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Title: Phenolic cross-links: building and de-constructing the plant cell wall.

Abstract

Covering: Up to 2019Phenolic cross-links and phenolic inter-unit linkages result from the oxidative coupling of two hydroxycinnamates or two molecules of tyrosine. Free dimers of hydroxycinnamates, lignans, play important roles in plant defence. Cross-linking of bound phenolics in the plant cell wall affects cell expansion, wall strength, digestibility, degradability, and pathogen resistance. Cross-links mediated by phenolic substituents are particularly important as they confer strength to the wall via the formation of new covalent bonds, and by excluding water from it. Four biopolymer classes are known to be involved in the formation of phenolic cross-links: lignins, extensins, glucuronoarabinoxylans, and side-chains of rhamnogalacturonan-I. Lignins and extensins are ubiquitous in streptophytes whereas aromatic substituents on xylan and pectic side-chains are commonly assumed to be particular features of Poales sensu lato and core Caryophyllales, respectively. Cross-linking of phenolic moieties proceeds via radical formation, is catalyzed by peroxidases and laccases, and involves monolignols, tyrosine in extensins, and ferulate esters on xylan and pectin. Ferulate substituents, on xylan in particular, are thought to be nucleation points for lignin polymerization and are, therefore, of paramount importance to wall architecture in grasses and for the development of technology for wall disassembly, e.g. for the use of grass biomassmore » for production of 2nd generation biofuels. This review summarizes current knowledge on the intra- and extracellular acylation of polysaccharides, and inter- and intra-molecular cross-linking of different constituents. Enzyme mediated lignan in vitro synthesis for pharmaceutical uses are covered as are industrial exploitation of mutant and transgenic approaches to control cell wall cross-linking.« less

Authors:
; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ;
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER)
OSTI Identifier:
1609110
DOE Contract Number:  
AC02-05CH11231
Resource Type:
Journal Article
Country of Publication:
United States
Language:
English

