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Flavonoid Metabolism and Challenges to Understanding Mechanisms of Health Effects

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Flavonoid Metabolism and Challenges to Understanding Mechanisms of Health Effects Journal of the Science of Food and Agriculture J Sci Food Agric 86:2487–2491 (2006) Perspective Flavonoid metabolism and challenges to understanding mechanisms of health effects Flavonoids comprise the most common group of plant metabolized to simple phenolic acids or conjugated polyphenols in fruits and vegetables. More than 5000 forms with glucuronic acid or sulfate. Flavan-3-ols different flavonoids have been described. The major (catechins) are unusual in that they are not glyco- subclasses of flavonoids (Fig. 1) include the flavones sylated in the natural form. Anthocyanins present a (e.g., apigenin, luteolin), flavonols (e.g., quercetin, major deviation from this generalization in that the myricetin), flavanones (e.g., naringenin, hesperidin), intact anthocyanin is absorbed and the aglycone is catechins or flavanols (e.g., epicatechin, gallocate- generally not present in plasma or urine.5,6 chin), anthocyanidins (e.g., cyanidin, pelargonidin), The potential role of microbial metabolism in the and isoflavones (e.g., genistein, daidzein). The proan- gastrointestinal tract is often overlooked. A large thocyanidins or condensed tannins are oligomeric and number of flavonoids and other phenolic compounds polymeric flavan-3-ols. Most of the flavonoids, except have recently been identified in colonic water of for proanthocyanidins, are present in plants with sug- the human.7 Some of the phenolic or aromatic ars attached (glycosides), although occasionally they compounds were probably generated after ring fission are found as aglycones. from flavonoids by human gut microflora. Compared Flavonoids can exhibit a wide range of health effects. to polyphenolic flavonoids, the monophenolics may However, without knowing whether the flavonoid be present in considerable excess both in terms ever reaches any of the tissues, we are left to make of concentration and number within the colon.7 numerous assumptions relative to relationships to Within the gastrointestinal tract the biological effect of health. Extensive work has been done in the field of monophenolics may be equal or more important than flavonoid bioavailability, pathways of absorption, and that of the polyphenolics. Anthocyanidin glycosides metabolism for some flavonoids.1,2 Some flavonoids, have been shown to be hydrolyzed by the intestinal such as quercetin, isoflavones, and catechins, are microflora within 20 min to 2 h of incubation reasonably well characterized; however, the health depending on the sugar moiety.8 Due to the high benefits for many of the flavonoids are still largely instability of the liberated anthocyanidin aglycones at unknown. Attempts to link dietary intake with neutral pH, primary phenolic degradation products health outcomes require further investigation. Studies were detected within 20 min of incubation. Further reported to date have been based on analysis of metabolism of the phenolic acids was accompanied plasma and urine concentrations of flavonoids or their by demethylation. Keppler8 suggested that because of metabolites after a single dose. Additional work is their higher chemical and microbial stability phenolic needed on tissue distribution of flavonoids after long- acids and/or other, not yet identified, anthocyanin term (more than a single dose) oral consumption. metabolites may be responsible for the observed Although there are some similar pathways of antioxidant activities and other physiological effects metabolism for some of the flavonoids, there are strik- in vivo. The formation of phenolic acids, as the major ing contrasts which present interesting challenges. stable degradation product, provides an important hint Similarities and contrasts are illustrated in antho- as to the fate of anthocyanins in vivo.9 Considerable cyanins, isoflavones, flavonols (quercetin), and proan- work remains to be done relative to the potential thocyanidins. Hydrolysis of the flavonoid to the agly- absorption, metabolism, and biological effects of the cone prior to absorption and subsequent conjugation phenolic acids. to the glucuronide or sulfate form is thought to occur Methylation is a common pathway of flavonoid via enteric bacteria or enteric mucosal metabolism. metabolism. Flavonoids that have a catechol struc- The action of the enzyme lactase-phlorizin hydrolase,3 ture in the B-ring are metabolized primarily to localized to the apical membrane of small intesti- the 3-O-methyl derivatives but some 4-O-methyl nal epithelial cells, and/or cytosolic β-glucosidase,3 is derivatives may be formed in smaller amounts (see important in the formation of the aglycone prior to Fig. 1). Flavonoids having a pyrogallol structure are absorption. Dietary flavonoid