Enzymatic basis for C‐lignin monomer biosynthesis in the seed coat of Cleome hassleriana

Zhuo, Chunliu; Rao, Xiaolan; Azad, Rajeev; Pandey, Ravi; Xiao, Xirong; Harkelroad, Aaron; Wang, Xiaoqiang; Chen, Fang; Dixon, Richard A.

doi:10.1111/tpj.14340

Title: Enzymatic basis for C‐lignin monomer biosynthesis in the seed coat of Cleome hassleriana

Abstract

Summary C‐lignin is a linear polymer of caffeyl alcohol, found in the seed coats of several exotic plant species, with promising properties for generation of carbon fibers and high value chemicals. In the ornamental plant Cleome hassleriana , guaiacyl (G) lignin is deposited in the seed coat for the first 6–12 days after pollination, after which G‐lignin deposition ceases and C‐lignin accumulates, providing an excellent model system to study C‐lignin biosynthesis. We performed RNA sequencing of seed coats harvested at 2‐day intervals throughout development. Bioinformatic analysis identified a complete set of lignin biosynthesis genes for Cleome . Transcript analysis coupled with kinetic analysis of recombinant enzymes in Escherichia coli revealed that the switch to C‐lignin formation was accompanied by down‐regulation of transcripts encoding functional caffeoyl CoA‐ and caffeic acid 3‐ O ‐methyltransferases ( CC o AOMT and COMT ) and a form of cinnamyl alcohol dehydrogenase (Ch CAD 4) with preference for coniferaldehyde as substrate, and up‐regulation of a form of CAD (Ch CAD 5) with preference for caffealdehyde. Based on these analyses, blockage of lignin monomer methylation by down‐regulation of both O ‐methyltransferases ( OMT s) and methionine synthase (for provision of C1 units) appears to be the major factormore »« less

Authors:

Zhuo, Chunliu ^[1]; Rao, Xiaolan ^[1]; Azad, Rajeev ^[2]; Pandey, Ravi ^[1]; Xiao, Xirong ^[3]; Harkelroad, Aaron ^[1]; Wang, Xiaoqiang ^[1]; Chen, Fang ^[3];

^[3]

BioDiscovery Institute University of North Texas Denton TX USA, Department of Biological Science University of North Texas Denton TX USA
BioDiscovery Institute University of North Texas Denton TX USA, Department of Biological Science University of North Texas Denton TX USA, Department of Mathematics University of North Texas Denton TX USA
BioDiscovery Institute University of North Texas Denton TX USA, Department of Biological Science University of North Texas Denton TX USA, Center for Bioenergy Innovation Oak Ridge National Laboratory Oak Ridge TX USA

Publication Date:: Fri May 17 00:00:00 EDT 2019

Sponsoring Org.:: USDOE

OSTI Identifier:: 1560226

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: The Plant Journal

Additional Journal Information:: Journal Name: The Plant Journal Journal Volume: 99 Journal Issue: 3; Journal ID: ISSN 0960-7412

Publisher:: Wiley-Blackwell

Country of Publication:: United Kingdom

Language:: English

Citation Formats


                    Zhuo, Chunliu, Rao, Xiaolan, Azad, Rajeev, Pandey, Ravi, Xiao, Xirong, Harkelroad, Aaron, Wang, Xiaoqiang, Chen, Fang, and Dixon, Richard A. Enzymatic basis for C‐lignin monomer biosynthesis in the seed coat of Cleome hassleriana.  United Kingdom: N. p., 2019. 
Web.  doi:10.1111/tpj.14340.

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                    Zhuo, Chunliu, Rao, Xiaolan, Azad, Rajeev, Pandey, Ravi, Xiao, Xirong, Harkelroad, Aaron, Wang, Xiaoqiang, Chen, Fang, & Dixon, Richard A. Enzymatic basis for C‐lignin monomer biosynthesis in the seed coat of Cleome hassleriana.  United Kingdom.  https://doi.org/10.1111/tpj.14340

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                    Zhuo, Chunliu, Rao, Xiaolan, Azad, Rajeev, Pandey, Ravi, Xiao, Xirong, Harkelroad, Aaron, Wang, Xiaoqiang, Chen, Fang, and Dixon, Richard A. Fri .  
"Enzymatic basis for C‐lignin monomer biosynthesis in the seed coat of Cleome hassleriana".  United Kingdom.  https://doi.org/10.1111/tpj.14340.

