[Show abstract][Hide abstract] ABSTRACT: Delay in gastric emptying (GE) lowers the blood ethanol concentration (BEC) after alcohol administration. We previously demonstrated that water-insoluble fractions, mainly comprising dietary fiber derived from many types of botanical foods, possessed the ability to absorb ethanol-containing aqueous solutions. Furthermore, there was a significant correlation between the absorption of ethanol and lowering of BEC because of delay in GE. Here we identified dietary nutrients that synergize with the water-insoluble fraction of tomatoes to lower BEC in rats. Consequently, unlike tomato juice without alanine, tomato juice with 5.0% alanine decreased BEC depending on the delay in GE and mediated the ethanol-induced decrease in the spontaneous motor activity (an indicator of drunkenness). Our findings indicate that the synergism between tomato juice and alanine to reduce the absorption of ethanol was attributable to the effect of alanine on precipitates such as the water-insoluble fraction of tomatoes.
Preview · Article · Dec 2015 · Journal of nutrition and metabolism
[Show abstract][Hide abstract] ABSTRACT: Background: Particulate pollution is associated with occurrence of asthma and allergy, acting together with allergens in initiating and exacerbating these diseases. Production of reactive oxygen species contributes to this effect of pollutants. We tested the hypothesis that oxygen radicals generated by granulocytes are key regulators in exacerbation of allergic responses by particulate pollution. Methods: Out of pollen season, granulocytes and serum were collected from 17 patients sensitive to pollen allergens and from 13 healthy volunteers. Oxygen radical generation, individual single nucleotide polymorphism types (SOD2, SOD3, GSTP1, CAT, FCER1B and IL4A) , gene expression differences and serum cytokine concentrations were compared with allergen-specific IgE, and histamine-release test results in ability to discriminate between groups. Results: Oxygen radical measurements predicted severity of pollinosis. Allergy (IgE receptor) related genotype FCER1B was associated with increased oxygen radical generation (P=0.04). RNA markers may also predict the onset of hay fever those symptoms getting worse. Interpretation. From our pilot study, genomic approaches and oxygen radical generation by granulocytes in response to pollen particles may be possible molecular markers of allergic inflammation that predicted pollinosis severity. Conclusion: New measurement technique and methodology may elucidate pollinosis patients in their prediction and prevention and may contribute to development of preventive medicine. It is only a pilot study with small sample, but might have possibilities of finding a cut end and a breakthrough in the difficulty of allergic pathophysiology from the viewpoint of genomic approach and radical oxygen measurement.
[Show abstract][Hide abstract] ABSTRACT: Apples are known to contain high concentrations of phenolic compounds such as condensed tannins. Consumption of condensed tannins has been reported to reduce the risk of many types of chronic diseases including allergies. However, their therapeutic effectiveness and potential in treating autoimmune disease remain controversial. Here, the effect of oral administration of apple condensed tannins (ACT) prepared from apples (Malus pumila cv. Fuji) on bovine type II collagen (CII)-induced arthritis in DBA1/J mice, a well-established murine model of human rheumatoid arthritis (RA), was evaluated. As compared to the control (without ACT administration) group, RA development was delayed and a significant reduction in the RA clinical score was observed in the ACT-administered group. Using cultured splenocytes isolated from CII-immunized mice, ACT-administration was shown to decrease the CII-induced increases in IL-17 expression and production in vitro. We propose that down-regulation of T helper (Th) 17 cells is responsible for the ACT-induced RA suppression This article is protected by copyright. All rights reserved.
This article is protected by copyright. All rights reserved.
