Molecular definition of black tea taste by means of quantitative studies, taste reconstitution, and omission experiments

Recently, bioresponse-guided fractionation of black tea infusions indicated that neither the high molecular weight thearubigens nor the theaflavins, but a series of 14 flavon-3-ol glycopyranosides besides some catechins, might be important contributors to black tea taste. To further bridge the gap between pure structural chemistry and human taste perception, in the present investigation 51 putative taste compounds have been quantified in a black tea infusion, and their dose-over-threshold (Dot) factors have been calculated on the basis of a dose/threshold relationship. To confirm these quantitative results, an aqueous taste model was prepared by blending aqueous solutions of 15 amino acids, 14 flavonol-glycosides, 8 flavan-3-ols, 5 theaflavins, 5 organic acids, 3 sugars, and caffeine in their "natural" concentrations. Sensory analyses revealed that the taste profile of this artificial cocktail did not differ significantly from the taste profile of the authentic tea infusion. To further narrow the number of key taste compounds, finally, taste omission experiments have been performed, on the basis of which a reduced recombinate was prepared containing the bitter-tasting caffeine, nine velvety astringent flavonol-3-glycosides, and the puckering astringent catechin as well as the astringent and bitter epigallocatechin-3-gallate. The taste profile of this reduced recombinate differed not significantly from that of the complete taste recombinate, thus confirming these 12 compounds as the key taste compounds of the tea infusion. Additional sensory studies demonstrated for the first time that the flavanol-3-glycosides not only impart a velvety astringent taste sensation to the oral cavity but also contribute to the bitter taste of tea infusions by amplifying the bitterness of caffeine.     

Identification and comparison of phenolic compounds in the preparation of oolong tea manufactured by semifermentation and drying processes

Oolong tea manufactured via a semifermentation process possesses a taste and color somewhere between green and black teas. Alteration of constituents, particularly phenolic compounds, in the infusion of oolong tea resulting from its manufacture, was analyzed by high-performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry. The identified constituents contained 2 alkaloids, 11 flavan-3-ols, 8 organic acids and esters, 11 proanthocyanidin dimers, 3 theaflavins, and 22 flavonoid glycosides, including 6 novel acylated flavonol glycosides. The tentative structures of these 6 novel compounds were depicted according to their mass fragmentation patterns in MS(n) (n = 1-4). In comparison with caffeine as an internal standard, relative contents of the constituents in the infusions of fresh tea shoot and different oolong tea preparations were examined. Approximately, 30% catechins and 20% proanthocyanidins were oxidized during the manufacture of oolong tea from fresh tea shoots, and 20% of total flavonoids were decomposed in a follow-up drying process. Gallocatechin-3-O-gallate and theaflavins putatively produced in the semifermentation process of oolong tea were not detected in fresh tea shoots, and the majority of theaflavins were presumably transformed into thearubigins after drying.     

New phenolic components and chromatographic profiles of green and fermented teas

A standardized profiling method based on liquid chromatography with diode array and electrospray ionization mass spectrometric detection (LC-DAD-ESI/MS) was applied to establish the phenolic profiles of 41 green teas and 25 fermented teas. More than 96 phenolic compounds were identified that allowed the teas to be organized into five groups. Epigallocatechin gallate (EGCG) was the major phenolic component of green tea made from mature leaves (group 2), while green tea made from the younger buds and leaves (group 1) contained lower flavonoid concentrations. Partially fermented teas (group 3) contained one-half the EGCG content of the green tea. Fully fermented black teas (group 4) had a trace of EGCG, but contained theaflavins. Highly overfermented black tea (group 5) contained only trace amounts of flavonol glycosides and theaflavins. Over 30 phenolics are new for tea, and this is the first phenolic profile to simultaneously detect C- and O-glycosylated flavonoids, catechins, proanthocyanidins, phenolic acid derivatives, and purine alkaloids.     

