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PubMed2006

Kinetic study of the thermal stability of tea catechins in aqueous systems using a microwave reactor.

Tea catechins may undergo complex reactions such as oxidation, polymerization, and epimerization during thermal processing. The thermal stability of tea catechins in an aqueous system, including degradation and epimerization reactions, was investigated using a microwave reactor. Reactions were controlled at high temperatures ranging from 100 to 165 degrees C with various durations up to 120 min. Three sources of tea catechins containing different levels of (-)-epigallocatechin gallate (EGCG), (-)-epicatechin gallate (ECG), and their epimers were studied. Kinetic models for the degradation/epimerization of tea catechins were developed and validated by the reactions at 145 degrees C. It was shown that the epimerization and degradation of tea catechins followed first-order reactions and the rate constants of reaction kinetics followed the Arrhenius equation. Values of the activation energy (E(a)) for the epimerization of EGCG from epi- to nonepi-structures, the epimerization of GCG from nonepi- to epi-structures, and the total degradation of EGCG and its epimer GCG were 117.6, 84.2, and 42.8 kJ/mol, respectively. For ECG and CG, the E(a) values were 119.3, 96.2, and 41.6 kJ/mol, respectively. The mathematical models may provide a useful prediction for the loss of tea catechins during any thermal processing.

Catechin↗
PubMed2006

New constituents related to 3-methyl-2,4-nonanedione identified in green tea.

The volatile constituents of two exquisite green tea varieties, Kiyosawa tea from Japan and Long Jing tea from China, were investigated in order to identify new compounds responsible for the characteristic flavor of a green tea brew. The extracts were prepared by solid-phase extraction using Oasis-HLB-cartridges. Besides the common compounds of green tea chemistry, the already described compounds 3-methyl-2,4-nonanedione (1) and 3-hydroxy-3-methyl-2,4-nonanedione (2), products of degradation of furan fatty acids, as well as three new compounds related to compound 1 were identified. These were 1-methyl-2-oxopropyl hexanoate (3), 1-methyl-2-oxoheptyl acetate (4) and 2-butyl-4,5-dimethyl-3(2H)-furanone (5). Their syntheses and spectroscopic data are reported. Compound 2 increases the sweet, creamy aroma and the characteristic mouthfeel of a green tea flavor, compounds 3 and 4 contribute to its floral, juicy notes and compound 5 exhibits an interesting sweet, buttery flavor.

Alkanes↗
PubMed2002

Accumulation of epigallocatechin quinone dimers during tea fermentation and formation of theasinensins.

Production and accumulation of catechin dimer quinones during tea fermentation were chemically confirmed for the first time by trapping as phenazine derivatives. Direct treatment of the fermented tea leaves with o-phenylenediamine yielded five phenazine derivatives (8-12) of o-quinones of an epigallocatechin dimer and its galloyl esters (13-16), in which two flavan units were linked at the B-rings through a C-C bond. Atrop isomerism of the biphenyl bonds was shown to be the R configuration, suggesting that the o-quinone dimers were generated by stereoselective coupling of monomeric quinones. The total concentration of the phenazine derivatives in the o-phenylenediamine-treated tea leaves was higher than that of theaflavins. In contrast, phenazine derivatives of monomeric quinones of epigallocatechin were not isolated. When the fermented tea leaves were heated, the quinone dimers were converted to theasinensins, which are constituents of black tea, suggesting that theasinensins are generated by reduction of the quinone dimers during the heating and drying steps in black tea manufacturing.

Camellia sinensis↗
PubMed2004

Hypoxia-inducible factor-1 activation by (-)-epicatechin gallate: potential adverse effects of cancer chemoprevention with high-dose green tea extracts.

