Molecular Interactions between Barley and Oat β-Glucans and Phenolic Derivatives

Equilibrium dialysis, molecular modeling, and multivariate data analysis were used to investigate the nature of the molecular interactions between 21 vanillin-inspired phenolic derivatives, 4 bile salts, and 2 commercially available β-glucan preparations, Glucagel and PromOat, from barley and oats....

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Bibliographic Details
Published in:	Journal of agricultural and food chemistry Vol. 57; no. 5; pp. 2056 - 2064
Main Authors:	Simonsen, Henrik Toft, Nielsen, Mette S, Christensen, Niels J, Christensen, Ulla, La Cour, Thomas V, Motawia, Mohammed Saddik, Jespersen, Birthe P. M, Engelsen, Søren B, Møller, Birger Lindberg
Format:	Journal Article
Language:	English
Published:	Washington, DC American Chemical Society 11-03-2009
Subjects:	adsorption Avena - chemistry barley beta-glucans beta-Glucans - chemistry Bile Acids and Salts - chemistry bile salts binding properties Biological and medical sciences Cereal and baking product industries food analysis Food Chemistry/Biochemistry food composition Food industries Fundamental and applied biological sciences. Psychology Hordeum - chemistry in vitro studies molecular conformation molecular models nutrition physiology oats phenolic compounds Phenols - chemistry phenolic derivatives barley oat β-Glucan bile salts β-glucosides Barley Oat Bile salt Glucoside Molecular interaction Glucan Phenols Cereal Polysaccharide
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Summary:	Equilibrium dialysis, molecular modeling, and multivariate data analysis were used to investigate the nature of the molecular interactions between 21 vanillin-inspired phenolic derivatives, 4 bile salts, and 2 commercially available β-glucan preparations, Glucagel and PromOat, from barley and oats. The two β-glucan products showed very similar binding properties. It was demonstrated that the two β-glucan products are able to absorb most phenolic derivatives at a level corresponding to the absorption of bile salts. Glucosides of the phenolic compounds showed poor or no absorption. The four phenolic derivatives that showed strongest retention in the dialysis assay shared the presence of a hydroxyl group in para-position to a CHO group. However, other compounds with the same structural feature but possessing a different set of additional functional groups showed less retention. Principal component analysis (PCA) and partial least-squares regression (PLS) calculations using a multitude of diverse descriptors related to electronic, geometrical, constitutional, hybrid, and topological features of the phenolic compounds showed a marked distinction between aglycon, glucosides, and bile salt retention. These analyses did not offer additional information with respect to the mode of interaction of the individual phenolics with the β-glucans. When the barley β-glucan was subjected to enzyme degradation, the ability to bind some but not all of the phenolic derivatives was lost. It is concluded that the binding must be dependent on multiple characteristics that are not captured by a single molecular descriptor.
Bibliography:	http://dx.doi.org/10.1021/jf802057v ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0021-8561 1520-5118
DOI:	10.1021/jf802057v