Recent Advances in Characterization of Lignin Polymer by Solution-State Nuclear Magnetic Resonance (NMR) Methodology

Overview

Journal Materials (Basel)

Publisher MDPI

Date 2017 Aug 16

PMID 28809313

Citations 75

Authors

Jia-Long Wen

Shao-Long Sun

Bai-Liang Xue

Run-Cang Sun

Affiliations

Soon will be listed here.

Abstract

The demand for efficient utilization of biomass induces a detailed analysis of the fundamental chemical structures of biomass, especially the complex structures of lignin polymers, which have long been recognized for their negative impact on biorefinery. Traditionally, it has been attempted to reveal the complicated and heterogeneous structure of lignin by a series of chemical analyses, such as thioacidolysis (TA), nitrobenzene oxidation (NBO), and derivatization followed by reductive cleavage (DFRC). Recent advances in nuclear magnetic resonance (NMR) technology undoubtedly have made solution-state NMR become the most widely used technique in structural characterization of lignin due to its versatility in illustrating structural features and structural transformations of lignin polymers. As one of the most promising diagnostic tools, NMR provides unambiguous evidence for specific structures as well as quantitative structural information. The recent advances in two-dimensional solution-state NMR techniques for structural analysis of lignin in isolated and whole cell wall states (), as well as their applications are reviewed.

Citing Articles

Solvent-Free Catalytic Hydrotreatment of Lignin to Biobased Aromatics: Current Trends, Industrial Approach, and Future Perspectives.

Chowdari R, Ganji P, Likozar B Energy Fuels. 2025; 39(6):2943-2985.

PMID: 39967748 PMC: 11831597. DOI: 10.1021/acs.energyfuels.4c05174.

Thermal Condensation of Dehydrogenation Polymer (DHP) with Xylose.

Wang P, Xie J, Peng W, Xie J, An J, Zhang G Polymers (Basel). 2024; 16(22).

PMID: 39599230 PMC: 11597921. DOI: 10.3390/polym16223139.

Study on the Thermal Condensation Mechanism of Dehydrogenated Polymer (DHP) and Glucuronic Acid.

Wang P, Zhang X, Peng W, Chen J, An J, Zhang G Int J Mol Sci. 2024; 25(19).

PMID: 39408871 PMC: 11476454. DOI: 10.3390/ijms251910533.

The role of NMR spectroscopy in lignocellulosic biomass characterisation: A mini review.

Vukovic J, Tisma M Food Chem (Oxf). 2024; 9:100219.

PMID: 39263258 PMC: 11388798. DOI: 10.1016/j.fochms.2024.100219.

Differential Studies on the Structure of Lignin-Carbohydrate Complexes (LCC) in Alkali-Extracted Plant Hemicelluloses.

Pang S, Wang X, Pu J, Liang C, Yao S, Qin C Polymers (Basel). 2024; 16(10).

PMID: 38794596 PMC: 11124851. DOI: 10.3390/polym16101403.

References

Kupce E, Freeman R . Compensated adiabatic inversion pulses: broadband INEPT and HSQC. J Magn Reson. 2007; 187(2):258-65. DOI: 10.1016/j.jmr.2007.05.009. View

Capanema E, Balakshin M, Kadla J . A comprehensive approach for quantitative lignin characterization by NMR spectroscopy. J Agric Food Chem. 2004; 52(7):1850-60. DOI: 10.1021/jf035282b. View

Martinez A, Rencoret J, Nieto L, Jimenez-Barbero J, Gutierrez A, Del Rio J . Selective lignin and polysaccharide removal in natural fungal decay of wood as evidenced by in situ structural analyses. Environ Microbiol. 2011; 13(1):96-107. DOI: 10.1111/j.1462-2920.2010.02312.x. View

Grabber J, Hatfield R, Lu F, Ralph J . Coniferyl ferulate incorporation into lignin enhances the alkaline delignification and enzymatic degradation of cell walls. Biomacromolecules. 2008; 9(9):2510-6. DOI: 10.1021/bm800528f. View

Kim H, Ralph J . Solution-state 2D NMR of ball-milled plant cell wall gels in DMSO-d(6)/pyridine-d(5). Org Biomol Chem. 2010; 8(3):576-91. PMC: 4070321. DOI: 10.1039/b916070a. View