Hypoxia-inducible factor-1 (HIF-1) is a transcription factor that induces oxygen-regulated genes in response to reduced oxygen conditions (hypoxia). Expression of the oxygen-regulated HIF-1alpha subunit correlates positively with advanced disease stages and poor prognosis in cancer patients. Green tea catechins are believed to be responsible for the cancer chemopreventive activities of green tea. We found that (-)-epicatechin-3-gallate (ECG, 1), one of the major green tea catechins, strongly activates HIF-1 in T47D human breast carcinoma cells. Among the green tea catechins tested, 1 demonstrated the strongest HIF-1-inducing activity, while (-)-epigallocatechin-3-gallate (EGCG, 2) was significantly less active. However, 2 is relatively unstable in the in vitro system studied. Compound 1 also increases the expression of HIF-1 target genes including GLUT-1, VEGF, and CDKN1A. In T47D cells, 1 induces nuclear HIF-1alpha protein without affecting HIF-1alpha mRNA. Both the induction of HIF-1alpha protein and activation of HIF-1 by 1 can be blocked by iron and ascorbate, indicating that 1 may activate HIF-1 through the chelation of iron. These results suggest that intended cancer chemoprevention with high-dose green tea extracts may be compromised, by the ability of tea catechins to promote tumor cell survival pathways associated with HIF-1 activation.

Catechin↗
PubMed2001

Analysis of urinary metabolites of tea catechins by liquid chromatography/electrospray ionization mass spectrometry.

Tea has been proposed to have beneficial health effects which have been attributed to the polyphenolic compounds known as catechins. The bioavailability and biotransformation of these compounds, however, are not clearly understood. In this study, we used liquid chromatography/electrospray ionization-mass spectrometry (LC/ESI-MS) to determine urinary glucuronidated and sulfated tea catechins and their metabolites (including methylated and ring-fission metabolites) based on the detection of deprotonated molecular ions and aglycone fragment ions. The compound resolution was achieved both chromatographically and mass spectroscopically. After green tea administration, the major conjugates appeared in human, mouse, and rat urine samples were identified as monoglucuronides and monosulfates of (-)-epigallocatechin (EGC) and (-)-epicatechin. We also found O-methyl-EGC-O-glucuronides and -O-sulfates and O-methyl-epicatechin-O-sulfates in human urine. (-)-5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone (M4) and (-)-5-(3',4'-dihydroxyphenyl)-gamma-valerolactone (M6), the ring-fission metabolites of EGC and (-)-epicatechin, respectively, were also predominantly in monoglucuronide and monosulfate forms in the urine. In comparison to rats, the urinary metabolite profiles of tea catechins in mice resemble more closely to those in humans. This is the first report describing direct simultaneous analysis of multiple tea catechin conjugates in urine samples. This method will allow more thorough investigations of the biotransformation of tea polyphenols.

Adult↗
PubMed2000

Structural identification of two metabolites of catechins and their kinetics in human urine and blood after tea ingestion.

Tea is a popular beverage consumed worldwide. The metabolic fate of its major constituents, catechins, however, is not well-known. In this study, two catechin metabolites were detected in the urine and plasma of human volunteers after ingestion of green tea. These metabolites were identified by LC/ESI-MS and NMR as (-)-5-(3',4', 5'-trihydroxyphenyl)-gamma-valerolactone (M4) and (-)-5-(3', 4'-dihydroxyphenyl)-gamma-valerolactone (M6). The renal excretion of M4 and M6 had a 3 h lag time and peaked 7.5-13.5 h after ingestion of a single dose of green tea, while (-)-epigallocatechin (EGC) and (-)-epicatechin peaked at 2 h. M4 and M6 were two major tea metabolites with urinary cumulative excretions as high as 8-25 times the levels of EGC and (-)-epicatechin in some of our subjects, and accounted for 6-39% of the amounts of ingested EGC and (-)-epicatechin. Both the metabolites appeared to be produced by intestinal microorganisms, with EGC and (-)-epicatechin as the precursors of M4 and M6, respectively. Repeated ingestion of green tea produced a slight accumulative effect of the metabolites. They were also detected in the plasma, exhibiting kinetics similar to those of the urinary metabolites, and in the feces. Study on these metabolites may help us further understand the cancer chemopreventive actions and other beneficial effects of tea.

Adult↗
PubMed2002

Improvement of periodontal status by green tea catechin using a local delivery system: a clinical pilot study.

