Skip to main navigation menu Skip to main content Skip to site footer
Plant Science Today (PST)

Research Articles

Vol. 13 No. 3 (2026)

Analysis of sinapyl alcohol deposition patterns and lignification regulatory mechanisms in hardwoods using alkynyl-labelled sinapyl alcohol combined with click chemistry technology

DOI
https://doi.org/10.14719/pst.13230
Submitted
16 December 2025
Published
27-08-2026 — Updated on 29-09-2026
Versions

Abstract

Lignin is a major cell wall component in vascular plants and the second most abundant biopolymer accounting for 15–30 % of woody biomass. It maintains mechanical strength, supports xylem water transport, and contributes to defense against biotic stresses. Sinapyl alcohol is a major lignin precursor, but its deposition mechanism in hardwoods remains underexplored. In this study, an alkynyl-labelled sinapyl alcohol (SALK) probe was synthesised. Click chemistry combined with bioorthogonal labelling was applied to develop a visualisation system for tracking lignin monomer deposition in plant cell walls, enabling analysis of lignification mechanisms. Results showed that in Nerium oleander, fibre tracheids near the pith were less lignified, while lignin was deposited continuously in ray parenchyma cells. Lignin deposition starts at cell corners and middle lamellae and then moved to the secondary walls. Broussonetia papyrifera showed unique lignification process, in which vessel elements lignified non-autonomously, offering an ideal model for studying non-autonomous lignification. For the first time, the alkyne-tagged system developed in this study dynamically visualised sinapyl alcohol deposition in hardwood, revealing lignification differences across developmental stages and tissue types. It provides new technical insights into the autonomous and non-autonomous regulation of plant cell wall lignification.