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@article{osti_1560226,

  title        = {Enzymatic basis for C‐lignin monomer biosynthesis in the seed coat of Cleome hassleriana},

  author       = {Zhuo, Chunliu and Rao, Xiaolan and Azad, Rajeev and Pandey, Ravi and Xiao, Xirong and Harkelroad, Aaron and Wang, Xiaoqiang and Chen, Fang and Dixon, Richard A.},

  abstractNote = {Summary C‐lignin is a linear polymer of caffeyl alcohol, found in the seed coats of several exotic plant species, with promising properties for generation of carbon fibers and high value chemicals. In the ornamental plant Cleome hassleriana , guaiacyl (G) lignin is deposited in the seed coat for the first 6–12 days after pollination, after which G‐lignin deposition ceases and C‐lignin accumulates, providing an excellent model system to study C‐lignin biosynthesis. We performed RNA sequencing of seed coats harvested at 2‐day intervals throughout development. Bioinformatic analysis identified a complete set of lignin biosynthesis genes for Cleome . Transcript analysis coupled with kinetic analysis of recombinant enzymes in Escherichia coli revealed that the switch to C‐lignin formation was accompanied by down‐regulation of transcripts encoding functional caffeoyl CoA‐ and caffeic acid 3‐ O ‐methyltransferases ( CC o AOMT and COMT ) and a form of cinnamyl alcohol dehydrogenase (Ch CAD 4) with preference for coniferaldehyde as substrate, and up‐regulation of a form of CAD (Ch CAD 5) with preference for caffealdehyde. Based on these analyses, blockage of lignin monomer methylation by down‐regulation of both O ‐methyltransferases ( OMT s) and methionine synthase (for provision of C1 units) appears to be the major factor in diversion of flux to C‐lignin in the Cleome seed coat, although the change in CAD specificity also contributes based on the reduction of C‐lignin levels in transgenic Cleome with down‐regulation of Ch CAD 5. Structure modeling and mutational analysis identified amino acid residues important for the preference of Ch CAD 5 for caffealdehyde.},

  doi          = {10.1111/tpj.14340},

  journal      = {The Plant Journal},

  number       = 3,

  volume       = 99,

  place        = {United Kingdom},

  year         = {Fri May 17 00:00:00 EDT 2019},

  month        = {Fri May 17 00:00:00 EDT 2019}

}

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Works referenced in this record:

Dual Methylation Pathways in Lignin Biosynthesis
journal, December 1998

Zhong, Ruiqin; Morrison, W. Herbert; Negrel, Jonathan
The Plant Cell, Vol. 10, Issue 12
DOI: 10.1105/tpc.10.12.2033

Lignin Biosynthesis
journal, June 2003

Boerjan, Wout; Ralph, John; Baucher, Marie
Annual Review of Plant Biology, Vol. 54, Issue 1, p. 519-546
DOI: 10.1146/annurev.arplant.54.031902.134938

A polymer of caffeyl alcohol in plant seeds
journal, January 2012

Chen, F.; Tobimatsu, Y.; Havkin-Frenkel, D.
Proceedings of the National Academy of Sciences, Vol. 109, Issue 5
DOI: 10.1073/pnas.1120992109

Functional reclassification of the putative cinnamyl alcohol dehydrogenase multigene family in Arabidopsis
journal, January 2004

Kim, S. -J.; Kim, M. -R.; Bedgar, D. L.
Proceedings of the National Academy of Sciences, Vol. 101, Issue 6
DOI: 10.1073/pnas.0307987100

Structure-Function Analyses of a Caffeic Acid O -Methyltransferase from Perennial Ryegrass Reveal the Molecular Basis for Substrate Preference
journal, December 2010

Louie, Gordon V.; Bowman, Marianne E.; Tu, Yi
The Plant Cell, Vol. 22, Issue 12
DOI: 10.1105/tpc.110.077578

Multi-site genetic modulation of monolignol biosynthesis suggests new routes for formation of syringyl lignin and wall-bound ferulic acid in alfalfa ( Medicago sativa L.)
journal, October 2006

Chen, Fang; Srinivasa Reddy, Marry S.; Temple, Stephen
The Plant Journal, Vol. 48, Issue 1
DOI: 10.1111/j.1365-313X.2006.02857.x

AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility
journal, December 2009

Morris, Garrett M.; Huey, Ruth; Lindstrom, William
Journal of Computational Chemistry, Vol. 30, Issue 16
DOI: 10.1002/jcc.21256

A novel lignin in poplar trees with a reduced caffeic acid/5-hydroxyferulic acid O-methyltransferase activity: A novel lignin in poplar trees
journal, December 1995

Doorsselaere, Jan; Baucher, Marie; Chognot, Emmanuelle
The Plant Journal, Vol. 8, Issue 6
DOI: 10.1046/j.1365-313X.1995.8060855.x

