ISSN 0253-2778

CN 34-1054/N

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2D HSQC NMR analysis of plant cell wall material in DMSO-d6/HMPA-d18

  • 1.

    Department of Chemistry, University of Science and Technology of China, Hefei 230026, China

  • 2.

    Technology Center, China Tobacco Jiangxi Industry Co., Ltd., Nanchang 330096, China

Cite this:
https://doi.org/10.3969/j.issn.0253-2778.2020.08.006
  • Received Date: 06 June 2020
  • Accepted Date: 28 June 2020
  • Rev Recd Date: 28 June 2020
  • Publish Date: 31 August 2020
    Abstract

  • Abstract

    The cell wall material gel is the product of the cell wall material directly formed with deuterated solvent in the nuclear magnetic resonance tube. The well-resolved/dispersed 2D 13C-1H related nuclear magnetic resonance spectra (2D HSQC NMR)can be obtained without the separation of components. Deuterated dimethyl sulfoxide (DMSO-d6), deuterated dimethyl sulfoxide/deuterated pyridine (DMSO-d6/pyridine-d5) and deuterated dimethyl sulfoxide/deuterated hexamethylphosphoryltriamine (DMSO-d6/HMPA-d18) were selected to dissolve the cell wall of poplar (angiosperm). The spectrum signals under DMSO-d6/HMPA-d18 were the most abundant, and the correlation of p-hydroxyphenyl signals could be easily obtained. Therefore, DMSO-d6/ HMPA-d18 improves the resolution and intensity of the spectrum. DMSO-d6/HMPA-d18 was used to characterize the two-dimensional NMR structure of pine (gymnosperms), and the spectrum showed high-resolution polysaccharide correlation and lignin structure. Studies have shown that this method is suitable for the detection of cell wall substances in plants.Therefore, the 2D HSQC NMR study under DMSO-d6/HMPA-d18 is a faster and greener method to evaluate the structure of plant cell wall.