References

  1. 1. Kolb HC, Finn MG, Sharpless KB. Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed Engl. 2001;40:2004–21. https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
  2. 2. Bukowski N, Pandey JL, Doyle L, Richard TL, Anderson CT, Zhu Y. Development of a clickable designer monolignol for interrogation of lignification in plant cell walls. Bioconjugate Chem. 2014;25:2189–96. https://doi.org/10.1021/bc500411u
  3. 3. Tobimatsu Y, Wagner A, Donaldson L, Mitra P, Niculaes C, Dima O, et al. Visualization of plant cell wall lignification using fluorescence-tagged monolignols. Plant J. 2013;76(3):357–66. https://doi.org/10.1111/tpj.12299
  4. 4. Simon C, Lion C, Spriet C, Baldacci-Cresp F, Hawkins S, Biot C. One, two, three: a bioorthogonal triple labelling strategy for studying the dynamics of plant cell wall formation in vivo. Angew Chem. 2019;57(51):16665–71. https://doi.org/10.1002/anie.201808493
  5. 5. Simon C, Morel O, Neutelings G, Baldacci-Cresp F, Baucher M, Spriet C, et al. Exploring lignification complexity in plant cell walls with airyscan super-resolution microscopy and bioorthogonal chemistry. Chem Biomed Imaging. 2023;1:479–87. https://doi.org/10.1021/cbmi.3c00052
  6. 6. Pomar F, Merino F, Barceló AR. O-4-Linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction. Protoplasma. 2002;220:17–28. https://doi.org/10.1007/s00709-002-0030-y
  7. 7. Lapierre C, Monties B, Rolando C, Chirale L de. Thioacidolysis of Lignin: Comparison with Acidolysis. J Wood Chem Technol. 1985;5:277–92. https://doi.org/10.1080/02773818508085193
  8. 8. Naron DR, Collard F-X, Tyhoda L, Görgens JF. Characterisation of lignins from different sources by appropriate analytical methods: Introducing thermogravimetric analysis-thermal desorption-gas chromatography-mass spectroscopy. Ind Crop Prod. 2017;101:61–74. https://doi.org/10.1016/j.indcrop.2017.02.041
  9. 9. Ralph J, Lapierre C, Boerjan W. Lignin structure and its engineering. Curr Opin Biotech. 2019;56:240–9. https://doi.org/10.1016/j.copbio.2019.02.019
  10. 10. Zhang S, Chen Y, Liu Z, Zhao Z. Advances in lignin valorization from a biorefinery concept. Sheng Wu Gong Cheng Xue Bao. 2021;37:3108–28.
  11. 11. Anterola AM, Lewis NG. Trends in lignin modification: a comprehensive analysis of the effects of genetic manipulations/mutations on lignification and vascular integrity. Phytochemistry. 2002;61:221–94. https://doi.org/10.1016/S0031-9422(02)00211-X
  12. 12. Lion C, Simon C, Huss B, Blervacq A-S, Tirot L, Toybou D, et al. BLISS: a bioorthogonal dual-labeling strategy to unravel lignification dynamics in plants. Cell Chem Biol. 2017;24:326–38. https://doi.org/10.1016/j.chembiol.2017.02.009
  13. 13. Yamauchi K, Yasuda S, Fukushima K. Evidence for the biosynthetic pathway from sinapic acid to syringyl lignin using labeled sinapic acid with stable isotope at both methoxy groups in Robinia pseudoacacia and Nerium indicum. J Agric Food Chem. 2002;50:3222–7. https://doi.org/10.1021/jf011565x
  14. 14. Sun J, Liu S, Zhang C, Yu L, Bi J, Zhu F, Yang Q. Chemical composition and antioxidant activities of Broussonetia papyrifera fruits. PLoS One. 2012;7:e32021. https://doi.org/10.1371/journal.pone.0032021
  15. 15. Yang H, Liu W, Sun Z, Yao L. Visualization of flax cell wall lignification using a novel click chemistry analogue of sinapyl alcohol. New J Chem. 2024;48:16599–608. https://doi.org/10.1039/D4NJ02847C
  16. 16. Pandey JL, Wang B, Diehl BG, Richard TL, Chen G, Anderson CT. A versatile click-compatible monolignol probe to study lignin deposition in plant cell walls. PLoS One. 2015;10:e0121334. https://doi.org/10.1371/journal.pone.0121334
  17. 17. Obame SN, Ziegler-Devin I, Safou-Tchima R, Brosse N. Homolytic and heterolytic cleavage of β-ether linkages in hardwood lignin by steam explosion. J Agric Food Chem. 2019;67(21):5989–96. https://doi.org/10.1021/acs.jafc.9b01744
  18. 18. Smith RA, Schuetz M, Roach M, Mansfield SD, Ellis B, Samuels L. Neighboring parenchyma cells contribute to Arabidopsis xylem lignification, while lignification of interfascicular fibers is cell autonomous. Plant Cell. 2013;25:3988–99. https://doi.org/10.1105/tpc.113.117176
  19. 19. Yao L, Wang R, Yoo CG, Zhang Y, Meng X, Liu W, et al. Visualization of lignification in flax stem cell walls with novel click-compatible monolignol analogs. Front Plant Sci. 2024;15:1423072. https://doi.org/10.3389/fpls.2024.1423072
