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MALDI-TOF mass spectrometry of oligomeric food polyphenols.

Reed JD, Krueger CG, Vestling MM

Department of Animal Science and Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA. jdreed@wisc.edu

The structural heterogeneity of polyphenols from cranberries, grape seed extracts, sorghum and pomegranate was characterized by MALDI-TOF MS. Polyphenolics were isolated by liquid chromatography and subjected to MALDI-TOF MS using trans-3-indoleacrylic acid as the matrix. Spectrometric analysis gave information on degree of polymerization, monomeric substitution, and the nature of intermolecular bonds. Cranberry polyflavan-3-ols had variation in interflavan bonds (A- and B-types) and contained polyflavan-3-ols linked to anthocyanins through a CH3-CH bridge. Polygalloyl-polyflavan-3-ols in grape seed extract had large variation in the degree of galloyl substitution. Sorghum polyflavans had structural heterogeneity in glycosylation and hydroxylation. Pomegranate hydrolyzable tannins that correspond to previously described structures were detected, such as punicalagin, but others that correspond to oligomeric ellgitannins in which two to five core glucose units are cross-linked by dehydrodigalloyl and or valoneoyl units were also observed. Results demonstrate that large heterogeneity occurs in degree of polymerization, intermolecular bonds, pattern of hydroxylation, and substitution with monosaccharides and gallic acid.

Published 12 September 2005 in Phytochemistry, 66(18): 2248-63.
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