralph J, Novel dibenzodioxocin structures involving p- hydroxyphenyl units on their biphenyl units,第53回リグニン討論会要旨集, 静岡, 66 (2009)
Ämmälahti E, Brunow G, Bardet M, Robert D and Kilpeläinen I, Identification of side-chain structures in a poplar lignin using three-dimensional HMQC-HOHAHA NMR spectroscopy, Journal of Agricultural and Food Chemistry, 46, 5113 (1998)
Björkman A, Studies on finely divided wood. Part 5. The effect of milling, Sevensk Papperstidn, 60, 329 (1957)
Bose SK, Wilson KL, Francis RC and Aoyama M, Lignin analysis by permanganate Oxidation. I. Native spruce lignin, Holzforschung, 52, 297 (1998)
Brunow G, Karhunen P, Lundquist K and Olson S, Investigation of lignin models of the biphenyl type by X-ray crystallography and NMR spectroscopy, Journal of Chemical Crystallography, 25, 1 (1995)
Capanema EA, Balakshin MY, Kadla JF, A comprehensive approach for quantitative lignin characterization by NMR spectroscopy, Journal of Agricultural and Food Chemistry, 52, 1850 (2004)
Chang HM and Allan GG, Oxidation, In: Lignins-occurrence, formation, structure and reactions, Eds. Sarkanen KV and Ludwig GH, Wiley-Interscience, New York, 433-485 (1971)
Chang HM, Cowling EB, Brown W, Adler E and Miksche G, Comparative studies on cellulolytic enzyme lignin and milled wood lignin of sweetgum and spruce, Holzforschung, 29, 153 (1975)
Chen CL, Characterization of lignin by oxidative degradation: use of gas chromatography-mass spectrometry technique, Methods in Enzymology, 161, 110 (1988)
Crestini C, Melone F, Sette M and Saladino R, Milled wood lignin: A linear oligomer, Biomacromolecules, 12, 3928 (2011)
Dershem SM, Fisher TH, Johnson S and Schultz TP, Substituent effects in nitrobenzene and copper (II) oxidations of some hydroxystilbene lignin model compounds, Holzforschung, 42, 163 (1988)
Dimmel D, Overview, In: Lignin and lignans, Eds. Heitner C, Dimmel DR and Schmidt JA, CRC Press (Taylor & Francis Group), Boca Raton, FL, 137-234 (2010)
Drumond M, Aoyama M, Chen CL and Robert D, Substituent effects on C-13 chemical shifts of aromatic carbons in biphenyl type lignin model compounds, Journal of Organic Chemistry, 9, 421 (1989)
Erickson M, Larsson S and Miksche GE, Gaschromatographische Analyse von ligninoxydations- produkten. VIII. Zur des lignins der fichte, Acta Chemica Scandinavica, 27, 903 (1973a)
Erickson M, Larsson S and Miksche GE, Zur der lignins des druckholzes von Pinus mugo, Acta Chemica Scandinavica, 27, 1673 (1973b)
Fujimoto A, Matsumoto Y, Chang HM and Meshitsuka Gyosuke, Quantitative evaluation of milling effects on lignin structure during the isolation process of milled wood lignin, Journal of Wood Science, 51, 89 (2005)
Karhunen P, Rummakko P, Sililä J and Brunow G, Dibenzodioxocins; A novel type of linkage in softwood lignins, Tetrahedron Letters, 36, 169 (1995)
Kishimoto T, Chiba W, Saito K, Fukushima K, Uraki Y and Ubukata M, Influence of syringyl to guaiacyl ratio on the structure of natural and synthetic lignins, Journal of Agricultural and Food Chemistry, 58, 895 (2010)
Lapierre C, Pollet B, Monties B and Roland C, Thioacidolysis of spruce lignin-GC-MS analysis of the main dimers recovered after raney-nickel desulfuration, Holzforschung, 45, 61 (1991)
