Tomomasa Kanda

Japan Food Research Laboratories, Ōsaka, Ōsaka, Japan

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Publications (67)166.7 Total impact

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    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.
    Bioscience Biotechnology and Biochemistry 07/2014; 78(7):1140-1146. · 1.27 Impact Factor
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    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.
    Bioscience Biotechnology and Biochemistry 05/2014; 78(5):806-11. · 1.27 Impact Factor
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    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.
    Current pharmaceutical design 03/2014; 20(6):892-905. · 4.41 Impact Factor
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    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.
    Journal of Agricultural and Food Chemistry 02/2014; · 3.11 Impact Factor
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    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.
    BioMed research international. 01/2014; 2014:704291.
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    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.
    Journal of Agricultural and Food Chemistry 12/2013; · 3.11 Impact Factor
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    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.
    Food Chemistry 06/2013; 138(2-3):757-61. · 3.33 Impact Factor
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    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.
    Journal of Agricultural and Food Chemistry 03/2013; 61:3306-3310. · 3.11 Impact Factor
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    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.
    Food and chemical toxicology: an international journal published for the British Industrial Biological Research Association 02/2013; · 2.99 Impact Factor
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    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.
    Phytochemistry 08/2012; 83:144-52. · 3.35 Impact Factor
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    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.
    European journal of pharmacology 07/2012; 692(1-3):52-60. · 2.59 Impact Factor
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    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.
    International Journal of Life Science and Medical Research. 01/2012; 2(3):46-51.
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    ABSTRACT: A chromanone glycoside, 5-β-d-glucopyranosyloxy-7-hydroxy-2-isopropylchromanone, and two acylphloroglucinol glycosides, 2-(3-methylbutyryl)phloroglucinol-4,6-di-C-β-d-glucopyranoside and 2-isobutyrylphloroglucinol-1,5-di-O-β-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.
    Phytochemistry Letters 01/2012; 5(3):514-518. · 1.18 Impact Factor
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    ABSTRACT: [This corrects the article on p. 104 in vol. 87.].
    Proceedings of the Japan Academy Ser B Physical and Biological Sciences 07/2011; 87(7):431. · 2.77 Impact Factor
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    ABSTRACT: Studies on metabolisms of alcohol and the metabolites (e.g.:acetaldehyde) after drinking give basic and important information to recognize the physiological influence of drinking to human bodies. The aims of these studies were to clarify the influences of ALDH2 genotype difference, kinds of alcohol beverages, and fasted or prandial state to alcohol metabolisms at moderate drinking. The studies were conducted by a randomized cross-over design. After overnight fast, fifteen of ALDH2*1/*1 (Experiment 1) and twenty of ALDH21/*2 (Experiment 2) in Japanese healthy men aged 40 to 59 years old drank beer or shochu at a dose of 0.32g ethanol / kg body weight with or without test meal (460 kcal). The peak of blood ethanol (C(max)) was higher with shochu than with beer in the fasted condition in both ALDH2 genotypes, however, the difference between two types of alcohol beverages went out in the prandial condition. Simultaneous ingestion of test meal with alcohol beverage significantly decreased blood ethanol concentrations and increased ethanol disappearance rate (EDR) in the both genotypes. EDR values were significantly higher in ALDH2*1/*1 type than in ALDH2*1/*2 type in the both beverages with and without meal, whereas beta values showed no significant difference between two genotypes. The concentrations of blood acetaldehyde in ALDH2*1/*2 type were higher in prandial condition than in fasted condition with shochu. These results indicate that meal modified the differences of alcohol metabolism between beer and shochu and also between ALDH2 genotypes. Thus, alcohol metabolism in daily drinking is shown to be regulated by various combinatorial drinking conditions.
    Nihon Arukōru Yakubutsu Igakkai zasshi = Japanese journal of alcohol studies & drug dependence 06/2011; 46(3):357-67.
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    ABSTRACT: New red leaf tea cultivar 'Sunrouge' (Camellia taliensis × Camellia sinensis), for which an application for registration was made in 2009, is an anthocyanin-rich tea. The anthocyanin content of 'Sunrouge' was the highest among 4 tea cultivars, and was 8.4 times higher than that of 'Yabukita'. We purified and isolated 6 anthocyanins from 'Sunrouge' by chromatography, and identified them by LC/MS/MS and NMR analysis. As a result, the four anthocyanins were identified as delphinidin-3-O-β-D-(6-(E)-p-coumaroyl)galactopyranoside (2), delphinidin-3-O-β-D-(6-(E)-p-coumaroyl)glucopyranoside (3), cyanidin-3-O-β-D-(6-(E)-p-coumaroyl)galactopyranoside (4), and cyanidin-3-O-β-D-(6-(E)-p-coumaroyl)glucopyranoside (5), and the other two were estimated as delphinidin-(Z)-p-coumaroylgalactopyranoside (1), petunidin-(E)-p-coumaroylgalactopyranoside (6). Compound 3 was found in tea for the first time. In general, anthocyanins have various bioactivities, including relieving eyestrain and antioxidative effects, so it is expected that drinking 'Sunrouge' tea brings in similar bioactivities.
    Journal of Agricultural and Food Chemistry 05/2011; 59(9):4779-82. · 3.11 Impact Factor