Membrane protein complexes catalyze both 4- and 3-hydroxylation of cinnamic acid derivatives in monolignol biosynthesis
journal, December 2011

Chen, H. -C.; Li, Q.; Shuford, C. M.
Proceedings of the National Academy of Sciences, Vol. 108, Issue 52
DOI: 10.1073/pnas.1116416109

Mathematical models of lignin biosynthesis
journal, February 2018

Faraji, Mojdeh; Fonseca, Luis L.; Escamilla-Treviño, Luis
Biotechnology for Biofuels, Vol. 11, Issue 1
DOI: 10.1186/s13068-018-1028-9

Ultrafast and memory-efficient alignment of short DNA sequences to the human genome
journal, January 2009

Langmead, Ben; Trapnell, Cole; Pop, Mihai
Genome Biology, Vol. 10, Issue 3
DOI: 10.1186/gb-2009-10-3-r25

Biochemical transformation of lignin for deriving valued commodities from lignocellulose
journal, June 2017

Gall, Daniel L.; Ralph, John; Donohue, Timothy J.
Current Opinion in Biotechnology, Vol. 45
DOI: 10.1016/j.copbio.2017.02.015

Novel seed coat lignins in the Cactaceae: structure, distribution and implications for the evolution of lignin diversity
journal, November 2012

Chen, Fang; Tobimatsu, Yuki; Jackson, Lisa
The Plant Journal, Vol. 73, Issue 2
DOI: 10.1111/tpj.12012

Caffeoyl Shikimate Esterase (CSE) Is an Enzyme in the Lignin Biosynthetic Pathway in Arabidopsis
journal, August 2013

Vanholme, R.; Cesarino, I.; Rataj, K.
Science, Vol. 341, Issue 6150
DOI: 10.1126/science.1241602

Both caffeoyl Coenzyme A 3-O-methyltransferase 1 and caffeic acid O-methyltransferase 1 are involved in redundant functions for lignin, flavonoids and sinapoyl malate biosynthesis in Arabidopsis
journal, June 2007

Do, Cao-Trung; Pollet, Brigitte; Thévenin, Johanne
Planta, Vol. 226, Issue 5
DOI: 10.1007/s00425-007-0558-3

The biosynthesis of monolignols: a “metabolic grid”, or independent pathways to guaiacyl and syringyl units?
journal, August 2001

Dixon, Richard A.; Chen, Fang; Guo, Dianjing
Phytochemistry, Vol. 57, Issue 7
DOI: 10.1016/S0031-9422(01)00092-9

Purification, Cloning, and Properties of an Acyltransferase Controlling Shikimate and Quinate Ester Intermediates in Phenylpropanoid Metabolism
journal, October 2002

Hoffmann, Laurent; Maury, Stéphane; Martz, Françoise
Journal of Biological Chemistry, Vol. 278, Issue 1
DOI: 10.1074/jbc.M209362200

Structural Studies of Cinnamoyl-CoA Reductase and Cinnamyl-Alcohol Dehydrogenase, Key Enzymes of Monolignol Biosynthesis
journal, September 2014

Pan, H.; Zhou, R.; Louie, G. V.
The Plant Cell, Vol. 26, Issue 9
DOI: 10.1105/tpc.114.127399

Altered lignin composition in transgenic tobacco expressing O-methyltransferase sequences in sense and antisense orientation
journal, October 1995

Atanassova, Rossitza; Favet, Noelle; Martz, Francoise
The Plant Journal, Vol. 8, Issue 4
DOI: 10.1046/j.1365-313X.1995.8040465.x

Thioacidolysis of Lignin: Comparison with Acidolysis
journal, January 1985

Lapierre, Catherine; Monties, Bernard; Rolando, Christian
Journal of Wood Chemistry and Technology, Vol. 5, Issue 2
DOI: 10.1080/02773818508085193

Elucidation of new structures in lignins of CAD- and COMT-deficient plants by NMR
journal, July 2001

Ralph, John; Lapierre, Catherine; Marita, Jane M.
Phytochemistry, Vol. 57, Issue 6
DOI: 10.1016/S0031-9422(01)00109-1

A real-time PCR assay to estimate Leishmania chagasi load in its natural sand fly vector Lutzomyia longipalpis
journal, September 2008

Ranasinghe, Shalindra; Rogers, Matthew E.; Hamilton, James G. C.
Transactions of the Royal Society of Tropical Medicine and Hygiene, Vol. 102, Issue 9
DOI: 10.1016/j.trstmh.2008.04.003

Streaming fragment assignment for real-time analysis of sequencing experiments
journal, November 2012

Roberts, Adam; Pachter, Lior
Nature Methods, Vol. 10, Issue 1
DOI: 10.1038/nmeth.2251