    Abstract

    The cell wall material gel is the product of the cell wall material directly formed with deuterated solvent in the nuclear magnetic resonance tube. The well-resolved/dispersed 2D 13C-1H related nuclear magnetic resonance spectra (2D HSQC NMR)can be obtained without the separation of components. Deuterated dimethyl sulfoxide (DMSO-d6), deuterated dimethyl sulfoxide/deuterated pyridine (DMSO-d6/pyridine-d5) and deuterated dimethyl sulfoxide/deuterated hexamethylphosphoryltriamine (DMSO-d6/HMPA-d18) were selected to dissolve the cell wall of poplar (angiosperm). The spectrum signals under DMSO-d6/HMPA-d18 were the most abundant, and the correlation of p-hydroxyphenyl signals could be easily obtained. Therefore, DMSO-d6/ HMPA-d18 improves the resolution and intensity of the spectrum. DMSO-d6/HMPA-d18 was used to characterize the two-dimensional NMR structure of pine (gymnosperms), and the spectrum showed high-resolution polysaccharide correlation and lignin structure. Studies have shown that this method is suitable for the detection of cell wall substances in plants.Therefore, the 2D HSQC NMR study under DMSO-d6/HMPA-d18 is a faster and greener method to evaluate the structure of plant cell wall.
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    • References(20)
  • [1]
    BANERJEE A, DICK G R, YOSHINO T, et al. Carbon dioxide utilization via carbonate-promoted C-H carboxylation[J]. Nature, 2016, 531(7593): 215.
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    KERR R A. Peak oil production may already be here[J]. Science, 2011, 331(6024): 1510.
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    DELAUX J, ORTIZMELLET C, CANAFF C, et al. Impact of nonthermal atmospheric plasma on the structure of cellulose: Access to soluble branched glucans[J]. Chemistry - A European Journal, 2016, 22(46): 16522-16530.
    [4]
    DING J, YOO C G, PU Y, et al. Cellulolytic enzyme-aided extraction of hemicellulose from switchgrass and its characteristics[J]. Green Chemistry, 2019, 21(14): 3902-3910.
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    ROBINSON A R, MANSFIELD S D. Rapid analysis of poplar lignin monomer composition by a streamlined thioacidolysis procedure and near-infrared reflectance-based prediction modeling[J]. The Plant Journal, 2009, 58(4): 706-714.
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    DUVAL A, LAWOKO M. A review on lignin-based polymeric, micro- and nano-structured materials[J]. Reactive & Functional Polymers, 2014, 85(SI): 78-96.
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    FOSTON M, SAMUEL R, HE J, et al. A review of whole cell wall NMR by the direct-dissolution of biomass[J]. Green Chemistry, 2016, 18(3): 608-621.
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    YUAN T Q, SUN S N, XU F, et al. Structural characterization of lignin from triploid of populus tomentosa Carr[J]. Journal of Agricultural and Food Chemistry, 2011, 59(12): 6605-6615.
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    ZOIA L, TAMBURINI D, ORLANDI M, et al. Chemical characterisation of the whole plant cell wall of archaeological wood: An integrated approach[J]. Analytical and Bioanalytical Chemistry, 2017, 409(17): 4233-4245.
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    LU F, RALPH J. Non-degradative dissolution and acetylation of ball-milled plant cell walls: High-resolution solution-state NMR[J]. The Plant Journal, 2003, 35(4): 535-544.
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    CAPANEMA E A, BALAKSHIN M Y, KADLA J F. Quantitative characterization of a hardwood milled wood lignin by nuclear magnetic resonance spectroscopy[J]. Journal of Agricultural and Food Chemistry, 2005, 53(25): 9639-9649.
    [12]
    KIM H, RALPH J. Solution-state 2D NMR of ball-milled plant cell wall gels in DMSO-d6/pyridine-d5[J]. Organic and Biomolecular Chemistry, 2010, 8(3): 576-591.
    [13]
    YOO C G, PU Y, LI M, et al. Elucidating structural characteristics of biomass using solution-state 2?偆fD NMR with a mixture of deuterated dimethylsulfoxide and hexamethylphosphoramide[J]. ChemSusChem, 2016, 9(10): 1090-1095.
    [14]
    CHEN T Y, WANG B, WU Y Y, et al. Structural variations of lignin macromolecule from different growth years of triploid of populus tomentosa Carr[J]. Internal Journal of Biological Macromolecoles , 2017, 101: 747-757.
    [15]
    SUN R C, FANG J M, TOMKINSON J, et al. Fractional isolation, physico-chemical characterization and homogeneous esterification of hemicelluloses from fast-growing poplar wood[J]. Carbohydrate Polymers, 2001, 44(1): 29-39.
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    YAHIAOUI N, MARQUE C, MYTON K E, et al. Impact of different levels of cinnamyl alcohol dehydrogenase down-regulation on lignins of transgenic tobacco plants[J]. Planta, 1997, 204(1): 8-15.
    [17]
