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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis and Identification of An Unanticipated Ferulate 8-8 Coupling Product Present in Cereal Dietary Fibers

item Schatz, Paul
item Ralph, John
item Lu, Fachuang - UW-MADISON
item Guzei, I - U HAMBURG
item Steinhart, Hans - U HAMBURG
item Bunzel, Mirko - U HAMBURG

Submitted to: Meeting Proceedings
Publication Type: Proceedings
Publication Acceptance Date: February 20, 2005
Publication Date: September 21, 2005
Citation: Schatz, P.F., Ralph, J., Lu, F., Guzei, I.A., Steinhart, H., Bunzel, M. 2005. Synthesis and identification of an unanticipated ferulate 8-8-coupling product present in cereal dietary fibers. In: Edklund, T., Steinhart, H., Thier, H.-P., Winterhalter, P., editors. European Food Chemistry Conference XIII: Macromolecules and their degradation products in food — Physiological, analytical and technological aspects, September 21-23, 2005, Hamburg, Germany. p. 253-261.

Technical Abstract: Ferulate dimers and trimers act as cross-links between polysaccharides and between polysaccha-rides and lignin in grasses. In addition to two already identified 8-8-diferulic acids we identified another product of 8-8-coupling by its mass spectral data. This compound, 2,5-di(4´-hydroxy-3-methoxyphenyl)-2,3,4,5-tetrahydrofuran-3,4-dicarboxylic acid, has been authenticated by independent synthesis. In comparison to the formerly known 8-8-coupled diferulates, this diferulate incorporates additional water, probably by water addition to one of the incipient quinone methide moieties and internal trapping of the other. In insoluble cereal dietary fibres this dimer contributes between 2.5 and 4.9% to the absolute ferulate dimer content, showing that cell wall cross-linking is more extensive and variable than previously documented.

Last Modified: 4/22/2015
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