No preview · Article · Apr 2015 · Molecular Nutrition & Food Research
[Show abstract][Hide abstract] ABSTRACT: A novel O-methyltransferase gene was isolated from Flammulina velutipes. The isolated full-length cDNA was composed of a 690-nucleotide open reading frame encoding 230 amino acids. A database search revealed that the deduced amino acid sequence was similar to those of other O-methyltransferases; the highest identity was only 61.8% with Laccaria bicolor. The recombinant enzyme was expressed by Escherichia coli. BL21 (DE3) was assessed for its ability to methylate (-)-epigallocatechin-3-O-gallate (EGCG). LC-TOF-MS and NMR revealed that the enzyme produced five kinds of O-methylated EGCGs: (-)-epigallocatechin-3-O-(3-O-methyl)gallate, (-)-epigallocatechin-3-O-(4-O-methyl)gallate, (-)-epigallocatechin-3-O-(3,4-O-dimethyl)gallate, (-)-epigallocatechin-3-O-(3,5-O-dimethyl)gallate, and (-)-4'-O-methylepigallocatechin-3-O-(3,5-O-dimethyl)gallate. The substrate specificity of the enzyme for 20 kinds of polyphenols was assessed using the crude recombinant enzyme of O-methyltransferase. This enzyme introduced methyl group(s) into polyphenols with pyrocatechol and pyrogallol structures.
No preview · Article · Mar 2015 · Bioscience Biotechnology and Biochemistry
[Show abstract][Hide abstract] ABSTRACT: Seven new O-methylated theaflavins (TFs) were synthesized by using O-methyltransferase from an edible mushroom. Using TFs and O-methylated TFs, metabolic stability in pooled human liver S9 fractions and inhibitory effect on H2O2-induced oxidative damage in human HepG2 cells were investigated. In O-methylation of theaflavin 3'-O-gallate (TF3'G), metabolic stability was potentiated by an increase in the number of introduced methyl groups. O-methylation of TF3,3'G did not affect metabolic stability, which was likely because of a remaining 3-O-galloyl group. The inhibitory effect on oxidative damage was assessed by measuring the viability of H2O2-damaged HepG2 cells treated with TFs and O-methylated TFs. TF3,3'G and O-methylated TFs increased cell viabilities significantly compared with DMSO, which was the compound vehicle (p < 0.05), and improved to approximately 100%. Only TF3'G did not significantly increase cell viability. It was suggested that the inhibitory effect on H2O2-induced oxidative damage was potentiated by O-methylation or O-galloylation of TFs.
No preview · Article · Jul 2014 · Bioscience Biotechnology and Biochemistry
[Show abstract][Hide abstract] ABSTRACT: Extracts from immature fruit of the apple (Rosaceae, Malus sp.), which contain procyanidins (polymers of catechins) as the major ingredients, are known to inhibit histamine release from mast cells. We analyzed in this study the mechanism for the anti-allergic activity of two polyphenol-enriched apple extracts. These extracts, termed “crude apple polyphenol (CAP)” and “apple condensed tannin (ACT)”, reduced the degranulation of mast cells caused by cross-linking of the high-affinity receptor for IgE (FcεRI) with IgE and the antigen in a dose-dependent manner. Furthermore, western blotting revealed that phosphorylation of the intracellular signal-transduction molecules caused by cross-linking of FcεRI was markedly decreased by the addition of CAP or ACT. We then analyzed the effects of CAP and ACT on the binding of the IgE antibody to FcεRI on mast cells, which is the first key step in the allergic reaction mediated by mast cells, and found that this binding was markedly inhibited by both CAP and ACT. These results indicate that the inhibition of binding between FcεRI and IgE by either CAP or ACT was the probable cause of the suppression of mast cell activation. This is the first report demonstrating the molecular mechanism for the anti-allergic effect of procyanidin-enriched extracts from apples.
No preview · Article · May 2014 · Bioscience Biotechnology and Biochemistry
[Show abstract][Hide abstract] ABSTRACT: An enzyme catalyzing the methylation of phenolic hydroxyl groups in polyphenols was identified from mycelial cultures of edible mushrooms to synthesize O-methylated polyphenols. Enzyme activity was measured to assess whether methyl groups were introduced into (-)-epigallocatechin-3-O-gallate (EGCG) using SAM as a methyl donor, and (-)-epigallocatechin-3-O-(3-O-methyl)-gallate (EGCG3″Me), (-)-epigallocatechin-3-O-(4-O-methyl)-gallate (EGCG4″Me), and (-)-epigallocatechin-3-O-(3,5-O-dimethyl)-gallate (EGCG3″,5″diMe) peaks were detected using crude enzyme preparations from mycelial cultures of Flammulina velutipes. The enzyme was purified using chromatographic and two-dimensional electrophoresis. The purified enzyme was subsequently analyzed on the basis of the partial amino acid sequence using LC-MS/MS. Partial amino acid sequencing identified the 17 and 12 amino acid sequences, VLEVGTLGGYSTTWLAR and TGGIIIVDNVVR. In database searches, these sequences showed high identity with O-methyltransferases from other mushroom species and completely matched 11 of 17 and 9 of 12 amino acids from five other mushroom O-methyltransferases.
