malvidin-3-glucoside and procyanidin

Bitterness is a major sensory attribute of several common foods and beverages rich in polyphenol compounds. These compounds are reported as very important for health as chemopreventive compounds, but they are also known to taste bitter. In this work, the activation of the human bitter taste receptors, TAS2Rs, by six polyphenol compounds was analyzed. The compounds chosen are present in a wide range of plant-derived foods and beverages, namely, red wine, beer, tea, and chocolate. Pentagalloylglucose (PGG) is a hydrolyzable tannin, (-)-epicatechin is a precursor of condensed tannins, procyanidin dimer B3 and trimer C2 belong to the condensed tannins, and malvidin-3-glucoside and cyanidin-3-glucoside are anthocyanins. The results show that the different compounds activate different combinations of the ~25 TAS2Rs. (-)-Epicatechin activated three receptors, TAS2R4, TAS2R5, and TAS2R39, whereas only two receptors, TAS2R5 and TAS2R39, responded to PGG. In contrast, malvidin-3-glucoside and procyanidin trimer stimulated only one receptor, TAS2R7 and TAS2R5, respectively. Notably, tannins are the first natural agonists found for TAS2R5 that display high potency only toward this receptor. The catechol and/or galloyl groups appear to be important structural determinants that mediate the interaction of these polyphenolic compounds with TAS2R5. Overall, the EC(50) values obtained for the different compounds vary 100-fold, with the lowest values for PGG and malvidin-3-glucoside compounds, suggesting that they could be significant polyphenols responsible for the bitterness of fruits, vegetables, and derived products even if they are present in very low concentrations.

Topics: Anthocyanins; Beer; Beverages; Biflavonoids; Cacao; Catechin; Fruit; Glucosides; Humans; Hydrolyzable Tannins; Polyphenols; Proanthocyanidins; Taste; Taste Buds; Tea; Vegetables; Wine

The reaction between procyanidin dimer Ec-EcG (B2 3'-O-gallate) and malvidin 3-O-glucoside (Mv3glc) was studied in a model solution system at two different pH values, 2.0 and 3.8. Disappearance of both species was much faster at pH 3.8 than at pH 2.0. That of Mv3glc was increased in the presence of Ec-EcG, whereas that of Ec-EcG was the same in the presence or absence of the anthocyanin. Values of absorbance at 520 nm measured at pH 2.0 were correlated with the amount of residual Mv3glc. Those measured at pH 3.8 hardly changed during the incubation, but absorbance values at 420 and 620 nm as well as resistance to sulfite bleaching were much increased, confirming that Mv3glc was converted to other pigments. Anthocyanin-flavanol adducts were observed at both pH values, but their structures were different. At pH 2.0, cleavage of the procyanidin linkage followed by nucleophilic addition of flavanol or anthocyanin moieties led to (Ec)(n)-EcG and (Ec)(n)-Mv3glc, respectively. At pH 3.8, nucleophilic addition of Ec-EcG onto the anthocyanin yielded Mv3glc-(Ec-EcG).

Topics: Anthocyanins; Biflavonoids; Catechin; Chromatography, High Pressure Liquid; Dimerization; Glucosides; Hydrogen-Ion Concentration; Kinetics; Proanthocyanidins; Solutions; Spectrometry, Mass, Electrospray Ionization; Spectrophotometry; Sulfhydryl Compounds

Three newly formed Port wine pigments were isolated by Toyopearl HW-40(s) gel chromatography and semipreparative HPLC. Furthermore, the pigments were identified by mass spectrometry (LC/MS) and NMR techniques (1D and 2D). These anthocyanin-derived pigments showed UV-visible spectra different from those of the original grape anthocyanins. These pigments correspond to malvidin 3-glucoside linked through a vinyl bond to either (+)-catechin, (-)-epicatechin, or procyanidin dimer B3 [(+)-catechin-(+)-catechin]. NMR data of these pigments are reported for the first time.

Topics: Anthocyanins; Biflavonoids; Catechin; Flavonoids; Flavonols; Glucosides; Magnetic Resonance Spectroscopy; Mass Spectrometry; Pigments, Biological; Proanthocyanidins; Vitis; Wine