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    ABSTRACT: Apple procyanidins (AP), one of the polyphenol-rich compounds, showed an endothelial-dependent vasorelaxation in rat aorta, but the mechanisms of beneficial effects are still unclear. The present study was designed to clarify the potential role of AP in rat aorta endothelial cells (RAECs). The treatment of RAECs with AP (1-10 μg/ml) resulted in a dose-dependent hyperpolarization with a maximum effect at 10 μg/ml, and for this reason, AP (10 μg/ml) was used in all the following experiments. AP-induced hyperpolarization was significantly inhibited by pretreatment of nonspecific K(+) inhibitor, tetraethyl ammonium chloride or specific K(+) channel inhibitors, iberiotoxin, glibenclamide, 4-aminopyridine and BaCl(2), as well as by high KCl or Ca(2+)-free solution. AP-induced hyperpolarization was also proved using 64-channel multielectrode dish system that can monitor a direct and real-time change of membrane potential. Furthermore, AP treatment caused a significant increase of nitric oxide (NO) production and cyclic guanosine monophosphate levels via endothelial NO synthase messenger RNA expression. The NO production was inhibited by N(G)-monoethyl-l-arginine or Ca(2+)-free solution and was completely abolished by their combination. Also, AP inhibited endothelial proliferation, while the effect was significantly abolished by N(G)-monoethyl-l-arginine or tetraethyl ammonium chloride. These findings suggest that AP induces both hyperpolarization of RAECs via multiple activation of K(+) channels and activation of NO/cyclic guanosine monophosphate pathway via increasing NO production or is responsible for antiangiogenic effect. Diminishment of hyperpolarization as well as NO production of AP in Ca(2+)-free solution implicated that AP would play a crucial role in promoting Ca(2+) influx into endothelial cells so as to promote both actions.
    The Journal of nutritional biochemistry 05/2011; 23(3):278-86. · 4.29 Impact Factor
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    ABSTRACT: Porphyromonas gingivalis (Pg) is thought to be involved in the progression of occlusive arterial lesions, whereas vascular smooth muscle cell (SMC) proliferation is considered to be involved in occlusive arterial disease. We previously showed that bacteremia caused by Pg infection induced proliferation of mouse aortic SMCs. Furthermore, human SMCs stimulated with human plasma incubated with Pg showed a marked transformation from the contractile to proliferative phenotype. In the present study, we examine the involvement of Pg gingipains and fimbriae in induction of the SMC transformation and proliferation, and effective inhibitors. Pg strains including gingipain- and fimbria-null mutants were incubated in human plasma, after which the bacteria were removed and the supernatants were added to cultured SMCs. To evaluate the effects of inhibitors, Pg organisms were incubated in plasma in the presence of apple polyphenol (AP), epigallocatechin gallate, KYT-1 (Arg-gingipain inhibitor), and KYT-36 (Lys-gingipain inhibitor). Plasma supernatants from wild-type and fimbria-mutant cultures markedly stimulated cellular proliferation, whereas those containing gingipain-null mutants showed negligible effects. SMC proliferation was also induced by plasma treated with trypsin. Furthermore, plasma supernatants cultured in the presence of KYT-1/KYT-36 and AP showed significant inhibitory effects on SMC proliferation, whereas cultures with epigallocatechin gallate did not. Our results suggest that Pg gingipains are involved in the induction of SMC transformation and proliferation, whereas this was inhibited by AP.
    Journal of Periodontology 03/2011; 82(11):1616-22. · 2.40 Impact Factor
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    ABSTRACT: Caloric restriction (CR) is well known to expand lifespan in a variety of species and to retard many age-related diseases. The effects of relatively mild CR on the proteome profile in relation to lifespan have not yet been reported, despite the more extensive studies of the stricter CR conditions. Thus, the present study was conducted to elucidate the protein profiles in rat livers after mild CR for a relatively short time. Young growing rats were fed CR diets (10% and 30% CR) for 1month. We performed the differential proteomic analysis of the rat livers using two-dimensional electrophoresis combined with MALDI-TOF mass spectrometry. The most remarkable protein among the differentially expressed proteins was found to be prohibitin, the abundance of which was increased by 30% CR. Prohibitin is a ubiquitously expressed protein shown to suppress cell proliferation and to be related to longevity. The increase in prohibitin was observed both in 10% and 30% CR by Western blot analysis. Furthermore, induction of AMP-activated kinase (AMPK) protein, related to the actions of prohibitin in promoting longevity, was observed. The increased prohibitin level in response to subtle CR suggests that this increase may be one of the early events leading to the expansion of lifespan in response to CR.
    Biochemical and Biophysical Research Communications 02/2011; 405(3):462-7. · 2.28 Impact Factor
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    ABSTRACT: Procyanidins (PCs) are major components of the apple polyphenols (APs). We previously reported that treatment with PC extended the mean lifespan of Caenorhabditis elegans (Sunagawa et al., 2011). In order to estimate the neuroprotective effects of PC, we investigated the antiaggregative activity of PC on amyloid β-protein (Aβ) aggregation, which is a pathological hallmark of Alzheimer's disease. We herein report that PC significantly suppressed Aβ42 aggregation and dissociated Aβ42 aggregates in a dose-dependent manner, indicating that PC is a potent suppressor of Aβ aggregation. Furthermore, PC significantly inhibited Aβ42 neurotoxicity and stimulated proliferation in PC-12 cells. These results suggested that the PC and AP acted as neuroprotective factors against toxic Aβ aggregates.
    Biochemistry research international. 01/2011; 2011:784698.

Publication Stats

978 Citations
166.70 Total Impact Points

Institutions

  • 2010–2013
    • Japan Food Research Laboratories
      Ōsaka, Ōsaka, Japan
  • 2006–2011
    • Osaka City University
      Ōsaka, Ōsaka, Japan
  • 2009
    • Kyushu University
      • Faculty of Agriculture
      Fukuoka-shi, Fukuoka-ken, Japan
  • 2005
    • Fujitsu Ltd.
      Kawasaki Si, Kanagawa, Japan
  • 2002
    • Tokyo University of Pharmacy and Life Science
      • School of Pharmacy
      Tokyo, Tokyo-to, Japan