No preview · Article · May 2014 · Bioscience Biotechnology and Biochemistry
[Show abstract][Hide abstract] ABSTRACT: Cardiac electrophysiological alterations induced by chronic exposure to reactive oxygen species and protective effects of dietary antioxidant have not been thoroughly examined. We recorded surface electrocardiograms (ECG) and evaluated cellular electrophysiological abnormalities in enzymatically-dissociated left ventricular (LV) myocytes in heart/muscle-specific manganese-superoxide dismutase-deficient (H/M-Sod2 (-/-)) mice, which exhibit dilated cardiomyopathy due to increased oxidative stress. We also investigated the influences of intake of apple polyphenols (AP) containing mainly procyanidins with potent antioxidant activity. The QRS and QT intervals of ECG recorded in H/M-Sod2 (-/-) mice were prolonged. The effective refractory period in the LV myocardium of H/M-Sod2 (-/-) mice was prolonged, and susceptibility to ventricular tachycardia or fibrillation induced by rapid ventricular pacing was increased. Action potential duration in H/M-Sod2 (-/-) LV myocytes was prolonged, and automaticity was enhanced. The density of the inwardly rectifier K(+) current (I K1) was decreased in the LV cells of H/M-Sod2 (-/-) mice. The AP intake partially improved these electrophysiological alterations and extended the lifespan in H/M-Sod2 (-/-) mice. Thus, chronic exposure of the heart to oxidative stress produces a variety of electrophysiological abnormalities, increased susceptibility to ventricular arrhythmias, and action potential changes associated with the reduced density of I K1. Dietary intake of antioxidant nutrients may prevent oxidative stress-induced electrophysiological disturbances.
[Show abstract][Hide abstract] ABSTRACT: A fundamental means of allergic disease prevention, via the use of functional food factors, is desirable. A number of studies on the role of functional food factors in preventing allergic diseases have been reported. In this review, the preventive effects of polyphenols, carotenoids, polysaccharides, and non-digestible oligosaccharides on allergic diseases are discussed.
No preview · Article · Mar 2014 · Current pharmaceutical design
[Show abstract][Hide abstract] ABSTRACT: A novel sequential chromatographic technique was applied to the comprehensive separation of polyphenols and related compounds from a hop bract extract. Over 100 types of constituents were effectively isolated from only 25 g of extract in high yields by high-speed countercurrent chromatography followed by hydrophilic interaction chromatography and reversed-phase high performance liquid chromatography. Among the materials isolated, the structures of 39 compounds were elucidated on the basis of their spectroscopic data including electrospray ionization time-of-flight mass spectrometry and 1D/2D nuclear magnetic resonance. Three new compounds, 1 known compound identified for the first time in plants, and 20 known compounds that have not been reported in hops were found. The hop bract extract also contained an abundance of highly oligomeric proanthocyanidins, which consisted of B-type procyanidin structures.
No preview · Article · Feb 2014 · Journal of Agricultural and Food Chemistry
[Show abstract][Hide abstract] ABSTRACT: A known O-methylated theaflavin, theaflavin 3-O-(3-O-methyl)gallate (3MeTF3G), and the new theaflavin 3-O-(3,5-di-O-methyl)gallate (3,5diMeTF3G) were synthesized via the O-methylation of theaflavin 3-O-gallate (TF3G). Both 3MeTF3G and 3,5diMeTF3G are more stable than TF3G at pH 7.5 in the order 3,5diMeTF3G > 3MeTF3G > TF3G. The inhibitory effects of these compounds on the intracellular accumulation of triglycerides from terminally differentiated human visceral adipocytes were investigated. Compound 3MeTF3G exhibited a similar inhibitory effect as TF3G at 3 µM and a slightly lower effect than that of TF3G at 10 µM. The result suggested that the degradants and oxidatively polymerized products of TF3G may also have inhibitory effects. For cells treated with 3,5diMeTF3G at 3 and 10 µM, intracellular triglyceride accumulation was dose dependent and significantly lower compared with that for other compounds. The higher inhibitory effect of 3,5diMeTF3G may be due to its greater stability and enhanced ability for absorption owing to di-O-methylation.
