Relationship between the flavanol composition of fresh tea shoots and the theaflavin content of manufactured tea

Under field conditions, where the phenolic composition of shoots of tea varied under the effect of seasonal, genetic and agronomic factors, the level of theaflavins produced by these shoots during fermentation was highly correlated to the concentration of (?)-epigallocatechin in the shoots.     

Polyphenols of tea. IV.—Qualitative and quantitative study of the polyphenols of different organs and some cultivated varieties of tea plant

A method is described for the estimation of individual polyphenols of tea leaf. Polyphenols separated by two-way paper chromatography of a methanolic extract of the material were located under ultra-violet light. The excised spots were eluted with water and estimated from extinctions at 275 nm. Three of the polyphenols, (?)-epigallocatechin gallate, (?)-epigallocatechin and (?)-epicatechin gallate, which comprise 10-19% of the dry matter of tea shoots from Assam, are partly consumed during the manufacture of black tea. Seasonal variation in the polyphenolic content of some jats and clones grown in North East India are described. The phenolic content of the tea shoots was higher during rains. Changes in the phenolic pattern during the growth and development of tea flower, fruit and seed are described. Organs of tea, such as sepals, petals and pericarp with closer morphological affinities to the leaf, showed a greater degree of similarity in their phenolic pattern compared with other organs such as stigma, style, carpel, anther and testa. The gallates were mostly confined to the chlorophyll-bearing organs.     

Changes in major polyphenolic compounds of tea (<Emphasis Type="Italic">Camellia sinensis</Emphasis>) leaves during the production of black tea

The objective of this study was to quantify the polyphenolic compounds present in tea samples during black tea processing, and to determine the correlation between the contents of individual catechins and theaflavins. Nine monomeric and four dimeric compounds were identified and quantified by HPLC. During black tea processing, the catechins content decreased, whereas the gallic acid content increased. The decrease in the catechins-in particular, the cis-catechins-was due to the formation of dimeric theaflavins. In the present study, we found a significant negative correlation between the changes in the catechins and theaflavins contents during black tea processing. Theaflavin-3-gallate showed the strongest correlations with the cis-catechins ((?)-epigallocatechin: r=0.713; (?)-epicatechin: r=0.755; (?)-epigallocatechin gallate: r=0.681; and (?)-epicatechin gallate: r=0.771).     

Changes in content of organic acids and tea polyphenols during kombucha tea fermentation

Kombucha tea is a fermented tea beverage produced by fermenting sugared black tea with tea fungus (kombucha). Tea polyphenols which includes (-)-epicatechin (EC), (-)-epicatechin gallate (ECG), (-)-epigallocatechin (EGC), (-)-epigallocatechin gallate (EGCG) and theaflavin (TF) have been reported to possess various biological activities. The present study focused on changes in content of organic acid and tea polyphenols in kombucha tea prepared from green tea (GTK), black tea (BTK) and tea manufacture waste (TWK) during fermentation. Concentration of acetic acid has reached maximum up to 9.5 g/l in GTK on 15th day and glucuronic acid concentration was reached maximum upto 2.3 g/l in BTK on 12th day of fermentation. Very less concentration of lactic acid was observed during the fermentation period and citric acid was detected only on 3rd day of fermentation in GTK and BTK but not in TWK. When compared to BTK and TWK very less degradation of EGCG (18%) and ECG (23%) was observed in GTK. TF and thearubigen (TR) were relatively stable when compared to epicatechin isomers. The biodegradation of tea catechins, TF and TR during kombucha fermentation might be due to some unknown enzymes excreted by yeasts and bacteria in kombucha culture.     

