Elucidating Tricin-Lignin Structures: Assigning Correlations in HSQC Spectra of Monocot Lignins
Abstract
Tricin [5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-4-one] is a flavone that has been found to be incorporated in grass lignin polymers via 4'–O–β coupling. Herein, we investigated the tricin-lignin structure using nuclear magnetic resonance (NMR) methods by comparing the 1H–13C heteronuclear correlation (HSQC) NMR spectra of the isolated lignin with a series of dimeric and trimeric tricin-4'–O–β-ether model compounds. Results showed that the tricin moiety significantly affects the chemical shift of the Cβ/Hβ of 4'–O–β unit, producing peaks at around δC/δH 82.5–83.5/4.15–4.45, that differ from the Cβ/Hβ correlations from normal 4–O–β units formed solely by monolignols, and that have to date been unassigned.
- Authors:
-
[4];
- South China Univ. of Technology, Guangzhou (China). State Key Lab. of Pulp and Paper Engineering; Univ. of Wisconsin, Madison, WI (United States). DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Inst., and Dept. of Biological System Engineering
- South China Univ. of Technology, Guangzhou (China). State Key Lab. of Pulp and Paper Engineering; Univ. of Wisconsin, Madison, WI (United States). DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Inst., and Dept. of Biochemistry
- Inst. de Recursos Naturales y Agrobiologia de Sevilla (IRNAS), Seville (Spain)
- Vlaams Inst. voor Biotechnologie (VIB), Ghent (Belgium). Dept. of Plant Systems Biology; Ghent Univ., Ghent (Belgium). Dept. of Plant Biotechnology and Bioinformatics
- Univ. of Wisconsin, Madison, WI (United States). DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Inst., and Dept. of Biochemistry
- Publication Date:
- Research Org.:
- Univ. of Wisconsin, Madison, WI (United States); Great Lakes Bioenergy Research Center (GLBRC), Madison, WI (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Biological and Environmental Research (BER)
- Contributing Org.:
- China Scholarship Council, State Education Department
- OSTI Identifier:
- 1499895
- Alternate Identifier(s):
- OSTI ID: 1506468
- Grant/Contract Number:
- FC02-07ER64494; SC0018409
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Polymers
- Additional Journal Information:
- Journal Volume: 10; Journal Issue: 8; Journal ID: ISSN 2073-4360
- Publisher:
- MDPI
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 59 BASIC BIOLOGICAL SCIENCES; tricin; lignin; model compound; HSQC; nuclear magnetic resonance (NMR); monocot; NMR
Citation Formats
Lan, Wu, Yue, Fengxia, Rencoret, Jorge, del Río, José, Boerjan, Wout, Lu, Fachuang, and Ralph, John. Elucidating Tricin-Lignin Structures: Assigning Correlations in HSQC Spectra of Monocot Lignins. United States: N. p., 2018.
Web. doi:10.3390/polym10080916.
Lan, Wu, Yue, Fengxia, Rencoret, Jorge, del Río, José, Boerjan, Wout, Lu, Fachuang, & Ralph, John. Elucidating Tricin-Lignin Structures: Assigning Correlations in HSQC Spectra of Monocot Lignins. United States. https://doi.org/10.3390/polym10080916
Lan, Wu, Yue, Fengxia, Rencoret, Jorge, del Río, José, Boerjan, Wout, Lu, Fachuang, and Ralph, John. Wed .
"Elucidating Tricin-Lignin Structures: Assigning Correlations in HSQC Spectra of Monocot Lignins". United States. https://doi.org/10.3390/polym10080916. https://www.osti.gov/servlets/purl/1499895.
@article{osti_1499895,
title = {Elucidating Tricin-Lignin Structures: Assigning Correlations in HSQC Spectra of Monocot Lignins},
author = {Lan, Wu and Yue, Fengxia and Rencoret, Jorge and del Río, José and Boerjan, Wout and Lu, Fachuang and Ralph, John},
abstractNote = {Tricin [5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-4-one] is a flavone that has been found to be incorporated in grass lignin polymers via 4'–O–β coupling. Herein, we investigated the tricin-lignin structure using nuclear magnetic resonance (NMR) methods by comparing the 1H–13C heteronuclear correlation (HSQC) NMR spectra of the isolated lignin with a series of dimeric and trimeric tricin-4'–O–β-ether model compounds. Results showed that the tricin moiety significantly affects the chemical shift of the Cβ/Hβ of 4'–O–β unit, producing peaks at around δC/δH 82.5–83.5/4.15–4.45, that differ from the Cβ/Hβ correlations from normal 4–O–β units formed solely by monolignols, and that have to date been unassigned.},
doi = {10.3390/polym10080916},
journal = {Polymers},
number = 8,
volume = 10,
place = {United States},
year = {Wed Aug 01 00:00:00 EDT 2018},
month = {Wed Aug 01 00:00:00 EDT 2018}
}
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Figures / Tables:
Figure 1: 1H–13C heteronuclear correlation (HSQC) spectra of acetylated (a) and non-acetylated (b) milled wood lignin of wheat straw overlaid with the nuclear magnetic resonance (NMR) data from four tricin-containing model compounds.
