This review will discuss recent progress in the chemistry of secondary polyphenols produced during food processing. The production mechanism of the secondary polyphenols in black tea, whisky, cinnamon, and persimmon fruits will be introduced. In the process of black tea production, tea leaf catechins are enzymatically oxidized to yield a complex mixture of oxidation products, including theaflavins and thearubigins. Despite the importance of the beverage, most of the chemical constituents have not yet been confirmed due to the complexity of the mixture. However, the reaction mechanisms at the initial stages of catechin oxidation are explained by simple quinone–phenol coupling reactions. In vitro model experiments indicated the presence of interesting regio- and stereoselective reactions. Recent results on the reaction mechanisms will be introduced. During the aging of whisky in oak wood barrels, ellagitannins originating from oak wood are oxidized and react with ethanol to give characteristic secondary ellagitannins. The major part of the cinnamon procyanidins is polymerized by copolymerization with cinnamaldehyde. In addition, anthocyanidin structural units are generated in the polymer molecules by oxidation which accounts for the reddish coloration of the cinnamon extract. This reaction is related to the insolubilization of proanthocyanidins in persimmon fruits by condensation with acetaldehyde. In addition to oxidation, the reaction of polyphenols with aldehydes may be important in food processing.
The bark extract of Acacia mearnsii showed strong lipase and α-amylase inhibition activities. Fractionation of the extract by column chromatography and subsequent (13)C NMR and MALDI-TOF-MS analysis revealed that the active substances are proanthocyanidin oligomers mainly composed of 5-deoxyflavan-3-ol units. In addition, 4'-O-methylrobinetinidol 3'-O-β-D-glucopyranoside, fisetinidol-(4α,6)-gallocatechin, and epirobinetinidol-(4β,8)-catechin were isolated as new compounds, and their structures were determined from spectroscopic data. Furthermore, a modified thiol degradation method using strongly acidic conditions was applied to the extract to yield three thiol degradation products derived from robinetinidol units. This method is useful for characterizing acacia proanthocyanidins (wattle tannins).
The quality of 18 F-FDG PET/CT images of overweight patients is often degraded. We evaluated the effect of optimizing injected dose or acquisition time on the quality of images of overweight patients using lutetium oxyorthosilicate PET/CT with high-performance detector electronics. Methods: We initially retrospectively measured radioactivity concentrations and signal-to-noise ratios (SNRs) in the liver relative to body weight for 80 patients who had undergone 18 F-FDG PET/CT according to our standard protocol (injected dose, 3.7 MBq/kg; acquisition time, 2 min/bed position). The patients were grouped (n 5 20 per group) according to baseline body weight as G1 (#59 kg), G2 (60-69 kg), G3 (70-84 kg), and G4 ($85 kg). We compared the SNRs of G1 with those of G2, G3, and G4 and calculated the ratio squared as a factor to correct the acquisition parameters for overweight patients. We then prospectively enrolled 120 patients according to the same body weight criteria. We multiplied the correction factors to optimize injected doses or acquisition times and defined dose-adjusted groups (n 5 20 per group) and timeadjusted groups (n 5 20 per group). G2 dose was defined as 5.59 6 0.19 MBq/kg, G3 dose as 7.29 6 0.33 MBq/kg, and G4 dose as 8.88 6 0.43 MBq/kg. G2 time was defined as 3 min/bed position, G3 time as 4 min/bed position, and G4 time as 5 min/ bed position. Results: Although liver activities did not significantly differ among G1 through G4 irrespective of patient weight, SNR progressively decreased as patient weight increased. The liver activities of G2 dose, G3 dose, and G4 dose were, respectively, 1.4-, 1.9-, and 2.5-fold higher than those of the baseline counterparts. Nevertheless, the increased liver activities of G2 dose, G3 dose, and G4 dose did not significantly affect SNR, compared with the baseline groups. In contrast, the SNR of G4 time was significantly higher than that of G4. Conclusion: Our findings suggest that the quality of images acquired from heavier patients can be maintained only by scanning for longer periods. Increasing the dose per kilogram of body weight did not improve the quality of lutetium oxyorthosilicate PET/CT images.
Myocardial fat is often seen at cardiac computed tomography (CT) and magnetic resonance (MR) imaging of healthy adults and patients with myocardial diseases. Physiologic myocardial fat develops with aging and is commonly seen at CT in the anterolateral right ventricular (RV) free wall and RV outflow tract with normal or thickened RV myocardium and a normal-sized RV in elderly patients. Pathologic conditions with myocardial fat include healed myocardial infarction (MI); arrhythmogenic RV cardiomyopathy or dysplasia (ARVC); and others, such as cardiac lipoma, lipomatous hypertrophy of the interatrial septum, tuberous sclerosis complex, dilated cardiomyopathy, and cardiomyopathy with muscular dystrophy. In patients with healed MI, CT and MR imaging show fat in left ventricular myocardium that is of normal thickness or thin and follows the distribution of the coronary artery; CT often depicts fat in mostly subendocardial regions. In patients with ARVC, characteristic CT and MR imaging findings include a thin RV outflow tract and free wall caused by subepicardial fatty infiltration; fat in the RV moderator band, trabeculae, and ventricular septum; and RV enlargement and wall motion abnormality. Recognition of patient age, characteristic locations of myocardial fat, myocardial thickness, and ventricular size helps in differentiating physiologic and pathologic myocardial fat at cardiac imaging; findings of wall motion abnormality and late gadolinium enhancement at MR imaging help narrow the diagnosis.