The purpose of this study was to determine the usefulness of green tea catechin for the improvement of periodontal disease. The minimum inhibitory concentration (MIC) and bactericidal activity of green tea catechin against black-pigmented, Gram-negative anaerobic rods (BPR) were measured. Hydroxypropylcellulose strips containing green tea catechin as a slow release local delivery system were applied in pockets in patients once a week for 8 weeks. The clinical, enzymatic and microbiological effects of the catechin were determined. Green tea catechin showed a bactericidal effect against Porphyromonas gingivalis and Prevotella spp. in vitro with an MIC of 1.0 mg/ml. In the in vivo experiment, the pocket depth (PD) and the proportion of BPR were markedly decreased in the catechin group with mechanical treatment at week 8 compared with the baseline with significant difference. In contrast, PD and BPR were similar to the baseline and the value at the end of the experimental period in the placebo sites of scaled groups. The peptidase activities in the gingival fluid were maintained at lower levels during the experimental period in the test sites, while it reached 70% of that at baseline in the placebo sites. No morbidity was observed in the placebo and catechin groups without mechanical treatment. Green tea catechin showed a bactericidal effect against BPR and the combined use of mechanical treatment and the application of green tea catechin using a slow release local delivery system was effective in improving periodontal status.

Administration, Topical↗
PubMed2004

Reproducibility and validity of coffee and tea consumption in Italy.

OBJECTIVE: The reproducibility and validity of coffee, decaffeinated coffee and tea intake has not been adequately studied, particularly in Italy, where coffee drinking is peculiar in terms of type and amount of coffee consumed. DESIGN: We compared coffee and tea consumption, measured by two interviewer-administered food frequency questionnaires (FFQ), with average intake derived from two 7-day dietary (DD) records (the reference method) on 395 volunteers. The Pearson correlation coefficients (r) were used to assess both reproducibility and validity of information on coffee intake. RESULTS: A satisfactory level of reproducibility and validity of the pattern consumption was observed for coffee, decaffeinated coffee and tea. The reproducibility for both sex combined showed r of 0.74-0.78 for coffee, 0.57-0.65 for decaffeinated coffee and 0.61-0.67 for tea. The validity was about 0.70 for coffee, around 0.58 for decaffeinated coffee and 0.56-0.60 for tea intake. CONCLUSIONS: The FFQ is a satisfactorily reliable and valid instrument for collecting information on coffee, decaffeinated coffee and tea intake.

Adult↗
PubMed2002

Beneficial effects of tea catechins on diet-induced obesity: stimulation of lipid catabolism in the liver.

OBJECTIVE: Obesity has increased at an alarming rate in recent years and is now a worldwide health problem. We investigated the effects of long-term feeding with tea catechins, which are naturally occurring polyphenolic compounds widely consumed in Asian countries, on the development of obesity in C57BL/6J mice. DESIGN: We measured body weight, adipose tissue mass and liver fat content in mice fed diets containing either low-fat (5% triglyceride (TG)), high-fat (30% TG), or high-fat supplemented with 0.1-0.5% (w/w) tea catechins for 11 months. The beta-oxidation activities and related mRNA levels were measured after 1 month of feeding. RESULTS: Supplementation with tea catechins resulted in a significant reduction of high-fat diet-induced body weight gain, visceral and liver fat accumulation, and the development of hyperinsulinemia and hyperleptinemia. Feeding with tea catechins for 1 month significantly increased acyl-CoA oxidase and medium chain acyl-CoA dehydrogenase mRNA expression as well as beta-oxidation activity in the liver. CONCLUSION: The stimulation of hepatic lipid metabolism might be a factor responsible for the anti-obesity effects of tea catechins. The present results suggest that long-term consumption of tea catechins is beneficial for the suppression of diet-induced obesity, and it may reduce the risk of associated diseases including diabetes and coronary heart disease.

Adipose Tissue↗
PubMed2006

Reduction of diet-induced obesity by a combination of tea-catechin intake and regular swimming.

