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

Journal Article ·
DOI:https://doi.org/10.1039/c9np00028c· OSTI ID:1609110

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.

Research Organization:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
DOE Contract Number:
AC02-05CH11231
OSTI ID:
1609110
Country of Publication:
United States
Language:
English

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  • del Río, José C.; Rencoret, Jorge; Marques, Gisela
  • Journal of Agricultural and Food Chemistry, Vol. 56, Issue 20, p. 9525-9534 https://doi.org/10.1021/jf800806h
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Hydroxystilbenes Are Monomers in Palm Fruit Endocarp Lignins journal June 2017
Enzyme catalyzed cross-linking of spruce galactoglucomannan improves its applicability in barrier films journal June 2013
Ectopic expression of a novel OsExtensin-like gene consistently enhances plant lodging resistance by regulating cell elongation and cell wall thickening in rice journal July 2017
Simultaneously disrupting AtPrx2 , AtPrx25 and AtPrx71 alters lignin content and structure in Arabidopsis stem : Lignin alteration by simultaneous disruption of journal March 2015
Journal club journal February 2010
Coupling and Reactions of 5-Hydroxyconiferyl Alcohol in Lignin Formation journal June 2016
Ferulic acid in cereals – a review [Ferulic acid in cereals – a review] journal June 2016
Coniferylaldehydgruppem im Holz und in isolierten Ligninpräparaten. journal January 1948
Lignin degradation: microorganisms, enzymes involved, genomes analysis and evolution journal October 2017
Bioinspired assemblies of plant cell wall polymers unravel the affinity properties of carbohydrate-binding modules journal January 2015
Pectin RG-I rhamnosyltransferases represent a novel plant-specific glycosyltransferase family journal August 2018
Differences in S/G ratio in natural poplar variants do not predict catalytic depolymerization monomer yields journal May 2019
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
On the formation of lignin polysaccharide networks in Norway spruce journal March 2015
PeroxiBase: a database for large-scale evolutionary analysis of peroxidases journal November 2012
Isolation and characterization of Burkholderia sp. strain CCA53 exhibiting ligninolytic potential journal May 2016
Expression of a fungal glucuronoyl esterase in Populus: Effects on wood properties and saccharification efficiency journal April 2015
6 Lignin-protein complex in cell walls of Pinus elliottii: Amino acid constituents journal January 1982
Direct evidence for α ether linkage between lignin and carbohydrates in wood cell walls journal April 2018
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
ARAD proteins associated with pectic Arabinan biosynthesis form complexes when transiently overexpressed in planta journal January 2012
Ferulate Cross-Links Limit the Enzymatic Degradation of Synthetically Lignified Primary Walls of Maize journal July 1998
Surveillance of cell wall diffusion barrier integrity modulates water and solute transport in plants journal March 2019
Covalent bond formation between amino acids and lignin: Cross-coupling between proteins and lignin journal December 2013
Correlation between cell wall extensibility and the content of diferulic and ferulic acids in cell walls of Oryza sativa coleoptiles grown under water and in air journal November 1991
Dityrosine Cross-Linking in Designing Biomaterials journal October 2016
Impact of engineered lignin composition on biomass recalcitrance and ionic liquid pretreatment efficiency journal January 2016
Molecular characterization of two Arabidopsis thaliana glycosyltransferase mutants, rra1 and rra2, which have a reduced residual arabinose content in a polymer tightly associated with the cellulosic wall residue journal March 2007
Silencing CHALCONE SYNTHASE in Maize Impedes the Incorporation of Tricin into Lignin and Increases Lignin Content journal December 2016
Enzymic feruloylation of arabinoxylan-trisaccharide by feruloyl-CoA:arabinoxylan-trisaccharide O -hydroxycinnamoyl transferase from Oryza sativa journal February 2001
Regiochemical control of monolignol radical coupling: A new paradigm for lignin and lignan biosynthesis journal March 1999
O-Glycosylated Cell Wall Proteins Are Essential in Root Hair Growth journal June 2011
Diferulic and ferulic acid in the cell wall of Avena coleoptiles-Their relationships to mechanical properties of the cell wall journal January 1990
Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae journal October 2015
Accumulation of phenolic acid conjugates and betacyanins, and changes in the activities of enzymes involved in feruloylglucose metabolism in cell-suspension cultures of Chenopodium rubrum L. journal May 1991
Laccase application in medium density fibreboard to prepare a bio-composite journal January 2014
Monolignol ferulate conjugates are naturally incorporated into plant lignins journal October 2016
Structural Basis of Stereospecificity in the Bacterial Enzymatic Cleavage of β-Aryl Ether Bonds in Lignin journal December 2015
Characterization and heterologous expression of hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/benzoyltransferase from elicited cell cultures of carnation, Dianthus caryophyllus L. journal December 1997
Supramolecular Self-Assembled Chaos: Polyphenolic Lignin’s Barrier to Cost-Effective Lignocellulosic Biofuels journal November 2010
Repression of lignin biosynthesis promotes cellulose accumulation and growth in transgenic trees journal August 1999
SbCOMT (Bmr12) is involved in the biosynthesis of tricin-lignin in sorghum journal June 2017
Lignins: Natural polymers from oxidative coupling of 4-hydroxyphenyl- propanoids journal January 2004
Identification and suppression of the p‐ coumaroyl CoA:hydroxycinnamyl alcohol transferase in Zea mays L. journal May 2014