Two cinnamoyl-CoA reductase (CCR) genes from Arabidopsis thaliana are differentially expressed during development and in response to infection with pathogenic bacteria
journal, August 2001

Lauvergeat, Virginie; Lacomme, Christophe; Lacombe, Eric
Phytochemistry, Vol. 57, Issue 7
DOI: 10.1016/S0031-9422(01)00053-X

Radical Nature of C-Lignin
journal, May 2016

Berstis, Laura; Elder, Thomas; Crowley, Michael
ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 10
DOI: 10.1021/acssuschemeng.6b00520

Coexistence but Independent Biosynthesis of Catechyl and Guaiacyl/Syringyl Lignin Polymers in Seed Coats
journal, July 2013

Tobimatsu, Y.; Chen, F.; Nakashima, J.
The Plant Cell, Vol. 25, Issue 7
DOI: 10.1105/tpc.113.113142

Loss of function of folylpolyglutamate synthetase 1 reduces lignin content and improves cell wall digestibility in Arabidopsis
journal, December 2015

Srivastava, Avinash C.; Chen, Fang; Ray, Tui
Biotechnology for Biofuels, Vol. 8, Article No. 224
DOI: 10.1186/s13068-015-0403-z

Purification and Characterization of Cinnamoyl-Coenzyme A:NADP Oxidoreductase in Eucalyptus gunnii
journal, October 1994

Goffner, D.; Campbell, M. M.; Campargue, C.
Plant Physiology, Vol. 106, Issue 2
DOI: 10.1104/pp.106.2.625

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

del Río, José C.; Rencoret, Jorge; Prinsen, Pepijn
Journal of Agricultural and Food Chemistry, Vol. 60, Issue 23
DOI: 10.1021/jf301002n

Increase of Cinnamaldehyde Groups in Lignin of Transgenic Tobacco Plants Carrying an Antisense Gene for Cinnamyl Alcohol Dehydrogenase
journal, January 1995

Hibino, Takashi; Takabe, Keiji; Kawazu, Tetsu
Bioscience, Biotechnology, and Biochemistry, Vol. 59, Issue 5
DOI: 10.1271/bbb.59.929

Expression of cinnamyl alcohol dehydrogenases and their putative homologues during Arabidopsis thaliana growth and development: Lessons for database annotations?
journal, July 2007

Kim, Sung-Jin; Kim, Kye-Won; Cho, Man-Ho
Phytochemistry, Vol. 68, Issue 14
DOI: 10.1016/j.phytochem.2007.02.032

Lignification in Transgenic Poplars with Extremely Reduced Caffeic Acid O -Methyltransferase Activity
journal, August 2000

Jouanin, Lise; Goujon, Thomas; de Nadaı̈, Véronique
Plant Physiology, Vol. 123, Issue 4
DOI: 10.1104/pp.123.4.1363

Crystal structures and catalytic mechanism of the Arabidopsis cinnamyl alcohol dehydrogenases AtCAD5 and AtCAD4
journal, January 2006

Youn, Buhyun; Camacho, Roy; Moinuddin, Syed G. A.
Organic & Biomolecular Chemistry, Vol. 4, Issue 9
DOI: 10.1039/b601672c

The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism
journal, April 2002

Franke, Rochus; Humphreys, John M.; Hemm, Matthew R.
The Plant Journal, Vol. 30, Issue 1, p. 33-45
DOI: 10.1046/j.1365-313X.2002.01266.x

The Reliability of Molecular Weight Determinations by Dodecyl Sulfate-Polyacrylamide Gel Electrophoresis
journal, August 1969

Weber, K.; Osborn, M.
Journal of Biological Chemistry, Vol. 244, Issue 16
DOI: 10.1016/S0021-9258(18)94333-4

The rapid generation of mutation data matrices from protein sequences
journal, January 1992

Jones, David T.; Taylor, William R.; Thornton, Janet M.
Bioinformatics, Vol. 8, Issue 3
DOI: 10.1093/bioinformatics/8.3.275

Coot model-building tools for molecular graphics
journal, November 2004

Emsley, Paul; Cowtan, Kevin
Acta Crystallographica Section D Biological Crystallography, Vol. 60, Issue 12, p. 2126-2132
DOI: 10.1107/S0907444904019158

Downregulation of Caffeic Acid 3- O -Methyltransferase and Caffeoyl CoA 3- O -Methyltransferase in Transgenic Alfalfa: Impacts on Lignin Structure and Implications for the Biosynthesis of G and S Lignin
journal, January 2001

Guo, Dianjing; Chen, Fang; Inoue, Kentaro
The Plant Cell, Vol. 13, Issue 1
DOI: 10.1105/tpc.13.1.73