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Works referenced in this record:
Lignin Biosynthesis
journal, June 2003
- Boerjan, Wout; Ralph, John; Baucher, Marie
- Annual Review of Plant Biology, Vol. 54, Issue 1, p. 519-546
Tricin, a Flavonoid Monomer in Monocot Lignification
journal, February 2015
- Lan, Wu; Lu, Fachuang; Regner, Matthew
- Plant Physiology, Vol. 167, Issue 4
A polymer of caffeyl alcohol in plant seeds
journal, January 2012
- Chen, F.; Tobimatsu, Y.; Havkin-Frenkel, D.
- Proceedings of the National Academy of Sciences, Vol. 109, Issue 5
Silencing CHALCONE SYNTHASE in Maize Impedes the Incorporation of Tricin into Lignin and Increases Lignin Content
journal, December 2016
- Eloy, Nubia B.; Voorend, Wannes; Lan, Wu
- Plant Physiology, Vol. 173, Issue 2
Successive and quantitative fractionation and extensive structural characterization of lignin from wheat straw
journal, November 2014
- Zikeli, Florian; Ters, Thomas; Fackler, Karin
- Industrial Crops and Products, Vol. 61
Lignification in Sugarcane: Biochemical Characterization, Gene Discovery, and Expression Analysis in Two Genotypes Contrasting for Lignin Content
journal, October 2013
- Bottcher, A.; Cesarino, I.; Brombini dos Santos, A.
- PLANT PHYSIOLOGY, Vol. 163, Issue 4
Quantification of Wheat Straw Lignin Structure by Comprehensive NMR Analysis
journal, November 2013
- Zeng, Jijiao; Helms, Gregory L.; Gao, Xin
- Journal of Agricultural and Food Chemistry, Vol. 61, Issue 46
Structural Characterization of the Lignin in the Cortex and Pith of Elephant Grass ( Pennisetum purpureum ) Stems
journal, March 2012
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- Journal of Agricultural and Food Chemistry, Vol. 60, Issue 14
Isolation and Structural Characterization of the Milled Wood Lignin, Dioxane Lignin, and Cellulolytic Lignin Preparations from Brewer’s Spent Grain
journal, January 2015
- Rencoret, Jorge; Prinsen, Pepijn; Gutiérrez, Ana
- Journal of Agricultural and Food Chemistry, Vol. 63, Issue 2
Differences in the chemical structure of the lignins from sugarcane bagasse and straw
journal, October 2015
- del Río, José C.; Lino, Alessandro G.; Colodette, Jorge L.
- Biomass and Bioenergy, Vol. 81
The dibenzodioxocin lignin substructure is abundant in the inner part of the secondary wall in Norway spruce and silver birch xylem
journal, January 2004
- Kukkola, Eija M.; Koutaniemi, Sanna; P�ll�nen, Eija
- Planta, Vol. 218, Issue 3
Structural Characterization of Wheat Straw Lignin as Revealed by Analytical Pyrolysis, 2D-NMR, and Reductive Cleavage Methods
journal, December 2011
- del Río, José C.; Rencoret, Jorge; Prinsen, Pepijn
- Journal of Agricultural and Food Chemistry, Vol. 60, Issue 23
Structural Characterization of Lignin Isolated from Coconut ( Cocos nucifera ) Coir Fibers
journal, February 2013
- Rencoret, Jorge; Ralph, John; Marques, Gisela
- Journal of Agricultural and Food Chemistry, Vol. 61, Issue 10
Maize Tricin-Oligolignol Metabolites and their Implications for Monocot Lignification
journal, April 2016
- Lan, Wu; Morreel, Kris; Lu, Fachuang
- Plant Physiology
Tricin-lignins: occurrence and quantitation of tricin in relation to phylogeny
journal, November 2016
- Lan, Wu; Rencoret, Jorge; Lu, Fachuang
- The Plant Journal, Vol. 88, Issue 6
The dibenzodioxocin lignin substructure is abundant in the inner part of the secondary wall in Norway spruce and silver birch xylem
journal, January 2004
- Kukkola, Eija M.; Koutaniemi, Sanna; P�ll�nen, Eija
- Planta, Vol. 218, Issue 3
Differences in the chemical structure of the lignins from sugarcane bagasse and straw
journal, October 2015
- del Río, José C.; Lino, Alessandro G.; Colodette, Jorge L.