Orosensory-directed identification of astringent mouthfeel and bitter-tasting compounds in red wine

Application of sequential solvent extraction, followed by HPLC combined with the taste dilution analysis, enabled the localization of the most intense velvety astringent, drying, and puckering astringent, as well as bitter-tasting, compounds in red wine, respectively. Isolation of the taste components involving gel adsorption chromatography, ultrafiltration, and synthesis revealed the identification of 26 sensory-active nonvolatiles, among which several hydroxybenzoic acids, hydroxycinnamic acids, flavon-3-ol glycosides, and dihydroflavon-3-ol rhamnosides as well as a structurally undefined polymeric fraction (>5 kDa) were identified as the key astringent components. In contradiction to literature suggestions, flavan-3-ols were found to be not of major importance for astringency and bitter taste, respectively. Surprisingly, a series of hydroxybenzoic acid ethyl esters and hydroxycinnamic acid ethyl esters were identified as bitter compounds in wine. Taste qualities and taste threshold concentrations of the individual wine components were determined by means of a three-alternative forced-choice test and the half-mouth test, respectively.     

Role of polyphenol oxidase and peroxidase in the generation of black tea theaflavins.

It has been reported earlier that when macerated tea leaf is fermented at lower pH, the resultant black tea contains increased levels of theaflavin, an important quality marker in black tea. In an attempt to investigate the biochemistry and chemistry underlying this observation, in vitro oxidation experiments using polyphenol oxidase (PPO) from fresh tea leaves, horseradish peroxidase (POD), and tea catechins, precursors for theaflavins, were carried out. In vitro oxidation experiments using crude tea PPO resulted in higher content of theaflavins at pH 4.5 in comparison with pH 5.5, the normal pH of the macerated tea leaf. When purified PPO was used in the in vitro system, surprisingly a reversal of this trend was observed, with more theaflavins being formed at the higher pH. A combination of pure tea PPO and POD led to an observation similar to that with the crude enzyme preparation, suggesting a possible role for POD in the formation or degradation of theaflavin. POD was observed to oxidize theaflavins in the presence of H(2)O(2), leading to the formation of thearubigin, another black tea pigment. This paper demonstrates that tea PPO, while oxidizing catechins, generates H(2)O(2). The amount of H(2)O(2) produced is greater at pH 5.5, the optimum pH for PPO activity, than at pH 4.5. Hence, an observed increase of theaflavins in black teas fermented at pH 4.5 appears to be due to lower turnover of formed theaflavins into thearubigins.     

Isolation, structure determination, and sensory activity of mouth-drying and astringent nitrogen-containing phytochemicals isolated from red currants (Ribes rubrum)

Application of chromatographic separation and taste dilution analyses recently revealed, besides a series of flavon-3-ol glycosides and (E)/(Z)-aconitic acid, four nitrogen-containing phytochemicals as the key astringent and mouth-drying compounds in red currants (Ribes rubrum). The isolation and structure determination of the astringent indoles 3-carboxymethyl-indole-1-N-beta-D-glucopyranoside (1) and 3-methylcarboxymethyl-indole-1-N-beta-D-glucopyranoside (2), as well as the astringent, noncyanogenic nitriles 2-(4-hydroxybenzoyloxymethyl)-4-beta-D-glucopyranosyloxy-2(E)-butenenitrile (3) and 2-(4-hydroxy-3-methoxybenzoyloxymethyl)-4-beta-D-glucopyranosyloxy-2(E)-butenenitrile (4) by means of 1D/2D NMR, LC-MS/MS, and UV-vis spectroscopy are reported. The structures of compounds 1 and 2 were confirmed by synthesis. Using the recently developed half-tongue test, human recognition thresholds for the astringent and mouth-drying nitrogen compounds were determined to be between 0.0003 and 5.9 micromol/L (water). In particular, the extraordinarily low threshold of 0.0003 micromol/L evaluated for the indole 1 represents the lowest recognition threshold of any astringent phytochemical reported to date.     