No preview · Article · Dec 2013 · Journal of Agricultural and Food Chemistry
[Show abstract][Hide abstract] ABSTRACT: Apple polyphenol extract (AP) and procyanidin contained in AP were investigated for their immunomodulatory effects using THP-1-derived human dendritic cells (TDDCs). The expression levels of HLA-DR (MHC class II) and CD86 (costimulatory molecule) were measured as an indicator of antigen presentation in TDDCs. A significant decrease in HLA-DR expression was observed in the AP and fractionated procyanidin-treated cells in the presence of ovalbumin (OVA), but no effect on CD86 expression was observed. The uptake of OVA was not inhibited by AP treatment, and the gene expression of membrane-associated RING-CH ubiquitin E3 ligase, MARCH1, was up-regulated by AP treatment. It can therefore be presumed that AP suppresses HLA-DR expression via the ubiquitin-proteasome pathway. Furthermore, the up-regulation of IL-12 and TNF-α was found in the procyanidin trimers-treated cells in the presence of OVA. These results suggest that apple polyphenols would be an effective factor for the development of immunomodulatory agents with suppressive effects of antigen presentation.
[Show abstract][Hide abstract] ABSTRACT: Zijuan tea is a new cultivar produced in Yunnan province of China. Unlike most tea cultivars, Zijuan tea is anthocyanin-rich. The composition and antioxidant activities of anthocyanins of Zijuan tea were studied for the first time in this paper. Anthocyanins were extracted with acidified methanol and quantified as 707±28 μg/g of dry weight (cyanidin-3-O-β-D-glucoside equivalent) by high-performance liquid chromatography (HPLC) analysis. Four anthocyanins were successfully identified, after over Amberlite XAD-7HP adsorption column chromatography and octadecyl silane (ODS) flash chromatography. Among the four, delphinidin-3-O-β-D-galactoside (1) and cyanidin-3-O-β-D-galactoside (2) were confirmed by Liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) and HPLC. Delphinidin-3-O-β-D-(6-(E)-p-coumaroyl) galactopyranoside (3) and cyanidin-3-O-β-D-(6-(E)-p-coumaroyl) galactopyranoside (4) were characterized by the high-resolution time-of-flight-mass spectrometry (HRTOF-MS) and nuclear magnetic resonance (NMR) spectrometry. The antioxidant activities of compounds 3 and 4, which composed approximately 75% of the total anthocyanins content in HPLC analysis, were evaluated by DPPH and FRAP assays. Results showed that both had higher antioxidant activities than commercial antioxidants butylated hydroxytoluene (BHT) used as one of controls in these assays.
No preview · Article · Mar 2013 · Journal of Agricultural and Food Chemistry
[Show abstract][Hide abstract] ABSTRACT: To examine the safety of dietary Applephenon® (AP) in feed, Crl: CD (SD) rats of each sex were divided into four groups and given diets containing AP at 0, 1.25, 2.5, or 5.0% for 90 days. All rats survived and toxic changes were not observed throughout the study. Body weight and food efficiency in the 5.0% AP group of both sexes were significantly decreased compared with that in controls. These changes were considered to be caused by the physiological effects of AP (including the inhibitory effects on pancreatic lipase activity). Slight hypertrophy in acinar cells in the parotid and submandibular glands appeared in the 2.5 and 5.0% groups. These were suggested not to be toxicological but physiologic adaptive responses to oral stimuli by the lower pH of AP-containing diets. In conclusion, dietary AP in feed, up to a maximum level of 5.0% for 90 days, given to rats did not induce toxicological effects.