The chemical oxidation of catechins and other phenolics: A study of the formation of black tea pigments

The chemical oxidation of polyphenols has been used to produce black tea pigments. (+)-Catechin, (?)-epicatechin, (?)-epicatechin gallate and (?)-epigallocatechin gallate were isolated from convenient sources, their identity being confirmed by mass spectrometry and HPLC. The oxidation of a mixture of (?)-epicatechin gallate and gallic acid gave an oxidation product of (?)-epicatechin gallate in addition to epitheaflavic acid 3-gallate. The catechins were oxidised chemically and the products analysed by HPLC, the chromatograms being compared with a black tea chromatogram. The reactions gave both resolved and unresolved pigments, and many of the resolved pigments had HPLC retention times close to black tea pigments. Each catechin behaved differently, the chromatograms of the oxidation products from each starting material being clearly distinguishable. Resolved pigments were obtained by the chemical oxidation of other phenolic compounds. This work provides a convenient method for studying the formation of resolved and unresolved black tea pigments.     

Comparison of catechins and purine alkaloids in albino and normal green tea cultivars (Camellia sinensis L.) by HPLC

The variations in the contents of catechins and purine alkaloids in relation to the chlorophyll contents in albino tea cultivar ‘Anji baicha’ and normal cultivar ‘Longjing 43’, grown in Anji and Guilin, were determined. The results showed that, compared to ‘Anji baicha’, ‘Longjing 43’ had significantly higher (?)-epigallocatechin (EGC), (?)-epicatechin (EC), (?)-epicatechin gallate (ECG), theobromine and caffeine contents in Anji, and significantly higher (+)-catechin (C), ECG and caffeine contents in Guilin. ‘Anji baicha’ only had C content significantly higher than ‘Longjing 43’ in Anji. Correlation analysis indicated that C, EGC and (?)-epigallocatechin gallate (EGCG) were significantly and negatively correlated with chlorophyll contents, suggesting that chlorophylls might play vital roles in the regulation of catechin biosynthesis. Moreover, no significant correlation was observed between purine alkaloids and chlorophylls, indicating that the biosynthesis of purine alkaloids might be affected by genotypic factors other than chlorophyll biosynthesis.     

Effect of process unit operations and long-term storage on catechin contents in EGCG-enriched tea drink

Due to the increasing market for functional foods and the chemopreventive action of (?)-epigallocatechin gallate (EGCG), manufacturers produce ready-to-drink green tea infusions enriched or not in EGCG. However, the maintenance of green tea catechins stability in drinks is always a challenge. In this context, the objectives of this study were (1) to assess the catechin stability in tea drink during a 6-month storage, (2) to evaluate the impact of process unit operations on catechin stability and (3) to compare the catechin and caffeine contents of commercially available tea drinks. It appeared that the stability of catechins during long-term storage was optimum at low temperature (4 °C) and acidic pH (pH 4.0). During the processing of the EGCG-enriched green tea drink, all the process unit operations, except heat-treatment, had no impact on catechin concentrations. In addition, in commercially available tea drinks, except enriched green tea drinks, their catechin contents are very low to provide health benefits.     

Epimerisation of tea polyphenols in tea drinks

The present study was carried out to quantify green tea epicatechin (GTE) derivatives and to investigate the origin of epicatechin epimers present in 18 selected canned or bottled tea drinks. The major GTEs present in tea are (?)‐epigallocatechin gallate (EGCG), (?)‐epigallocatechin (EGC), (?)‐epicatechin gallate (ECG) and (?)‐epicatechin (EC). HPLC analysis showed that the content of total GTEs was lower (16.4–268.3 mg l^?1) in the canned and bottled tea drinks than in tea traditionally prepared as a beverage in a cup or teapot (3–5 g l^?1). The major finding was that they contained higher levels of epicatechin epimers, namely (?)‐gallocatechin gallate (GCG), (?)‐gallocatechin (GC), catechin gallate (CG) and (?)‐catechin (C), than of GTEs, ranging from 7.6 to 331.8 mg l^?1. To investigate the origin of these epimers, GTEs were extracted from longjing green tea and autoclaved at various temperatures for 10–60 min. It was found that at least 50% of GTEs were epimerised to their corresponding epimers when autoclaved at 120 °C for 20 min. It is concluded that epicatechin epimers in tea drinks are not originally present in green tea leaf but are instead derived from thermal conversion of GTEs. Copyright © 2003 Society of Chemical Industry     

