Document Detail


Identification of ferulate oligomers from corn stover.
MedLine Citation:
PMID:  20549649     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
BACKGROUND: Cross-links between plant cell wall polymers negatively impact forage digestibility. Hydroxycinnamates and their oligomers act as cross-links between polysaccharides and/or polysaccharides and lignin. Higher ferulate oligomers such as dehydrotrimers were identified in cereal grains but not in vegetative organs of grasses. The aim of this study was to characterize ester-linked hydroxycinnamate oligomers from corn stover with special emphasis on ferulate dehydrotrimers.
RESULTS: With the exception of the 4-O-5-dehydrodiferulic acid all known ferulate dehydrodimers, including the recently described 8-8(tetrahydrofuran) dimer, were identified in the alkaline hydrolyzate of corn stover after chromatographic fractionation. Next to dehydrodimers, 18 cyclobutane dimers made up of ferulic acid and/or p-coumaric acid were identified by GC-MS of the dimeric size exclusion chromatography fraction. Ferulate dehydrotrimers were isolated by using multiple chromatographic procedures and identified by UV spectroscopy, MS and NMR. Four trimers were unambiguously identified as 5-5/8-O-4-, 8-O-4/8-O-4-, 8-8(aryltetralin)/8-O-4-, and 8-O-4/8-5-dehydrotriferulic acids, a fifth tentatively as 8-5/5-5-dehydrotriferulic acid.
CONCLUSION: The formation of ferulate dehydrotrimers is not limited to reproductive organs of grasses but also contribute to network formation in the cell walls of vegetative organs. Although radically coupled hydroxycinnamate dimers and oligomers were in the focus of researchers over the last decade, the earlier described cyclobutane dimers significantly contribute to cell wall cross-linking.
Authors:
Diane Dobberstein; Mirko Bunzel
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of the science of food and agriculture     Volume:  90     ISSN:  1097-0010     ISO Abbreviation:  J. Sci. Food Agric.     Publication Date:  2010 Aug 
Date Detail:
Created Date:  2010-07-12     Completed Date:  2011-01-19     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0376334     Medline TA:  J Sci Food Agric     Country:  England    
Other Details:
Languages:  eng     Pagination:  1802-10     Citation Subset:  IM    
Copyright Information:
Copyright (c) 2010 Society of Chemical Industry.
Affiliation:
Department of Biochemistry and Food Chemistry, University of Hamburg, Grindelallee 117, 20146 Hamburg, Germany.
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MeSH Terms
Descriptor/Qualifier:
Animal Feed
Cell Wall / chemistry*
Coumaric Acids / isolation & purification*
Cyclobutanes / isolation & purification*
Dimerization
Gas Chromatography-Mass Spectrometry
Hydrolysis
Plant Leaves
Plant Stems
Zea mays / chemistry*
Chemical
Reg. No./Substance:
0/Coumaric Acids; 0/Cyclobutanes

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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