Citation Formats

Mnich, Ewelina, Bjarnholt, Nanna, Eudes, Aymerick, Harholt, Jesper, Holland, Claire, Jørgensen, Bodil, Larsen, Flemming Hofmann, Liu, Ming, Manat, Renil, Meyer, Anne S, Mikkelsen, Jørn Dalgaard, Motawia, Mohammed Saddik, Muschiol, Jan, Møller, Birger Lindberg, Møller, Svenning Rune, Perzon, Alixander, Petersen, Bent Larsen, Ravn, Jonas Laukkonen, and Ulvskov, Peter. Phenolic cross-links: building and de-constructing the plant cell wall.. United States: N. p., 2020. Web. doi:10.1039/c9np00028c.
Mnich, Ewelina, Bjarnholt, Nanna, Eudes, Aymerick, Harholt, Jesper, Holland, Claire, Jørgensen, Bodil, Larsen, Flemming Hofmann, Liu, Ming, Manat, Renil, Meyer, Anne S, Mikkelsen, Jørn Dalgaard, Motawia, Mohammed Saddik, Muschiol, Jan, Møller, Birger Lindberg, Møller, Svenning Rune, Perzon, Alixander, Petersen, Bent Larsen, Ravn, Jonas Laukkonen, & Ulvskov, Peter. Phenolic cross-links: building and de-constructing the plant cell wall.. United States. doi:10.1039/c9np00028c.
Mnich, Ewelina, Bjarnholt, Nanna, Eudes, Aymerick, Harholt, Jesper, Holland, Claire, Jørgensen, Bodil, Larsen, Flemming Hofmann, Liu, Ming, Manat, Renil, Meyer, Anne S, Mikkelsen, Jørn Dalgaard, Motawia, Mohammed Saddik, Muschiol, Jan, Møller, Birger Lindberg, Møller, Svenning Rune, Perzon, Alixander, Petersen, Bent Larsen, Ravn, Jonas Laukkonen, and Ulvskov, Peter. Thu . "Phenolic cross-links: building and de-constructing the plant cell wall.". United States. doi:10.1039/c9np00028c.
@article{osti_1609110,
title = {Phenolic cross-links: building and de-constructing the plant cell wall.},
author = {Mnich, Ewelina and Bjarnholt, Nanna and Eudes, Aymerick and Harholt, Jesper and Holland, Claire and Jørgensen, Bodil and Larsen, Flemming Hofmann and Liu, Ming and Manat, Renil and Meyer, Anne S and Mikkelsen, Jørn Dalgaard and Motawia, Mohammed Saddik and Muschiol, Jan and Møller, Birger Lindberg and Møller, Svenning Rune and Perzon, Alixander and Petersen, Bent Larsen and Ravn, Jonas Laukkonen and Ulvskov, Peter},
abstractNote = {Covering: Up to 2019Phenolic cross-links and phenolic inter-unit linkages result from the oxidative coupling of two hydroxycinnamates or two molecules of tyrosine. Free dimers of hydroxycinnamates, lignans, play important roles in plant defence. Cross-linking of bound phenolics in the plant cell wall affects cell expansion, wall strength, digestibility, degradability, and pathogen resistance. Cross-links mediated by phenolic substituents are particularly important as they confer strength to the wall via the formation of new covalent bonds, and by excluding water from it. Four biopolymer classes are known to be involved in the formation of phenolic cross-links: lignins, extensins, glucuronoarabinoxylans, and side-chains of rhamnogalacturonan-I. Lignins and extensins are ubiquitous in streptophytes whereas aromatic substituents on xylan and pectic side-chains are commonly assumed to be particular features of Poales sensu lato and core Caryophyllales, respectively. Cross-linking of phenolic moieties proceeds via radical formation, is catalyzed by peroxidases and laccases, and involves monolignols, tyrosine in extensins, and ferulate esters on xylan and pectin. Ferulate substituents, on xylan in particular, are thought to be nucleation points for lignin polymerization and are, therefore, of paramount importance to wall architecture in grasses and for the development of technology for wall disassembly, e.g. for the use of grass biomass for production of 2nd generation biofuels. This review summarizes current knowledge on the intra- and extracellular acylation of polysaccharides, and inter- and intra-molecular cross-linking of different constituents. Enzyme mediated lignan in vitro synthesis for pharmaceutical uses are covered as are industrial exploitation of mutant and transgenic approaches to control cell wall cross-linking.},
doi = {10.1039/c9np00028c},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2020},
month = {1}
}

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Jute/polypropylene composites: Effect of enzymatic modification on thermo-mechanical and dynamic mechanical properties
journal, October 2015


Properties of fibre boards obtained by activation of the middle lamella lignin of wood fibres with peroxidase and H2O2 before conventional pressing
journal, January 1998

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Modeling Progression of Fluorescent Probes in Bioinspired Lignocellulosic Assemblies
journal, June 2013

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Bioinspired assemblies of plant cell wall polymers unravel the affinity properties of carbohydrate-binding modules
journal, January 2015

  • Paës, Gabriel; von Schantz, Laura; Ohlin, Mats
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A new procedure for the hydrophobization of cellulose fibre using laccase and a hydrophobic phenolic compound
journal, May 2012


Antimicrobial and antioxidant linen via laccase-assisted grafting
journal, July 2011


Enzymatic grafting of natural phenols to flax fibres: Development of antimicrobial properties
journal, January 2012


Native lignin for bonding of fiber boards—evaluation of bonding mechanisms in boards made from laccase-treated fibers of beech (Fagus sylvatica)
journal, September 2004


Pilot-scale production of fiberboards made by laccase oxidized wood fibers: board properties and evidence for cross-linking of lignin
journal, November 2002


