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.     

Determination and comparison of γ-aminobutyric acid (GABA) content in pu-erh and other types of Chinese tea

Two previous studies have reported that pu-erh tea contains a high level of γ-aminobutyric acid (GABA), which is the major inhibitory neurotransmitter in the central nervous system and has several physiological functions. However, two other researchers have demonstrated that the GABA content of several pu-erh teas was low. Due to the high value and health benefits of GABA, analysis of mass-produced pu-erh tea is necessary to determine whether it is actually enriched with GABA. A high-performance liquid chromatography (HPLC) method was developed for the determination of GABA in tea, the results of which were verified by amino acid analysis using an Amino Acid Analyzer (AAA). A total of 114 samples of various types of Chinese tea, including 62 pu-erh teas, 13 green teas, 8 oolong teas, 8 black teas, 3 white teas, 4 GABA teas, and 16 process samples from two industrial fermentations of pu-erh tea (including the raw material and the first to seventh turnings), were analyzed using HPLC. Statistical analysis demonstrated that the GABA content in pu-erh tea was significantly lower than that in other types of tea (p < 0.05) and that the GABA content decreased during industrial fermentation of pu-erh tea (p < 0.05). This mass analysis and comparison suggested GABA was not a major bioactive constituent and resolved the disagreement GABA content in pu-erh tea. In addition, the GABA content in white tea was found to be significantly higher than that in the other types of tea (p < 0.05), leading to the possibility of producing GABA-enriched white tea.     

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.     

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.     

Determination of theanine, GABA, and other amino acids in green, oolong, black, and Pu-erh teas with dabsylation and high-performance liquid chromatography

Dabsyl chloride (dimethylaminoazobenzene sulfonyl chloride), a useful chromophoric labeling reagent for amino acids and amines, was developed in this laboratory in 1975. Although several methods have been developed to determine various types of amino acids, a quick and easy method of determining theanine, GABA, and other amino acids has not been developed in one HPLC system. In this paper are analyzed the free amino acid contents of theanine and GABA in different teas (green tea, black tea, oolong tea, Pu-erh tea, and GABA tea) with a dabsylation and reverse phase high-performance liquid chromatography (HPLC) system coupled with a detector at 425 nm absorbance. Two reverse phase columns, Hypersil GOLD and Zorbax ODS, were used and gave different resolutions of dabsyl amino acids in the gradient elution program. The data suggest that the tea source or the steps of tea-making may contribute to the theanine contents variations. High theanine contents of high-mountain tea were observed in both green tea and oolong tea. Furthermore, the raw (natural fermented) Pu-erh tea contained more theanine than ripe (wet fermented) Pu-erh tea, and the GABA contents in normal teas were generally lower than that in GABA tea.     

Antioxidative activities of volatile extracts from green tea, oolong tea, and black tea

Antioxidative activities of volatile extracts from six teas (one green tea, one oolong tea, one roasted green tea, and three black teas) were investigated using an aldehyde/carboxylic acid assay and a conjugated diene assay. The samples were tested at levels of 20, 50, 100, and 200 micrograms/mL of dichloromethane. The results obtained from the two assays were consistent. All extracts except roasted green tea exhibited dose-dependent inhibitory activity in the aldehyde/carboxylic acid assay. A volatile extract from green tea exhibited the most potent activity in both assays among the six extracts. It inhibited hexanal oxidation by almost 100% over 40 days at the level of 200 micrograms/mL. The extract from oolong tea inhibited hexanal oxidation by 50% in 15 days. In the case of the extract from roasted green tea, the lowest antioxidative activity was obtained at the level of 200 micrograms/mL, suggesting that the extract from roasted green tea contained some pro-oxidants. The extracts from the three black teas showed slight anti- or proactivities in both assays. The major volatile constituents of green tea and roasted green tea extracts, which exhibited significant antioxidative activities, were analyzed using gas chromatography-mass spectrometry. The major volatile chemicals with possible antioxidative activity identified were alkyl compounds with double bond(s), such as 3,7-dimethyl-1,6-octadien-3-ol (8.04 mg/kg), in the extract from green tea and heterocyclic compounds, such as furfural (7.67 mg/kg), in the extract from roasted green tea. Benzyl alcohol, which was proved to be an antioxidant, was identified both in a green tea extract (4.67 mg/kg) and in a roasted tea extract (1.35 mg/kg).     