A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
journal, May 1976

Bradford, Marion M.
Analytical Biochemistry, Vol. 72, Issue 1-2
DOI: 10.1016/0003-2697(76)90527-3

Distinct cinnamoyl CoA reductases involved in parallel routes to lignin in Medicago truncatula
journal, September 2010

Zhou, Rui; Jackson, Lisa; Shadle, Gail
Proceedings of the National Academy of Sciences, Vol. 107, Issue 41, p. 17803-17808
DOI: 10.1073/pnas.1012900107

Basic local alignment search tool
journal, October 1990

Altschul, Stephen F.; Gish, Warren; Miller, Webb
Journal of Molecular Biology, Vol. 215, Issue 3, p. 403-410
DOI: 10.1016/S0022-2836(05)80360-2

MEGA7: Molecular Evolutionary Genetics Analysis Version 7.0 for Bigger Datasets
journal, March 2016

Kumar, Sudhir; Stecher, Glen; Tamura, Koichiro
Molecular Biology and Evolution, Vol. 33, Issue 7
DOI: 10.1093/molbev/msw054

Substrate preferences of O-methyltransferases in alfalfa suggest new pathways for 3-O-methylation of monolignols: Monolignol methylation in alfalfa
journal, January 2001

Parvathi, Kota; Chen, Fang; Guo, Dianjing
The Plant Journal, Vol. 25, Issue 2
DOI: 10.1111/j.1365-313X.2001.00956.x

Comparison of the Acetyl Bromide Spectrophotometric Method with Other Analytical Lignin Methods for Determining Lignin Concentration in Forage Samples
journal, June 2004

Fukushima, Romualdo S.; Hatfield, Ronald D.
Journal of Agricultural and Food Chemistry, Vol. 52, Issue 12, p. 3713-3720
DOI: 10.1021/jf035497l

Superior plant based carbon fibers from electrospun poly-(caffeyl alcohol) lignin
journal, July 2016

Nar, Mangesh; Rizvi, Hussain R.; Dixon, Richard A.
Carbon, Vol. 103
DOI: 10.1016/j.carbon.2016.02.053

Thioacidolysis of Poplar Lignins: Identification of Monomeric Syringyl Products and Characterization of Guaiacyl-Syringyl Lignin Fractions
journal, January 1986

Lapierre, Catherine; Monties, Bernard; Rolando, Christian
Holzforschung, Vol. 40, Issue 2
DOI: 10.1515/hfsg.1986.40.2.113

Reductive Catalytic Fractionation of C-Lignin
journal, August 2018

Stone, Michael L.; Anderson, Eric M.; Meek, Kelly M.
ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 9
DOI: 10.1021/acssuschemeng.8b02741

CYP98A3 from Arabidopsis thaliana Is a 3′-Hydroxylase of Phenolic Esters, a Missing Link in the Phenylpropanoid Pathway
journal, June 2001

Schoch, Guillaume; Goepfert, Simon; Morant, Marc
Journal of Biological Chemistry, Vol. 276, Issue 39
DOI: 10.1074/jbc.M104047200

CAD 1 and CCR 2 protein complex formation in monolignol biosynthesis in Populus trichocarpa
journal, October 2018

Yan, Xiaojing; Liu, Jie; Kim, Hoon
New Phytologist, Vol. 222, Issue 1
DOI: 10.1111/nph.15505

An “ideal lignin” facilitates full biomass utilization
journal, September 2018

Li, Yanding; Shuai, Li; Kim, Hoon
Science Advances, Vol. 4, Issue 9
DOI: 10.1126/sciadv.aau2968

The Tarenaya hassleriana Genome Provides Insight into Reproductive Trait and Genome Evolution of Crucifers
journal, August 2013

Cheng, Shifeng; van den Bergh, Erik; Zeng, Peng
The Plant Cell, Vol. 25, Issue 8
DOI: 10.1105/tpc.113.113480

Designer lignins: harnessing the plasticity of lignification
journal, February 2016

Mottiar, Yaseen; Vanholme, Ruben; Boerjan, Wout
Current Opinion in Biotechnology, Vol. 37
DOI: 10.1016/j.copbio.2015.10.009

CINNAMYL ALCOHOL DEHYDROGENASE-C and -D Are the Primary Genes Involved in Lignin Biosynthesis in the Floral Stem of Arabidopsis
journal, June 2005

Sibout, Richard; Eudes, Aymerick; Mouille, Gregory
The Plant Cell, Vol. 17, Issue 7
DOI: 10.1105/tpc.105.030767

