[...]... stomach to a limited extent,1 glycosides (of quercetin) are not.2 The limited capacity of the stomach to F-glu enterocyte 1 F 2 F hepatocyte F 3 F 4 5 F-glcA 6 F-glcA 7 F-glcA 8 F 13 17 F-glcA Me-F-glcA 11 F-SO4 12 F-rha F-glcA 9 10 Me-F-glcA F-SO4 14 F-glcA 8 16 F 15 F 3 F 18 colonocyte PA 19 PA 20 PA conjugation then urinary excretion COMMON FEATURES IN THE PATHWAYS OF FLAVONOIDS Figure 2.1 23 Key step:... 23.2 ± 4.8 mg or 0.004% of dose Matsumoto et al.16 reported that the cumulative urinary excretion of the four anthocyanins from black currant (delphinidin 3-O-b-rutinoside, cyanidin 3-O-brutinoside, delphinidin 3-O-b-glucoside, and cyanidin 3-O-b-glucoside) during the first 8 h after intake was 0.11 ± 0.05% of the dose ingested.16 Gut Metabolism of Anthocyanins The metabolism of anthocyanins in the gut... (cyanidin-3-glucoside and cyanidin-3-sambubioside) were detected as glycosides in both plasma and urine of humans Mulleder and Murkovic26 observed a greater urinary excretion of cyanidin-3-sambubioside than cyanidin-3-glucoside (0.014 vs 0.004% of dose) and that addition of sucrose to the elderberry juice led to a reduced and delayed excretion of the anthocyanins The reduced excretion of cyanidin-3-glucoside... catechins are (+)-catechin-5-O-b-glucuronide and (-) -epicatechin-5-O-bglucuronide.63 Generally, renal excretion is not a major pathway for intact flavonoids62 and the urinary content of flavonoids cannot be used as a biomarker of bioavailability or dietary intake DEGLYCOSYLATION AND FURTHER BREAKDOWN OF FLAVONOIDS OCCURS IN THE COLON BY MICROFLORA Certain flavonoids, such as rutin (quercetin-3-rhamnoglucoside),... cyanidin-3-glucoside (C-3-G) orally (0.9 mmol/kg body weight), C-3-G rapidly appeared in the plasma, but the aglycone of C-3-G (cyanidin) was not detected, although it was present in the jejunum.25 Protocatechuic acid (PC), which may be produced by degradation of cyanidin, was present in the plasma of the rat at concentrations eightfold higher than that of C-3-G We have not detected PC in the plasma of. .. contents of rats after adaptation to consumption of a diet containing blackberry anthocyanins The blackberries contained primarily cyanidin-3-glucoside with a small amount of malvidin-3-glucoside (~1.9% of C-3-G) Recovery of cyanidin plus C-3-G in the total cecal contents was ~0.25% Interestingly, about the same amount of cyanidin products (~0.26%) was recovered in the urine However, larger amounts of malvidin-3-glucoside... activity In vivo antioxidant activity Paraquat-induced oxidative stress CCl4-induced liver damage Hepatic ischemia reperfusion Ischemia reperfusion t-Butyl Hydroperoxide (0.2 mm/kg)-induced liver cytotoxicity Vitamin E deficiency 7 8 9 10 6 2 3 4 5 1 600 mg/day; 2 mo 1.2 g 690 mg; 10 mg/kg body wt) 33 mg/kg; 1.7 mg D-3-Rut, 1.24 mg Cy-3-Rut, 0.5 mg D-3-G, 0.2 mg Cy-3-G/kg body weight N/A 25 to 100 mg/kg i.p... b-glucuronidase and then sulfated, or the intact 26 PHYTOCHEMICALS: MECHANISMS OF ACTION Table 2.1 “Pharmacokinetic” parameters of flavonoids in blood after consumption by volunteers Source Red wine Green tea Green tea Green tea Green tea Onion Quercetin-4¢-glucoside Quercetin-4¢-glucoside Buckwheat tea Quercetin-3-rutinoside Quercetin-3-rutinoside Soy Soy flour Soy flour Soy flour Soy Soy flour a Flavonoida... 5 d Species Rat Dose of Anthocyanins N/A 49 36 50 27 44 46 35 30 33 34 12 29 Reference Table 1.4 Summary of in vivo models and dose of anthocyanins used in studies of biological effects of anthocyanins or foods rich in anthocyanins 10 PHYTOCHEMICALS: MECHANISMS OF ACTION CCl4-induced liver damage Hepatic ischemia reperfusion Ischemia reperfusion t-Butyl hydroperoxide (0.2 mm/kg)-induced liver cytotoxicity... Am J Clin Nutr 76, 798–804, 2002 32 PHYTOCHEMICALS: MECHANISMS OF ACTION 47 O’Leary, K.A., Day, A.J., Needs, P., Mellon, F.A., O’Brien, N.M., and Williamson, G., Metabolism of quercetin- 7- and quercetin-3-glucuronides by an in vitro hepatic model: the role of human b-glucuronidase, sulfotransferase, catechol-O-methyltransferase and multi-resistant protein 2 (MRP2) in flavonoid metabolism Biochem Pharmacol., . - - - - - - - + - - - - - Apple + ++ + - - - - - - - - + - - - - - Pear - ++ + - - - - - - - - + - Strawberry ++ - - + - - - - - - + + - - ++ - - Chokeberry + ++ + - - - - - - - - + - - - - - Black. + - - + - + - - - - - +++ - - + - - Cherry, sour + - - + + + ++ - - - - ++ - - - + - Cherry, sweet + - - ++ - - - - - - - ++ - - - + - Plum ++ - - + - - - - - - - ++ - - - + - Peach ++ - - + -. + - - ++ - - - - - - - + + - - - - Red currant + - - + + + + - - - - + - - - - - Grape + - + + + +++ +-+ ++ Chokeberry + ++ + - - - - - - - + ++ - - - - - Pomegranate ++ - - - - - - - - - + ++ -