COMPARATIVE ANALYSIS OF LIGNINS OF VARIOUS PLANT FORMS BY 31P-NMR

UDC 543.632.538

  • Yuliya Aleksandrovna Popova Northern (Arctic) Federal University named after M.V. Lomonosov Email: yuliya.popova01@mail.ru
  • Semen Leonidovich Shestakov Northern (Arctic) Federal University named after M.V. Lomonosov Email: s.shestakov@narfu.ru
  • Aleksandr Yur'yevich Kozhevnikov Northern (Arctic) Federal University named after M.V. Lomonosov Email: akozhevnikov@mail.ru
  • Dmitriy Sergeyevich Kosyakov Northern (Arctic) Federal University named after M.V. Lomonosov Email: kosyakov@mail.ru
  • Sergey Aleksandrovich Sypalov Northern (Arctic) Federal University named after M.V. Lomonosov Email: sypych.one@yandex.ru
DOI_disc_logo https://doi.org/10.14258/jcprm.2019045119
Keywords: lignins, NMR, 31P-NMR, functional analysis, phosphitylation

Abstract

Lignin is one of the most abundant biopolymers. Information about the functional composition and structure of various lignins may be useful in the study of biosynthesis processes in plants. The subject of the article is the determination of 31P-NMR spectroscopy possibilities to identify lignins obtained from various plant forms. To obtain spectra on 31P nuclei, a modification of the studied samples was applied by phosphitylating their OH-groups with a special reagent. We obtained qualitative and quantitative analysis of samples of softwood and hardwood lignins and herbaceous plants. According to the NMR spectra we noted the differences in composition and structure of the studied lignins. We confirmed that the structure of lignins of softwood and hardwood wood mainly contain guaiacilpropane and syringylpropane structural units, respectively. We found that lignins of herbaceous plants contain all types of OH-groups characteristic for lignins, including p-hydroxyphenyl groups. It was observed that samples of herbaceous plants lignins contain fragments of flavonoid structures in most cases. The 31P-NMR spectrum of quercetin, as the flavonoids representative, was registered and also modeled using the ACDLabs software package to confirm the presence of flavone structures in the macromolecules of the herbaceous lignins.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Author Biographies

Yuliya Aleksandrovna Popova, Northern (Arctic) Federal University named after M.V. Lomonosov

инженер центра коллективного пользования научным оборудованием «Арктика»

Semen Leonidovich Shestakov, Northern (Arctic) Federal University named after M.V. Lomonosov

старший научный сотрудник центра коллективного пользования научным оборудованием «Арктика», кандидат физико-математических наук

Aleksandr Yur'yevich Kozhevnikov, Northern (Arctic) Federal University named after M.V. Lomonosov

заместитель директора центра коллективного пользования научным оборудованием «Арктика»,  кандидат химических наук

Dmitriy Sergeyevich Kosyakov, Northern (Arctic) Federal University named after M.V. Lomonosov

директор центра коллективного пользования научным оборудованием «Арктика», кандидат химических наук

Sergey Aleksandrovich Sypalov, Northern (Arctic) Federal University named after M.V. Lomonosov

инженер центра коллективного пользования научным оборудованием «Арктика»

References

Balakshin M.Yu, Capanema E.A. Journal of Wood Chemistry and Technology, 2015, vol. 35, no. 3, pp. 220–237, DOI: 10.1080/02773813.2014.928328.

Crestini C., Argyropoulos D.S. J. Agric. Food Chem., 1997, vol. 45, no. 4, pp. 1212–1219, DOI: 10.1021/jf960568k.

Kalabin G.A., Kanitskaya L.V., Kushnarev D.F. Kolichestvennaya spektroskopiya YaMR prirodnogo organicheskogo syr'ya i produktov yego pererabotki. [Quantitative NMR spectroscopy of natural organic raw materials and products of its processing]. Moscow, 2000, 408 p. (in Russ.).

Sarkanen K.V., Ludwig C.H. Lignins: Occurrence, formation, structure and reactions, New-York: Wiley-Interscience, 1971, 916 p.

Dashtban M., Schraft H., Syed T.A., Qin W. International Journal of Biochemistry and Molecular Biology, 2010, vol. 1, no. 1, pp. 36–50.

Capanema E.A., Balakshin M.Yu., Kadla J.F. J. Agric. Food Chem., 2005, vol. 53 (25), pp. 9639–9649, DOI: 10.1021/jf0515330.

