Lignin -Hydroxybenzoylation Is Negatively Correlated With Syringyl Units in Poplar

Overview

Journal Front Plant Sci

Date 2022 Aug 8

PMID 35937345

Authors

Yaseen Mottiar

Shawn D Mansfield

Affiliations

Soon will be listed here.

Abstract

The lignin found in the cell walls of poplar fibres is decorated with ester-linked -hydroxybenzoate moieties that originate from the participation of acylated monolignols in lignin polymerisation. Although little is known about the biological implications of these cell-wall constituents, it has historically been postulated that acylated monolignols might promote lignification in syringyl lignin-rich species such as poplar. However, cell-wall-bound -hydroxybenzoate groups were negatively correlated with syringyl units in a collection of 316 unrelated genotypes of black cottonwood (). Based upon this observation, several alternative hypotheses on the occurrence of lignin acylation are presented.

Citing Articles

Lignin deoxygenation for the production of sustainable aviation fuel blendstocks.

Webber M, Watson J, Zhu J, Jang J, Caglayan M, Heyne J Nat Mater. 2024; 23(12):1622-1638.

PMID: 39592761 DOI: 10.1038/s41563-024-02024-6.

Cell wall response of field grown to infection.

Bryant N, Muchero W, Weber R, Barros J, Chen J, Tschaplinski T Front Plant Sci. 2023; 14:1089011.

PMID: 37351208 PMC: 10282658. DOI: 10.3389/fpls.2023.1089011.

Novel candidate genes for lignin structure identified through genome-wide association study of naturally varying .

Bryant N, Zhang J, Feng K, Shu M, Ployet R, Chen J Front Plant Sci. 2023; 14:1153113.

PMID: 37215291 PMC: 10197963. DOI: 10.3389/fpls.2023.1153113.

Evolution of p-coumaroylated lignin in eudicots provides new tools for cell wall engineering.

Mottiar Y, Smith R, Karlen S, Ralph J, Mansfield S New Phytol. 2022; 237(1):251-264.

PMID: 36196006 PMC: 10099755. DOI: 10.1111/nph.18518.

Metabolic engineering of p-hydroxybenzoate in poplar lignin.

Mottiar Y, Karlen S, Goacher R, Ralph J, Mansfield S Plant Biotechnol J. 2022; 21(1):176-188.

PMID: 36161690 PMC: 9829402. DOI: 10.1111/pbi.13935.

References

Marjamaa K, Kukkola E, Fagerstedt K . The role of xylem class III peroxidases in lignification. J Exp Bot. 2009; 60(2):367-76. DOI: 10.1093/jxb/ern278. View

Zhao Y, Yu X, Lam P, Zhang K, Tobimatsu Y, Liu C . Monolignol acyltransferase for lignin p-hydroxybenzoylation in Populus. Nat Plants. 2021; 7(9):1288-1300. DOI: 10.1038/s41477-021-00975-1. View

Kirui A, Zhao W, Deligey F, Yang H, Kang X, Mentink-Vigier F . Carbohydrate-aromatic interface and molecular architecture of lignocellulose. Nat Commun. 2022; 13(1):538. PMC: 8795156. DOI: 10.1038/s41467-022-28165-3. View

Lapierre C, Sibout R, Laurans F, Lesage-Descauses M, Dejardin A, Pilate G . p-Coumaroylation of poplar lignins impacts lignin structure and improves wood saccharification. Plant Physiol. 2021; 187(3):1374-1386. PMC: 8566233. DOI: 10.1093/plphys/kiab359. View

Marita J, Hatfield R, Rancour D, Frost K . Identification and suppression of the p-coumaroyl CoA:hydroxycinnamyl alcohol transferase in Zea mays L. Plant J. 2014; 78(5):850-64. PMC: 4282748. DOI: 10.1111/tpj.12510. View

Bose S, Francis R, Govender M, Bush T, Spark A . Lignin content versus syringyl to guaiacyl ratio amongst poplars. Bioresour Technol. 2008; 100(4):1628-33. DOI: 10.1016/j.biortech.2008.08.046. View