- Biomass and Bioenergy, Vol. 81
Structural Characterization of Wheat Straw Lignin as Revealed by Analytical Pyrolysis, 2D-NMR, and Reductive Cleavage Methods
journal, December 2011
- del Río, José C.; Rencoret, Jorge; Prinsen, Pepijn
- Journal of Agricultural and Food Chemistry, Vol. 60, Issue 23
Quantification of Wheat Straw Lignin Structure by Comprehensive NMR Analysis
journal, November 2013
- Zeng, Jijiao; Helms, Gregory L.; Gao, Xin
- Journal of Agricultural and Food Chemistry, Vol. 61, Issue 46
Isolation and Structural Characterization of the Milled Wood Lignin, Dioxane Lignin, and Cellulolytic Lignin Preparations from Brewer’s Spent Grain
journal, January 2015
- Rencoret, Jorge; Prinsen, Pepijn; Gutiérrez, Ana
- Journal of Agricultural and Food Chemistry, Vol. 63, Issue 2
A polymer of caffeyl alcohol in plant seeds
journal, January 2012
- Chen, F.; Tobimatsu, Y.; Havkin-Frenkel, D.
- Proceedings of the National Academy of Sciences, Vol. 109, Issue 5
Lignification in Sugarcane: Biochemical Characterization, Gene Discovery, and Expression Analysis in Two Genotypes Contrasting for Lignin Content
journal, October 2013
- Bottcher, A.; Cesarino, I.; Brombini dos Santos, A.
- PLANT PHYSIOLOGY, Vol. 163, Issue 4
Tricin, a Flavonoid Monomer in Monocot Lignification
journal, February 2015
- Lan, Wu; Lu, Fachuang; Regner, Matthew
- Plant Physiology, Vol. 167, Issue 4
Silencing CHALCONE SYNTHASE in Maize Impedes the Incorporation of Tricin into Lignin and Increases Lignin Content
journal, December 2016
- Eloy, Nubia B.; Voorend, Wannes; Lan, Wu
- Plant Physiology, Vol. 173, Issue 2
Maize Tricin-Oligolignol Metabolites and their Implications for Monocot Lignification
journal, April 2016
- Lan, Wu; Morreel, Kris; Lu, Fachuang
- Plant Physiology
Tricin-lignins: occurrence and quantitation of tricin in relation to phylogeny
journal, November 2016
- Lan, Wu; Rencoret, Jorge; Lu, Fachuang
- The Plant Journal, Vol. 88, Issue 6
Lignin Biosynthesis
journal, June 2003
- Boerjan, Wout; Ralph, John; Baucher, Marie
- Annual Review of Plant Biology, Vol. 54, Issue 1, p. 519-546
Works referencing / citing this record:
Structural characteristics of different softwood lignins according to 1D and 2D NMR spectroscopy
journal, February 2020
- Faleva, Anna V.; Kozhevnikov, Aleksandr Yu.; Pokryshkin, Sergey A.
- Journal of Wood Chemistry and Technology, Vol. 40, Issue 3
Miscanthus x giganteus Stem Versus Leaf-Derived Lignins Differing in Monolignol Ratio and Linkage
journal, March 2019
- Bergs, Michel; Völkering, Georg; Kraska, Thorsten
- International Journal of Molecular Sciences, Vol. 20, Issue 5
Structural characteristics of different softwood lignins according to 1D and 2D NMR spectroscopy
text, January 2020
- Faleva, Anna V.; Kozhevnikov, Aleksandr Yu.; Pokryshkin, Sergey A.
- Taylor & Francis
Structural characteristics of different softwood lignins according to 1D and 2D NMR spectroscopy
text, January 2020
- Faleva, Anna V.; Kozhevnikov, Aleksandr Yu.; Pokryshkin, Sergey A.
- Taylor & Francis
Structural Motifs of Wheat Straw Lignin Differ in Susceptibility to Degradation by the White-Rot Fungus Ceriporiopsis subvermispora
journal, November 2019
- van Erven, Gijs; Wang, Jianli; Sun, Peicheng
- ACS Sustainable Chemistry & Engineering, Vol. 7, Issue 24
Figures / Tables found in this record:
Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.