Application of microwave energy in the manufacture of enhanced-quality green tea

Green tea manufacture was standardized with respect to the inactivation of polyphenol oxidase (PPO), rolling, and drying for quality manufacture. Inactivation of PPO by parching, steaming, microwave heating, and oven heating was monitored in tea shoots. The inactivated shoots were rolled under regimens of high and low pressures and dried by microwave heating, oven heating, or sun-drying; total phenols and catechins were estimated. Parched and sun-dried teas contained the lowest levels of total phenols and catechins, and their infusions were dull in color with a slightly burnt odor. Microwave-inactivated and-dried teas showed the highest levels of total phenols and catechins, and their infusions were bright in color and sweet in taste with a subtle pleasant odor. In steam-inactivated and oven/microwave-dried teas, total phenol and catechin contents were intermediate between parched and sun-dried teas and microwave-inactivated and microwave-dried teas, and their infusions were bright with a umami taste.     

Structure-activity relationships of tea compounds against human cancer cells

The content of the biologically active amino acid theanine in 15 commercial black, green, specialty, and herbal tea leaves was determined as the 2,4-dinitrophenyltheanine derivative (DNP-theanine) by a validated HPLC method. To define relative anticarcinogenic potencies of tea compounds and teas, nine green tea catechins, three black tea theaflavins, and theanine as well as aqueous and 80% ethanol/water extracts of the same tea leaves were evaluated for their ability to induce cell death in human cancer and normal cells using a tetrazolium microculture (MTT) assay. Compared to untreated controls, most catechins, theaflavins, theanine, and all tea extracts reduced the numbers of the following human cancer cell lines: breast (MCF-7), colon (HT-29), hepatoma (liver) (HepG2), and prostate (PC-3) as well as normal human liver cells (Chang). The growth of normal human lung (HEL299) cells was not inhibited. The destruction of cancer cells was also observed visually by reverse phase microscopy. Statistical analysis of the data showed that (a) the anticarcinogenic effects of tea compounds and of tea leaf extracts varied widely and were concentration dependent over the ranges from 50 to 400 microg/mL of tea compound and from 50 to 400 microg/g of tea solids; (b) the different cancer cells varied in their susceptibilities to destruction; (c) 80% ethanol/water extracts with higher levels of flavonoids determined by HPLC were in most cases more active than the corresponding water extracts; and (d) flavonoid levels of the teas did not directly correlate with anticarcinogenic activities. The findings extend related observations on the anticarcinogenic potential of tea ingredients and suggest that consumers may benefit more by drinking both green and black teas.     