Diabetes mellitus is a leading cause of many complications, such as atherosclerosis, cardiac dysfunction, retinopathy, neuropathy, and nephropathy. In longitudinal hyperglycemia, advanced glycation end-product (AGE) formation, resulting from the non-enzymatic reactions of carbohydrates and oxidized lipids with proteins, is increased and is also stimulated by oxidative stress which is closely linked with the pathogenesis of diabetic complications as well as the polyol pathway and protein kinase C pathway.1,2) Therefore, interference with AGE formation has the therapeutic potential to prevent the progression of diabetic complications.Traditional medicines are recently being focused on to treat diabetes and its complications because of their absence of toxic-and/or side-effects. In our previous study, we reported that Hachimi-jio-gan ameliorated functional and structural features associated with experimental type 1 and 2 diabetic nephropathy rat models, 3,4) and according to the three-dimensional HPLC profile of Hachimi-jio-gan, morroniside and loganin obtained from Corni Fructus (Cornus officinalis SIEB. et ZUCC.) are the major compounds. It was previously discovered that Corni Fructus could ameliorate glucose-associated metabolic disorders, and its mechanisms were intimately related to the formation of AGEs, as well as those of Hachimi-jio-gan. 5) To add to these findings, we evaluated the major active components in Corni Fructus. As the first step, we prepared five fractions from Corni Fructus extract, that is, one sugar with organic acid fraction (S1D1), one iridoid glycoside fraction (S1D2), and three polyphenol fractions (from low to high molecular weights: S2, S3, and S4) as shown in Fig. 1A. Next, we examined the effect of Corni Fructus and its five fractions on hydroxyl radical scavenging activity associated with the glycation reaction, because this reaction is, in part, mediated by hydrogen peroxide and transition metal ions, called the Fenton reaction.6) As a result, only the fraction of S1D1 was weaker than Corni Fructus and S1D2 was similar to Corni Fructus; that is, the relation of these activities was as follows, "S1D1
The development and progression of diabetic nephropathy is dependent on glucose homeostasis and many other contributing factors. In the present study, we examined the effect of nitecapone, an inhibitor of the dopaminemetabolizing enzyme catechol-O-methyl transferase (COMT) and a potent antioxidant, on functional and cellular determinants of renal function in rats with streptozotocin-induced diabetes. Administration of nitecapone to diabetic rats normalized urinary sodium excretion in a manner consistent with the dopaminedependent inhibition of proximal tubule Na,K-ATPase activity. Hyperfiltration, focal glomerulosclerosis, and albuminuria were also reversed by nitecapone, but in a manner that is more readily attributed to the antioxidant potential of the agent. A pattern of elevated oxidative stress, measured as CuZn superoxide dismutase gene expression and thiobarbituric acid-reactive substance content, was noted in diabetic rats, and both parameters were normalized by nitecapone treatment. In diabetic rats, activation of glomerular protein kinase C (PKC) was confirmed by isoform-specific translocation and Ser23 phosphorylation of the PKC substrate Na,KATPase. PKC-dependent changes in Na,K-ATPase phosphorylation were associated with decreased glomerular Na,K-ATPase activity. Nitecapone-treated diabetic rats were protected from these intracellular modifications. The combined results suggest that the COMTinhibitory and antioxidant properties of nitecapone provide a protective therapy against the development of diabetic nephropathy. Diabetes 49:1381-1389, 2000
During tea fermentation, oxidation-reduction dismutation of a number of quinone metabolites of tea catechins yields numerous minor products, which make it difficult to separate and purify black tea polyphenols. In this study, epigallocatechin-3-O-gallate was enzymatically oxidized and then the unstable quinone metabolites in the oxidation mixture were hydrogenated with 2-mercaptoethanol to reduce production of inseparable minor dismutation products. As a result, three new oxidation products including a new black tea pigment were isolated, and their structures were determined based on chemical and spectroscopic data. Dehydrotheasinensin AQ is a new reddish-orange pigment with a 1,2-diketone structure, and its presence in commercial black tea was confirmed. In addition, a new quinone dimer with a complex caged structure and a trimer of epigallocatechin-3-O-gallate were also isolated and their production mechanisms are proposed. The presence of this trimer suggested participation of galloyl quinones in production of minor polyphenols in black tea.
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