The formation of thearubigin-like substances by in-vitro polyphenol oxidase-mediated fermentation of individual flavan-3-ols

An enzymic in-vitro model tea fermentation system has been used in combination with gradient elution reversed-phase high-performance liquid chromatography to study the formation from individual fiavan-3-ols of resolvable and unresolvable thearubigin-like substances. It has been found that in 30 min at pH 5.6 tea polyphenol oxidase (EC 1.14.18.1) produces a distinctive range of resolvable thearubigin-like products from each flavan-3-ot substrate examined ((+)-catechin, (?)-epicatechin, (?)-epigallocatechin, (?)-epicatechin gallate and (?)-epigallocatechin gallate). However, (?)-epicatechin, and to a much lesser extent (+ )-catechin, were the only flavan-3-ols converted to an unresolvable thearubigin-like hump under these conditions. In addition, it was demonstrated that varying the pH of incubation in the range 5.0–6.0 had little effect on the profile of products obtained from the simple catechins, but a pronounced effect in the case of the gallocatechins. It is concluded that the combination of (?)-epicatechin and polyphenol oxidase is the simplest model of tea fermentation that can be used to generate in quantity thearubigin-like materials for structure elucidation.     

远安黄茶啤酒抗氧化物质的分离与鉴定

以抗氧化活性为筛选导向,采用醇沉、溶剂萃取、大孔树脂分离和半制备型液相色谱联用技术从远安黄茶啤酒中分离出8 个具有抗氧化作用的关键组分。进一步结合超高效液相色谱-四极杆飞行时间质谱联用技术对抗氧化组分进行分析,共鉴定出8 种化合物,分别为表没食子儿茶素（(－)-epigallocatechin,EGC）、咖啡因、表没食子儿茶素没食子酸酯（(－)-epigallocatechin gallate,EGCG）、表儿茶素（epicatechin,EC）、1,2,6-三没食子酰-β-D-葡萄糖、表儿茶素没食子酸酯（(－)-epicatechin gallate,ECG）、柯里拉京（corilagin,Cor）和色氨酸（Trp）。抗氧化活性和定量研究发现,EGC、EGCG、EC、ECG和Cor是远安黄茶啤酒中的主要抗氧化物质,对酒体的抗氧化活性贡献可达54.61%。其中,EGCG的贡献值最大,其次为EGC、ECG、EC和Cor。本研究为鉴定茶啤酒中的关键抗氧化成分,实现高抗氧化啤酒产品的选择性研发提供了技术支撑。     

Biological and chemical factors affecting the valuation of North East Indian plains teas. III. Statistical Evaluation of the Biochemical Constituents and their Effects on Colour,Brightness and Strength of Black Teas

Regardless of tasters and methods of manufacture five biochemical factors, total oxygen uptake of unprocessed tea shoots and theaflavins (TF), thearubigins (TR), (?)-epigallocatechin gallate (EGCE) and theogallin (TG), of black tea are the main contributing factors of colour of North East India plains tea. Similarly, three constituents, TF, TR and (?)-epicatechin gallate (ECG) of black tea, are main the factors for brightness. Four factors, total oxygen uptake and ECG of unprocessed tea shoots and TF and moisture of black tea are the main contributing factors of strength of North East Indian plains tea.     

Correlation between leaf age,shade levels,and characteristic beneficial natural constituents of tea (Camellia sinensis) grown in Hawaii

This study showed the relationship between tea leaf age, bud and first two leaves, and shade levels, on the relative concentrations of six major compounds of tea leaf, namely l-theanine, caffeine, and the major tea catechins; (−)-epigallocatechin gallate (EGCG), (−)-epigallocatechin (EGC), (−)-epicatechin (EC), and (−)-epicatechin gallate (ECG), all of which are reported to have positive effects on human health, as well as at the ferric reducing antioxidant power of bud and leaf extracts. The concentration of l-theanine and caffeine decreased as leaf age increased moving from bud to first and then second leaf, while the concentration of the four catechins increased from the bud to first and second leaves. In most cases this increase was generally relatively small but in the case of EGC it was 7 to 10-fold. Certain chemical components of freshly picked, minimally processed and essentially unoxidised tea may potentially be used as markers for age, quality, authenticity and area of growth.     