Modifications in Lignin and Accumulation of Phenolic Glucosides in Poplar Xylem upon Down-regulation of Caffeoyl-Coenzyme A O-Methyltransferase, an Enzyme Involved in Lignin Biosynthesis
journal, August 2000

Meyermans, Hugo; Morreel, Kris; Lapierre, Catherine
Journal of Biological Chemistry, Vol. 275, Issue 47, p. 36899-36909
DOI: 10.1074/jbc.M006915200

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Title: Enzymatic basis for C‐lignin monomer biosynthesis in the seed coat of Cleome hassleriana

Abstract

Citation Formats

Dual Methylation Pathways in Lignin Biosynthesis journal, December 1998

Lignin Biosynthesis journal, June 2003

A polymer of caffeyl alcohol in plant seeds journal, January 2012

Functional reclassification of the putative cinnamyl alcohol dehydrogenase multigene family in Arabidopsis journal, January 2004

Structure-Function Analyses of a Caffeic Acid O -Methyltransferase from Perennial Ryegrass Reveal the Molecular Basis for Substrate Preference journal, December 2010

Multi-site genetic modulation of monolignol biosynthesis suggests new routes for formation of syringyl lignin and wall-bound ferulic acid in alfalfa ( Medicago sativa L.) journal, October 2006

AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility journal, December 2009

A novel lignin in poplar trees with a reduced caffeic acid/5-hydroxyferulic acid O-methyltransferase activity: A novel lignin in poplar trees journal, December 1995

Membrane protein complexes catalyze both 4- and 3-hydroxylation of cinnamic acid derivatives in monolignol biosynthesis journal, December 2011

Mathematical models of lignin biosynthesis journal, February 2018

Ultrafast and memory-efficient alignment of short DNA sequences to the human genome journal, January 2009

Biochemical transformation of lignin for deriving valued commodities from lignocellulose journal, June 2017

Novel seed coat lignins in the Cactaceae: structure, distribution and implications for the evolution of lignin diversity journal, November 2012

Caffeoyl Shikimate Esterase (CSE) Is an Enzyme in the Lignin Biosynthetic Pathway in Arabidopsis journal, August 2013

Both caffeoyl Coenzyme A 3-O-methyltransferase 1 and caffeic acid O-methyltransferase 1 are involved in redundant functions for lignin, flavonoids and sinapoyl malate biosynthesis in Arabidopsis journal, June 2007

The biosynthesis of monolignols: a “metabolic grid”, or independent pathways to guaiacyl and syringyl units? journal, August 2001

Purification, Cloning, and Properties of an Acyltransferase Controlling Shikimate and Quinate Ester Intermediates in Phenylpropanoid Metabolism journal, October 2002

Structural Studies of Cinnamoyl-CoA Reductase and Cinnamyl-Alcohol Dehydrogenase, Key Enzymes of Monolignol Biosynthesis journal, September 2014

Altered lignin composition in transgenic tobacco expressing O-methyltransferase sequences in sense and antisense orientation journal, October 1995

Thioacidolysis of Lignin: Comparison with Acidolysis journal, January 1985

Elucidation of new structures in lignins of CAD- and COMT-deficient plants by NMR journal, July 2001

A real-time PCR assay to estimate Leishmania chagasi load in its natural sand fly vector Lutzomyia longipalpis journal, September 2008

Streaming fragment assignment for real-time analysis of sequencing experiments journal, November 2012

Two cinnamoyl-CoA reductase (CCR) genes from Arabidopsis thaliana are differentially expressed during development and in response to infection with pathogenic bacteria journal, August 2001

Radical Nature of C-Lignin journal, May 2016

Coexistence but Independent Biosynthesis of Catechyl and Guaiacyl/Syringyl Lignin Polymers in Seed Coats journal, July 2013

Loss of function of folylpolyglutamate synthetase 1 reduces lignin content and improves cell wall digestibility in Arabidopsis journal, December 2015

Purification and Characterization of Cinnamoyl-Coenzyme A:NADP Oxidoreductase in Eucalyptus gunnii journal, October 1994

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

Increase of Cinnamaldehyde Groups in Lignin of Transgenic Tobacco Plants Carrying an Antisense Gene for Cinnamyl Alcohol Dehydrogenase journal, January 1995

Expression of cinnamyl alcohol dehydrogenases and their putative homologues during Arabidopsis thaliana growth and development: Lessons for database annotations? journal, July 2007

Lignification in Transgenic Poplars with Extremely Reduced Caffeic Acid O -Methyltransferase Activity journal, August 2000

Crystal structures and catalytic mechanism of the Arabidopsis cinnamyl alcohol dehydrogenases AtCAD5 and AtCAD4 journal, January 2006