采用PLS-DA分析毛火方式对工夫红茶品质的影响

为探究不同毛火方式对工夫红茶品质的影响,明确新型电磁内热式滚筒-热风耦合干燥设备的毛火效果,该研究以一芽一二叶初展嫩度的"福鼎大白"品种为原料进行工夫红茶加工,设定电磁滚筒-热风耦合(Rotary pot-Hot air coupling First-Drying with electromagnetic heat,RHFD)、链板热风(Chain plate Hot air First-Drying,CHFD)、箱式热风(Box Hot air First-Drying,BHFD)、滚筒式滚炒(Rotary pot First-Drying,RFD)等4种毛火方式,比较所制茶样的茶多酚、儿茶素、茶色素、可溶性糖、咖啡碱、氨基酸等29个非挥发性指标,114个气相色谱-质谱技术(GasChromatography-Mass Spectrometry,GC-MS)检测的挥发性香气指标,10个外形和汤色色泽客观评价指标,同时进行了毛火方式的热效率、生产效率、生产成本等性能指标的分析比较,通过偏最小二乘判别统计(PartialLeastSquaresDiscriminationAnalysis,PLS-DA)分析毛火方式对优质工夫红茶品质的影响,并获得标志性差异化合物。结果表明:电磁内热式滚筒-热风耦合毛火处理下茶多酚和儿茶素总量显著最低(P<0.05),简单儿茶素含量较高,茶红素和可溶性糖含量、茶黄素综合指标TDE和茶色素综合指标10TFRB最高(P<0.05),毛火方式对茶黄素总量影响不显著(P>0.05);挥发性化合物总量以RHFD方式最高,RFD方式次之,CHFD方式最低;RHFD毛火方式芳香类、萜烯类等化合物含量最高。电磁内热式滚筒-热风耦合毛火升温快、温度分布均匀且稳定性好,热效率和生产效率高(分别为50.0%、220 kg/h),生产成本较低(仅0.32元/kg),预热时间仅14min;所制红茶在汤色透亮度、香气甜久度、滋味甜醇度等方面均得到提升,感官总分最高(P<0.05),达88.1。PLS-DA分析从挥发性和非挥发性角度均可将工夫红茶4种毛火方式显著区分,并分别获得了43种和18种差异化合物,结合差异性分析获得标志性差异化合物,2,4,6-三(1,1-二甲基乙基)-4-甲基环己-2,5-二烯-1-酮、香叶醇、3-辛酮、水杨酸甲酯、茶黄素、茶褐素、可溶性糖、表儿茶素等,可作为区分工夫红茶毛火方式,以及定向加工甜香、甜醇、高亮等优质工夫红茶的指标物质。该研究为红茶加工基础和品质提升提供技术参考和理论指导。     

Black tea polyphenols, theaflavins, prevent cellular DNA damage by inhibiting oxidative stress and suppressing cytochrome P450 1A1 in cell cultures.

Tea polyphenols have been demonstrated as chemopreventive agents in a number of experimental models. However, less is known about the mechanism of chemoprevention by black tea compared with that of green tea. Some beneficial properties of theaflavins, the black tea polyphenols, were investigated in the present study. Theaflavins showed inhibitory effects on H(2)O(2)- and tert-butyl hydroperoxide (tBuOOH)-induced cytotoxicity (evaluated by tetrazolium bromide reduction), cellular oxidative stress (detected by oxidation of 2', 7'-dichlorofluorescin), and DNA damage (measured by amount of 8-OHdG and comet assay) in rat normal liver epithelium cell RL-34 cell lines. In addition, theaflavins also exhibited suppression of cytochrome P450 1A1 induced by omeprazole in the human hepatoma HepG2 cell line. Furthermore, when HepG2 cells were pretreated with omeprazole to induce CYP1A1, then exposed to benzo[a]pyrene (B[a]P), DNA damage was observed using the comet assay. However, theaflavins could inhibit this DNA damage. These results indicated that theaflavins could prevent cellular DNA damage by inhibiting oxidative stress and suppressing cytochrome P450 1A1 in cell cultures.     

Preparative separation of polyphenols from tea by high-speed countercurrent chromatography

High-speed countercurrent chromatography (HSCCC) was applied to the separation of polyphenols from tea leaves (Camellia sinensis L.). The capability of HSCCC to isolate pure tea polyphenols from complex mixtures on a preparative scale was demonstrated for catechins, flavonol glycosides, proanthocyanidins, and strictinin from green and black tea. The purity and identity of isolated compounds was confirmed by (1)H NMR and HPLC-ESI-MS/MS. Gram quantities of polyphenols from tea can be isolated with the procedure described.     