Capillary electrophoretic determination of theanine, caffeine, and catechins in fresh tea leaves and oolong tea and their effects on rat neurosphere adhesion and migration

Theanine, caffeine, and catechins in fresh tea leaves and oolong tea were determined by using capillary electrophoresis (CE). CE separated these tea polyphenols from three other tea ingredients, namely, caffeine, theophylline, and theanine, within 8 min. The young leaves (apical bud and the two youngest leaves) were found to be richer in caffeine, (-)-epigallocatechin gallate (EGCg), and (-)-epicatechin gallate (ECg) than old leaves (from 5th to 7th leaves). On the other hand, the old leaves (from 8th to 10th leaves) contained higher levels of theanine, (-)-epigallocatechin (EGC), and (-)-epicatechin (EC). Results from a comparison of fresh young tea and oolong tea compositions indicated oolong tea contained more theanine and catechins than fresh young tea. Furthermore, it was found that the levels of theanine, EGC, and EGCg in young leaves rose markedly with the withering process. Caffeine did not markedly change. However, fully or partially fermented teas (oolong tea or pauchong tea) have a common initial step in the withering process. Fresh tea leaves or oolong tea extract (0.1%, w/v) markedly inhibited neurosphere adhesion, cell migration, and neurite outgrowth in rat neurospheres. Theanine (348 micrograms/mL) and caffeine at high concentration (50 micrograms/mL) did not inhibit neurosphere adhesion or migration activities, but EGCg at 20 micrograms/mL effectively inhibited neurosphere adhesion for 24 h. These results indicated that EGCg might affect neural stem cell survival or differentiation.     

Effects of pu-erh tea on oxidative damage and nitric oxide scavenging

The effects of pu-erh tea, which is prepared by fermentation of tea, on oxidative damage and nitric oxide scavenging, compared with various other brands of tea were investigated. The total antioxidant activity was determined using the Trolox equivalent antioxidant capacity (TEAC) assay. The results showed that TEAC values of the 200 microg/mL water extracts of pu-erh tea (WEPT), green tea, oolong tea, and black tea were 86.3, 85.3, 87.4, and 80.3 (microg/mL), respectively, indicating that WEPT showed a significant antioxidant activity. WEPT, like green tea extract, oolong tea extract, and black tea extract, exhibited a remarkable protective effect in lipid (liposome) and nonlipid (protein and deoxyribose) model systems, implying that it is an inhibitor of lipid and nonlipid oxidative damage. It also exhibited metal-binding ability, reducing power, and scavenging effect for free radicals. Moreover, WEPT showed a decreasing effect on nitric oxide production of lipopolysaccharide-induced RAW 264.7 macrophages. In addition, the results revealed that epicatechin (EC), flavonoid, ascorbic acid, and polyphenolic compounds are present in WEPT, which may partially account for the protective effect on oxidative damage. Thus, WEPT may have potential as an antioxidant and as a nitric oxide scavenging agent.     