The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism journal, April 2002

The Reliability of Molecular Weight Determinations by Dodecyl Sulfate-Polyacrylamide Gel Electrophoresis journal, August 1969

The rapid generation of mutation data matrices from protein sequences journal, January 1992

Coot model-building tools for molecular graphics journal, November 2004

Downregulation of Caffeic Acid 3- O -Methyltransferase and Caffeoyl CoA 3- O -Methyltransferase in Transgenic Alfalfa: Impacts on Lignin Structure and Implications for the Biosynthesis of G and S Lignin journal, January 2001

A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding journal, May 1976

Distinct cinnamoyl CoA reductases involved in parallel routes to lignin in Medicago truncatula journal, September 2010

Basic local alignment search tool journal, October 1990

MEGA7: Molecular Evolutionary Genetics Analysis Version 7.0 for Bigger Datasets journal, March 2016

Substrate preferences of O-methyltransferases in alfalfa suggest new pathways for 3-O-methylation of monolignols: Monolignol methylation in alfalfa journal, January 2001

Comparison of the Acetyl Bromide Spectrophotometric Method with Other Analytical Lignin Methods for Determining Lignin Concentration in Forage Samples journal, June 2004

Superior plant based carbon fibers from electrospun poly-(caffeyl alcohol) lignin journal, July 2016

Thioacidolysis of Poplar Lignins: Identification of Monomeric Syringyl Products and Characterization of Guaiacyl-Syringyl Lignin Fractions journal, January 1986

Reductive Catalytic Fractionation of C-Lignin journal, August 2018

CYP98A3 from Arabidopsis thaliana Is a 3′-Hydroxylase of Phenolic Esters, a Missing Link in the Phenylpropanoid Pathway journal, June 2001

CAD 1 and CCR 2 protein complex formation in monolignol biosynthesis in Populus trichocarpa journal, October 2018

An “ideal lignin” facilitates full biomass utilization journal, September 2018

The Tarenaya hassleriana Genome Provides Insight into Reproductive Trait and Genome Evolution of Crucifers journal, August 2013

Designer lignins: harnessing the plasticity of lignification journal, February 2016

CINNAMYL ALCOHOL DEHYDROGENASE-C and -D Are the Primary Genes Involved in Lignin Biosynthesis in the Floral Stem of Arabidopsis journal, June 2005

Modifications in Lignin and Accumulation of Phenolic Glucosides in Poplar Xylem upon Down-regulation of Caffeoyl-Coenzyme A O-Methyltransferase, an Enzyme Involved in Lignin Biosynthesis journal, August 2000

Dual Methylation Pathways in Lignin Biosynthesis
journal, December 1998

Lignin Biosynthesis
journal, June 2003

A polymer of caffeyl alcohol in plant seeds
journal, January 2012

Functional reclassification of the putative cinnamyl alcohol dehydrogenase multigene family in Arabidopsis
journal, January 2004

Structure-Function Analyses of a Caffeic Acid O -Methyltransferase from Perennial Ryegrass Reveal the Molecular Basis for Substrate Preference
journal, December 2010

Multi-site genetic modulation of monolignol biosynthesis suggests new routes for formation of syringyl lignin and wall-bound ferulic acid in alfalfa ( Medicago sativa L.)
journal, October 2006

AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility
journal, December 2009

A novel lignin in poplar trees with a reduced caffeic acid/5-hydroxyferulic acid O-methyltransferase activity: A novel lignin in poplar trees
journal, December 1995

Membrane protein complexes catalyze both 4- and 3-hydroxylation of cinnamic acid derivatives in monolignol biosynthesis
journal, December 2011

Mathematical models of lignin biosynthesis
journal, February 2018

Ultrafast and memory-efficient alignment of short DNA sequences to the human genome
journal, January 2009

Biochemical transformation of lignin for deriving valued commodities from lignocellulose
journal, June 2017

Novel seed coat lignins in the Cactaceae: structure, distribution and implications for the evolution of lignin diversity
journal, November 2012

Caffeoyl Shikimate Esterase (CSE) Is an Enzyme in the Lignin Biosynthetic Pathway in Arabidopsis
journal, August 2013

Both caffeoyl Coenzyme A 3-O-methyltransferase 1 and caffeic acid O-methyltransferase 1 are involved in redundant functions for lignin, flavonoids and sinapoyl malate biosynthesis in Arabidopsis
journal, June 2007

The biosynthesis of monolignols: a “metabolic grid”, or independent pathways to guaiacyl and syringyl units?
journal, August 2001

Purification, Cloning, and Properties of an Acyltransferase Controlling Shikimate and Quinate Ester Intermediates in Phenylpropanoid Metabolism
journal, October 2002

