Epicatechin from

Extraction of the catechin and epicatechin from the green tea was carried out by liquid extraction with methanol. 

Flavanols and procyanidins Flavanols, or flavan-3-ols, are synthesized via two routes, with (+) catechins formed from flavan-3,4-diols via leucoanthocyanidin reductase (LAR), and (—) epicatechins from anthocyanidins via anthocyanidin reductase (ANR) (see Fig. 5.4). These flavan-3-ol molecules are then polymerized to condensed tannins (proanthocyanidins or procyanidins), widely varying in the number and nature of their component monomers and linkages (Aron and Kennedy 2008 Deluc and others 2008). It is still not known whether these polymerization reactions happen spontaneously, are enzyme catalyzed, or result from a mixture of both. 

Absorption of (-)-epicatechin from chocolate has been studied by different authors [104-106]. Baba et al [104] found maximum levels of total EC metabolites in plasma after 2 h of chocolate or cocoa intake. Sulfate, glucuronide and sulfoglucuronide conjugates of non-methylated EC were the main metabolites present rather than methylated forms. In urine samples, excretion of total EC metabolites within 24 h was about 30% of total EC intake after chocolate and 25 % after cocoa consumption. 

M. Richelle, 1. Tavazzi, M. Enslen et al. Plasma kinetics in man of epicatechin from black chocolate. European Journal of Clinical Nutrition 53 (1999) 22-26. 

Hofmann, T., Albert, L., and Retfalvi, T., Quantitative TLC analysis of (-1-)-catechin and (—)-epicatechin from Fagus sylvatica L. with and without red heartwood, J. Planar Chromatogr, 17, 350, 2004. 

Each of the four theaflavins theoretically are derived from the reactions the quinones of epicatechin or its gallate with those of epigallocatechin or its gallate has been identified in black tea and its structure authenticated.50... 

Red wine contains quercetin, rutin, catechin, and epicatechin, among other flavonoids (Frankel and others 1993). Quercetin and other phenolic compounds isolated from wines were found to be more effective than a-tocopherol in inhibiting copper-catalyzed LDL oxidation. It has been determined that quercetin has also several anti-inflammatory effects it inhibits inflammatory cytokine production (Boots and others 2008), inducible NO synthase expression and activation of inflammatory transcription factors (Hamalainen and others 2007), and activity of cyclooxygenase and lipooxygenase (Issa 2006), among others. 

Wang J, Schramm D and Holt R. 2000. A dose-response effect from chocolate consumption on plasma epicatechin and oxidative damage. J Nutr 130 2115S-2119S. 

Jo and others (2006) applied this assay to determine the antioxidant properties of methanolic extracts from Japanese apricot in chicken breast meat. Likewise, Pearson and others (1998) assessed two types of Japanese green tea from Japan and two of their active compounds, catechin and epicatechin, for their relative abilities to inhibit the oxidation of LDL. Also, Pearson and others (1999) assessed the ability of compounds in apple juices and extracts from fresh apple to protect LDL. Heinonen and others (1998b) observed that berry phenolics inhibited hexanal formation in oxidized human LDL. 

The effects of flavonoids on in vitro and in vivo lipid peroxidation have been thoroughly studied [123]. Torel et al. [124] found that the inhibitory effects of flavonoids on autoxidation of linoleic acid increased in the order fustin < catechin < quercetin < rutin = luteolin < kaempferol < morin. Robak and Gryglewski [109] determined /50 values for the inhibition of ascorbate-stimulated lipid peroxidation of boiled rat liver microsomes. All the flavonoids studied were very effective inhibitors of lipid peroxidation in model system, with I50 values changing from 1.4 pmol l-1 for myricetin to 71.9 pmol I 1 for rutin. However, as seen below, these /50 values differed significantly from those determined in other in vitro systems. Terao et al. [125] described the protective effect of epicatechin, epicatechin gallate, and quercetin on lipid peroxidation of phospholipid bilayers. 

Flavonoids exhibit protective action against LDL oxidation. It has been shown [145] that the pretreatment of macrophages and endothelial cells with tea flavonoids such as theaflavin digallate diminished cell-mediated LDL oxidation probably due to the interaction with superoxide and the chelation of iron ions. Quercetin and epicatechin inhibited LDL oxidation catalyzed by mammalian 15-lipoxygenase, and are much more effective antioxidants than ascorbic acid and a-tocopherol [146], Luteolin, rutin, quercetin, and catechin suppressed copper-stimulated LDL oxidation and protected endogenous urate from oxidative degradation [147]. Quercetin was also able to suppress peroxynitrite-induced oxidative modification of LDL [148],... 

Fig. 2.56. HPLC chromatogram of (a) Golden peel and (b) Golden pulp extracts at 280 nm. Peaks 1 = procyanidin B3 2 = procyanidin Bl 3 = ( + )-catechin 4 = procyanin B2 5 = chlorogenic acid 6 = ( — )-epicatechin 7 = caffeic acid 8 = phloretin derivative 9 = phloridzin 10 = rutin 11, 12 and 13 = flavonol glucosides. Reprinted with permission from A. Escarpa et al. [160].

Fig. 2.61. Separation of grape seed extract (a) and grape seed extract spiked with mixture of eight compounds (b) using optimized conditions. Chromatographic conditions are discussed in the text. Peak identification 1 = 2-phenylethanol 2 = vanillin 3 = ferulic acid 4 = protocatechoic acid 5 = caffeic acid 6 = gallic acid 7 = catechin 8 = epicatechin. Reprinted with permission from A. Kamangerpour et al. [167].

Fig. 2.62. HPLC chromatogram of (a) jasmin (green) tea, (b) Fujian Oolong tea, (c) pu-erh tea and (d) black tea at 280 nm. Peak identification 1 = gallic acid (GA) 2 = (-)-epigallocatechin (EGC) 3 = (-)-epigallocatechin gallate (EGCG) 4 = epicatechin (EC) 5 = (-)-epicatechin gallate (ECG) 6 = caffeine (CA) 7 = ( — )-catechin gallate (CG). Reprinted with permission from Y. Zuo et al. [178].

Fig. 2.64. Representative chromatogram of tea infusions. Conditions C18 column acetonitrile-aqueous acetate buffer gradient absorbance at 210 nm. Peak identities 1 = epigallocatechin (EGC) 2 = caffeine 3 = epicatechin (EC) 4 = epigallocatechin gallate EGCG) 5 = epicatechin gallate (ECG) 6 = internal standard (naringenin). Reprinted with permission from W. E. Bronner et al. [180].

Fig. 2.79. Chromatograms of a white (I) and red wine sample (II). (LC-DAD signals at three different wavelenghts 256, 324, 365 nm). Peak identification 1 = gallic acid 2 = protocatechuic acid 3 = p-hydroxybenzoic acid 4 = vanillic acid 5 = caffeic acid 6 = (+)-catechin 7 = syringic acid 8 = p-coumaric acid 9 = ( — )-epicatechin 10 = ferulic acid 11 = fraras-resveratrol 12 = rutin 13 = myricetin 14 = cw-resveratrol 15 = quercetin A = caftaric acid B = coutaric acid. Reprinted with permission from M. Castellari et al. [196],...

Fig. 2.82. Chromatograms for a red wine sample using gradient elution and photodiode array detection. Flow rate, lml/min. Peak identification 1 = catechin 2 = epicatechin 4 = irans-resveratrol 6 = quercetin. Reprinted with permission from P. Vinas et al. [198].

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