Highly Decorated Lignins in Leaf Tissues of the Canary Island Date Palm

Overview

Journal Plant Physiol

Specialty Physiology

Date 2017 Sep 13

PMID 28894022

Citations 9

Authors

Steven D Karlen

Rebecca A Smith

Hoon Kim

Dharshana Padmakshan

Allison Bartuce

Justin K Mobley

Heather C A Free

Bronwen G Smith

Philip J Harris

John Ralph

Affiliations

Soon will be listed here.

Abstract

The cell walls of leaf base tissues of the Canary Island date palm () contain lignins with the most complex compositions described to date. The lignin composition varies by tissue region and is derived from traditional monolignols (ML) along with an unprecedented range of ML conjugates: ML-acetate, ML-benzoate, ML--hydroxybenzoate, ML-vanillate, ML--coumarate, and ML-ferulate. The specific functions of such complex lignin compositions are unknown. However, the distribution of the ML conjugates varies depending on the tissue region, indicating that they may play specific roles in the cell walls of these tissues and/or in the plant's defense system.

Citing Articles

-Coumaroylated Lignins Are Natively Produced in Three Rosales Families.

Hellinger J, Ralph J, Karlen S ACS Omega. 2025; 10(6):6220-6227.

PMID: 39989774 PMC: 11840785. DOI: 10.1021/acsomega.4c11429.

The Covalent Linking of Organophosphorus Heterocycles to Date Palm Wood-Derived Lignin: Hunting for New Materials with Flame-Retardant Potential.

Davidson D, McKay A, Cordes D, Woollins J, Westwood N Molecules. 2023; 28(23).

PMID: 38067614 PMC: 10707890. DOI: 10.3390/molecules28237885.

Lignin Hydrogenolysis: Phenolic Monomers from Lignin and Associated Phenolates across Plant Clades.

Chen M, Li Y, Lu F, Luterbacher J, Ralph J ACS Sustain Chem Eng. 2023; 11(27):10001-10017.

PMID: 37448721 PMC: 10337261. DOI: 10.1021/acssuschemeng.3c01320.

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.

Monolignol acyltransferase for lignin p-hydroxybenzoylation in Populus.

Zhao Y, Yu X, Lam P, Zhang K, Tobimatsu Y, Liu C Nat Plants. 2021; 7(9):1288-1300.

PMID: 34354261 DOI: 10.1038/s41477-021-00975-1.

References

Chen F, Tobimatsu Y, Havkin-Frenkel D, Dixon R, Ralph J . A polymer of caffeyl alcohol in plant seeds. Proc Natl Acad Sci U S A. 2012; 109(5):1772-7. PMC: 3277123. DOI: 10.1073/pnas.1120992109. View

Vanholme R, Morreel K, Darrah C, Oyarce P, Grabber J, Ralph J . Metabolic engineering of novel lignin in biomass crops. New Phytol. 2012; 196(4):978-1000. DOI: 10.1111/j.1469-8137.2012.04337.x. View

Petrik D, Karlen S, Cass C, Padmakshan D, Lu F, Liu S . p-Coumaroyl-CoA:monolignol transferase (PMT) acts specifically in the lignin biosynthetic pathway in Brachypodium distachyon. Plant J. 2013; 77(5):713-26. PMC: 4282527. DOI: 10.1111/tpj.12420. View

Coleman H, Park J, Nair R, Chapple C, Mansfield S . RNAi-mediated suppression of p-coumaroyl-CoA 3'-hydroxylase in hybrid poplar impacts lignin deposition and soluble secondary metabolism. Proc Natl Acad Sci U S A. 2008; 105(11):4501-6. PMC: 2393750. DOI: 10.1073/pnas.0706537105. View

Bartley L, Peck M, Kim S, Ebert B, Manisseri C, Chiniquy D . Overexpression of a BAHD acyltransferase, OsAt10, alters rice cell wall hydroxycinnamic acid content and saccharification. Plant Physiol. 2013; 161(4):1615-33. PMC: 3613443. DOI: 10.1104/pp.112.208694. View

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

Schuetz M, Smith R, Ellis B . Xylem tissue specification, patterning, and differentiation mechanisms. J Exp Bot. 2012; 64(1):11-31. DOI: 10.1093/jxb/ers287. View

Sun , Mott , Bolton . Isolation and Fractional Characterization of Ball-Milled and Enzyme Lignins from Oil Palm Trunk. J Agric Food Chem. 2001; 46(2):718-723. DOI: 10.1021/jf9705532. View

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

10.

Sibout R, Le Bris P, Legee F, Cezard L, Renault H, Lapierre C . Structural Redesigning Arabidopsis Lignins into Alkali-Soluble Lignins through the Expression of p-Coumaroyl-CoA:Monolignol Transferase PMT. Plant Physiol. 2016; 170(3):1358-66. PMC: 4775143. DOI: 10.1104/pp.15.01877. View

11.

Rencoret J, Ralph J, Marques G, Gutierrez A, Martinez A, Del Rio J . Structural characterization of lignin isolated from coconut (Cocos nucifera) coir fibers. J Agric Food Chem. 2013; 61(10):2434-45. DOI: 10.1021/jf304686x. View

12.

Sun R, Sun X, Zhang S . Quantitative determination of hydroxycinnamic acids in wheat, rice, rye, and barley straws, maize stems, oil palm frond fiber, and fast-growing poplar wood. J Agric Food Chem. 2001; 49(11):5122-9. DOI: 10.1021/jf010500r. View

13.

Wagner A, Ralph J, Akiyama T, Flint H, Phillips L, Torr K . Exploring lignification in conifers by silencing hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyltransferase in Pinus radiata. Proc Natl Acad Sci U S A. 2007; 104(28):11856-61. PMC: 1913891. DOI: 10.1073/pnas.0701428104. View

14.

Del Rio J, Rencoret J, Prinsen P, Martinez A, Ralph J, Gutierrez A . Structural characterization of wheat straw lignin as revealed by analytical pyrolysis, 2D-NMR, and reductive cleavage methods. J Agric Food Chem. 2012; 60(23):5922-35. DOI: 10.1021/jf301002n. View

15.

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

16.

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

17.

Lu , Ralph . The DFRC Method for Lignin Analysis. 2. Monomers from Isolated Lignins. J Agric Food Chem. 2001; 46(2):547-552. DOI: 10.1021/jf970676m. View

18.

Kishimoto T, Uraki Y, Ubukata M . Synthesis of beta-O-4-type artificial lignin polymers and their analysis by NMR spectroscopy. Org Biomol Chem. 2008; 6(16):2982-7. DOI: 10.1039/b805460f. View

19.

Lu F, Ralph J . Detection and determination of p-coumaroylated units in lignins. J Agric Food Chem. 1999; 47(5):1988-92. DOI: 10.1021/jf981140j. View

20.

Kim H, Ralph J . Solution-state 2D NMR of ball-milled plant cell wall gels in DMSO-d(6)/pyridine-d(5). Org Biomol Chem. 2010; 8(3):576-91. PMC: 4070321. DOI: 10.1039/b916070a. View