Nanocelluloses: A New Family of Nature-Based Materials
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Nanocellulose as a natural source for groundbreaking applications in materials science: Today’s state
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Cellulose nanomaterials review: structure, properties and nanocomposites
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Nanocomposite materials from latex and cellulose whiskers
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Nanocellulose: a new ageless bionanomaterial
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Biomimetic engineering of cellulose-based materials
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Enzyme catalyzed cross-linking of spruce galactoglucomannan improves its applicability in barrier films
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Hydrogel: Preparation, characterization, and applications: A review
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Cellulose-based hydrogels: Present status and application prospects
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Dityrosine Cross-Linking in Designing Biomaterials
journal, October 2016

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Kinetics of Enzyme-Catalyzed Cross-Linking of Feruloylated Arabinan from Sugar Beet
journal, November 2011

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  • Journal of Agricultural and Food Chemistry, Vol. 59, Issue 21
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Bright Side of Lignin Depolymerization: Toward New Platform Chemicals
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Nanofibers Produced from Agro-Industrial Plant Waste Using Entirely Enzymatic Pretreatments
journal, November 2018


Generation of transgenic wheat ( Triticum aestivum L.) accumulating heterologous endo-xylanase or ferulic acid esterase in the endosperm
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Quantification of lignin–carbohydrate linkages with high-resolution NMR spectroscopy
journal, February 2011


Expression of a fungal glucuronoyl esterase in Populus: Effects on wood properties and saccharification efficiency
journal, April 2015


Degradation of lignosulfonic and tannic acids by ligninolytic soil fungi cultivated under icroaerobic conditions
journal, June 2010

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Phoma herbarum, a soil fungus able to grow on natural lignin and synthetic lignin (DHP) as sole carbon source and cause lignin degradation
journal, June 2016

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Enzyme activities of aerobic lignocellulolytic bacteria isolated from wet tropical forest soils
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Biodegradation of kraft-lignin by Bacillus sp. isolated from sludge of pulp and paper mill
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Biodegradation of kraft lignin by a newly isolated bacterial strain, Aneurinibacillus aneurinilyticus from the sludge of a pulp paper mill
journal, November 2006

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Isolation and characterization of Burkholderia sp. strain CCA53 exhibiting ligninolytic potential
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Isolation of bacterial strains able to metabolize lignin and lignin-related compounds
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Degradation of lignin and lignin derivatives by Acinetobacter sp.
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Genome sequence and description of the anaerobic lignin-degrading bacterium Tolumonas lignolytica sp. nov.
journal, November 2015

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Evidence supporting dissimilatory and assimilatory lignin degradation in Enterobacter lignolyticus SCF1
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Characterization of a newly isolated Bacterium Pandoraea sp. B-6 capable of degrading kraft lignin
journal, March 2013

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Biodegradation of kraft lignin by a bacterial strain Comamonas sp. B-9 isolated from eroded bamboo slips: Biodegradation of kraft lignin
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New and classic families of secreted fungal heme peroxidases
journal, May 2010

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Towards understanding of laccase-catalysed oxidative oligomerisation of dimeric lignin model compounds
journal, January 2017

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Direct rate assessment of laccase catalysed radical formation in lignin by electron paramagnetic resonance spectroscopy
journal, November 2017


Laccase and Its Role in Production of Extracellular Reactive Oxygen Species during Wood Decay by the Brown Rot Basidiomycete Postia placenta
journal, February 2010

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Active and total microbial communities in forest soil are largely different and highly stratified during decomposition
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Synergistic enzymatic and microbial lignin conversion
journal, January 2016

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Lignin degradation: microorganisms, enzymes involved, genomes analysis and evolution
journal, October 2017

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Lignin engineering through laccase modification: a promising field for energy plant improvement
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Lignin bioengineering
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Genetic manipulation of lignocellulosic biomass for bioenergy
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Chemical Pulping Advantages of Zip-lignin Hybrid Poplar
journal, August 2017


Impact of lignin polymer backbone esters on ionic liquid pretreatment of poplar
journal, April 2017


Apoplastic pH and Monolignol Addition Rate Effects on Lignin Formation and Cell Wall Degradability in Maize
journal, August 2003