No preview · Article · Feb 2013 · Food and chemical toxicology: an international journal published for the British Industrial Biological Research Association
[Show abstract][Hide abstract] ABSTRACT: Apple polyphenols (AP), which contain procyanidins as major components, have been reported to display potent antioxidant activity and several beneficial health effects. To investigate the protective effect of AP intake against murine cardiomyopathy caused by endogenous oxidative stress, we orally administered AP to heart/muscle-specific manganese-superoxide dismutase (Mn-SOD)-deficient (H/M-Sod2-/-) mice [Nojiri et al., 2006]. Dietary AP significantly increased the survival of the mutant mice, extending their mean lifespan by 29%. Dietary AP also suppressed the progression of cardiac dilatation and fibrosis in the H/M-Sod2-/- mice. In vitro experiments revealed that AP treatment strongly suppressed the production of hydrogen peroxide induced reactive oxygen species (ROS) in C2C12 myoblast cells and endogenous superoxide production in Mn-SOD-deficient cells. Furthermore, dietary AP suppressed ROS production in Mn-SOD-deficient cardiomyocytes and oxidative DNA damage in vivo. These results indicate that dietary AP improved the survival and pathology of short-lived mice with cardiomyopathy by suppressing mitochondrial superoxide production.
[Show abstract][Hide abstract] ABSTRACT: A chromanone glycoside, 5-Œ≤-d-glucopyranosyloxy-7-hydroxy-2-isopropylchromanone, and two acylphloroglucinol glycosides, 2-(3-methylbutyryl)phloroglucinol-4,6-di-C-Œ≤-d-glucopyranoside and 2-isobutyrylphloroglucinol-1,5-di-O-Œ≤-d-glucopyranoside, along with 15 known compounds were isolated from the bracts of hops (Humulus lupulus L.). Their structures were elucidated based on spectroscopic data, including TOFMS and 1D/2D NMR.
No preview · Article · Sep 2012 · Phytochemistry Letters
[Show abstract][Hide abstract] ABSTRACT: Procyanidins are plant secondary metabolites widely consumed and known to have various physiological functions, but their bioavailability and mechanism of action are still unclear especially for larger oligomers. One of the reasons is scarce information about the detailed structure of oligomeric procyanidins. As for apple, structures of procyanidin components larger than trimers are scarcely known. In this study, 11 tetrameric procyanidins including two known compounds were isolated from unripe apples (Malus pumila cv. Fuji) and identified by NMR spectroscopic analysis and phloroglucinol degradation. As a result, the detailed structural diversity of tetrameric procyanidins in apple was established.
[Show abstract][Hide abstract] ABSTRACT: Procyanidins, which are condensed catechins, have been elucidated as absorbable polyphenols, but their health-benefits remain unclear. The aim of this study was, thus, to clarify the efficacy and mechanism of each procyanidin oligomer in NO activation in rat aortic endothelial cells (RAECs). Treatment of RAECs with 50μM procyanidin C1 (4β→8 trimer) resulted in a time- and dose-dependent hyperpolarization using the membrane potential-sensitive probe bis-(1,3-dibutylbarbituric acid) trimethine oxonol, while no effect was observed for (-)-epicatechin (a monomer) and procyanidin B2 (4β→8 dimer). The C1-induced hyperpolarization was inhibited by iberiotoxin, a specific inhibitor of large-conductance Ca(2+)-activated K(+) (BK(Ca)) channel, as well as 2-aminoethyl diphenylborinate (2-APB), a store-operated Ca(2+) entry inhibitor. Procyanidin C1 caused a significant increase in NO production from RAECs via phosphorylation of both eNOS and Akt, and the effect was completely inhibited by N(G)-monomethyl-l-arginine or combined treatment with iberiotoxin and the phosphatidylinositol 3-kinase (PI3K) specific inhibitor, wortmannin, as well as combined treatment with 2-APB and wortmannin. Taken together, these findings provide critical evidence that procyanidin C1, but not B2, has potential to induce NO production in RAECs via both Ca(2+)-dependent BK(Ca) channel-mediated hyperpolarization and Ca(2+)-independent PI3K/Akt pathways.
No preview · Article · Jul 2012 · European journal of pharmacology