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Title: Elucidating Tricin-Lignin Structures: Assigning Correlations in HSQC Spectra of Monocot Lignins

Journal Article · · Polymers
 [1];  [2];  [3];  [3]; ORCiD logo [4];  [2];  [5]
  1. 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
  2. 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
  3. Inst. de Recursos Naturales y Agrobiologia de Sevilla (IRNAS), Seville (Spain)
  4. Vlaams Inst. voor Biotechnologie (VIB), Ghent (Belgium). Dept. of Plant Systems Biology; Ghent Univ., Ghent (Belgium). Dept. of Plant Biotechnology and Bioinformatics
  5. Univ. of Wisconsin, Madison, WI (United States). DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Inst., and Dept. of Biochemistry
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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.

Research Organization:
Univ. of Wisconsin, Madison, WI (United States); Great Lakes Bioenergy Research Center (GLBRC), Madison, WI (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Biological and Environmental Research (BER)
Contributing Organization:
China Scholarship Council, State Education Department
Grant/Contract Number:
FC02-07ER64494; SC0018409
OSTI ID:
1499895
Alternate ID(s):
OSTI ID: 1506468
Journal Information:
Polymers, Vol. 10, Issue 8; ISSN 2073-4360
Publisher:
MDPICopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 24 works
Citation information provided by
Web of Science

References (15)

Lignin Biosynthesis journal June 2003
Tricin, a Flavonoid Monomer in Monocot Lignification journal February 2015
A polymer of caffeyl alcohol in plant seeds journal January 2012
Silencing CHALCONE SYNTHASE in Maize Impedes the Incorporation of Tricin into Lignin and Increases Lignin Content journal December 2016
Successive and quantitative fractionation and extensive structural characterization of lignin from wheat straw journal November 2014
Lignification in Sugarcane: Biochemical Characterization, Gene Discovery, and Expression Analysis in Two Genotypes Contrasting for Lignin Content journal October 2013
Quantification of Wheat Straw Lignin Structure by Comprehensive NMR Analysis journal November 2013
Structural Characterization of the Lignin in the Cortex and Pith of Elephant Grass ( Pennisetum purpureum ) Stems journal March 2012
Isolation and Structural Characterization of the Milled Wood Lignin, Dioxane Lignin, and Cellulolytic Lignin Preparations from Brewer’s Spent Grain journal January 2015
Differences in the chemical structure of the lignins from sugarcane bagasse and straw journal October 2015
The dibenzodioxocin lignin substructure is abundant in the inner part of the secondary wall in Norway spruce and silver birch xylem journal January 2004
Structural Characterization of Wheat Straw Lignin as Revealed by Analytical Pyrolysis, 2D-NMR, and Reductive Cleavage Methods journal December 2011
Structural Characterization of Lignin Isolated from Coconut ( Cocos nucifera ) Coir Fibers journal February 2013
Maize Tricin-Oligolignol Metabolites and their Implications for Monocot Lignification journal April 2016
Tricin-lignins: occurrence and quantitation of tricin in relation to phylogeny journal November 2016

Cited By (5)

Structural characteristics of different softwood lignins according to 1D and 2D NMR spectroscopy journal February 2020
Miscanthus x giganteus Stem Versus Leaf-Derived Lignins Differing in Monolignol Ratio and Linkage journal March 2019
Structural characteristics of different softwood lignins according to 1D and 2D NMR spectroscopy text January 2020
Structural characteristics of different softwood lignins according to 1D and 2D NMR spectroscopy text January 2020
Structural Motifs of Wheat Straw Lignin Differ in Susceptibility to Degradation by the White-Rot Fungus Ceriporiopsis subvermispora journal November 2019

Figures / Tables (3)

Figure 1(p. 4)figure Figure 1
Figure 2(p. 4)figure Figure 2
Table 1(p. 4)table Table 1

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Related Subjects

59 BASIC BIOLOGICAL SCIENCES
tricin
lignin
model compound
HSQC
nuclear magnetic resonance (NMR)
monocot
NMR