Larsson S and Miksche GE, Gaschromatographische analyse von ligninoxydationsprodukten. IV. Zur struktur des lignins der brike, Acta Chemica Scandinavica, 25, 647 (1971)
Lange W and Faix O, Lignin-polyphenol interaction in azobe (Lophira alata) heartwood. A study on milled wood lignin (MWL) and Klason residues, Holzforschung, 53, 519 (1999)
Lee ZZ, Meshitsuka G, Cho NS and Nakano J, Characterization of milled wood lignins isolated with different milling times, Mokuzai Gakkaishi, 27, 671 (1981)
Leopold B, Studies on lignin III. Oxidation of wood from Picea abis(L.) Karst.(Norway Spruce) with nitrobenzene and alkali, Acta Chemica Scandinavica, 6, 38 (1952)
Li Y, Akiyama T, Yokoyama T and Matsumoto Y, NMR assignment for diaryl ether structures (4-O-5 structures) in pine wood lignin, Biomacromolecules, 17, 1921 (2016)
Lu F and Ralph J, Non-degradative dissolution and acetylation of ball-milled plant cell walls: high- resolution solution-state NMR, The Plant Journal, 35, 535 (2003)
Lundquist K, Isolation and purification: wood. In: Methods in lignin chemistry. Eds. Lin SY, Dence CW, Springer-Verlag, Berlin, 65-70 (1992)
Matsukura M and Sakakibara A, On the heterogeneous distribution of chemical structure in lignin, Mokuzai Gakkaishi, 15, 35 (1969)
Obst JR and Kirk TK, Isolation of lignin, Methods Enzymol, 161(Biomass, Pt. B), 3-12 (1988)
Parkas J, Brunow G and Lundquist K, Quantitative lignin analysis based on permanganate oxidation, Bioresources, 2, 169 (2007)
Pew JC, Nitrobenzene oxidation of lignin model compounds, spruce wood and spruce “native lignin”, Journal of the American Chemical Society, 77, 2831 (1955)
Pew JC, Evidence of a biphenyl group in lignin, Journal of Organic Chemistry, 28, 1048 (1963)
Ralph J, Akiyama T, Kim H, Lu F, Schatz PF, Marita JM, Ralph SA, Reddy MSS, Chen F and Dixon RA, Effects of coumarate 3-hydroxylase down-regulation on lignin structure, The Journal of Biological Chemistry, 281, 8843 (2006)
Saito K and Fukushima K, Distribution of lignin interunit bonds in the differentiating xylem of compression and normal woods of Pinus thunbergii, Journal of Wood Science, 51, 246 (2005)
Schultz TP and Templeton MC, Proposed mechanism for the nitrobenzene oxidation of lignin, Holzforschung, 40, 93 (1986)
Schultz TP, Fisher TH and Dershem SM, Role of the p-hydroxyl group in the nitrobenzene oxidation of p-hydroxybenzyl alcohols, The Journal of Organic Chemistry, 52, 279 (1987)
Tamai A, Goto H, Akiyama T and Matsumoto Y, Revisiting alkaline nitrobenzene oxidation: Quantitative evaluation of biphenyl structures in cedar wood lignin (cryptomeria japonica) by a modified nitrobenzene oxidation method, Holzforschung, 69, 951 (2015)
Tanaka J and Kondo T, Studies on degradation of lignin. Ⅱ. Nitrobenzene oxidation products of hardwood lignin, Mokuzai Gakkaishi, 4, No.1, 34 (1958)
Yamasaki T and Higuchi T, p-Hydroxyphenyl component of grass lignin, Mokuzai Gakkaishi, 17, 117 (1971)
Yamasaki T and Higuchi T, Chemical properties of enzymic dehydrogenation polymer from p- coumaryl alcohol, Mokuzai Gakkaishi, 18, 361 (1972)
Yasuda S and Sakakibara A, Hydrogenolysis of protolignin in compression wood. III. Isolation of four dimeric compounds with carbon to carbon linkage, Mokuzai Gakkaishi, 23, 114 (1977)
Yue F, Lu F, Ralph S and Ralph J, Identification of 4-O-5-units in softwood lignins via definitive lignin models and NMR, Biomacromolecules, 17, 1909 (2016)