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Methyl Esterification Divergently Affects the Degradability of Pectic Uronosyls in Nonlignified and Lignified Maize Cell Walls
journal, March 2005

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Coupling and Reactions of 5-Hydroxyconiferyl Alcohol in Lignin Formation
journal, June 2016

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Enhancing digestibility and ethanol yield of Populus wood via expression of an engineered monolignol 4-O-methyltransferase
journal, June 2016

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Vanillin formation from ferulic acid in Vanilla planifolia is catalysed by a single enzyme
journal, June 2014

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The Intracellular Localization of the Vanillin Biosynthetic Machinery in Pods of Vanilla planifolia
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SbCOMT (Bmr12) is involved in the biosynthesis of tricin-lignin in sorghum
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Cytochrome P450 93G1 Is a Flavone Synthase II That Channels Flavanones to the Biosynthesis of Tricin O -Linked Conjugates in Rice
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Completion of Tricin Biosynthesis Pathway in Rice: Cytochrome P450 75B4 Is a Unique Chrysoeriol 5′-Hydroxylase
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Silencing CHALCONE SYNTHASE in Maize Impedes the Incorporation of Tricin into Lignin and Increases Lignin Content
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Current Understanding of the Correlation of Lignin Structure with Biomass Recalcitrance
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CINNAMYL ALCOHOL DEHYDROGENASE-C and -D Are the Primary Genes Involved in Lignin Biosynthesis in the Floral Stem of Arabidopsis
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Different Routes for Conifer- and Sinapaldehyde and Higher Saccharification upon Deficiency in the Dehydrogenase CAD1
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Why genetic modification of lignin leads to low-recalcitrance biomass
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Impact of engineered lignin composition on biomass recalcitrance and ionic liquid pretreatment efficiency
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Lignin modification improves fermentable sugar yields for biofuel production
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Natural acetylation impacts carbohydrate recovery during deconstruction of Populus trichocarpa wood
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Introduction of chemically labile substructures into Arabidopsis lignin through the use of LigD, the Cα-dehydrogenase from Sphingobium sp. strain SYK-6
journal, January 2015

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Degradation of lignin β-aryl ether units in Arabidopsis thaliana expressing LigD , LigF and LigG from Sphingomonas paucimobilis SYK-6
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Roles of the Enantioselective Glutathione S-Transferases in Cleavage of  -Aryl Ether
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Roles for Stress-inducible Lambda Glutathione Transferases in Flavonoid Metabolism in Plants as Identified by Ligand Fishing
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Glutathione transferases catalyze recycling of auto-toxic cyanogenic glucosides in sorghum
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An Inducible Glutathione S-Transferase in Soybean Hypocotyl Is Localized in the Apoplast
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Characterization of the extracellular γ-glutamyl transpeptidases, GGT1 and GGT2, in Arabidopsis: Apoplastic glutathione degradation in Arabidopsis
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Proteome readjustments in the apoplastic space of Arabidopsis thaliana ggt1 mutant leaves exposed to UV-B radiation
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Pathogen-Induced Changes in the Antioxidant Status of the Apoplast in Barley Leaves
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Enzymatic cleavage of lignin β-O-4 aryl ether bonds via net internal hydrogen transfer
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Structural Basis of Stereospecificity in the Bacterial Enzymatic Cleavage of β-Aryl Ether Bonds in Lignin
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Cascade enzymatic cleavage of the β-O-4 linkage in a lignin model compound
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Bacterial catabolism of lignin-derived aromatics: New findings in a recent decade: Update on bacterial lignin catabolism: Bacterial catabolism of lignin-derived aromatics
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A Group of Sequence-Related Sphingomonad Enzymes Catalyzes Cleavage of β-Aryl Ether Linkages in Lignin β-Guaiacyl and β-Syringyl Ether Dimers
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From Gene Towards Selective Biomass Valorization: Bacterial β-Etherases with Catalytic Activity on Lignin-Like Polymers
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Characterization of the primary cell walls of seedlings of Brachypodium distachyon – A potential model plant for temperate grasses
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