749
Views
24
CrossRef citations to date
0
Altmetric
Original Articles

Structural characteristics of different softwood lignins according to 1D and 2D NMR spectroscopy

ORCID Icon, ORCID Icon, , ORCID Icon, &

References

  • Heitner, C.; Dimmel, D. R.; Schmidt, J. A. Lignin and Lignans: Advances in Chemistry; Boca Raton: CRC Press, 2010; pp. 683.
  • Abe, A.; Dusek, K.; Kobayashi, S. Biopolymers. Lignin, Proteins, Bioactive Nanocomposites; Berlin: Springer-Verlag, 2010; pp. 212.
  • Ralph, J.; Lundquist, K.; Brunow, G.; Lu, F.; Kim, H.; Schatz, P. F.; Marita, J. M.; Hatfield, R. D.; Ralph, S. A.; Christensen, J. H.; et al. Lignins: Natural Polymers from Oxidative Coupling of 4-Hydroxyphenyl- Propanoids. Phytochem. Rev. 2004, 3, 29–60. DOI: 10.1023/B:PHYT.0000047809.65444.a4.
  • Lupoi, J. S.; Singh, S.; Parthasarathi, R.; Simmons, B. A.; Henry, R. J. Recent Innovations in Analytical Methods for the Qualitative and Quantitative Assessment of Lignin. Renew Sust Energ Rev 2015, 49, 871–906. DOI: 10.1016/j.rser.2015.04.091.
  • Lin, S. Y.; Dence, C. W. Methods in Lignin Chemistry; Berlin: Springer-Verlag, 1992; pp. 578.
  • Balakshin, M. Y.; Capanema, E. A.; Santos, R. B.; Chang, H-m.; Hasan Jameel, H. Structural analysis of hardwood native lignins by quantitative 13C NMR spectroscopy. Holzforschung 2015, 70, 95–108. DOI: 10.1515/hf-2014-0328.
  • Ralph, J.; Lapierre, C.; Lu, F.; Marita, J. M.; Pilate, G.; Van Doorsselaere, J.; Boerjan, W.; Jouanin, L. NMR Evidence for Benzodioxane Structures Resulting from Incorporation of 5-Hydroxyconiferyl Alcohol into Lignins of O -Methyltransferase-Deficient Poplars. J. Agric. Food Chem. 2001, 49, 86–91. DOI: 10.1021/jf001042+.
  • Zhang, L. M.; Gellerstedt, G.; Ralph, J.; Lu, F. NMR Studies on the Occurrence of Spirodienone Structures in Lignins. J. Wood Chem. Technol. 2006, 26, 65–79. DOI: 10.1080/02773810600580271.
  • Yelle, D. J.; Ralph, J.; Frihart, C. R. Characterization of Nonderivatized Plant Cell Walls Using High-Resolution Solution-State NMR Spectroscopy. Magn. Reson. Chem. 2008, 46, 508–517. DOI: 10.1002/mrc.2201.
  • Kim, H.; Ralph, J.; Akiyama, T. Solution-State 2D NMR of Ball-Milled Plant Cell Wall Gels in DMSO-d 6. Bioenerg. Res. 2008, 1, 56–66. DOI: 10.1007/s12155-008-9004-z.
  • Kim, H.; Ralph, J. Solution-State 2D NMR of Ball-Milled Plant Cell Wall Gels in DMSO-d6/Pyridine-d5. Org. Biomol. Chem. 2010, 8, 576–591. DOI: 10.1039/B916070A.
  • Sluiter, J. B.; Ruiz, R. O.; Scarlata, C. J.; Sluiter, A. D.; Templeton, D. W. Compositional Analysis of Lignocellulosic Feedstocks. 1. Review and Description of Methods. J. Agric. Food Chem. 2010, 58, 9043–9053. DOI: 10.1021/jf1008023.
  • Pepper, J. M.; Baylis, P. E. T.; Adler, E. The Isolation and Properties of Lignins Obtained by the Acidolysis of Spruce and Aspen Woods in Dioxane–Water Medium. Can. J. Chem. 1959, 37, 1241–1248. DOI: 10.1139/v59-183.
  • Zakis, G. F.; Mozheiko, L. N.; Telysheva, G. M. Methods for Determining Lignin Functional Groups [in Russian]; Zinatne: Riga, 1975; pp. 176.
  • Constant, S.; Wienk, H. L. J.; Frissen, A. E.; Peinder, P. d.; Boelens, R.; van Es, D. S.; Grisel, R. J. H.; Weckhuysen, B. M.; Huijgen, W. J. J.; Gosselink, R. J. A.; Bruijnincx, P. C. A. New Insights into the Structure and Composition of Technical Lignins: A Comparative Characterisation Study. Green Chem. 2016, 18, 2651–2665. DOI: 10.1039/C5GC03043A.