做青工艺对夏季祁门红茶品质形成影响

对舒茶早夏季鲜叶晒青、摇青处理后,采用祁门红茶加工工艺,对加工得到的毛茶进行感官审评及儿茶素、香气成分分析,探讨了做青工艺对祁门红茶品质的影响。结果表明,经做青加工而成的祁门红茶香气、滋味品质得到明显的改善。与未做青加工的红茶相比,轻做青能够显著降低夏季红茶中表没食子儿茶素EGC、儿茶素C、表儿茶素EC、表没食子儿茶素没食子酸酯EGCG、表儿茶素没食子酸酯ECG、儿茶素总量、茶红素(TR_S)和茶黄素(TF_S)的含量(p<0.05),提高了夏季红茶滋味鲜爽度;轻做青工艺能够显著降低红茶醇类香气含量(p<0.05),显著提高醛类、酯类、酸类和酮类香气的含量(p<0.05),干茶带有花香。轻做青更有利于香气、滋味品质的形成。      

Effects of enzyme treatment on volatile and non-volatile compounds in dried green tea leaves

Food Science and Biotechnology - Green tea contains polyphenols, mainly four catechins, including (−)-epigallocatechin gallate, (−)-epicatechin gallate, (−)-epigallocatechin, and...     

Isolation and identification of (—)-gallocatechin gallate and circular dichroism of green tea flavanols

Partly raceme (—)-gallocatechin gallate was isolated from green tea by counter-current distributins and column chromatography on Sephadex LH-20. The structure was proven by mass spectroscopy of the pertrimethylsilyl ether and by n.m.r. and circular dichroism (c.d.). The compound is probably an artifact produced by heating (—)-epigallocatechin gallate. Circular dichroism curves of several tea flavanols are presented.     

Trapping reactions of reactive carbonyl species with tea polyphenols in simulated physiological conditions

The carbonyl stress that leads to the formation of advanced glycation end products (AGEs) in diabetes mellitus has drawn much attention recently. Reactive alpha-dicarbonyl compounds, such as glyoxal (GO) and methylglyoxal (MGO), have been shown to be a high potential glycation agent in vitro and in vivo. In this study, epicatechins in green tea and theaflavins in black tea were found to be able to reduce the concentration of MGO in physiological phosphate buffer conditions. Modified MGO derivatization for GC/flame ionization detector (FID) method in quantification was systematically conducted. In molar ratio of 3 (MGO/polyphenol), theaflavin-3,3'-digallate (TF3) in theaflavins and (-)-epigallocatechin (EGC) in epicatechins showed the highest MGO reduction at 66.65 and 45.74%, respectively, after 1 h of incubation. In kinetic study (molar ratio of MGO/polyphenol = 1:1), rapid MGO reduction occurred within 10 min. Identities of primary adducts between (-)-epigallocatechin gallate (EGCG) and MGO were determined. Newly generated stereoisomers at the C8 position of EGCG A-ring were isolated with a chiral column, and structurally confirmed by 2-D NMR analyses.     

Taste characterisation of green tea catechins

There has been interest in biological activities of green tea catechins. However, little is known about the taste characteristics of catechins. To assess the taste characteristics of catechins ((?)–epicatechin (EC), (?)–epicatechin gallate (ECg), (?)–epigallocatechin (EGC) and (?)–epigallocatechin gallate (EGCg)), sensory evaluations were performed. The taste intensity increased with increased catechins concentration. Among them, ECg showed the strongest taste. Catechins had tastes that consisted primarily of astringency and bitterness. Therefore, taste palatability decreased with increasing catechin concentrations. In line with taste intensity, taste palatability of ECg was the lowest. Taste sensor analysis and mouse behavioural assays showed same results. EC and ECg were more stable in Ringer’s solution than EGC and EGCg. Furthermore, taste cell responses to ECg that had the strong taste and better stability among catechins used were recorded. Some taste cells responded to ECg. This result suggests that ECg might be recognised by taste cells.     