OBJECTIVE: Obesity is a metabolic disorder resulting from imbalance between metabolizable energy intake and energy expenditure. It is known to be a strong risk factor for lifestyle-related diseases. Here, we investigated the effects of long-term intake of tea catechins (Cat) in combination with regular exercise (Ex) on the development of obesity in C57BL/6 mice. DESIGN: We compared body weight, adipose tissue mass, plasma parameters and beta-oxidation activity in mice fed a low-fat diet (5% triglyceride (TG); LF), a high-fat diet (30% TG; HF), a HF diet supplemented with 0.5% (w/w) tea Cat, a HF diet in addition to swimming Ex or a HF diet plus 0.5% tea Cat in addition to swimming Ex (Cat+Ex) for 15 weeks. Oxygen consumption and respiratory quotients were measured using indirect calorimetry. RESULTS: Tea-Cat intake in combination with swimming Ex suppressed HF diet-induced body-weight gain by 18 and 22%, respectively, compared to Ex and tea-Cat intake on their own. Visceral fat accumulation and the development of hyperinsulinemia and hyperleptinemia were also reduced in the HF+Cat+Ex group. Muscular beta-oxidation activity in this group was 69 and 52% higher, respectively, than that in the HF and HF+Cat groups. Lipid oxidation, determined using indirect calorimetry, was higher in the HF+Cat+Ex group, suggesting increased lipid utilization at the individual level. CONCLUSION: These results indicate that intake of tea Cat, together with regular Ex helps to reduce diet-induced obesity. This effect might be attributed, at least in part, to the activation of whole-body energy metabolism.

Adipose Tissue↗
PubMed1973

Metabolism of methylamine in the tea plant (Thea sinensis L.).

1. The metabolism of methylamine in excised shoot tips of tea was studied with micromolar amounts of [(14)C]methylamine. Of the [(14)C]methylamine supplied 57% was utilized by tea shoots during the 10h experimental period. 2. The main products of [(14)C]methylamine metabolism in tea shoots were serine, gamma-glutamylmethylamide, theobromine, caffeine and CO(2). There was also incorporation of the label into glutamate, aspartate, RNA purine nucleotides and S-adenosylmethionine. 3. The formation of methylamine from gamma-glutamylmethylamide was confirmed by feeding tea shoots with gamma-glutamyl[(14)C]methylamide. The products of gamma-glutamyl[(14)C]methylamide metabolism in tea plants were serine, theobromine, caffeine, glutamate and aspartate. 4. The results indicate that the oxidation of methylamine to formaldehyde is the first step of methylamine utilization. Labelled formaldehyde released by the metabolism of methylamine leads to the incorporation of the label into metabolites on the C(1) pathways of this compound. It is also suggested that formaldehyde is further oxidized via formate to CO(2). 5. The role of gamma-glutamylmethylamide in methylamine metabolism in tea plants is discussed. 6. Results support the view that theobromine is the immediate precursor of caffeine.

Amino Acids↗
PubMed2000

Anti-Helicobacter pylori activity of Chinese tea: in vitro study.

BACKGROUND: Chinese tea has an antibacterial activity against a wide range of bacteria. However, its activity against Helicobacter pylori has not been reported. METHOD: In this study the anti-Helicobacter pylori effects of a Chinese tea (Lung Chen tea), and two tea catechins, epigallocatechin gallate and epicatechin and their minimum inhibitory concentrations (MICs) were examined. The effect of Lung Chen on metronidazole resistance was also studied using the E-test. RESULTS: Lung Chen, epigallocatechin gallate and epicatechin all inhibited the growth of H. pylori. The MIC90 for Lung Chen was 0. 25-0.5% (w/w) and that of epigallocatechin gallate and epicatechin were 50-100 and 800-1600 microg/mL, respectively. Epigallocatechin gallate is probably the active ingredient responsible for most of the anti-H. pylori activity of Chinese tea. Lung Chen did not reverse metronidazole resistance. CONCLUSIONS: Chinese tea has anti-H. pylori activity in a daily consumed concentration, and epigallocatechin gallate is probably the active ingredient responsible for the action.

Anti-Bacterial Agents↗
PubMed2003

Preventive effects of urinary bladder tumors induced by N-butyl-N-(4-hydroxybutyl)-nitrosamine in rat by green tea leaves.

BACKGROUND: Recently, the anticarcinogenic effects of green tea have been studied in sites other than the urinary tract. Although the incidence of bladder cancer has increased, responses to therapy have been limited. The present work examined the preventive effects of green tea against bladder tumors induced in rats by the carcinogen, N-butyl-N-(4-hydroxybutyl)-nitrosamine(BBN). METHODS: From week 5 to week 9, all the groups were exposed to 0.05% BBN in the drinking water for 5 weeks. Rats were divided into four groups. Group 1 was fed a CE-2 diet and tap water for the entire experimental period and served as the control group. Group 2 was fed the green tea leaves after carcinogen exposure. Groups 3 and 4 received green tea leaves before carcinogen exposure. All rats were killed and examined at 44 weeks. RESULTS: Green tea leaves prevented the growth of BBN-induced urinary bladder tumors when given before the carcinogen. CONCLUSION: Green tea may inhibit tumor initiation in the bladder.