Del Rio J, Marques G, Rencoret J, Martinez A, Gutierrez A . Occurrence of naturally acetylated lignin units. J Agric Food Chem. 2007; 55(14):5461-8. DOI: 10.1021/jf0705264. View

Robinson A, Mansfield S . Rapid analysis of poplar lignin monomer composition by a streamlined thioacidolysis procedure and near-infrared reflectance-based prediction modeling. Plant J. 2009; 58(4):706-14. DOI: 10.1111/j.1365-313X.2009.03808.x. View

Ranocha P, McDougall G, Hawkins S, Sterjiades R, Borderies G, Stewart D . Biochemical characterization, molecular cloning and expression of laccases - a divergent gene family - in poplar. Eur J Biochem. 1999; 259(1-2):485-95. DOI: 10.1046/j.1432-1327.1999.00061.x. View

10.

Lu F, Ralph J . Novel tetrahydrofuran structures derived from beta-beta-coupling reactions involving sinapyl acetate in Kenaf lignins. Org Biomol Chem. 2008; 6(20):3681-94. DOI: 10.1039/b809464k. View

11.

Busse-Wicher M, Gomes T, Tryfona T, Nikolovski N, Stott K, Grantham N . The pattern of xylan acetylation suggests xylan may interact with cellulose microfibrils as a twofold helical screw in the secondary plant cell wall of Arabidopsis thaliana. Plant J. 2014; 79(3):492-506. PMC: 4140553. DOI: 10.1111/tpj.12575. View

12.

Stewart J, Akiyama T, Chapple C, Ralph J, Mansfield S . The effects on lignin structure of overexpression of ferulate 5-hydroxylase in hybrid poplar. Plant Physiol. 2009; 150(2):621-35. PMC: 2689994. DOI: 10.1104/pp.109.137059. View

13.

Lu F, Ralph J, Morreel K, Messens E, Boerjan W . Preparation and relevance of a cross-coupling product between sinapyl alcohol and sinapyl p-hydroxybenzoate. Org Biomol Chem. 2004; 2(20):2888-90. DOI: 10.1039/B411428K. View

14.

Mottiar Y, Vanholme R, Boerjan W, Ralph J, Mansfield S . Designer lignins: harnessing the plasticity of lignification. Curr Opin Biotechnol. 2016; 37:190-200. DOI: 10.1016/j.copbio.2015.10.009. View

15.

Karlen S, Zhang C, Peck M, Smith R, Padmakshan D, Helmich K . Monolignol ferulate conjugates are naturally incorporated into plant lignins. Sci Adv. 2016; 2(10):e1600393. PMC: 5065250. DOI: 10.1126/sciadv.1600393. View

16.

Wilkerson C, Mansfield S, Lu F, Withers S, Park J, Karlen S . Monolignol ferulate transferase introduces chemically labile linkages into the lignin backbone. Science. 2014; 344(6179):90-3. DOI: 10.1126/science.1250161. View

17.

Boerjan W, Ralph J, Baucher M . Lignin biosynthesis. Annu Rev Plant Biol. 2003; 54:519-46. DOI: 10.1146/annurev.arplant.54.031902.134938. View

18.

Smith R, Beebe E, Bingman C, Vander Meulen K, Eugene A, Steiner A . Identification and characterization of a set of monocot BAHD monolignol transferases. Plant Physiol. 2022; 189(1):37-48. PMC: 9070852. DOI: 10.1093/plphys/kiac035. View

19.

Zhao Y, Yu X, Liu C . The Inducible Accumulation of Cell Wall-Bound -Hydroxybenzoates Is Involved in the Regulation of Gravitropic Response of Poplar. Front Plant Sci. 2021; 12:755576. PMC: 8712735. DOI: 10.3389/fpls.2021.755576. View

20.

Sasaki S, Nishida T, Tsutsumi Y, Kondo R . Lignin dehydrogenative polymerization mechanism: a poplar cell wall peroxidase directly oxidizes polymer lignin and produces in vitro dehydrogenative polymer rich in beta-O-4 linkage. FEBS Lett. 2004; 562(1-3):197-201. DOI: 10.1016/S0014-5793(04)00224-8. View