skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: A Versatile Click-Compatible Monolignol Probe to Study Lignin Deposition in Plant Cell Walls

Abstract

Here, lignin plays important structural and functional roles in plants by forming a hydrophobic matrix in secondary cell walls that enhances mechanical strength and resists microbial decay. While the importance of the lignin matrix is well documented and the biosynthetic pathways for monolignols are known, the process by which lignin precursors or monolignols are transported and polymerized to form this matrix remains a subject of considerable debate. In this study, we have synthesized and tested an analog of coniferyl alcohol that has been modified to contain an ethynyl group at the C-3 position. This modification enables fluorescent tagging and imaging of this molecule after its incorporation into plant tissue by click chemistry-assisted covalent labeling with a fluorescent azide dye, and confers a distinct Raman signature that could be used for Raman imaging. We found that this monolignol analog is incorporated into in vitro-polymerized dehydrogenation polymer (DHP) lignin and into root epidermal cell walls of 4-day-old Arabidopsis seedlings. Incorporation of the analog in stem sections of 6-week-old Arabidopsis thaliana plants and labeling with an Alexa-594 azide dye revealed the precise locations of new lignin polymerization. Results from this study indicate that this molecule can provide high-resolution localization of lignification during plantmore » cell wall maturation and lignin matrix assembly.« less

Authors:
 [1];  [1];  [1];  [1];  [1];  [1];  [2]
  1. The Pennsylvania State Univ., University Park, PA (United States)
  2. Iowa State Univ., Ames, IA (United States)
Publication Date:
Research Org.:
Pennsylvania State Univ., University Park, PA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1459346
Grant/Contract Number:  
SC0001090
Resource Type:
Accepted Manuscript
Journal Name:
PLoS ONE
Additional Journal Information:
Journal Volume: 10; Journal Issue: 4; Journal ID: ISSN 1932-6203
Publisher:
Public Library of Science
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; lignin; seedlings; fluorescence imaging; alcohols; NMR spectroscopy; Arabidopsis thaliana; polymerization; alkynes

Citation Formats

Pandey, Jyotsna L., Wang, Bo, Diehl, Brett G., Richard, Tom L., Chen, Gong, Anderson, Charles T., and Zabotina, Olga A. A Versatile Click-Compatible Monolignol Probe to Study Lignin Deposition in Plant Cell Walls. United States: N. p., 2015. Web. doi:10.1371/journal.pone.0121334.
Pandey, Jyotsna L., Wang, Bo, Diehl, Brett G., Richard, Tom L., Chen, Gong, Anderson, Charles T., & Zabotina, Olga A. A Versatile Click-Compatible Monolignol Probe to Study Lignin Deposition in Plant Cell Walls. United States. doi:10.1371/journal.pone.0121334.
Pandey, Jyotsna L., Wang, Bo, Diehl, Brett G., Richard, Tom L., Chen, Gong, Anderson, Charles T., and Zabotina, Olga A. Fri . "A Versatile Click-Compatible Monolignol Probe to Study Lignin Deposition in Plant Cell Walls". United States. doi:10.1371/journal.pone.0121334. https://www.osti.gov/servlets/purl/1459346.
@article{osti_1459346,
title = {A Versatile Click-Compatible Monolignol Probe to Study Lignin Deposition in Plant Cell Walls},
author = {Pandey, Jyotsna L. and Wang, Bo and Diehl, Brett G. and Richard, Tom L. and Chen, Gong and Anderson, Charles T. and Zabotina, Olga A.},
abstractNote = {Here, lignin plays important structural and functional roles in plants by forming a hydrophobic matrix in secondary cell walls that enhances mechanical strength and resists microbial decay. While the importance of the lignin matrix is well documented and the biosynthetic pathways for monolignols are known, the process by which lignin precursors or monolignols are transported and polymerized to form this matrix remains a subject of considerable debate. In this study, we have synthesized and tested an analog of coniferyl alcohol that has been modified to contain an ethynyl group at the C-3 position. This modification enables fluorescent tagging and imaging of this molecule after its incorporation into plant tissue by click chemistry-assisted covalent labeling with a fluorescent azide dye, and confers a distinct Raman signature that could be used for Raman imaging. We found that this monolignol analog is incorporated into in vitro-polymerized dehydrogenation polymer (DHP) lignin and into root epidermal cell walls of 4-day-old Arabidopsis seedlings. Incorporation of the analog in stem sections of 6-week-old Arabidopsis thaliana plants and labeling with an Alexa-594 azide dye revealed the precise locations of new lignin polymerization. Results from this study indicate that this molecule can provide high-resolution localization of lignification during plant cell wall maturation and lignin matrix assembly.},
doi = {10.1371/journal.pone.0121334},
journal = {PLoS ONE},
number = 4,
volume = 10,
place = {United States},
year = {2015},
month = {4}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 5 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Advances in modifying lignin for enhanced biofuel production
journal, June 2010

  • Simmons, Blake A.; Loqué, Dominique; Ralph, John
  • Current Opinion in Plant Biology, Vol. 13, Issue 3, p. 312-319
  • DOI: 10.1016/j.pbi.2010.03.001

Monolignol Ferulate Transferase Introduces Chemically Labile Linkages into the Lignin Backbone
journal, April 2014


Lignin Biosynthesis and Structure
journal, May 2010

  • Vanholme, R.; Demedts, B.; Morreel, K.
  • Plant Physiology, Vol. 153, Issue 3, p. 895-905
  • DOI: 10.1104/pp.110.155119

Visualization of biomass solubilization and cellulose regeneration during ionic liquid pretreatment of switchgrass
journal, September 2009

  • Singh, Seema; Simmons, Blake A.; Vogel, Kenneth P.
  • Biotechnology and Bioengineering, Vol. 104, Issue 1, p. 68-75
  • DOI: 10.1002/bit.22386

Lignin Biosynthesis
journal, June 2003


Lignification and lignin topochemistry — an ultrastructural view
journal, July 2001


Lignin modification improves fermentable sugar yields for biofuel production
journal, June 2007

  • Chen, Fang; Dixon, Richard A.
  • Nature Biotechnology, Vol. 25, Issue 7, p. 759-761
  • DOI: 10.1038/nbt1316

Lignins: Natural polymers from oxidative coupling of 4-hydroxyphenyl- propanoids
journal, January 2004


Cloning and characterization of irregular xylem4 (irx4):a severely lignin-deficient mutant of Arabidopsis
journal, April 2001