Animals↗
PubMed2005

Coffee and tea consumption are associated with a lower incidence of chronic liver disease in the United States.

BACKGROUND & AIMS: Coffee drinking has been suggested to protect against liver injury, but it is uncertain whether this is of clinical significance. We examined the relationship of coffee and tea consumption with the incidence of hospitalization or death from chronic liver disease (CLD). METHODS: Participants in the population-based, first National Health and Nutrition Examination Survey, 1971-1975, were asked about coffee and tea consumption, which was categorized as <1 cup (mean, 0.2 cups), 1 to 2 cups, and >2 cups per day (mean, 4.0 cups). A second analysis included persons who, in 1982-1984, were asked more detailed questions on coffee and tea drinking. Participants were followed through 1992-1993 for a hospital or death certificate diagnosis of CLD or cirrhosis (ICD-9-CM 571). Hazard rate ratios for CLD according to coffee and tea intake were calculated using Cox proportional hazards analysis. RESULTS: Among 9849 persons followed for a median of 19.0 years (range, 0.02-22.1), the cumulative incidence of CLD was 1.4%. In multivariate analysis, participants who drank >2 cups per day had less than half the rate of CLD as those who drank <1 cup per day (hazard ratio, 0.43, 95% confidence interval: 0.24-0.78). Protection by coffee and tea was limited to persons at higher risk for liver diseases from heavier alcohol intake, overweight, diabetes, or high iron saturation. Among 9650 participants who provided detailed drink information in 1982-1984, intake of regular ground coffee and of caffeine was associated with lower incidence of CLD. CONCLUSIONS: Coffee and tea drinking decreases the risk of clinically significant CLD.

Adult↗
PubMed2001

Green tea and the risk of gastric cancer in Japan.

BACKGROUND: Although laboratory experiments and case-control studies have suggested that the consumption of green tea provides protection against gastric cancer, few prospective studies have been performed. METHODS: In January 1984, a total of 26,311 residents in three municipalities of Miyagi Prefecture, in northern Japan (11,902 men and 14,409 women 40 years of age or older), completed a self-administered questionnaire that included questions about the frequency of consumption of green tea. During 199,748 person-years of follow-up, through December 1992, we identified 419 cases of gastric cancer (in 296 men and 123 women). We used Cox regression to estimate the relative risk of gastric cancer according to the consumption of green tea. RESULTS: Green-tea consumption was not associated with the risk of gastric cancer. After adjustment for sex, age, presence or absence of a history of peptic ulcer smoking status, alcohol consumption, other dietary elements, and type of health insurance, the relative risks associated with drinking one or two, three or four, and five or more cups of green tea per day, as compared with less than one cup per day, were 1.1 (95 percent confidence interval, 0.8 to 1.6), 1.0 (95 percent confidence interval, 0.7 to 1.4), and 1.2 (95 percent confidence interval, 0.9 to 1.6), respectively (P for trend=0.13). The results were similar after the 117 cases of gastric cancer that were diagnosed in the first three years of follow-up had been excluded, with respective relative risks of 1.2 (95 percent confidence interval, 0.8 to 1.8) 1.0 (95 percent confidence interval, 0.7 to 1.5), and 1.4 (95 percent confidence interval, 1.0 to 1.9) (P for trend=0.07). CONCLUSIONS: In a population-based, prospective cohort study in Japan, we found no association between green-tea consumption and the risk of gastric cancer.

Adult↗
PubMed2004

Activation of endothelial nitric-oxide synthase by the p38 MAPK in response to black tea polyphenols.