glucosides may also be metabolized to 4-O-methyl derivatives. Metabolism hydrolyzed in the oral cavity by both bacteria and of quercetin to isorhamnetin (3-O-methyl-quercetin) sloughed intestinal epithelial cells to deliver the bio- as the primary metabolite and tamarixetin (4- logically active aglycones at the surface of the epithelial O-methyl-quercetin) as a secondary metabolite cells.4 The aglycone can be absorbed and/or further accounted for 0–50% of the total depending upon Published online 16 August 2006; DOI: 10.1002/jsfa.2611 2006 Society of Chemical Industry. J Sci Food Agric 0022–5142/2006/$30.00 Perspective Figure 1. Structure of common flavonoid subclasses. the amount of quercetin consumed and identi- Flavonoids that contained a 3, 4-ortho-dihydroxy (or fiedintissues.10 Likewise, anthocyanins (cyanidin- catechol) B-ring were transferred predominantly as 3-O-glycoside) have been shown to be metabo- glucuronides, whereas the monohydroxylated B-ring lized to the 3-O-methyl derivatives (peonidin-3-O- phenolics were less predisposed to glucuronidation. glycosides) and 4-O-methyl derivatives (isopeonidin- Flavonoids with monohydroxymethylated B-rings 3-O-glycosides).5,6,11 Delphinidin-3-O-glucoside has seem to be less susceptible to glucuronidation in the been reported to be methylated at the 4 position in small intestine but may be glucuronidated in the liver. the B-ring of delphinidin,12 which is expected since Anthocyanins have been shown to be conjugated with delphinidin has the pyrogallol structure in the B-ring. glucuronide.5,6,11 Glucuronide/sulfate and methylated Conjugation of flavonoids with glucuronic acid or conjugates of quercetin appeared in the lymph sulfate is also common. Glucuronidation of flavonols, of rats after quercetin administration.13 Catechin flavanones, flavones and their glycosides have been and epicatechin are extensively O-methylated during observed. The extent of glucuronidation seems to transfer across the jejunum, consistent with the be dependent on the available hydroxyl groups. reported activity of catechol-O-methyltransferases in 2488 J Sci Food Agric 86:2487–2491 (2006) DOI: 10.1002/jsfa Perspective the jejunum. Up to 30% of flavan-3-ol compounds been identified in pig or human plasma following from catechin and epicatechin detected in the jejunal consumption of anthocyanins. As indicated above, serosal fluid were O-methylated and an additional 20% the glucuronide conjugates and/or methylated forms were O-methylated and glucuronidated.14 Catechin of (−)-epicatechin were different between the human and epicatechin, which may enter the portal vein and rats.17 at relatively high concentrations from ileal transfer, An area of investigation that has received little may be further metabolized to O-methylated and attention is the possibility of interaction or syn- glucuronidated forms by phase II metabolism in the ergism of different flavonoids and/or phenolic acid liver. metabolites. Rechner27 demonstrated that a mixture Proanthocyanidins represent another class of of anthocyanins and colonic metabolites were active polyphenolics that are oligomers or polymers of in lowering (10–40%) the activation of platelets (P- flavan-3-ols. The common occurrence of proan- selectin expression) at ten times lower concentrations thocyanidins in foods makes them an important compared to the individual components. No activity part of the human diet.15 Procyanidins present a could be identified when the components were tested special situation when it comes to metabolism in individually at the equivalent concentration, indicat- that a significant proportion may exist as larger ing that synergism of the different components was molecular weight polymers.15 In addition to poly- causing the effect. Platelet reactivity to strong agonists mers, procyanidins are present as monomers (cat- such as collagen and ADP was not influenced.27 echin and epicatechin) and as oligomers. Epicate- chin (and catechin) is absorbed from the intestinal tract and conjugated to glucuronide and/or sulfate IN VITRO VERSUS IN VIVO STUDIES form.16 Natsume et al.17 identified (−)-epicatechin- In terms of individual flavonoids, the aglycone 3 -O-glucuronide as the main metabolite in plasma quercetin has been commercially available for some and urine from humans and also the metabolites time. Thus, this compound has been used for of 4 -O-methyl-(−)-epicatechin-3 -O-glucuronide and numerous in vitro studies, with many of the published 4 -O-methyl-(−)-epicatechin-5 or 7-O-glucuroide. In biological effects based mainly on these in vitro studies. rats, 3 -O-methyl-(−)-epicatechin, (−)-epicatechin- However, quercetin is rapidly metabolized during the 7-O-glucuronide and 3 -O-methyl-(−)-epicatechin-7- in vivo digestion/absorption processes. Until recently, O-glucuronide were identified. In humans, (−)- we have had little knowledge of the presence of epicatechin
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