Yue F, Lu F, Regner M, Sun R and Ralph J, Lignin-derived thioacidolysis dimers: Reevaluation, new products, authentication, and quantification, ChemSusChem, 10, 830 (2017)
黒田健一、リグニンの単離、日本木材学会編、木質の化学、文永堂出版株式会社、173-178 (2010)
越島哲夫、単離法、中野準三編、リグニンの化学―基礎と応用―(増強改訂版)、ユニ出版株式会社、37-49 (1990)
第2章
Akiyama T, Goto H, Nawawi SD, Syafii W, Matsumoto Y and Meshitsuka G, Erythro/threo ratio of β-O-4-structures as an important structural characteristic of lignin. Part 4: Variation in the erythro/threo ratio in softwood and hardwood lignins and its relation to syringyl/guaiacyl ratio, Holzforschung, 59, 276 (2005)
Bose SK, Wilson KL, Francis RC and Aoyama M, Lignin analysis by permanganate Oxidation. I. Native spruce lignin, Holzforschung, 52, 297 (1998)
Capanema EA, Balakshin MY, Kadla JF, A comprehensive approach for quantitative lignin characterization by NMR spectroscopy, Journal of Agricultural and Food Chemistry, 52, 1850 (2004)
Chen CL, Characterization of lignin by oxidative degradation: use of gas chromatography-mass spectrometry technique, Methods in Enzymology, 161, 110 (1988)
Drumond M, Aoyama M, Chen CL and Robert D, Substituent effects on C-13 chemical shifts of aromatic carbons in biphenyl type lignin model compounds, Journal of Organic Chemistry, 9, 421 (1989)
Kishimoto T, Chiba W, Saito K, Fukushima K, Uraki Y and Ubukata M, Influence of syringyl to guaiacyl ratio on the structure of natural and synthetic lignins, Journal of Agricultural and Food Chemistry, 58, 895 (2010)
Li Y, Akiyama T, Yokoyama T and Matsumoto Y, NMR assignment for diaryl ether structures (4-O-5 structures) in pine wood lignin, Biomacromolecules, 17, 1921 (2016)
Pew JC, Evidence of a biphenyl group in lignin, Journal of Organic Chemistry, 28, 1048 (1963)
Ralph J, Akiyama T, Kim H, Lu F, Schatz PF, Marita JM, Ralph SA, Reddy MSS, Chen F and Dixon RA, Effects of coumarate 3-hydroxylase down-regulation on lignin structure, The Journal of Biological Chemistry, 281, 8843 (2006)
Tamai A, Goto H, Akiyama T and Matsumoto Y, Revisiting alkaline nitrobenzene oxidation: Quantitative evaluation of biphenyl structures in cedar wood lignin (cryptomeria japonica) by a modified nitrobenzene oxidation method, Holzforschung, 69, 951 (2015)
Yamasaki T and Higuchi T, p-Hydroxyphenyl component of grass lignin, Mokuzai Gakkaishi, 17, 117 (1971)
Yue F, Lu F, Sun RC and Ralph J, Syntheses of lignin-derived thioacidolysis monomers and their uses as quantitation standards, Journal of Agricultural and Food Chemistry, 60, 922 (2012)
Yue F, Lu F, Regner M, Sun R and Ralph J, Lignin-derived thioacidolysis dimers: reevaluation, new products, authentication, and quantification, ChemSusChem, 10, 830 (2017)
第3章
Billa E, Tollies MT and Monties B, Characterization of the monomeric composition of in situ wheat straw lignins by alkaline nitrobenzene oxidation: Effect of temperature and reaction time, Journal of the Science of Food and Agriculture, 72, 250 (1996)
Chan FD, Nguyen KL and Wallis AFA, Contribution of lignin sub-structures to nitrobenzene oxidation products, Journal of Wood Chemistry and Technology, 15, 329 (1995)
Iiyama K and Lam TBT, Lignin in wheat internodes. Part 1: The reactivities of lignin units during alkaline nitrobenzene oxidation, Journal of Agricultural and Food Chemistry, 51, 481 (1990)
