Anthocyanin derivative

Polyphenols are not found free in the blood but are bound to plasma proteins. Albumin is the primary protein responsible for the bindings of several polyphenols and their metabolites (i.e., quercetin, kempferol, isorhamnetin), but no data are available for anthocyanins. However it is probable that anthocyanin derivatives also bind to albumin and the degree of that binding may affect the clearance rate and the delivery to tissues of these compounds as well. 

Revilla, 1. et al.. Identification of anthocyanin derivatives in grape skin extracts and red wines by liquid chromatography with diode array and mass spectrometric detection, J. Chromatogr. A, 847, 83, 1999. 

CZE is particularly useful for separating anthocyanin dimers or polymeric anthocyanins. Calvo et al. (2004)" separated 13 anthocyanins by CZE including acylated and non-acylated anthocyanins, pyranoanthocyanins, and flavonol derivatives in wine. Saenz-Lopez et al. (2004)" applied CZE to analyze wine aging (1 to 14 yr) as related to monomeric anthocyanins, anthocyanin derivatives, tannins, and fla-vonols. Bicard et al. (1999)" reported the improved detection sensitivity of anthocyanin chemical degradation analysis by CZE. 

Pati, S. et al.. Simultaneous separation and identification of oligomeric procyanidins and anthocyanin-derived pigments in raw red wine by HPLC-UV-ESI-MS, J. Mass Spectrom., 41, 861, 2006. 

Use of Extracted Anthocyanin Derivatives in Nanostructures for Solar Energy Conversion... 

Fig. 2.71. HPLC chromatogram of the neutral (a) and acidic fractions (b) and the acid-catalysed hydrolysed product of freshly squeezed cranberry juice (c) at 280 nnm. Peaks in a 1 = ( + )-cate-chin 2 = myicetin 3 = quercetin (added as internal standard). Peaks in b 1 = anthocyanin derivative I 2 = benzoic acid 3 = p-anisic acid 4 = quercetin (added as internal standard). Peaks in c 1 = ( + )-catechin 2 = anthocyanin derivative I 3 = anthocyanin derivative II 4 = benzoic acid 5 = anthocyanin derivative III 6 = p-anisic acid 7 = myricetin 8 = quercetin. Reprinted with permission from H. Chen et al. [188].

The optimum conditions for the MS detection of anthocyanin derivatives have also been intensively studied. Grape skin extract was prepared by macerating skins with methanol-formic acid (95 5) for three days changing the extracting agent each day. The combined extracts were evaporated and diluted with water. RP-HPLC measurements were carried out in an ODS column (150 X 4.6 mm i.d. particle size 5 /an) at 30°C. The solvents were water-formic acid (90 10, v/v, A) and methanol-water-formic acid (45 45 10, v/v, B). The gradient was from 35 to 95 per cent B in 20 min to 100 per cent B in 5 min final hold... 

The synthesis of two new red wine pigments by nucleophilic addition of vinylphenols to malvidin 3-glucoside has been described. The structures of the two new pigments and their formation are shown in Fig. 2.105. HPLC-DAD and HPLCMS confirmed the occurrence of these two anthocyanin derivatives in red wine [239],... 

N. Mateus, S.de Pascual-Teresa, J.C. Rivas-Gonzalo, C.Santos-Buelga and V. de Freitas, Structural diversity of anthocyanin-derived pigments in port wines. Food Chem. 76 (2002) 335-342. 

A.M. Vivar-Quintana, C. Santos-Buelga and J.C. Rivas-Gonzalo, Anthocyanin-derived pigments and colour of red wines. Anal. Chim. Acta 458 (2002) 147-155. 

M.S. Narayan and L.V. Venkataraman, Characterisation of anthocyanins derived from carrot (Daucus carota) cell culture. Food Chem. 70 (2000) 361-363. 

Shortly after the discovery of phenyl pyranoanthocyanins, another series of anthocyanin derivatives showing similar UV-visible spectra, suggesting that they were also derived from a pyranoanthocyanin chromophore, and masses differing from those of grape anthocyanins by... 

Fulcrand, H. et al., Structure of new anthocyanin-derived wine pigments. J. Chem. Soc. Perkin Trans. 17, 735, 1996. 

Mateus, N. et al., A new class of blue anthocyanin-derived pigments isolated from red wines. J. Agric. Food Chem. 51, 1919, 2003. 

Sarni-Manchado, P. et al., Stability and color of unreported wine anthocyanin-derived pigments. /. Food Sci. 61, 938, 1996. 

Cameira dos Santos, J.P. et al., Detection and partial characterization of new anthocyanin-derived pigments in wine. J. Sci. Food Agric. 70, 204, 1996. 

Vivar-Quintana, A.M. et al.. Formation of anthocyanin-derived pigments in experimental red wines. Food Sci. Technol. Int. 5, 347, 1999. 

Matsui, T., Ebuchi, S., Kobayashi, M., Fukui, K., Sugita, K., Terahara, N., and Matsumoto, K., Anti-hyperglycemic effect of diacylated anthocyanin derived from Ipomoea batatas cultivar Ayamurasaki can be achieved through the a-glucosidase inhibitory action, J. Agric. Food Chem., 50, 7244, 2002. 

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