Factors affecting the levels of tea polyphenols and caffeine in tea leaves

An isocratic HPLC procedure was developed for the simultaneous determination of caffeine and six catechins in tea samples. When 31 commercial teas extracted by boiling water or 75% ethanol were analyzed by HPLC, the levels of (-)-epigallocatechin 3-gallate (EGCG), and total catechins in teas were in the order green tea (old leaves) > green tea (young leaves) and oolong tea > black tea and pu-erh tea. Tea samples extracted by 75% ethanol could yield higher levels of EGCG and total catechins. The contents of caffeine and catechins also have been measured in fresh tea leaves from the Tea Experiment Station in Wen-Shan or Taitung; the old tea leaves contain less caffeine but more EGCG and total catechins than young ones. To compare caffeine and catechins in the same tea but manufactured by different fermentation processes, the level of caffeine in different manufactured teas was in the order black tea > oolong tea > green tea > fresh tea leaf, but the levels of EGCG and total catechins were in the order green tea > oolong tea > fresh tea leaf > black tea. In addition, six commercial tea extracts were used to test the biological functions including hydroxyl radical scavenging, nitric oxide suppressing, and apoptotic effects. The pu-erh tea extracts protected the plasmid DNA from damage by the Fenton reaction as well as the control at a concentration of 100 microg/mL. The nitric oxide suppressing effect of tea extracts was in the order pu-erh tea >/= black tea > green tea > oolong tea. The induction of apoptosis by tea extract has been demonstrated by DNA fragmentation ladder and flow cytometry. It appeared that the ability of tea extracts to induce HL-60 cells apoptosis was in the order green tea > oolong > black tea > pu-erh tea. All tea extracts extracted by 75% ethanol have stronger biological functions than those extracted by boiling water.     

Effect of milk and brewing method on black tea catechin bioaccessibility

The aim of this study was to investigate whether milk reduces the bioaccessibility of tea catechins, which would compromise tea beneficial effects ascribed to polyphenols. Adding milk to black tea has been shown to lead to polyphenol-protein complexes. So far, data on the intestinal stability of polyphenol-protein complexes are scarce. English black tea (0.93 ± 0.06 mol/L total catechins) and Indian black tea (1.83 ± 0.08 mol/L catechins) were prepared with skimmed or full-fat milk and subjected to simulated gastric, small intestinal, and brush border digestion. Adding milk (5.6-40%) to tea results in a decrease of total catechin (TCAT) recovery. However, the bioaccessibilities of TCAT of tea with milk versus tea controls were comparable (p > 0.05). The type of milk did not influence TCAT recovery during all digestive stages (p > 0.05). Polyphenol-protein complexes are degraded during digestion. It is very unlikely that consumption of tea with or without milk will result in differences in catechin plasma concentration.     

Determination of theaflavins including methylated theaflavins in black tea leaves by solid-phase extraction and HPLC analysis

A quantitative method for four theaflavins and two methylated theaflavin derivatives in black tea leaves was developed by solid-phase extraction and a high-performance liquid chromatographic method with photodiode array detection. The theaflavins in black tea leaves were extracted three times with 40 vol 50% aqueous ethanol (mg dry tea powder/mL) containing 2% ascorbic acid. The ethanol extracts were diluted 4-fold with distilled water. All diluted extracts were directly applied to the solid-phase C18 cartridge column without concentration. The fraction of theaflavins was obtained by 40% ethanol extraction after rinsing with water followed with 15% ethanol extraction. An aliquot of theaflavins after concentration was injected onto an ODS C18 reversed-phase column, and four theaflavins and two methylated theaflavins were sufficiently separated by a linear gradient system using distilled water and acetonitrile with 0.5% acetic acid. This analytical method is sensitive for the determination of a small amount of methylated theaflavins, since various interfering substances produced during the fermentation process were eliminated in advance by solid-phase extraction. Using this analytical method, we also demonstrated that methylated theaflavins were easily produced during the manufacture of black tea.     