Tea enhances insulin activity

The most widely known health benefits of tea relate to the polyphenols as the principal active ingredients in protection against oxidative damage and in antibacterial, antiviral, anticarcinogenic, and antimutagenic activities, but polyphenols in tea may also increase insulin activity. The objective of this study was to determine the insulin-enhancing properties of tea and its components. Tea, as normally consumed, was shown to increase insulin activity >15-fold in vitro in an epididymal fat cell assay. Black, green, and oolong teas but not herbal teas, which are not teas in the traditional sense because they do not contain leaves of Camellia senensis, were all shown to increase insulin activity. High-performance liquid chromatography fractionation of tea extracts utilizing a Waters SymmetryPrep C18 column showed that the majority of the insulin-potentiating activity for green and oolong teas was due to epigallocatechin gallate. For black tea, the activity was present in several regions of the chromatogram corresponding to, in addition to epigallocatechin gallate, tannins, theaflavins, and other undefined compounds. Several known compounds found in tea were shown to enhance insulin with the greatest activity due to epigallocatechin gallate followed by epicatechin gallate, tannins, and theaflavins. Caffeine, catechin, and epicatechin displayed insignificant insulin-enhancing activities. Addition of lemon to the tea did not affect the insulin-potentiating activity. Addition of 5 g of 2% milk per cup decreased the insulin-potentiating activity one-third, and addition of 50 g of milk per cup decreased the insulin-potentiating activity approximately 90%. Nondairy creamers and soy milk also decreased the insulin-enhancing activity. These data demonstrate that tea contains in vitro insulin-enhancing activity and the predominant active ingredient is epigallocatechin gallate.     

Profiles of purine and pyrimidine nucleotides in fresh and manufactured tea leaves

Profiles of nucleotide levels in two varieties of Japanese green teas (cv. Yabukita and Saemidori), a Chinese green tea (Longjing), and two Japanese black teas (cv. Benifuuki and Benihikari) were determined and compared with that of fresh tea leaves. The concentration of 5'-nucleotides in green tea was much higher than in black tea. Nucleoside diphosphates were present in larger amounts than nucleoside triphosphates in manufactured green and black teas, whereas the triphosphates predominated in fresh tea leaves. Low levels of 3'-nucleotides were found in green and black teas. Inosine 5'-monophosphate, which is utilized as a seasoning component, was found in all manufactured teas in concentrations ranging from 50 to 200 nmol/g of dry weight. The levels of both inosine 5'-monophosphate and guanosine 5'-monophosphate were high in Chinese Longjing green tea. The unique profiles of nucleotides in manufactured teas may be a consequence of the action of degradation enzymes, such as ribonuclease, apyrase, phosphatase, nucleotidase, and adenosine 5'-monophsphate deaminase during the commercial processing of the young leaves.     

Comparison of the chemical constituents of aged pu-erh tea, ripened pu-erh tea, and other teas using HPLC-DAD-ESI-MSn

Pu-erh tea is a popular beverage in southwestern China and South Asian countries. To explain the differences of aged pu-erh tea and ripened pu-erh tea, the chemical constituents of these teas were identified by HPLC-DAD-ESI-MS(n). In addition, HPLC was used to determine the contents of the major polyphenols, gallic acid, caffeine, and theobromine, in various types of teas. These results showed that the majority of chemical constituents in ripened pu-erh tea and aged pu-erh tea were similar, but the contents of catechins and gallic acid presented significant differences between these two teas. After fermentation by microorganism, the levels of catechins in ripened pu-erh tea were decreased, but the contents of gallic acid and caffeine were conversely elevated compared with aged pu-erh tea.     

Chain-breaking antioxidant activity and cyclic voltammetry characterization of polyphenols in a range of green,oolong, and black teas

A series of eight green, eight oolong, and 17 black teas have been analyzed for polyphenol content by absorbance at 272 nm and cyclic voltammetry response at an inert carbon electrode, a new method developed to provide a rapid measure of easily oxidizable polyphenols in beverages. The chain-breaking antioxidant activity of the teas has also been determined during the chain oxidation of methyl linoleate in a pH 7.4 micellar solution, for which realistic kinetic parameters have been derived. While higher mean values were obtained for green teas than for oolong and black teas, the differences were not large, and the spread of values within each type was considerable. The absorbance at 272 nm correlated well with the cyclic voltammetry response only for green teas and black teas taken on their own. The cyclic voltammetry measure and the antioxidant activity correlated well only for the green teas, where the polyphenol content is dominated by epigallocatechin gallate.     