Structural Studies of Cinnamoyl-CoA Reductase and Cinnamyl-Alcohol Dehydrogenase, Key Enzymes of Monolignol Biosynthesis
journal, September 2014

Altered lignin composition in transgenic tobacco expressing O-methyltransferase sequences in sense and antisense orientation
journal, October 1995

Thioacidolysis of Lignin: Comparison with Acidolysis
journal, January 1985

Elucidation of new structures in lignins of CAD- and COMT-deficient plants by NMR
journal, July 2001

A real-time PCR assay to estimate Leishmania chagasi load in its natural sand fly vector Lutzomyia longipalpis
journal, September 2008

Streaming fragment assignment for real-time analysis of sequencing experiments
journal, November 2012

Two cinnamoyl-CoA reductase (CCR) genes from Arabidopsis thaliana are differentially expressed during development and in response to infection with pathogenic bacteria
journal, August 2001

Radical Nature of C-Lignin
journal, May 2016

Coexistence but Independent Biosynthesis of Catechyl and Guaiacyl/Syringyl Lignin Polymers in Seed Coats
journal, July 2013

Loss of function of folylpolyglutamate synthetase 1 reduces lignin content and improves cell wall digestibility in Arabidopsis
journal, December 2015

Purification and Characterization of Cinnamoyl-Coenzyme A:NADP Oxidoreductase in Eucalyptus gunnii
journal, October 1994

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

Increase of Cinnamaldehyde Groups in Lignin of Transgenic Tobacco Plants Carrying an Antisense Gene for Cinnamyl Alcohol Dehydrogenase
journal, January 1995

Expression of cinnamyl alcohol dehydrogenases and their putative homologues during Arabidopsis thaliana growth and development: Lessons for database annotations?
journal, July 2007

Lignification in Transgenic Poplars with Extremely Reduced Caffeic Acid O -Methyltransferase Activity
journal, August 2000

Crystal structures and catalytic mechanism of the Arabidopsis cinnamyl alcohol dehydrogenases AtCAD5 and AtCAD4
journal, January 2006

The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism
journal, April 2002

The Reliability of Molecular Weight Determinations by Dodecyl Sulfate-Polyacrylamide Gel Electrophoresis
journal, August 1969

The rapid generation of mutation data matrices from protein sequences
journal, January 1992

Coot model-building tools for molecular graphics
journal, November 2004

Downregulation of Caffeic Acid 3- O -Methyltransferase and Caffeoyl CoA 3- O -Methyltransferase in Transgenic Alfalfa: Impacts on Lignin Structure and Implications for the Biosynthesis of G and S Lignin
journal, January 2001

A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
journal, May 1976

Distinct cinnamoyl CoA reductases involved in parallel routes to lignin in Medicago truncatula
journal, September 2010

Basic local alignment search tool
journal, October 1990

MEGA7: Molecular Evolutionary Genetics Analysis Version 7.0 for Bigger Datasets
journal, March 2016

Substrate preferences of O-methyltransferases in alfalfa suggest new pathways for 3-O-methylation of monolignols: Monolignol methylation in alfalfa
journal, January 2001

Comparison of the Acetyl Bromide Spectrophotometric Method with Other Analytical Lignin Methods for Determining Lignin Concentration in Forage Samples
journal, June 2004

Superior plant based carbon fibers from electrospun poly-(caffeyl alcohol) lignin
journal, July 2016

Thioacidolysis of Poplar Lignins: Identification of Monomeric Syringyl Products and Characterization of Guaiacyl-Syringyl Lignin Fractions
journal, January 1986

Reductive Catalytic Fractionation of C-Lignin
journal, August 2018

CYP98A3 from Arabidopsis thaliana Is a 3′-Hydroxylase of Phenolic Esters, a Missing Link in the Phenylpropanoid Pathway
journal, June 2001

CAD 1 and CCR 2 protein complex formation in monolignol biosynthesis in Populus trichocarpa
journal, October 2018

An “ideal lignin” facilitates full biomass utilization
journal, September 2018

The Tarenaya hassleriana Genome Provides Insight into Reproductive Trait and Genome Evolution of Crucifers
journal, August 2013

Designer lignins: harnessing the plasticity of lignification
journal, February 2016

CINNAMYL ALCOHOL DEHYDROGENASE-C and -D Are the Primary Genes Involved in Lignin Biosynthesis in the Floral Stem of Arabidopsis
journal, June 2005

Modifications in Lignin and Accumulation of Phenolic Glucosides in Poplar Xylem upon Down-regulation of Caffeoyl-Coenzyme A O-Methyltransferase, an Enzyme Involved in Lignin Biosynthesis
journal, August 2000