Carbon-13 nuclear magnetic resonance spectra of lignins

Lüdemann, H.‐D.; Nimz, Horst

doi:10.1016/0006-291x(73)90622-0

Cited by 121 publications

(55 citation statements)

References 4 publications

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“…Moreover, the resistance of most aromatic groups to chemical depolymerization treatments supports a prior hypothesis that these functionalities are located primarily within the cell wall (6). In contrast to these results for suberin, cutin from limes is found to be predominantly an aliphatic polyester (18,22), and lignins have been described as complex phenylpropanoid networks (10)(11)(12).…”

Section: Discussionsupporting

confidence: 73%

“…Despite substantial overlap of the NMR signals from the two polymeric components, prior studies ofcutin, lignin, cellulose, and synthetic polyesters (3, 4, 10-13, 22) make possible the chemical shift assignments summarized in Table I. The resonances at 62, 72, 83, and 101 ppm may be assigned to carbons (12). Some ofthese spectral features have been observed previously for lime cutin (18,22).…”

Section: Potato Cell Wallmentioning

confidence: 76%

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¹³C Nuclear Magnetic Resonance Study of Suberized Potato Cell Wall

Garbow¹,

Ferrantello²,

Stark³

1989

Plant Physiol.

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High-resolution, solid-state 13C nuclear magnetic resonance (NMR) spectra are reported for suberized cell wall from potatoes (Solanum tuberosum L.). Through experiments combining the techniques of cross polarization and magic-angle spinning, we verified that suberin, like cutin, is a polyester and demonstrated that it also has phenylpropanoid groups characteristic of lignin. Roughly 50% of the suberized material consists of cell-wall polymers; aromatics and other unsaturated linkages outnumber methylene groups 2:1. In conjunction with traditional direct-polarization NMR results, these experiments provide support for prior suggestions that suberin and cell-wall components are chemically bonded via aromatic groups.Suberin and cutin are biopolymers with important protective functions in higher plants, serving as barriers against moisture loss for underground and aerial organs, respectively. For example, the formation of suberin within cell walls helps to prevent moisture loss and decay in potatoes, while the cuticular layer of fruits mitigates the effects of evaporation, wind, and fungal pathogens. Suberization also occurs as a defensive response, with polymer deposition occurring for approximately 1 week following wounding of the tissue. The ultrastructure, biosynthesis, and chemical identification of these materials have been the subject of much study during the past 20 years, with the goal of developing a molecular rationale for their physiological functions (5, 6).Spectroscopic analysis of intact cutin and suberin has been limited by their insolubility, and because the suberized cell wall forms an inseparable and chemically complex unit. Instead, research in this area has focused on characterization of the soluble, monomeric products of chemical depolymerization treatments. Using primarily GC-MS, both materials have been identified as polyesters. An incomplete picture of biopolymer structure emerges from such studies, however, since much of the plant material is resistant to degradation and the identification of monomeric constituents alone provides little clue as to how the units are linked together in living plants.A new spectroscopic approach to plant polyester structure ' (22). In the latter case, it was possible to determine the identity, number, and motional characteristics of the major carbon types and to develop a working model of cutin as a flexible netting with some cross-link constraints.In the current work, we present high-resolution naturalabundance '3C NMR results for suberized cell-wall tissue from wound-healing potatoes (18). CPMAS is employed to identify major chemical functionalities of both the suberin and cellwall components and to estimate the relative numbers of each carbon type present. These results allow compositional comparisons to be made with cutin, lignin, and the soluble depolymerization products of suberized potato tissue. In conjunction with traditional DPMAS, the CPMAS spectra are examined in light of proposed models for the attachment of suberin and polysaccharide co...

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Section: Discussionsupporting

confidence: 73%

Section: Potato Cell Wallmentioning

confidence: 76%

¹³C Nuclear Magnetic Resonance Study of Suberized Potato Cell Wall

Garbow¹,

Ferrantello²,

Stark³

1989

Plant Physiol.