Determination of tea components with antioxidant activity

Levels of essential elements with antioxidant activity, as well as catechins, gallic acid, and caffeine levels, in a total of 45 samples of different teas commercialized in Spain have been evaluated. Chromium, manganese, selenium, and zinc were determined in the samples mineralized with HNO(3) and V(2)O(5), using ETAAS as the analytical technique. The reliability of the procedure was checked by analysis of a certified reference material. Large variations in the trace element composition of teas were observed. The levels ranged from 50.6 to 371.4 ng/g for Cr, from 76.1 to 987.6 microg/g for Mn, from 48.5 to 114.6 ng/g for Se, and from 56.3 to 78.6 ng/g for Zn. The four major catechins [(-)-epigallocatechin gallate (EGCG), (-)-epigallocatechin (EGC), (-)-epicatechin gallate (ECG), and (-)-epicatechin (EC)], gallic acid (GA), and caffeine were simultaneously determined by a simple and fast HPLC method using a photodiode array detector. In all analyzed samples, EGCG ranged from 1.4 to 103.5 mg/g, EGC from 3.9 to 45.3 mg/g, ECG from 0.2 to 45.6 mg/g, and EC ranged from 0.6 to 21.2 mg/g. These results indicated that green tea has a higher content of catechins than both oolong and fermented teas (red and black teas); the fermentation process during tea manufacturing reduces the levels of catechins significantly. Gallic acid content ranged from 0.039 to 6.7 mg/g; the fermentation process also elevated remarkably gallic acid levels in black teas (mean level of 3.9 +/- 1.5 mg/g). The amount of caffeine in the analyzed samples ranged from 7.5 to 86.6 mg/g, and the lower values were detected in green and oolong teas. This study will be useful for the appraisal of trace elements and antioxidant components in various teas, and it will also be of interest for people who like drinking this beverage.     

Microwave heating of tea residue yields polysaccharides, polyphenols, and plant biopolyester

Microwave heating was used to produce aqueous-soluble components from green, oolong, and black tea residues. Heating at 200-230 degrees C for 2 min extracted 40-50% of polysaccharides and 60-70% of the polyphenols. Solubilization of arabinose and galactose by autohydrolysis occurred with heating above 170 degrees C, whereas heating above 200 degrees C was necessary to solubilize xylose. Catechins were soluble in water by heating at low temperature (110 degrees C); however, new polyphenols having strong antioxidant activity were produced above 200 degrees C. The amount of solubilized materials and antioxidant activity increased with increased fermentation of harvested tea leaves (green tea < oolong tea < black tea). Cutin, a plant biopolyester, remained in the residue after heating as did cellulose and lignin/tannin. The predominant cutin monomer that was recovered was 9,10-epoxy-18-hydroxyoctadecanoic acid, followed by dihydroxyhexadecanoic acid and 9,10,18-trihydroxyoctadecanoic acid.     

Effect of species variation and processing on phenolic composition and in vitro antioxidant activity of aqueous extracts of Cyclopia spp. (Honeybush Tea)

The in vitro antioxidant activity of aqueous extracts prepared from four Cyclopia spp. (unfermented and fermented) was assessed using radical (ABTS *+) scavenging, ferric ion reduction, and inhibition of Fe2+-induced microsomal lipid peroxidation as criteria. Aqueous extracts of unfermented and fermented Aspalathus linearis (rooibos) and Camellia sinensis teas (green, oolong, and black) were included as reference samples. Qualitative and quantitative differences in phenolic composition were demonstrated for the Cyclopia spp. The xanthone glycoside, a.k.a. mangiferin, was the major monomeric polyphenol present in the Cyclopia extracts, with both unfermented and fermented C. genistoides extracts containing the highest quantities. Fermentation resulted in a significant reduction in extract yields and their total polyphenolic and individual polyphenol contents. Unfermented plant material should preferentially be used for preparation of extracts, as fermentation significantly ( P < 0.05) lowered antioxidant activity of all species, except in the case of C. genistoides, where the ability to inhibit lipid peroxidation was not affected. Unfermented plant material also retained the highest concentration of mangiferin. Overall, extracts of unfermented Cyclopia were either of similar or lower antioxidant activity as compared to the other teas. However, the presence of high levels of mangiferin merits the use of Cyclopia spp. and, in particular, C. genistoides, as an alternative herbal tea and potential dietary supplement.     

