Structural elucidation of new ferulic acid-containing phenolic dimers and trimers isolated from maize bran

The structures of four new phenolic dimers and trimers that contain ferulic acid moieties isolated from maize bran fiber were established by 1D/2D NMR and mass spectrometry. The trimers were found to expand the number of products potentially involved in cell wall cross-linking whereas the biological...

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Bibliographic Details
Published in:Tetrahedron letters 2005-08, Vol.46 (35), p.5845-5850
Main Authors: Bunzel, Mirko, Ralph, John, Funk, Carola, Steinhart, Hans
Format: Article
Language:English
Subjects:
Arabinoxylans
Cell wall cross-linking
Dietary fiber
Ferulate
Ferulic acid
Gramineae
Oxidative degradation
Phenolic dimers
Triferulate
Triferulic acid
Vanillin
Zea mays L
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Summary:The structures of four new phenolic dimers and trimers that contain ferulic acid moieties isolated from maize bran fiber were established by 1D/2D NMR and mass spectrometry. The trimers were found to expand the number of products potentially involved in cell wall cross-linking whereas the biological role of the dimers partially remains uncertain. Four new phenolic dimers and trimers that contain ferulic acid moieties were isolated from the alkaline hydrolyzate of insoluble maize bran fiber and their structures were established by 1D/2D NMR and mass spectrometry. The biological role of one dimer remains unclear whereas the dimeric vanillin-ferulic acid-cross-product probably represents an oxidative degradation product from the corresponding diferulate. Both ferulic acid dehydrotrimers are able to cross-link polysaccharide chains. However, the 5-5/8-O-4(H 2O)-triferulic acid may be a cross-link in its identified structure whereas we assume that the identified 8-O-4/8-5(non-cyclic)-triferulic acid arose from a natural 8-O-4/8-5(cyclic)-triferulate analog during the saponification process.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.06.140