Oolong tea theasinensins attenuate cyclooxygenase-2 expression in lipopolysaccharide (LPS)-activated mouse macrophages: structure-activity relationship and molecular mechanisms

Oolong tea theasinensins are a group of tea polyphenols different from green tea catechins and black tea theaflavins. The present study reports the inhibitory effects of oolong tea theasinensins on the expression of cyclooxygenase-2 (COX-2) and underlying molecular mechanisms in lipopolysaccharide (LPS)-activated murine macrophage RAW264 cells. The structure-activity data revealed that the galloyl moiety of theasinensins played an important role in the inhibitory actions. Theasinensin A, a more potent inhibitor, caused a dose-dependent inhibition of mRNA, protein, and promoter activity of COX-2. An electrophoretic mobility shift assay (EMSA) revealed that theasinensin A reduced the complex of NF-κB- and AP-1-DNA in the promoter of COX-2. Signaling analysis demonstrated that theasinensin A attenuated IκB-α degradation, nuclear p65 accumulation, and c-Jun phosphorylation. Furthermore, theasinensin A suppressed the phosphorylation of MAPKs, IκB kinase α/β (IKKα/β), and TGF-β activated kinase (TAK1). These data demonstrated that the down-regulation of TAK1-mediated MAPKs and NF-κB signaling pathways might be involved in the inhibition of COX-2 expression by theasinensin A. These findings provide the first molecular basis for the anti-inflammatory properties of oolong tea theasinensins.     

Total phenol, catechin, and caffeine contents of teas commonly consumed in the United kingdom.

Levels of total phenol, catechins, and caffeine in teas commonly consumed in the United Kingdom have been determined using reversed phase high-performance liquid chromatography. Tea bags or tea leaves were purchased from local supermarkets and extracted in boiling water for 5 min. The resulting data showed considerable variability in both total phenols [80.5-134.9 mg/g of dry matter (DM) in black teas and 87-106.2 mg/g of DM in green teas] and catechins (5.6-47.5, 51.5-84.3, and 8.5-13.9 mg/g of DM in black, green, and fruit teas, respectively); this was most probably a result of differing agronomic conditions, leaf age, and storage during and after transport, as well as the degree of fermentation. Caffeine contents of black teas (22-28 mg/g of DM) were significantly higher than in less fermented green teas (11-20 mg/g of DM). The relative concentration of the five major tea catechins ranked EGCG > ECG > EC > EGC > C. The estimated U.K. dietary intakes of total tea catechins, calculated on the basis of an average tea consumption of three cups of tea (200 mL cup, 1% tea leaves w/v), were 61.5, 92.7, and 405.5 mg/day from fruit teas, black teas, and green teas, respectively. The coefficients of variation were 19.4, 88.6, and 17.3%, respectively, indicating the wide variation in these intakes. The calculated caffeine intake ranged between 92 and 146 mg/day. In addition, many individuals will consume much larger quantities of tea, of various strengths (as determined by the brewing conditions employed). This broad spread of U.K. daily intakes further emphasizes the need for additional research to relate intake and effect in various population groups.     

基于数据融合策略的红茶发酵程度判别

发酵是红茶加工过程中关键的一道工序,对红茶的品质形成有着重要影响。该研究以大叶种英德红茶中的英红九号为研究对象,试验收集了204份不同发酵时间的红茶样品并使用便携式近红外光谱仪和工业相机获取红茶发酵中的信息,基于近红外光谱数据、图像数据和数据融合策略分别建立了红茶发酵程度判别模型。通过分析茶多酚和儿茶素类含量的变化,将红茶的发酵划分为3个阶段,即发酵不足、发酵适度和发酵过度。采用Savitzky-Golay光滑对原始光谱进行预处理,利用竞争自适应重加权采样（Competitive Adaptive Reweighted Sampling, CARS）、连续投影算法（Successive Projections Algorithm, SPA）和主成分分析（Principal Components Analysis, PCA）对近红外光谱变量进行降维处理;相应地,图像进行去阴影后提取了9个颜色特征变量,采用皮尔森（Pearson）相关分析和主成分分析进行特征变量提取。最后采用线性判别分析（Linear Discriminant Analysis, LDA）和支持向量机（Support Vector Machine, SVM）分别建立了基于近红外、图像和两者数据融合的分类模型。结果表明,在建模数据相同的条件下,非线性的支持向量机模型性能优于线性判别分析模型。单一传感器数据建模效果不佳,近红外光谱和图像判别模型的预测集最大准确率仅为83.82%和73.53%。低层次数据融合建模效果较单一传感器数据建模无明显提升,而中层次的数据融合建模效果比单一数据建模均有显著提高,其中SPA提取光谱变量结合Pearson提取图像变量建立的判别模型效果较佳,校正集和预测集准确率分别达到了97.06%和95.59%。研究表明,近红外光谱和视觉结合的中层次融合策略可以作为一种快速判别红茶发酵程度的方法,研究结果为红茶发酵程度构建等级模型与判别奠定了一定的理论基础,为红茶发酵的自动化检测提供了重要依据。     

