3-O-Glucosides

The effects of pH under model conditions (0.6 to 5.5 for 24 hr) were covered by Nielsen et al. for four anthocyanins (3-O-glucoside, glycosylated cyanidin, rutinoside, and delphinidin rutinoside). After 24 hr, over 90% of the anthocyanins were intact up to pH 3.3, while instabihty greatly increased at pH greater than 4.5. 

Escribano-Bailon, T. et al.. Color and stability of pigments derived from the acetaldehyde-mediated condensation between malvidin 3-O-glucoside and (-t-)-catechin, J. Agric. Food Chem., 49, 1213, 2001. 

Trihydroxyflavone-7-0-glucoside Luteolin-7-O-glucoside Seed exudate Medicago saliva S. meliloli... 

Kovacs, M. F. "Dhurrin (p-hydroxy mandelonitrile-B-O-glucoside) An allelopath Identified In johnsongrass (Sorghum halapense (L.) Fers.) rhizome exudates", Ph.D. Thesis. University of Maryland, College Park, MD. 1972. 

A. Agarwal, S. Rani, and Y. D. Vankar, Protic acid (HC104 supported on silica gel)-mediated synthesis of 2, 3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals, J. Org. Chem., 69 (2004) 6137-6140. 

Es-Safi NE, Meudec E, Bouchut C, Fulcrand H, Ducrot PH, Herbette G and Cheynier V. 2008. New compounds obtained by evolution and oxidation of malvidin 3-O-glucoside in ethanolic medium. J Agric Food Chem 56(12) 4584-4591. 

Arteel and Sies (1999) examined procyanidin oligomers of different size, isolated from the seeds of Theobroma cacao, for their ability to protect against nitration of tyrosine. Serraino and others (2003) investigated antioxidant activity of the blackberry juice and cyanidin-3-O-glucoside on endothelial dysfunction in cells and in vascular rings exposed to peroxynitrite. However, more work is needed in this area, and the confounding effects of oxidized protein/amino acids in the diet need to be elucidated. 

Serraino I, Dugo L, Dugo P, Mondello L, Mazzon E, Dugo G, Caputi AP and Cuzzocre S. 2003. Protective effects of cyanidin-3-O-glucoside from blackberry extract against peroxynitrite-induced endothelial dysfunction and vascular failure. Life Sci 73(9) 1097-1114. 

Compounds 1 = 4-hydroxycoumarin 2 = umbelliferon 3 = 4-methyl-esculetin 4 = isopimpinellin 5 = esculin 6 = flavone 7 = a-naphtoflavone 8 = kaempferol 9 = quercetin 10 = isoquercitrin 11 = robinetin 12 = robinin 13 = myricetin 14 = luteolin 7-O-glucoside 15 = rutin 16 = hes-peretin 17 = hespiridin 18 = naringin 19 = pelargonin chloride 20 = polargonin chloride 21 = malvin chloride. 

Fig. 2.50. Profiles of calendula (a), milk-thistle (b) and passion flower (c) tinctures (each 60 per cent v/v, ethanol) with the HPLC-MS attributions of the components detected, lc = quercetin-3-O-ruti-nosylrhamnoside 2c = rutin 3c = isorhamnetin-3-O-ruti-nosylrhamnoside 4c = isoquercitrin 5c = isorhamnetin-3-O-gluco-sylglucoside 6c = narcissin 7c = isorhamnetin-3-O-glucoside lm = taxifolin 2m = siliydianin 3m = silychristin 4m = oxy derivative of silybin/isosilybin isomers 5m and 6m = 2,3-dehydro derivatives of silybin/isosilybin isomers 7m = silybin 8m = isosilybin lp = 6,8-diC-glucosylapigenin 2p = isoschaftoside 3p = shaftoside 4p = homoorientin 5p = isovetexin-2"-0-glucoside 6p = vitexin. Reprinted with permission from A. R. Biha et al. [150].

Fig. 2.101. Chromatograms of Cabernet Sauvignon and TempraniUo wines recorded at 520 nm. Peak identification Df-3-GL = delphinidin-3-O-glucoside Cy-3-Gl = cyanidin-3-O-glucoside Pt-3-Gl = petunidin-3-O-glucoside Pn-3-Gl = peonidin-3-O-glucoside Mv-3-Gl = maMdin-3-O-glucoside Pn-3-Gl-Ac = paeonidin-3-O-acetylglucoside Mv-3-Gl-Ac = maMdin-3-O-acetylglucoside Pn-3-Gl-Cm = peonidin-3-coumaroylglucoside Mv-3-Gl-Cm = malvidin-3-coumarylglucoside. Reprinted with permission from E. Revilla et al. [235].

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