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“…5). The signals were assigned based on the reports of Lüdemann and Nimz (1973), Xie andTerashima (1993), andSun et al (2005). The presence of the absorption peaks at 166.7 ppm, 162.8 ppm, 160.2 ppm, 130.5 ppm, 125.4 ppm, and 111.6 ppm originated from ferulic acid (FA) and p-coumaric acid (CA), indicating that there were ferulic acid and p-coumaric acid substructures in the lignin samples of the corn stalk (Fig.…”

Section: C-nmr Analysismentioning

confidence: 99%

Investigation of the Structural Characteristics of Corn Stalk during Hot-Pressing

Zhang

et al. 2016

BioResources

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Corn stalk is one of the most abundant agricultural residues in China. In this experiment, corn stalks were hot-pressed to prepare formalin-free particleboard. Milled wood lignin (MWL) samples were isolated from original and hot-pressed corn stalks. To illuminate the self-bonding mechanism of binderless particleboard, the structural characteristics of original corn stalk, hot-pressed corn stalk, and MWL samples were thoroughly investigated by Fourier transform infrared spectroscopy (FT-IR), solid-state cross-polarization magic angle spinning carbon-13 nuclear magnetic resonance spectroscopy (CP-MAS 13 C-NMR), X-ray diffraction (XRD), carbon-13 nuclear magnetic resonance spectroscopy ( 13 C-NMR) and gel permeation chromatography(GPC). The degradation of hemicellulose and a portion of amorphous cellulose occurred during hot-pressing. Hot-pressing increased the crystallinity and crystallite size of cellulose in treated corn stalk. The analysis of MWL showed that hotpressing resulted in corn stalk lignin depolymerization through cleavage of a substantial portion of the β-O-4 linkages in lignin, as well as the decrease of molecular weight of lignin in corn stalk. In addition, acidcatalyzed condensation occurred between lignin and xylose when liberated from hemicellulose. These results demonstrated that condensation between lignin and xylose may contribute to the selfbonding mechanism and improve board properties.

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“…and to C3 and C5 carbon of the syringyl unit at 154 p.p.m. (Lu¨demann & Nimz, 1973). On the other hand, these split peaks are also characteristic of tannins and tannin-like structures (Lorenz et al, 2000); the signal near 145 p.p.m.…”

mentioning

confidence: 97%

Changes in soil organic matter composition are associated with forest encroachment into grassland with long‐term fire history

Dümig

Knicker

Schád

et al. 2009

European J Soil Science

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Summary This study investigates if Araucaria forest (C3 metabolism) expansion on frequently burnt grassland (C4 metabolism) in the southern Brazilian highland is linked to the chemical composition of soil organic matter (SOM) in non‐allophanic Andosols. We used the 13C/12C isotopic signature to group heavy organo‐mineral fractions according to source vegetation and 13C NMR spectroscopy, lignin analyses (CuO oxidation) and measurement of soil colour lightness to characterize their chemical compositions. Large proportions of aromatic carbon (C) combined with small contents of lignin‐derived phenols in the heavy fractions of grassland soils and grass‐derived lower horizons of Araucaria forest soils indicate the presence of charred grass residues in SOM. The contribution of this material may have led to the unusual increase in C/N ratios with depth in burnt grassland soils and to the differentiation of C3‐ and C4‐derived SOM, because heavy fractions from unburnt Araucaria forest and shrubland soils have smaller proportions of aromatic C, smaller C/N ratios and are paler compared with those with C4 signatures. We found that lignins are not applicable as biomarkers for plant origin in these soils with small contents of strongly degraded and modified lignins as the plant‐specific lignin patterns are absent in heavy fractions. In contrast, the characteristic contents of alkyl C and O/N‐alkyl C of C3 trees or shrubs and C4 grasses are reflected in the heavy fractions. They show consistent changes of the (alkyl C)/(O/N‐alkyl C) ratio and the 13C/12C isotopic signature with soil depth, indicating their association with C4 and C3 vegetation origin. This study demonstrates that soils may preserve organic matter components from earlier vegetation and land‐use, indicating that the knowledge of past vegetation covers is necessary to interpret SOM composition.

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Carbon-13 nuclear magnetic resonance spectra of lignins

Cited by 121 publications

References 4 publications

¹³C Nuclear Magnetic Resonance Study of Suberized Potato Cell Wall

¹³C Nuclear Magnetic Resonance Study of Suberized Potato Cell Wall

Investigation of the Structural Characteristics of Corn Stalk during Hot-Pressing

Changes in soil organic matter composition are associated with forest encroachment into grassland with long‐term fire history

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Carbon-13 nuclear magnetic resonance spectra of lignins

Cited by 121 publications

References 4 publications

13C Nuclear Magnetic Resonance Study of Suberized Potato Cell Wall

13C Nuclear Magnetic Resonance Study of Suberized Potato Cell Wall

Investigation of the Structural Characteristics of Corn Stalk during Hot-Pressing

Changes in soil organic matter composition are associated with forest encroachment into grassland with long‐term fire history

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¹³C Nuclear Magnetic Resonance Study of Suberized Potato Cell Wall

¹³C Nuclear Magnetic Resonance Study of Suberized Potato Cell Wall