    HALPIN C, KNIGHT M E, GRIMAPETTENATI J, et al. Purification and characterization of cinnamyl alcohol dehydrogenase from tobacco stems[J]. Plant Physiology, 1992, 98(1): 12-16.
    [18]
    VAILHE M A B, BESLE J M, MAILLOT M P, et al. Effect of down-regulation of cinnamyl alcohol dehydrogenase on cell wall composition and on degradability of tobacco stems[J]. Journal of the Science of Food and Agriculture, 1998, 76(4): 505-514.
    [19]
    AKPINAR O, ERDOGAN K, BAKIR U, et al. Comparison of acid and enzymatic hydrolysis of tobacco stalk xylan for preparation of xylooligosaccharides[J]. Lwt - Food Science and Technology, 2010, 43(1): 119-125.
    [20]
    BALAKSHIN M, CAPANEMA E, GRACZ H, et al. Quantification of lignin-carbohydrate linkages with high-resolution NMR spectroscopy[J]. Planta, 2011, 233(6): 1097-1110.)
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    [1]
    BANERJEE A, DICK G R, YOSHINO T, et al. Carbon dioxide utilization via carbonate-promoted C-H carboxylation[J]. Nature, 2016, 531(7593): 215.
    [2]
    KERR R A. Peak oil production may already be here[J]. Science, 2011, 331(6024): 1510.
    [3]
    DELAUX J, ORTIZMELLET C, CANAFF C, et al. Impact of nonthermal atmospheric plasma on the structure of cellulose: Access to soluble branched glucans[J]. Chemistry - A European Journal, 2016, 22(46): 16522-16530.
    [4]
    DING J, YOO C G, PU Y, et al. Cellulolytic enzyme-aided extraction of hemicellulose from switchgrass and its characteristics[J]. Green Chemistry, 2019, 21(14): 3902-3910.
    [5]
    ROBINSON A R, MANSFIELD S D. Rapid analysis of poplar lignin monomer composition by a streamlined thioacidolysis procedure and near-infrared reflectance-based prediction modeling[J]. The Plant Journal, 2009, 58(4): 706-714.
    [6]
    DUVAL A, LAWOKO M. A review on lignin-based polymeric, micro- and nano-structured materials[J]. Reactive & Functional Polymers, 2014, 85(SI): 78-96.
    [7]
    FOSTON M, SAMUEL R, HE J, et al. A review of whole cell wall NMR by the direct-dissolution of biomass[J]. Green Chemistry, 2016, 18(3): 608-621.
    [8]
    YUAN T Q, SUN S N, XU F, et al. Structural characterization of lignin from triploid of populus tomentosa Carr[J]. Journal of Agricultural and Food Chemistry, 2011, 59(12): 6605-6615.
    [9]
    ZOIA L, TAMBURINI D, ORLANDI M, et al. Chemical characterisation of the whole plant cell wall of archaeological wood: An integrated approach[J]. Analytical and Bioanalytical Chemistry, 2017, 409(17): 4233-4245.
    [10]
    LU F, RALPH J. Non-degradative dissolution and acetylation of ball-milled plant cell walls: High-resolution solution-state NMR[J]. The Plant Journal, 2003, 35(4): 535-544.
    [11]
    CAPANEMA E A, BALAKSHIN M Y, KADLA J F. Quantitative characterization of a hardwood milled wood lignin by nuclear magnetic resonance spectroscopy[J]. Journal of Agricultural and Food Chemistry, 2005, 53(25): 9639-9649.
    [12]
    KIM H, RALPH J. Solution-state 2D NMR of ball-milled plant cell wall gels in DMSO-d6/pyridine-d5[J]. Organic and Biomolecular Chemistry, 2010, 8(3): 576-591.
    [13]
    YOO C G, PU Y, LI M, et al. Elucidating structural characteristics of biomass using solution-state 2?偆fD NMR with a mixture of deuterated dimethylsulfoxide and hexamethylphosphoramide[J]. ChemSusChem, 2016, 9(10): 1090-1095.
    [14]
    CHEN T Y, WANG B, WU Y Y, et al. Structural variations of lignin macromolecule from different growth years of triploid of populus tomentosa Carr[J]. Internal Journal of Biological Macromolecoles , 2017, 101: 747-757.
    [15]
    SUN R C, FANG J M, TOMKINSON J, et al. Fractional isolation, physico-chemical characterization and homogeneous esterification of hemicelluloses from fast-growing poplar wood[J]. Carbohydrate Polymers, 2001, 44(1): 29-39.
    [16]
    YAHIAOUI N, MARQUE C, MYTON K E, et al. Impact of different levels of cinnamyl alcohol dehydrogenase down-regulation on lignins of transgenic tobacco plants[J]. Planta, 1997, 204(1): 8-15.
    [17]
    HALPIN C, KNIGHT M E, GRIMAPETTENATI J, et al. Purification and characterization of cinnamyl alcohol dehydrogenase from tobacco stems[J]. Plant Physiology, 1992, 98(1): 12-16.
    [18]
    VAILHE M A B, BESLE J M, MAILLOT M P, et al. Effect of down-regulation of cinnamyl alcohol dehydrogenase on cell wall composition and on degradability of tobacco stems[J]. Journal of the Science of Food and Agriculture, 1998, 76(4): 505-514.
    [19]
    AKPINAR O, ERDOGAN K, BAKIR U, et al. Comparison of acid and enzymatic hydrolysis of tobacco stalk xylan for preparation of xylooligosaccharides[J]. Lwt - Food Science and Technology, 2010, 43(1): 119-125.
    [20]
    BALAKSHIN M, CAPANEMA E, GRACZ H, et al. Quantification of lignin-carbohydrate linkages with high-resolution NMR spectroscopy[J]. Planta, 2011, 233(6): 1097-1110.)
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