Study of Nettle (Urtica dióica) Lignin by Atmospheric Pressure Photoionization Orbitrap Mass Spectrometry

Pikovskoi, Ilya I.; Kosyakov, D. S.; Shavrina, I. S.; Ul’yanovskii, N. V.

doi:10.1134/s1061934819140090

Cited by 10 publications

(3 citation statements)

References 20 publications

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“…Following studies from the group successfully applied their APPI‐HRMS method to characterize products from the alkaline decomposition of hydrolysis lignin, revealing oligomers of up to ten aromatic rings with an average MW of 150 Da (Kosyakov et al, 2017) and the structure of grass lignins from nettle ( Urtica dióica ), revealing formation of lignins by the addition of guaiacyl‐ and syringylpropane units followed by etherification by p ‐coumaric, ferulic, and dihydroferulic acids (Pikovskoi et al, 2019).…”

Section: High Resolution Ms Methodsmentioning

confidence: 99%

Mass spectrometry‐based methods for the advanced characterization and structural analysis of lignin: A review

Letourneau

Volmer

2021

Mass Spectrometry Reviews

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Lignin is currently one of the most promising biologically derived resources, due to its abundance and application in biofuels, materials and conversion to value aromatic chemicals. The need to better characterize and understand this complex biopolymer has led to the development of many different analytical approaches, several of which involve mass spectrometry and subsequent data analysis. This review surveys the most important analytical methods for lignin involving mass spectrometry, first looking at methods involving gas chromatography, liquid chromatography and then continuing with more contemporary methods such as matrix assisted laser desorption ionization and time-of-flight-secondary ion mass spectrometry. Following that will be techniques that directly ionize lignin mixtures-without chromatographic separation-using softer atmospheric ionization techniques that leave the lignin oligomers intact. Finally, ultra-high resolution mass analyzers such as FT-ICR have enabled lignin analysis without major sample preparation and chromatography steps. Concurrent with an increase in the resolution of mass spectrometers, there have been a wealth of complementary data analyses and visualization methods that have allowed researchers to probe deeper into the "lignome" than ever before. These approaches extract trends such as compound series and even important analytical information about lignin substructures without performing lignin degradation either chemically or during MS analysis. These innovative methods are paving the way for a more comprehensiveThis is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

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Section: High Resolution Ms Methodsmentioning

confidence: 99%

Mass spectrometry‐based methods for the advanced characterization and structural analysis of lignin: A review

Letourneau

Volmer

2021

Mass Spectrometry Reviews

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“…One of the most promising analytical tools for molecular characterization of lignin is an orbital ion trap (Orbitrap) HRMS with atmospheric pressure photoionization (APPI) demonstrating a high efficiency of ionization of biopolymers in the wide range of molecular weights (up to 2 kDa) and a capability to simultaneously detect several thousands of oligomers [ 19 , 20 ]. This technique has been successfully used to characterize extremely complex mixtures of lignin depolymerization products [ 21 , 22 ], as well as to study the structure of nettle and sedge grass lignins [ 15 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Features of the Chemical Composition and Structure of Birch Phloem Dioxane Lignin: A Comprehensive Study

et al. 2022

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Understanding the chemical structure of lignin in the plant phloem contributes to the systematics of lignins of various biological origins, as well as the development of plant biomass valorization. In this study, the structure of the lignin from birch phloem has been characterized using the combination of three analytical techniques, including 2D NMR, Py-GC/MS, and APPI-Orbitrap-HRMS. Due to the specifics of the phloem chemical composition, two lignin preparations were analyzed: a sample obtained as dioxane lignin (DL) by the Pepper’s method and DL obtained after preliminary alkaline hydrolysis of the phloem. The obtained results demonstrated that birch phloem lignin possesses a guaiacyl–syringyl (G-S) nature with a unit ratio of (S/G) 0.7–0.9 and a higher degree of condensation compared to xylem lignin. It was indicated that its macromolecules are constructed from β-aryl ethers followed by phenylcoumaran and resinol structures as well as terminal groups in the form of cinnamic aldehyde and dihydroconiferyl alcohol. The presence of fatty acids and flavonoids removed during alkaline treatment was established. Tandem mass spectrometry made it possible to demonstrate that the polyphenolic components are impurities and are not incorporated into the structure of lignin macromolecules. An important component of phloem lignin is lignin–carbohydrate complexes incorporating xylopyranose moieties.

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“…In addition to bmim acetate, as an object we have also used bmim methylsulfate, which belongs to another class of ILs and also has a high dissolving power towards wood [17]. As the main methods of research two-dimensional NMR [21] and atmospheric pressure photoionization high-resolution mass spectrometry (APPI HRMS) [22,23] were chosen. Their combined use allows obtaining the most complete structural information for lignin characterization [24].…”

Section: Introductionmentioning

confidence: 99%

Characterization of Ionic Liquid Lignins Isolated from Spruce Wood with 1-Butyl-3-methylimidazolium Acetate and Methyl Sulfate and Their Binary Mixtures with DMSO

et al. 2020

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Ionic liquids (ILs) based on 1-butyl-3-methylimidazolium (bmim) cation have proved to be promising solvents for the fractionation of plant biomass with the production of cellulose and lignin. This study deals with the characterization of lignins isolated from coniferous (spruce) wood using [bmim]OAc and [bmim]MeSO4 ionic liquids and their binary mixtures with DMSO (80:20). Molecular weight distributions, functional composition, and structural features of IL lignins were studied by size-exclusion chromatography, NMR spectroscopy (1D and 2D) and atmospheric pressure photoionization high-resolution mass spectrometry. It was shown that the interaction of ILs with lignin leads to significant chemical changes in the biopolymer; a decrease in the degree of polymerization and in the content of free phenolic hydroxyl groups due to alkylation, the disappearance (in the case of [bmim]OAc) of carbonyl groups and a significant destruction of β-O-4 bonds. The chemical reactions between lignin and 1-butyl-3-methylidazolium cation with covalent binding of ionic liquids or products of their decomposition is evidenced by the presence of a large number of nitrogen-containing oligomers in IL lignins.

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Study of Nettle (Urtica dióica) Lignin by Atmospheric Pressure Photoionization Orbitrap Mass Spectrometry

Cited by 10 publications

References 20 publications

Mass spectrometry‐based methods for the advanced characterization and structural analysis of lignin: A review

Mass spectrometry‐based methods for the advanced characterization and structural analysis of lignin: A review

Features of the Chemical Composition and Structure of Birch Phloem Dioxane Lignin: A Comprehensive Study

Characterization of Ionic Liquid Lignins Isolated from Spruce Wood with 1-Butyl-3-methylimidazolium Acetate and Methyl Sulfate and Their Binary Mixtures with DMSO

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