Xia Z, Akim L, Argyropoulos D . Quantitative (13)C NMR analysis of lignins with internal standards. J Agric Food Chem. 2001; 49(8):3573-8. DOI: 10.1021/jf010333v. View

Zhang A, Lu F, Liu C, Sun R . Isolation and characterization of lignins from Eucalyptus tereticornis (12ABL). J Agric Food Chem. 2010; 58(21):11287-93. DOI: 10.1021/jf103354x. View

Sette M, Wechselberger R, Crestini C . Elucidation of lignin structure by quantitative 2D NMR. Chemistry. 2011; 17(34):9529-35. DOI: 10.1002/chem.201003045. View

Rencoret J, Gutierrez A, Nieto L, Jimenez-Barbero J, Faulds C, Kim H . Lignin composition and structure in young versus adult Eucalyptus globulus plants. Plant Physiol. 2010; 155(2):667-82. PMC: 3032458. DOI: 10.1104/pp.110.167254. View

10.

Balakshin M, Capanema E, Gracz H, Chang H, Jameel H . Quantification of lignin-carbohydrate linkages with high-resolution NMR spectroscopy. Planta. 2011; 233(6):1097-110. DOI: 10.1007/s00425-011-1359-2. View

11.

Calvo-Flores F, Dobado J . Lignin as renewable raw material. ChemSusChem. 2010; 3(11):1227-35. DOI: 10.1002/cssc.201000157. View

12.

Heikkinen S, Toikka M, Karhunen P, Kilpelainen I . Quantitative 2D HSQC (Q-HSQC) via suppression of J-dependence of polarization transfer in NMR spectroscopy: application to wood lignin. J Am Chem Soc. 2003; 125(14):4362-7. DOI: 10.1021/ja029035k. View

13.

Yelle D, Ralph J, Lu F, Hammel K . Evidence for cleavage of lignin by a brown rot basidiomycete. Environ Microbiol. 2008; 10(7):1844-9. DOI: 10.1111/j.1462-2920.2008.01605.x. View

14.

Yelle D, Wei D, Ralph J, Hammel K . Multidimensional NMR analysis reveals truncated lignin structures in wood decayed by the brown rot basidiomycete Postia placenta. Environ Microbiol. 2011; 13(4):1091-100. DOI: 10.1111/j.1462-2920.2010.02417.x. View

15.

Zhang A, Lu F, Sun R, Ralph J . Isolation of cellulolytic enzyme lignin from wood preswollen/dissolved in dimethyl sulfoxide/n-methylimidazole. J Agric Food Chem. 2010; 58(6):3446-50. DOI: 10.1021/jf903998d. View

16.

Capanema E, Balakshin M, Kadla J . Quantitative characterization of a hardwood milled wood lignin by nuclear magnetic resonance spectroscopy. J Agric Food Chem. 2005; 53(25):9639-49. DOI: 10.1021/jf0515330. View

17.

Wagner A, Donaldson L, Kim H, Phillips L, Flint H, Steward D . Suppression of 4-coumarate-CoA ligase in the coniferous gymnosperm Pinus radiata. Plant Physiol. 2008; 149(1):370-83. PMC: 2613735. DOI: 10.1104/pp.108.125765. View

18.

Del Rio J, Rencoret J, Marques G, Li J, Gellerstedt G, Jimenez-Barbero J . Structural characterization of the lignin from jute (Corchorus capsularis) fibers. J Agric Food Chem. 2009; 57(21):10271-81. DOI: 10.1021/jf900815x. View

19.

Yuan T, Sun S, Xu F, Sun R . Structural characterization of lignin from triploid of Populus tomentosa Carr. J Agric Food Chem. 2011; 59(12):6605-15. DOI: 10.1021/jf2003865. View

20.

Del Rio J, Rencoret J, Prinsen P, Martinez A, Ralph J, Gutierrez A . Structural characterization of wheat straw lignin as revealed by analytical pyrolysis, 2D-NMR, and reductive cleavage methods. J Agric Food Chem. 2012; 60(23):5922-35. DOI: 10.1021/jf301002n. View