Density functional theory study on the coupling and reactions of diferuloylputrescine as a lignin monomer

Elder, Thomas; del Río, José C.; Ralph, John; Rencoret, Jorge; Kim, Hoon

doi:10.1016/j.phytochem.2022.113122

Title: Density functional theory study on the coupling and reactions of diferuloylputrescine as a lignin monomer

Abstract

Diferuloylputrescine has been found in a variety of plant species, and recent work has provided evidence of its covalent bonding into lignin. Results from nuclear magnetic resonance spectroscopy revealed the presence of bonding patterns consistent with homo-coupling of diferuloylputrescine and the possibility of cross-coupling with lignin. In the present work, density functional theory calculations have been applied to assess the energetics associated with radical coupling, rearomatization, and dehydrogenation for possible homo-coupled dimers of diferuloylputrescine and cross-coupled dimers of diferuloylputrescine and coniferyl alcohol. Furthermore, the values obtained for these reaction energetics are consistent with those reported for monolignols and other novel lignin monomers. As such, this study shows that there would be no thermodynamic impediment to the incorporation of diferuloylputrescine into the lignin polymer and its addition to the growing list of non-canonical lignin monomers.

Authors:

^[1];

^[2];

^[3];

^[2];

^[3]

USDA-Forest Service, Auburn, AL (United States)
Inst. de Recursos Naturales y Agrobiología de Sevilla (IRNAS), Seville (Spain)
Univ. of Wisconsin, Madison, WI (United States)

Publication Date:: Sat Feb 05 00:00:00 EST 2022

Research Org.:: Great Lakes Bioenergy Research Center (GLBRC), Madison, WI (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Biological and Environmental Research (BER)

OSTI Identifier:: 1845445

Alternate Identifier(s):: OSTI ID: 1962891

Grant/Contract Number:: SC0018409; BER DE-SC0018409

Resource Type:: Accepted Manuscript

Journal Name:: Phytochemistry

Additional Journal Information:: Journal Volume: 197; Journal ID: ISSN 0031-9422

Publisher:: Elsevier

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Diferuloylputrescine; Homo-couple; Cross-couple; Density functional theory; Coniferyl alcohol; Lignin; Lignification; Feruloyl amide; Radical coupling

Citation Formats


                    Elder, Thomas, del Río, José C., Ralph, John, Rencoret, Jorge, and Kim, Hoon. Density functional theory study on the coupling and reactions of diferuloylputrescine as a lignin monomer.  United States: N. p., 2022. 
Web.  doi:10.1016/j.phytochem.2022.113122.

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                    Elder, Thomas, del Río, José C., Ralph, John, Rencoret, Jorge, & Kim, Hoon. Density functional theory study on the coupling and reactions of diferuloylputrescine as a lignin monomer.  United States.  https://doi.org/10.1016/j.phytochem.2022.113122

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                    Elder, Thomas, del Río, José C., Ralph, John, Rencoret, Jorge, and Kim, Hoon. Sat .  
"Density functional theory study on the coupling and reactions of diferuloylputrescine as a lignin monomer".  United States.  https://doi.org/10.1016/j.phytochem.2022.113122.  https://www.osti.gov/servlets/purl/1845445.

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@article{osti_1845445,

  title        = {Density functional theory study on the coupling and reactions of diferuloylputrescine as a lignin monomer},

  author       = {Elder, Thomas and del Río, José C. and Ralph, John and Rencoret, Jorge and Kim, Hoon},

  abstractNote = {Diferuloylputrescine has been found in a variety of plant species, and recent work has provided evidence of its covalent bonding into lignin. Results from nuclear magnetic resonance spectroscopy revealed the presence of bonding patterns consistent with homo-coupling of diferuloylputrescine and the possibility of cross-coupling with lignin. In the present work, density functional theory calculations have been applied to assess the energetics associated with radical coupling, rearomatization, and dehydrogenation for possible homo-coupled dimers of diferuloylputrescine and cross-coupled dimers of diferuloylputrescine and coniferyl alcohol. Furthermore, the values obtained for these reaction energetics are consistent with those reported for monolignols and other novel lignin monomers. As such, this study shows that there would be no thermodynamic impediment to the incorporation of diferuloylputrescine into the lignin polymer and its addition to the growing list of non-canonical lignin monomers.},

  doi          = {10.1016/j.phytochem.2022.113122},

  journal      = {Phytochemistry},

  number       = ,

  volume       = 197,

  place        = {United States},

  year         = {Sat Feb 05 00:00:00 EST 2022},

  month        = {Sat Feb 05 00:00:00 EST 2022}

}

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Title: Density functional theory study on the coupling and reactions of diferuloylputrescine as a lignin monomer

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Coupling of Flavonoid Initiation Sites with Monolignols Studied by Density Functional Theory
journal, January 2021

Monolignol ferulate conjugates are naturally incorporated into plant lignins
journal, October 2016

Chemical Factors that Control Lignin Polymerization
journal, December 2013

Radical Coupling Reactions of Hydroxystilbene Glucosides and Coniferyl Alcohol: A Density Functional Theory Study
journal, March 2021

Coupling and Reactions of Lignols and New Lignin Monomers: A Density Functional Theory Study
journal, July 2020

Hydroxystilbene Glucosides Are Incorporated into Norway Spruce Bark Lignin
journal, April 2019

Structural Characterization of Lignin from Maize ( Zea mays L.) Fibers: Evidence for Diferuloylputrescine Incorporated into the Lignin Polymer in Maize Kernels
journal, April 2018

Anti-inflammatory activity of hydroxycinnamic acid derivatives isolated from corn bran in lipopolysaccharide-stimulated Raw 264.7 macrophages
journal, May 2012

Lignin Monomers from beyond the Canonical Monolignol Biosynthetic Pathway: Another Brick in the Wall
journal, March 2020

Variability in Lignin Composition and Structure in Cell Walls of Different Parts of Macaúba ( Acrocomia aculeata ) Palm Fruit
journal, December 2017

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals
journal, July 2007

NMR characterization of altered lignins extracted from tobacco plants down-regulated for lignification enzymes cinnamylalcohol dehydrogenase and cinnamoyl-CoA reductase
journal, October 1998

Radical Nature of C-Lignin
journal, May 2016

Highly Decorated Lignins in Leaf Tissues of the Canary Island Date Palm Phoenix canariensis
journal, September 2017

Reassignment of relative stereochemistry at C-7 and C-8 in arylcoumaran neolignans
journal, November 1997

Naturally p-Hydroxybenzoylated Lignins in Palms
journal, February 2015

The composition of corn oil obtained by the alcohol extraction of ground corn
journal, November 2005

Hydroxystilbenes Are Monomers in Palm Fruit Endocarp Lignins
journal, June 2017

Structural Characterization of Wheat Straw Lignin as Revealed by Analytical Pyrolysis, 2D-NMR, and Reductive Cleavage Methods
journal, December 2011

Lignans, Amides, and Saponins from Haplophyllum tuberculatum and Their Antiprotozoal Activity
journal, June 2020

Inhibition of Aflatoxin Biosynthesis in Aspergillus flavus by Diferuloylputrescine and p -Coumaroylferuloylputrescine
journal, September 2004

Tricin-lignins: occurrence and quantitation of tricin in relation to phylogeny
journal, November 2016

Abnormal Lignin in a Loblolly Pine Mutant
journal, July 1997

Phenolic compounds from hydrolyzed and extracted fiber-rich by-products
journal, July 2012