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Title: Evaluation of Feruloylated and p -Coumaroylated Arabinosyl Units in Grass Arabinoxylans by Acidolysis in Dioxane/Methanol

Abstract

We report that the arabinosyl side chains of grass arabinoxylans are partially acylated by p-coumarate (pCA) and ferulate (FA). These aromatic side chains can cross-couple wall polymers resulting in modulation of cell wall physical properties. The determination of p-coumaroylated and feruloylated arabinose units has been the target of analytical efforts with trifluoroacetic acid hydrolysis the standard method to release feruloylated and p-coumaroylated arabinose units from arabinoxylans. Herein, we report on a more robust method to measure these acylated units. Acidolysis of extractive-free grass samples in a dioxane/methanol/aqueous 2 M HCl mixture provided the methyl 5-O-p-coumaroyl- and 5-O-feruloyl-l-arabinofuranoside anomers (pCA-MeAra and FA-MeAra). These conjugates were readily analyzed by liquid chromatography combined with both UV and MS detection. The method revealed the variability of the relative acylation of arabinose units by pCA or FA in grass cell walls. Finally, this methodology will permit delineation of hydroxycinnamate acylation patterns in arabinoxylans.

Authors:
ORCiD logo [1];  [1]; ORCiD logo [2];  [3]; ORCiD logo [2]
  1. Université Paris-Saclay (France). Institut Jean-Pierre Bourgin, INRA, AgroParisTech, CNRS
  2. Univ. of Wisconsin, Madison, WI (United States). Department of Biochemistry, and The Department of Energy’s Great Lakes Bioenergy Research Center, The Wisconsin Energy Institute
  3. Virginia Tech, Blacksburg, VA (United States). Department of Biochemistry
Publication Date:
Research Org.:
Great Lakes Bioenergy Research Center, Madison, WI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1459510
Grant/Contract Number:  
SC0018409; FC02-07ER64494
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Agricultural and Food Chemistry
Additional Journal Information:
Journal Volume: 66; Journal Issue: 21; Journal ID: ISSN 0021-8561
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 59 BASIC BIOLOGICAL SCIENCES; Acylation; arabinose; esterification; ferulate; grass cell walls; hemicellulose; p-coumarate; quantitative analysis

Citation Formats

Lapierre, Catherine, Voxeur, Aline, Karlen, Steven D., Helm, Richard F., and Ralph, John. Evaluation of Feruloylated and p -Coumaroylated Arabinosyl Units in Grass Arabinoxylans by Acidolysis in Dioxane/Methanol. United States: N. p., 2018. Web. doi:10.1021/acs.jafc.8b01618.
Lapierre, Catherine, Voxeur, Aline, Karlen, Steven D., Helm, Richard F., & Ralph, John. Evaluation of Feruloylated and p -Coumaroylated Arabinosyl Units in Grass Arabinoxylans by Acidolysis in Dioxane/Methanol. United States. doi:10.1021/acs.jafc.8b01618.
Lapierre, Catherine, Voxeur, Aline, Karlen, Steven D., Helm, Richard F., and Ralph, John. Tue . "Evaluation of Feruloylated and p -Coumaroylated Arabinosyl Units in Grass Arabinoxylans by Acidolysis in Dioxane/Methanol". United States. doi:10.1021/acs.jafc.8b01618. https://www.osti.gov/servlets/purl/1459510.
@article{osti_1459510,
title = {Evaluation of Feruloylated and p -Coumaroylated Arabinosyl Units in Grass Arabinoxylans by Acidolysis in Dioxane/Methanol},
author = {Lapierre, Catherine and Voxeur, Aline and Karlen, Steven D. and Helm, Richard F. and Ralph, John},
abstractNote = {We report that the arabinosyl side chains of grass arabinoxylans are partially acylated by p-coumarate (pCA) and ferulate (FA). These aromatic side chains can cross-couple wall polymers resulting in modulation of cell wall physical properties. The determination of p-coumaroylated and feruloylated arabinose units has been the target of analytical efforts with trifluoroacetic acid hydrolysis the standard method to release feruloylated and p-coumaroylated arabinose units from arabinoxylans. Herein, we report on a more robust method to measure these acylated units. Acidolysis of extractive-free grass samples in a dioxane/methanol/aqueous 2 M HCl mixture provided the methyl 5-O-p-coumaroyl- and 5-O-feruloyl-l-arabinofuranoside anomers (pCA-MeAra and FA-MeAra). These conjugates were readily analyzed by liquid chromatography combined with both UV and MS detection. The method revealed the variability of the relative acylation of arabinose units by pCA or FA in grass cell walls. Finally, this methodology will permit delineation of hydroxycinnamate acylation patterns in arabinoxylans.},
doi = {10.1021/acs.jafc.8b01618},
journal = {Journal of Agricultural and Food Chemistry},
number = 21,
volume = 66,
place = {United States},
year = {2018},
month = {5}
}

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