Tricin, a Flavonoid Monomer in Monocot Lignification journal February 2015
Dehydrodimers of Ferulic Acid in Maize Grain Pericarp and Aleurone: Resistance Factors to Fusarium graminearum journal June 2003
Overexpression of cotton (Gossypium hirsutum) dirigent1 gene enhances lignification that blocks the spread of Verticillium dahliae journal May 2012
Isolation and structural identification of complex feruloylated heteroxylan side-chains from maize bran journal June 2006
Lodging resistance of winter wheat (Triticum aestivum L.): Lignin accumulation and its related enzymes activities due to the application of paclobutrazol or gibberellin acid journal February 2014
Enzymatic Xylose Release from Pretreated Corn Bran Arabinoxylan: Differential Effects of Deacetylation and Deferuloylation on Insoluble and Soluble Substrate Fractions journal May 2010
Hydroxyproline O -arabinosyltransferase mutants oppositely alter tip growth in Arabidopsis thaliana and Physcomitrella patens journal December 2015
Biodegradation of kraft lignin by a bacterial strain Comamonas sp. B-9 isolated from eroded bamboo slips: Biodegradation of kraft lignin journal March 2012
Laccases Direct Lignification in the Discrete Secondary Cell Wall Domains of Protoxylem journal August 2014
Ferulic Acid Dehydrodimer and Dehydrotrimer Profiles of Distiller’s Dried Grains with Solubles from Different Cereal Species journal February 2015
Characterization of the extracellular γ-glutamyl transpeptidases, GGT1 and GGT2, in Arabidopsis: Apoplastic glutathione degradation in Arabidopsis journal February 2007
Characterization of a Second Arabidopsis thaliana Prolyl 4-Hydroxylase with Distinct Substrate Specificity journal November 2004
Identification of Novel Peptidyl Serine α-Galactosyltransferase Gene Family in Plants journal June 2014
Feruloylated Arabinoxylans Are Oxidatively Cross-Linked by Extracellular Maize Peroxidase but Not by Horseradish Peroxidase journal September 2009
Isolation from Sugar Beet Cell Walls of Arabinan Oligosaccharides Esterified by Two Ferulic Acid Monomers journal February 2004
Hydrogel: Preparation, characterization, and applications: A review journal March 2015
p -Coumaroyl-CoA:monolignol transferase (PMT) acts specifically in the lignin biosynthetic pathway in Brachypodium distachyon journal February 2014
Structural Identification of Dehydrotriferulic and Dehydrotetraferulic Acids Isolated from Insoluble Maize Bran Fiber journal August 2006
The Cell Walls of Green Algae: A Journey through Evolution and Diversity journal January 2012
p-Hydroxybenzoate groups in the lignin of aspen (populus tremula) journal January 1955
Laccase-initiated cross-linking of lignocellulose fibres using a ultra-filtered lignin isolated from kraft black liquor journal October 2007
Characterization of the primary cell walls of seedlings of Brachypodium distachyon – A potential model plant for temperate grasses journal January 2010
Hydroxyproline Arabinosides in the Plant Kingdom journal October 1971
Di-isodityrosine Is the Intermolecular Cross-link of Isodityrosine-rich Extensin Analogs Cross-linked in Vitro journal October 2004
Di-isodityrosine, a novel tetrametric derivative of tyrosine in plant cell wall proteins: a new potential cross-link journal April 1996
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
CINNAMYL ALCOHOL DEHYDROGENASE-C and -D Are the Primary Genes Involved in Lignin Biosynthesis in the Floral Stem of Arabidopsis journal June 2005
Characterization of Oligomeric Xylan Structures from Corn Fiber Resistant to Pretreatment and Simultaneous Saccharification and Fermentation journal November 2010
Acyltransferases in plants: a good time to be BAHD journal June 2006
Extensin and Arabinogalactan-Protein Biosynthesis: Glycosyltransferases, Research Challenges, and Biosensors journal June 2016
Expression analysis of the Arabidopsis peroxidase multigenic family journal May 2004
Production and in Vitro Fermentation of Soluble, Non-digestible, Feruloylated Oligo- and Polysaccharides from Maize and Wheat Brans journal December 2013
Cell Wall Lignin is Polymerised by Class III Secretable Plant Peroxidases in Norway Spruce journal February 2010
Reduced wood stiffness and strength, and altered stem form, in young antisense 4CL transgenic poplars with reduced lignin contents journal December 2010
One-Pot Enzymatic Production of Lignin-Composites journal April 2018
Identification of Zinc-Responsive Proteins in the Roots of Arabidopsis thaliana Using a Highly Improved Method of Two-Dimensional Electrophoresis journal September 2009
Cell Wall Esterified Phenolic Dimers: Identification and Quantification by Reverse Phase High Performance Liquid Chromatography and Diode Array Detection journal November 1996
Genetic and molecular basis of grass cell-wall degradability. I. Lignin–cell wall matrix interactions journal May 2004
Structural Redesigning Arabidopsis Lignins into Alkali-Soluble Lignins through the Expression of p- Coumaroyl-CoA:Monolignol Transferase PMT journal January 2016
A plant mutase that interconverts UDP-arabinofuranose and UDP-arabinopyranose journal December 2006
Structure and functions of feruloylated polysaccharides journal September 1997
Identification of Dehydro-Ferulic Acid-Tyrosine in Rye and Wheat:  Evidence for a Covalent Cross-Link between Arabinoxylans and Proteins journal June 2005
Genetic manipulation of lignocellulosic biomass for bioenergy journal December 2015
Elicitor-Induced Spruce Stress Lignin (Structural Similarity to Early Developmental Lignins) journal July 1995
Functional characterization of two acyltransferases from Populus trichocarpa capable of synthesizing benzyl benzoate and salicyl benzoate, potential intermediates in salicinoid phenolic glycoside biosynthesis journal May 2015
LACCASE5 Is Required for Lignification of the Brachypodium distachyon Culm journal March 2015

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