  20. 20. Blee KA, Choi JW, O'Connell AP, Schuch W, Lewis NG, Bolwell GP. A lignin-specific peroxidase in tobacco whose antisense suppression leads to vascular tissue modification. Phytochemistry. 2003;64:163–76. https://doi.org/10.1016/S0031-9422(03)00212-7
  21. 21. Liu Q, Luo L, Zheng L. Lignins: biosynthesis and biological functions in plants. Int J Mol Sci. 2018;19:335. https://doi.org/10.3390/ijms19020335
  22. 22. Burr SJ, Fry SC. Extracellular cross-linking of maize arabinoxylans by oxidation of feruloyl esters to form oligoferuloyl esters and ether-like bonds. Plant J. 2009;58:554–67. https://doi.org/10.1111/j.1365-313X.2009.03800.x
  23. 23. Day A, Ruel K, Neutelings G, Crônier D, David H, Hawkins S, Chabbert B. Lignification in the flax stem: evidence for an unusual lignin in bast fibers. Planta. 2005;222:234–45. https://doi.org/10.1007/s00425-005-1537-1
  24. 24. Secchi F, Pagliarani C, Zwieniecki MA. The functional role of xylem parenchyma cells and aquaporins during recovery from severe water stress. Plant Cell Environ. 2017;40:858–71. https://doi.org/10.1111/pce.12831
  25. 25. Falcioni R, Moriwaki T, de Oliveira DM, Andreotti GC, de Souza LA, dos Santos WD, et al. Increased gibberellins and light levels promotes cell wall thickness and enhance lignin deposition in xylem fibers. Front Plant Sci. 2018;9:1391. https://doi.org/10.3389/fpls.2018.01391
  26. 26. Gadjev I, Stone JM, Gechev TS. Chapter 3: Programmed cell death in plants: new insights into redox regulation and the role of hydrogen peroxide. In: International Review of Cell and Molecular Biology. Academic Press; 2008. p. 87–144. https://doi.org/10.1016/S1937-6448(08)01403-2
  27. 27. Agrawal SB, Singh S, Agrawal M. Role of light in plant development. Int J Plant Environ. 2015;1:43–56. https://doi.org/10.18811/ijpen.v1i1.7113
  28. 28. Zhu N, Zhao C, Wei Y, Sun C, Wu D, Chen K. Biosynthetic labeling with 3-O-propargylcaffeyl alcohol reveals in vivo cell-specific patterned lignification in loquat fruits during development and postharvest storage. Hortic Res. 2021;8:61. https://doi.org/10.1038/s41438-021-00497-z
  29. 29. Berthet S, Demont-Caulet N, Pollet B, Bidzinski P, Cézard L, Le Bris P, et al. Disruption of LACCASE4 and 17 results in tissue-specific alterations to lignification of Arabidopsis thaliana stems. Plant Cell. 2011;23:1124–37. https://doi.org/10.1105/tpc.110.082792
  30. 30. Sterjiades R, Dean JFD, Eriksson K-EL. Laccase from sycamore maple (Acer pseudoplatanus) polymerizes monolignols. Plant Physiol. 1992;99:1162–8. https://doi.org/10.1104/pp.99.3.1162
  31. 31. Zhang B, Sztojka B, Escamez S, Vanholme R, Hedenström M, Wang Y, et al. PIRIN2 suppresses S-type lignin accumulation in a noncell-autonomous manner in Arabidopsis xylem elements. New Phytol. 2020;225:1923–35. https://doi.org/10.1111/nph.16271
  32. 32. Voxeur A, Wang Y, Sibout R. Lignification: different mechanisms for a versatile polymer. Curr Opin Plant Biol. 2015;23:83–90. https://doi.org/10.1016/j.pbi.2014.11.006
  33. 33. Smith RA, Schuetz M, Karlen SD, Bird D, Tokunaga N, Sato Y, et al. Defining the diverse cell populations contributing to lignification in Arabidopsis stems. Plant Physiol. 2017;174:1028–36. https://doi.org/10.1104/pp.17.00434
  34. 34. Pesquet E, Zhang B, Gorzsás A, Puhakainen T, Serk H, Escamez S, et al. Non-cell-autonomous postmortem lignification of tracheary elements in Zinnia elegans. Plant Cell. 2013;25:1314–28. https://doi.org/10.1105/tpc.113.110593
  35. 35. OlusegunAdebisi O, Kayode-Isola TM, DeborahGbala I, Adukwu E. Impact of hydrogen peroxide tolerance on carbapenem susceptibility in bacteria isolated from poultry environments. Microbiol Arch. 2024;7(1):7–15. https://doi.org/10.51470/MA.2025.7.1.07
  36. 36. Tripathi S, Srivastava D. Trichoderma as a green catalyst: exploring its versatile roles in sustainable agriculture. Microbiol Arch. 2025;7(2):13–21. https://doi.org/10.51470/MA.2025.7.2.13
  37. 37. Sarker S, Noor E Alam SM, Rahim MdA, Deb P, Das DC, Fazle Akbar SM, et al. Intravenous albumin in treatment of acute on chronic liver failure: can it be an option for resource constrained situation. J Am Med Sci Res. 2025;4(2):42–6. https://doi.org/10.51470/AMSR.2025.04.02.42
  38. 38. Dash SK, Hansdah B, Rout JR, Baral B, Sahoo SL. Christella parasitica (L.) Lev.: a potent pharmacological and pesticidal pteridophyte. J Plant Biota. 2024;3(2):1–4. https://doi.org/10.51470/JPB.2024.3.2.01
  39. 39. Ahmed SF, Azmi N, Azmi Z. A theoretical understanding of drug abuse: situational analysis of Hyderabad. Acta Pharm Rep. 2024;3(2):1–6. https://doi.org/10.51470/APR.2024.03.02.01

Downloads

Download data is not yet available.