  • Del Río, J. C.; Rencoret, J.; Prinsen, P.; Martínez, A. T.; Ralph, J.; Gutiérrez, A. Structural Characterization of Wheat Straw Lignin as Revealed by Analytical Pyrolysis, 2D-NMR, and Reductive Cleavage Methods. J. Agric. Food Chem. 2012, 60, 5922–5935. DOI: 10.1021/jf301002n.
  • ACD/Structure Elucidator 2015, version 2014, Advanced Chemistry Development, Inc., Toronto, ON, Canada, www.acdlabs.com.
  • ACD/Spectrus Processor 2015, version 2014, Advanced Chemistry Development, Inc., Toronto, ON, Canada, www.acdlabs.com.
  • Zhang, L.; Gellerstedt, G. Quantitative 2D HSQC NMR Determination of Polymer Structures by Selecting Suitable Internal Standard References. Magn. Reson. Chem. 2007, 45, 37–45. DOI: 10.1002/mrc.1914.
  • Rokhin, A. V.; Kanitskaya, L. V.; Kushnarev, D. F.; Kalabin, G. A.; Abduazimov, H. A.; Smirnova, L. S.; Pulatov, B. H. Quantitative NMR spectroscopy 1H and 13C of cotton-plant dioxanlignins (Gossipium) [in Russian]. Chem. Nat. Compd. 1994, 6, 798–808.
  • Shestakov, S. L.; Kosyakov, D. S.; Kozhevnikov, A. Y.; Ulyanovskiy, N. V.; Popova, Y. A. Improvement of the method for determining hydroxylic lignin groups by NMR spectroscopy. Khimiya Rastitel’nogo Syr’ya. 2017, 2, 81–88. DOI: 10.14258/jcprm.2017021641.
  • Balakshin, M.; Capanema, E. On the Quantification of Lignin Hydroxyl Groups with 31P and 13C NMR Spectroscopy. J. Wood Chem. Technol. 2015, 35, 220–237. DOI: 10.1080/02773813.2014.928328.
  • Faix, O.; Meier, D.; Fortmann, I. Pyrolysis-Gas Chromatography-Mass Spectrometry of Two Trimeric Lignin Model Compounds with Alkyl-Aryl Ether Structure. J. Anal. Pyrolysis. 1988, 14, 135–148. DOI: 10.1016/0165-2370(88)85004-6.
  • Ralph, J.; Hatfield, D. Pyrolysis-GC-MS Characterization of Forage Materials. J. Agric. Food Chem. 1991, 39, 1426–1437. DOI: 10.1021/jf00008a014.
  • Adler, E. Structural Elements of Lignin. Ind. Eng. Chem. 1957, 49, 1377–1383. DOI: 10.1021/ie50573a031.
  • Kalabin, G. A.; Kanitskaya, L. V.; Kushnarev, D. F. Quantitative NMR Spectroscopy of Natural Organic Raw Materials and Their Products [in Russian]; Science: Moscow, 2000; pp. 408.
  • Bogolitsyn, K. G.; Gusakova, M. A.; Khviyuzov, S. S.; Zubov, I. N. Physicochemical Properties of Conifer Lignins Using Juniperus communis as an Example. Chem. Nat. Compd. 2014, 50, 337–341. DOI: 10.1007/s10600-014-0946-4.
  • Li, M.; Pu, Y.; Tschaplinski, T. J.; Ragauskas, A. J. 31P NMR Characterization of Tricin and Its Structurally Similar Flavonoids. Chemistry Select. 2017, 2, 3557–3561. DOI: 10.1002/slct.201700735.
  • Adler, E. Lignin Chemistry-past, present and future. Wood Sci. Technol. 1977, 11, 169–218. DOI: 10.1007/BF00365615.
  • Guo, H.; Miles-Barrett, D. M.; Neal, A. R.; Zhang, T.; Li, C.; Westwood, N. J. Unravelling the Enigma of Lignin OX: can the Oxidation of Lignin Be Controlled? Chem. Sci. 2018, 9, 702–711. DOI: 10.1039/C7SC03520A.
  • Lan, W.; Lu, F.; Regner, M.; Zhu, Y.; Rencoret, J.; Ralph, S. A.; Zakai, U. I.; Morreel, K.; Boerjan, W.; Ralph, J. Tricin, a Flavonoid Monomer in Monocot Lignification. Plant Physiol. 2015, 167, 1284–1295. DOI: 10.1104/pp.114.253757.
  • Lan, W.; Yue, F.; Rencoret, J.; del Río, J. C.; Boerjan, W.; Lu, F.; Ralph, J. Elucidating Tricin-Lignin Structures: Assigning Correlations in HSQC Spectra of Monocot Lignins. Polymers. 2018, 10, 916–921. DOI: 10.3390/polym10080916.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.