Potent inhibitory effects of black tea theaflavins on off-odor formation from citral

The present study was conducted to investigate the ability of black tea theaflavins to inhibit the off-odor formation from citral under acidic aqueous conditions. Acidic buffer solutions (pH 3.0) containing citral (10 mg/L) and an inhibitor (0-5 mg/L) were stored at 40 degrees C for 2 weeks. The formation of possible off-odorants p-cresol and p-methylacetophenone in the citral solutions was monitored by high-performance liquid chromatography. A mixture of the theaflavins showed inhibitory effects on the formation of both p-cresol and p-methylacetophenone with 50% inhibitory concentrations (IC(50)) of 0.18 and 0.10 mg/L, respectively. Individual theaflavins and a structurally related compound, purpurogallin, also inhibited the formation of both off-odorants, with the lowest IC(50) values for theaflavin 3,3'-digallate (0.17 and 0.06 mg/L for p-cresol and p-methylacetophenone, respectively). On the other hand, a mixture of green tea catechins and its major constituent, (-)-epigallocatechin gallate, showed relatively high IC(50) values for the formation of p-methylacetophenone (1.29 and 1.28 mg/L, respectively) and showed no inhibitory effect on the formation of p-cresol. The results of the sensory evaluation showed that the off-odor intensity of the stored citral solution was significantly decreased by the addition of the theaflavin mixture at concentrations of 0.5 mg/L and above. In addition, the calculation of the odor activity values (OAVs) for the volatile compounds detected by a gas chromatographic analysis indicated that the total OAVs of the major volatile compounds in the citral solution were significantly decreased by the addition of the theaflavins.     

Breast cancer prevention by green tea catechins and black tea theaflavins in the C3(1) SV40 T,t antigen transgenic mouse model is accompanied by increased apoptosis and a decrease in oxidative DNA adducts

Tea consumption is associated with a reduced risk of mammary cancer as reflected by epidemiological studies and experiments in carcinogen-induced rodent models of mammary carcinogenesis. We tested the hypothesis that green tea catechins (GTC) or theaflavins from black tea (BTT) interfere with mammary carcinogenesis in C3(1) SV40 T,t antigen transgenic multiple mammary adenocarcinoma (TAg) mice and that GTC/BTT affect tumor survival or oxidation status. TAg mice received GTC/BTT (0.05%) in drinking water for their lifetime. As compared to control mice, they survived longer and had smaller tumors. On microscopic inspection, the size of the largest tumor per mouse was decreased by 40-42% (p<0.01). GTC (0.01%) and BTT (0.05%) increased levels of cleaved caspase 3 in tumor tissue by 67 and 38%, respectively (p<0.05), intimating increased apoptosis. Tumor levels of the malondialdehyde-DNA adduct M1dG in mice receiving GTC or BTT (0.05%) were reduced by 78 (p<0.001) or 63% (p<0.05), respectively, as compared to controls. The results render the exploration of the breast cancer chemopreventive properties of tea preparations in humans worthwhile.     

A novel black tea pigment and two new oxidation products of epigallocatechin-3-O-gallate

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.