Black tea improves endothelial function in patients with coronary artery disease. We sought to determine the responsible components of black tea and elucidate the underlying cell signaling mechanisms. We exposed porcine aortic endothelial cells to components of black tea and found that the polyphenol fraction acutely enhanced nitric oxide bioactivity. This effect involved endothelial nitric-oxide synthase (eNOS) phosphorylation at Ser-1177 and dephosphorylation at Thr-495, consistent with increased eNOS activity. These effects were calcium-dependent, as removal of extracellular calcium prevented eNOS phosphorylation at Ser-1177, whereas inhibition of intracellular calcium mobilization with TMB-8 blunted Thr-495 dephosphorylation. Black tea polyphenol-induced eNOS activation appeared dependent upon the phosphatidylinositol 3-kinase-Akt pathway, as it was significantly inhibited by LY294002 and a dominant negative Akt, respectively. Pharmacological inhibition of p38 mitogen-activated protein kinase (p38 MAPK) with either SB202190 or SB203580 as well as overexpression of a dominant negative p38 MAPKalpha attenuated both eNOS activation and phosphorylation changes in response to black tea polyphenols. Inhibition of p38 MAPKalpha also blunted Akt activation in response to black tea polyphenols, suggesting that p38alpha MAPK is upstream of Akt in this pathway. Finally, a constitutively active mutant of MKK6bE, an upstream kinase for p38 MAPK, enhanced both the basal and stimulated activity of Akt, leading to increased eNOS activity. Taken together, these data identify the p38 MAPK as an upstream component of Akt-mediated eNOS activation.

Adenoviridae↗
PubMed2001

Dominant fungi in the rhizosphere of established tea bushes and their interaction with the dominant bacteria under in situ conditions.

Species of Penicillium and Trichoderma were found to dominate the rhizosphere of established tea bushes in a detailed study conducted from various tea growing locations in India. Penicillium erythromellis, P. janthinellum, P. raistrickii, Trichoderma pseudokoningii and T. koningii were found to be closely associated with tea roots. While seasonal fluctuation was observed in the case of Penicillium spp., the population of Trichoderma spp. showed less variation during the year. Both species were sensitive to low temperatures. In general, fungi associated with the tea rhizosphere were found to prefer a mesophillic temperature range (15 degrees C to 35 degrees C). The dominant species of Penicillium and Trichoderma also exhibited tolerance to lower temperatures, i.e., 5 to 10 degrees C on agar plates. Most fungi were able to grow in a wide range of pH (4 to 12). Lowering of soil pH in the rhizosphere of tea bushes was positively correlated with the age of the bush and may have affected the development of a specific microbial community in the rhizosphere. The populations of Penicillium and Trichoderma species were inversely correlated with the populations of two most dominant rhizosphere bacteria, Bacillus subtilis and B. mycoides. Both Bacillus species have been shown to have antagonistic activity against these two fungi under in vitro conditions. The present study demonstrates the existence of a similar antagonism under in situ conditions in the rhizosphere of established tea bushes.

Antibiosis↗
PubMed2006

High tea consumption diminishes salivary 17beta-estradiol concentration in Polish women.

We hypothesized that among reproductive-age women consuming large quantities of tea, the production of estradiol would be suppressed. It has been shown that catechins and theaflavines, the major constituents of tea, inhibit aromatase, an enzyme which catalyses the conversion of androgens to oestrogens. Our study included Polish women living in urban (n 61) and rural (n 48) areas. Women collected daily saliva samples for one complete menstrual cycle and filled out dietary questionnaires. Saliva samples were analysed by RIA for concentration of 17beta-estradiol (E2). Women with high (above the median) average daily consumption of black tea had reduced levels of salivary E2 in comparison with women who drank less black tea (below the median). This effect was observed within the whole study group, as well as separately within urban (P=0.0006) and rural (P=0.013) groups. High intake of the sum of subclasses of tea catechins and epigallocatechin gallate, assessed using the United States Department of Agriculture database (http://www.nal.usda.gov), was also associated with lower concentrations of E2 within all women (P=0.01 and P=0.0001, respectively) and within the urban group (P=0.0001 and P=0.004, respectively). Similar relationships were observed between the sum of subclasses of theaflavines and thearubigines and E2 levels for the whole group (P=0.002) and for urban women (P=0.02). Women with high consumption of tea had lower levels of E2 concentration throughout the entire menstrual cycle. These results may have implications for reducing hormone-related cancer risk by a relatively easy dietary intervention.

Adult↗