Wang H., Pu Y., Ragauskas A., Yang B. Bioresource Technology, 2019, vol. 271, pp. 449–461, DOI: 10.1016/j.biortech.2018.09.072.

Bogolitsyn K.G., Lunin V.V. Fizicheskaya khimiya lignina. [Physical chemistry of lignin]. Arkhangelsk, 2009, 489 p. (in Russ.).

Monteil-Rivera F., Phuong M., Ye M., Halasz A., Hawari J. Industrial Crops and Products, 2013, vol. 41, pp. 356–364, DOI: 10.1016/j.indcrop.2012.04.049.

Xia Z., Akim L.G., Argyropoulos D.S. Journal of agricultural and food chemistry, 2001, vol. 49, no. 8, pp. 3573–3578, DOI: 10.1021/jf010333v.

Stark N.M., Yelle D.J., Agarwal U.P. Lignin in polymer composites, Elsevier Inc., 2016, pp. 49–65, DOI: 10.1016/B978-0-323-35565-0.00004-7.

Fitigau I.F., Peter F., Boeriu C.G. International Journal of Chemical, Molecular, Nuclear, Materials and Metallurgical Engineering, 2013, vol. 7, no. 4, pp. 167–172.

Kanitskaya L.V., Gorotov A.F., Khai D.T.T., Rokhin A.V. Russ. J. Bioorg. Chem, 2012, vol. 38, no. 7, pp. 720–725, DOI: 10.1134/S1068162012070102.

Pu Y., Cao S., Ragauskas A.J. Energy Environ. Sci, 2011, vol. 4, pp. 3154–3166, DOI: 10.1039/C1EE01201K.

Granata A., Argyropoulos D.S. J. Agric. Food Chem, 1995, vol. 43, no. 6, pp. 1538–1544, DOI: 10.1021/jf00054a023.

Shestakov S.L., Kosyakov D.S., Kozhevnikov A.Yu., Ul'yanovskiy N.V., Popova Yu.A. Khimiya rastitel'nogo syr'ya, 2017, no. 2, pp. 81–88, DOI: 10.14258/jcprm.2017021641. (in Russ.).

Nimz H.H, Robert D, Faix O, Nemr M. Holzforschung, 1981, vol. 35, no. 1, pp. 16–26, DOI: 10.1515/hfsg.1981.35.1.16.

Pepper J.M., Baylis P.E.T., Adler E. Can. J. Chem., 1959, vol. 37, no. 8, pp. 1241–1248, DOI: 10.1139/v59-183.

Prech E., Byulmann F., Affolter K. Opredeleniye stroyeniya organicheskikh soyedineniy. Tablitsy spektral'nykh dan-nykh. [Determination of the structure of organic compounds. Spectral Data Tables]. Moscow, 2006, 438 p. (in Russ.).

Constant S., Wienk H.L.J., Frissen A.E, Peinder P., Boelens R. et al. Green Chem., 2016, vol. 18, pp. 2651–2665, DOI: 10.1039/c5gc03043a.

Published
2019-12-27
How to Cite
1. Popova Y. A., Shestakov S. L., Kozhevnikov A. Y., Kosyakov D. S., Sypalov S. A. COMPARATIVE ANALYSIS OF LIGNINS OF VARIOUS PLANT FORMS BY 31P-NMR // chemistry of plant raw material, 2019. № 4. P. 57-64. URL: http://journal.asu.ru/cw/article/view/5119.
Issue
No 4 (2019)
Section
Biopolymers of plants

Copyright (c) 2019 Khimiya Rastitel'nogo Syr'ya (Chemistry of plant raw material)

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.

The authors, which are published in this journal, agree to the following conditions:

1. Authors retain the copyright to the work and transfer to the journal the right of the first publication along with the work, at the same time licensing it under the terms of the Creative Commons Attribution License, which allows others to distribute this work with the obligatory indication of the authorship of this work and a link to the original publication in this journal .

2. The authors retain the right to enter into separate, additional contractual agreements for the non-exclusive distribution of the version of the work published by this journal (for example, to place it in the university depository or to publish it in a book), with reference to the original publication in this journal.

3. Authors are allowed to post their work on the Internet (for example, in a university repository or on their personal website) before and during the review process of this journal, as this may lead to a productive discussion, as well as more links to this published work.