Min D, Xiang Z, Liu J, Jameel H, Chiang V, Jin Y and Chang HM, Improved protocol for alkaline nitrobenzene oxidation of woody and non-woody biomass, Journal of Wood Chemistry and Technology, 35, 52 (2015)
Quideau S and Ralph J, Facile large-scale synthesis of coniferyl, sinapyl, and p-coumaryl alcohol, Journal of Agricultural and Food Chemistry, 40, 1108 (1992)
Reinhoudt DN, de Jong F, van de Vondervoort EM, Crown ethers with converging neutral binding sites: Synthesis and complexation with t-butylammonium hexafluorophosphate, Tetrahedron, 37, 1753(1981)
Tamai A, Goto H, Akiyama T and Matsumoto Y, Revisiting alkaline nitrobenzene oxidation: Quantitative evaluation of biphenyl structures in cedar wood lignin (Cryptomeria japonica) by a modified nitrobenzene oxidation method, Holzforschung, 69, 951 (2015)
奥野芳樹、グアイアシル型フェニルクマラン化合物のニトロベンゼン酸化、卒業論文 (2016)
第4章
Akiyama T, Dixon RA, Kim H and Ralph J, Novel dibenzodioxocin structures involving p- hydroxyphenyl units on their biphenyl units, 第53回リグニン討論会要旨集, 静岡, 66 (2009)
Billa E, Tollies MT and Monties B, Characterization of the monomeric composition of in situ wheat straw lignins by alkaline nitrobenzene oxidation: Effect of temperature and reaction time, Journal of the Science of Food and Agriculture, 72, 250 (1996)
Bland DE, The chemistry of reaction wood part I. The lignins of Eucalyptus goniocalyx and Pinus radiata, Holzforschung, 12, 36 (1958)
Bland DE, The properties of syringyl, guaiacyl and p-hydroxyphenyl artificial lignins, Biochemical Journal, 95, 515 (1965)
Dence CW, The determination of lignin, In: Methods in lignin chemistry, Eds. Lin SY and Dence CW, Springer-Verlag, Berlin, 33-58 (1992)
Erickson M, Larsson S and Miksche GE, Gaschromatographische analyse von ligninoxydations- produkten. VIII. Zur des lignins der fichte, Acta Chemica Scandinavica, 27, 903 (1973a)
Erickson M, Larsson S and Miksche GE, Zur der lignins des druckholzes von Pinus mugo, Acta Chemica Scandinavica, 27, 1673 (1973b)
Fukushima K and Terashima N, Heterogeneity in formation of lignin XV. Formation and structure of lignin in compression wood of Pinus thunbergii studied by microautoradiography, Wood Science and Technology, 25, 371 (1991)
Goto H, Koda K, Matsumoto Y and Meshitsuka G, Precise determination of methoxyl content as an important indication of the extent of lignin oxidation remaining in bleached pulp, Proceedings of the 11th ISWPC Main Symposium, 3, 417 (2001)
Iiyama K and Lam TBT, Lignin in wheat internodes. Part 1: The reactivities of lignin units during alkaline nitrobenzene oxidation, Journal of Agricultural and Food Chemistry, 51, 481 (1990)
Jacquet G, Brigitte P, Lapierre C, Francesch C, Roland C and Faix O, Thioacidolysis of enzymatic dehydrogenation polymers from p-hydroxyphenyl, guaiacyl, and syringyl precursers, Holzforschung, 51, 349 (1997)
Lapierre C and Monties B, Thioacidolyses of diazomethane methylated pine compression wood and wheat straw in situ lignins, Holzforschung, 42, 409 (1988)
Li Y, Akiyama T, Yokoyama T and Matsumoto Y, NMR assignment for diaryl ether structures (4-O-5 structures) in pine wood lignin, Biomacromolecules, 17, 1921(2016)
Meshitsuka G and Nakano J, Structural characteristics of compound middle lamella lignin, Journal of Wood Chemistry and Technology, 5, 391 (1985)