Polyphenolic composition and in vitro antioxidant activities of native‐ and tannase‐treated green tea extracts

The antioxidant activities of native‐ and tannase‐treated green tea extracts along with their major polyphenol components were investigated. The polyphenolic content and composition of the tea before and after tannase treatment were determined by liquid chromatography coupled with mass spectrometry (LC‐MS). Approximately 99% of the (?)‐epigallocatechin gallate (EGCG) and (?)‐epicatechin gallate (ECG) in green tea extract were converted by tannase to (?)‐epigallocatechin (EGC) and (?)‐epicatechin (EC), respectively, after 30 min. Biotransformed green tea exhibited a significantly higher DPPH˙ radical scavenging activities than native green tea (EC₅₀ value of 0.024 ± 0.001 and 0.044 ± 0.001 mg mL^?1, respectively). Kinetic parameters such as scavenging rate and stoichiometry were calculated. The rate of DPPH˙ radical scavenging activities for tannase‐treated green tea extract was shown to be higher than native green tea extract.     

Comparison of catechins and volatile compounds among different types of tea using high performance liquid chromatograph and gas chromatograph mass spectrometer

As tea is one of the most popular beverages consumed worldwide, it is important for customers and business investigators to develop an easy and reliable method to discriminate between different types of teas from each other. A total of eighty‐seven types of various white, green, oolong, black and Puer teas were collected from the major tea estates in China, and their catechin contents and volatile compounds were compared by high performance liquid chromatograph and gas chromatograph mass spectrometer. It was found green tea contained the highest concentrations of total catechins, (?)‐epicatechin gallate (ECG) and (?)‐epigallocatechin gallate (EGCG), while oolong teas contained the highest concentrations of (?)‐epigallocatechin (EGC) among these five types of teas. The aroma composition and their quantities in different types of teas varied quite widely. The concentration of ECG, EGCG, pentanal, hexanal, methyl jasmonate, indole, (E,E)‐2,4‐hexadienal and 1,2,3‐trimethoxybenzene was shown to be different and could be used to discriminate white, green, oolong, black and Puer teas. The result showed that different types of teas could be partially classified by cluster analysis using index of individual catechins and volatile components.     

冠突散囊菌固体发酵铁观音茶的主要活性成分及其抗氧化性分析

为提高铁观音茶青的利用率,采用冠突散囊菌固体发酵铁观音茶,检测发酵前后茶叶中化学成分和抗氧化性的变化。结果表明,铁观音茶叶经发酵后,与未发酵的对照组茶叶相比,多酚、表没食子儿茶素没食子酸酯（EGCG）、表儿茶素没食子酸酯（ECG）、茶黄素,游离氨基酸、麦芽糖、蔗糖和果糖等物质的含量显著性降低（P<0.05）,尤其EGCG和ECG分别下降了92.2%和88.1%,而总黄酮、表没食子儿茶素（EGC）、儿茶素（+C）、表儿茶素（EC）、总糖、葡萄糖、三萜类物质、茶红素和茶褐素等物质的含量显著性增加（P<0.05）,尤其茶褐素增加了68.4%。经过冠突散囊菌发酵过的茶叶与对照茶叶相比总还原力和Fe3+还原能力,清除DPPH自由基、ABTS+自由基、羟基自由基能力仍然很强。综上,冠突散囊菌的固体发酵降低了茶叶中具有苦涩味道的茶多酚,增加了总糖、茶红素、茶褐素、EGC、+C、EC等含量,研究为铁观音茶青的发酵利用提供了实验依据。