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Title: 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:
 [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
Publication Date:
Research Org.:
Univ. of Wisconsin, Madison, WI (United States); Great Lakes Bioenergy Research Center
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
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:
Journal Article: 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. doi: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. doi: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},
issn = {2073-4360},
number = 8,
volume = 10,
place = {United States},
year = {2018},
month = {8}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 9 works
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Figures / Tables:

Figure 1 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:

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    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
    • DOI: 10.1080/02773813.2020.1722702

      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.