Study of interactions between food phenolics and aromatic flavors using one- and two-dimensional (1)H NMR spectroscopy.
Changes in flavor release and aroma characteristics in a medium including food phenolics may be attributed to an intermolecular interaction between flavor compounds and phenolics. To investigate the interaction, one- and two-dimensional NMR studies have been carried out on the binding of two phenolics, gallic acid and naringin, with three aroma compounds, 2-methylpyrazine, vanillin, and ethyl benzoate. Evaluation of thermodynamic parameters and intermolecular nuclear Overhauser effects reveals that gallic acid can interact more strongly with aromatic flavors than naringin. The supramolecular complexation is also dependent on the structural nature of the flavors, with 2-methylpyrazine and vanillin interacting more strongly than ethyl benzoate. The interaction is principally pi-pi stacking between the galloyl ring and the aromatic ring of the aroma compounds, but secondary hydrogen-bonding effects help to stabilize the complex and enhance the specificity.
Jung
D M
DM
Department of Viticulture and Enology and NMR Instrumentation Facility, University of California, Davis, Davis, California 95616, USA.
de Ropp
J S
JS
Ebeler
S E
SE
D001547:Benzaldehydes / Q000378:metabolism; D001565:Benzoates / Q000378:metabolism; D044950:Flavanones; D005419:Flavonoids / Q000378:metabolism; D005421:Flavoring Agents / Q000378:metabolism*; D005504:Food Analysis; D005707:Gallic Acid / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D010636:Phenols / Q000378:metabolism*; D013816:Thermodynamics
D001547:Benzaldehydes; D001565:Benzoates; D044950:Flavanones; D005419:Flavonoids; D005421:Flavoring Agents; D010636:Phenols; D005707:Gallic Acid; C051230:4-ethylbenzoic acid; C100058:vanillin; C005274:naringin