Min D, Xiang Z, Liu J, Jameel H, Chiang V, Jin Y and Chang HM, Improved protocol for alkaline nitrobenzene oxidation of woody and non-woody biomass, Journal of Wood Chemistry and Technology, 35, 52 (2015)
Morohoshi N and Sakakibara A, The chemical composition of reaction wood. I., Mokuzai Gakkaishi, 17, 393 (1971a)
Morohoshi N and Sakakibara A, The chemical composition of reaction Wood. II., Mokuzai Gakkaishi, 17, 400 (1971b)
Nakano J and Meshitsuka G, The detection of lignin, In: Methods in lignin chemistry, Eds. Lin SY and Dence CW, Springer-Verlag, Berlin, 23-32 (1992)
Nanayakkara B, Harris MM and Sackling ID, Understanding the degree of condensation of phenolic and etherified C-9 units of in situ lignins, Journal of Agricultural and Food Chemistry, 59, 12514 (2011)
Nawawi SD, Akiyama T, Syafii W and Matsumoto Y, Characteristic of β-O-4 structures in different reaction wood lignins of Eusideroxylon zwageri T. et B. and four other woody species, Holzforschung, 71, 11 (2017)
Ralph J, Akiyama T, Kim H, Lu F, Schatz PF, Marita JM, Ralph SA, Reddy MSS, Chen F and Dixon RA, Effects of coumarate 3-hydroxylase down-regulation on lignin structure, The Journal of Biological Chemistry, 281, 8843 (2006)
Roland C, Monties B and Lapierre C, Thioacidolysis. In: Methods in lignin chemistry, Eds. Lin SY and Dence CW, Springer-Verlag, Berlin, 334-348 (1992)
Saito K and Fukushima K, Distribution of lignin interunit bonds in the differentiating xylem of compression and normal woods of Pinus thunbergii, Journal of Wood Science, 51, 246 (2005)
Terashima N and Fukushima K, Heterogeneity in formation of lignin XI. An autoradiographic study of the heterogeneous formation and structure of pine lignin, Wood Science and Technology, 22, 259 (1988)
Whiting P and Goring DAI, Chemical characterization of tissue fractions from the middle lamella and secondary wall of black spruce tracheids, Wood Science and Technology, 16, 261 (1982)
Yamasaki T and Higuchi T, p-Hydroxyphenyl component of grass lignin, Mokuzai Gakkaishi, 17, 117(1971)
Yamasaki T and Higuchi T, Chemical properties of enzymic dehydrogenation polymer from p- coumaryl alcohol, Mokuzai Gakkaishi, 18, 361 (1972)
Yasuda S and Sakakibara A, The chemical composition of lignin from reaction wood, Mokuzai Gakkaishi, 21, 363 (1975)
Yasuda S and Sakakibara A, Hydrogenolysis of protolignin in compression wood. III. Isolation of four dimeric compounds with carbon to carbon linkage, Mokuzai Gakkaishi, 23, 114 (1977)
Yoshihara K, Kobayashi T, Fujii T and Akamatsu I, A novel modification of Klason lignin quantitative method, Japan Tappi, 38, 466 (1984)
Yue F, Lu F, Sun RC and Ralph J, Syntheses of lignin-derived thioacidolysis monomers and their uses as quantitation standards, Journal of Agricultural and Food Chemistry, 60, 922 (2012)
Yue F, Lu F, Regner M, Sun R and Ralph J, Lignin-derived thioacidolysis dimers: reevaluation, new products, authentication, and quantification, ChemSusChem, 10, 830 (2017)
石栗太、横田信三、あて材の化学成分量、吉澤信夫監修、あて材の科学、海青社、125-126 (2016)
林徳子、一般的な圧縮あて材、吉澤信夫監修、あて材の科学、海青社、50-53 (2016)
馬場啓一、あて材の構造と形成、福島和彦ら編、木質の形成、海青社、105-108 (2011)
福島和彦、リグニンの生合成、日本木材学会編、木質の化学、文永堂出版株式会社、22-33 (2010)
松下泰幸、クラーソン法/酸可溶性リグニン、石井忠ら編、植物細胞壁実験法、弘前大学出版会、117-118 (2016)
飯塚堯介、フェノール類および芳香族アミン類による呈色反応、石井忠ら編、植物細胞壁実験法、弘前大学出版会、105-106 (2016)