Arabinose Conjugates Diagnostic of Ferulate-Ferulate and Ferulate-Monolignol Cross-Coupling Are Released by Mild Acidolysis of Grass Cell Walls
Abstract
Ferulate (FA) units esterified to grass arabinoxylans are involved in cross-linking cell wall polymers. Here, this contention is strengthened by the identification of FA homo- and heterodimers esterified to methyl arabinofuranoside (MeAra) units after their release from the xylan by mild acidolysis in dioxane/methanol/HCl. Acidolysis of poorly lignified maize bran cell walls provided diferulate (DFA) isomers, including those from 8–5, 8–O–4, and 5–5 interunit bonding, esterified to one or two MeAra units. Acidolysis of lignified grass samples released crossed dimers esterified to one MeAra unit and derived from the β–O–4 coupling of coniferyl alcohol to FA esters. The evaluation of these heterodimeric esters by LC-UV of their aglycones revealed that the parent structures occur in significant amounts in lignified cell walls (0.5–1 mg/g expressed as FA equivalents). The current results position mild acidolysis as an efficient strategy to obtain improved details regarding the FA-mediated cross-linking of grass cell walls.
- Authors:
-
[1];
[2]
- Univ. Paris-Saclay, Versailles (France)
- Univ. of Wisconsin, Madison, WI (United States)
- Publication Date:
- Research Org.:
- Univ. of Wisconsin, Madison, WI (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Biological and Environmental Research (BER)
- OSTI Identifier:
- 1600973
- Grant/Contract Number:
- SC0018409
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of Agricultural and Food Chemistry
- Additional Journal Information:
- Journal Volume: 67; Journal Issue: 46; Journal ID: ISSN 0021-8561
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Radical coupling; dehydrodimer; lignification; cell wall cross-link; diferulate; monocot
Citation Formats
Lapierre, Catherine, Voxeur, Aline, Boutet, Stéphanie, and Ralph, John. Arabinose Conjugates Diagnostic of Ferulate-Ferulate and Ferulate-Monolignol Cross-Coupling Are Released by Mild Acidolysis of Grass Cell Walls. United States: N. p., 2019.
Web. doi:10.1021/acs.jafc.9b05840.
Lapierre, Catherine, Voxeur, Aline, Boutet, Stéphanie, & Ralph, John. Arabinose Conjugates Diagnostic of Ferulate-Ferulate and Ferulate-Monolignol Cross-Coupling Are Released by Mild Acidolysis of Grass Cell Walls. United States. https://doi.org/10.1021/acs.jafc.9b05840
Lapierre, Catherine, Voxeur, Aline, Boutet, Stéphanie, and Ralph, John. Wed .
"Arabinose Conjugates Diagnostic of Ferulate-Ferulate and Ferulate-Monolignol Cross-Coupling Are Released by Mild Acidolysis of Grass Cell Walls". United States. https://doi.org/10.1021/acs.jafc.9b05840. https://www.osti.gov/servlets/purl/1600973.
@article{osti_1600973,
title = {Arabinose Conjugates Diagnostic of Ferulate-Ferulate and Ferulate-Monolignol Cross-Coupling Are Released by Mild Acidolysis of Grass Cell Walls},
author = {Lapierre, Catherine and Voxeur, Aline and Boutet, Stéphanie and Ralph, John},
abstractNote = {Ferulate (FA) units esterified to grass arabinoxylans are involved in cross-linking cell wall polymers. Here, this contention is strengthened by the identification of FA homo- and heterodimers esterified to methyl arabinofuranoside (MeAra) units after their release from the xylan by mild acidolysis in dioxane/methanol/HCl. Acidolysis of poorly lignified maize bran cell walls provided diferulate (DFA) isomers, including those from 8–5, 8–O–4, and 5–5 interunit bonding, esterified to one or two MeAra units. Acidolysis of lignified grass samples released crossed dimers esterified to one MeAra unit and derived from the β–O–4 coupling of coniferyl alcohol to FA esters. The evaluation of these heterodimeric esters by LC-UV of their aglycones revealed that the parent structures occur in significant amounts in lignified cell walls (0.5–1 mg/g expressed as FA equivalents). The current results position mild acidolysis as an efficient strategy to obtain improved details regarding the FA-mediated cross-linking of grass cell walls.},
doi = {10.1021/acs.jafc.9b05840},
journal = {Journal of Agricultural and Food Chemistry},
number = 46,
volume = 67,
place = {United States},
year = {2019},
month = {10}
}
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Figures / Tables:
Table 1: GC-MS analysis (electron-impact 70 eV) of the TMS phenolic dimers (analyzed as their TMS derivatives) recovered after alkaline hydrolysis of acidolysis samples. Peak numbers refer to peak notations in Figure 3.
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Improved analysis of arabinoxylan-bound hydroxycinnamate conjugates in grass cell walls
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Figures / Tables found in this record:
Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.