Document Detail

Bonding of hydroxycinnamic acids to lignin: ferulic and p-coumaric acids are predominantly linked at the benzyl position of lignin, not the beta-position, in grass cell walls.
MedLine Citation:
PMID:  11423145     Owner:  NLM     Status:  MEDLINE    
A suspension in dichloromethane-water (18:1, v/v) of various fractions containing hydroxycinnamic acid ester-ether bridges between lignin and polysaccharides prepared from cell walls of matured oat (Avena sativa L.) intemodes, and a solution of their acetates in the same solvent, were treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). This reagent selectively cleaves benzyl ether and ester linkages of negatively charged aromatic nuclei. The sample treated with DDQ was directly hydrolysed either under mild (1 M NaOH, overnight at 37 degrees C) or severe (4 M NaOH, for 2 h at 170 degrees C) conditions. The hydroxycinnamic acids released in the hydrolysate were methylated with diazomethane and analysed quantitatively using gas chromatography. Significant portions of ether linkages between hydroxycinnamic acids and lignin were cleaved with DDQ, which suggests that most of the hydroxycinnamic acids were ether-linked at the benzyl position, and not the beta-position, of the lignin side chain as previously claimed.
T B Lam; K Kadoya; K Iiyama
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Phytochemistry     Volume:  57     ISSN:  0031-9422     ISO Abbreviation:  Phytochemistry     Publication Date:  2001 Jul 
Date Detail:
Created Date:  2001-06-25     Completed Date:  2001-10-04     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0151434     Medline TA:  Phytochemistry     Country:  United States    
Other Details:
Languages:  eng     Pagination:  987-92     Citation Subset:  IM    
School of Biochemistry, La Trobe University, Bundoora, 3083, Victoria, Australia.
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MeSH Terms
Avena sativa / chemistry*
Cell Wall / chemistry
Coumaric Acids / chemistry*
Dimethyl Sulfoxide
Lignin / chemistry*,  isolation & purification
Phenylpropionates / chemistry*
Poaceae / chemistry*
Sodium Hydroxide
Reg. No./Substance:
0/Benzoquinones; 0/Coumaric Acids; 0/Dioxanes; 0/Phenylpropionates; 0/Solvents; 1135-24-6/ferulic acid; 123-91-1/1,4-dioxane; 1310-73-2/Sodium Hydroxide; 501-52-0/3-phenylpropionic acid; 67-68-5/Dimethyl Sulfoxide; 7400-08-0/4-coumaric acid; 84-58-2/dichlorodicyanobenzoquinone; 9005-53-2/Lignin

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