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.     

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.     

Fluoride content in tea and its relationship with tea quality

The tea plant is known as a fluorine accumulator. Fluoride (F) content in fresh leaves collected from 14 plantations in China was investigated. The F increased with maturity, and the F variation was remarkable in the tender shoots. Furthermore, significant negative relationships were observed between F content and the content of the quality parameters total polyphenols and amino acids. These substances are rich in young leaves and poor in mature ones. With regard to quality of tea products, the relationship with F content was studied using 12 brands of tea products in four categories: green tea, oolong tea, black tea, and jasmine tea collected from six provinces. The F level increased with the decline in quality and showed good correlation with the quality grades. The results suggest that the F content could be used as a quality indicator for tea evaluation.     

HPLC analysis of naturally occurring methylated catechins, 3' '- and 4' '-methyl-epigallocatechin gallate, in various fresh tea leaves and commercial teas and their potent inhibitory effects on inducible nitric oxide synthase in macrophages

(-)-Epigallocatechin-3-gallate (EGCG), a major polyphenol of green tea, undergoes substantial biotransformation to species that includes the methylated compounds. Recent studies have demonstrated that the methylated EGCG has many biological activities. In this study, we have investigated the composition of the three O-methylated EGCG derivatives, (-)-epigallocatechin-3-O-(3-O-methyl)gallate (3' '-Me-EGCG), (-)-epigallocatechin-3-O-(4-O-methyl)gallate (4' '-Me-EGCG) and (-)-4'-methyl epigallocatechin-3-O-(4-O-methyl)gallate (4',4' '-di-Me-EGCG) in tea leaves which were picked from various species and at various seasons, ages of leaves, locations, and fermentation levels. Higher levels of 3' '-Me-EGCG and 4' '-Me-EGCG were detected in Chinshin-Kanzai (a species of Camellia sinensis) cultivated in the mountain area of Sansia, Taipei County, Taiwan. Also, these O-methylated EGCG levels were found to be higher in autumn and winter than in spring and summer. The young leaves were found to be richer in the O-methylated compounds than old leaves and the amount of O-methylated EGCG was higher in unfermented longjin green tea than in semifermented oolong tea. However, the fermented black tea and puerh tea did not contain these compounds. 4',4' '-diMe-EGCG could not be detected in either fresh tea leaves or commercial tea leaves. We also found that 3' '-Me-EGCG has a higher inhibitory effect on the nitric oxide generation and inducible nitric oxide synthase (iNOS) expression as compared with EGCG, while 4' '-Me-EGCG and 4',4' '-di-Me-EGCG were less effective.     

Novel antiallergic catechin derivatives isolated from oolong tea.

Two catechin derivatives (C-1 and C-2) with potent antiallergic activity were isolated from Taiwanese oolong tea by HPLC techniques. From NMR and FAB-MS analyses, the structures of C-1 and C-2 were elucidated as (-)-epigallocatechin 3-O-(3-O-methyl)gallate and (-)-epigallocatechin 3-O-(4-O-methyl)gallate, respectively. The oolong tea leaves contained 0.34% (dry weight) C-1 and 0.20% C-2. Traces of C-2 were detected in only 1 of 15 varieties of green tea tested. C-1 was detected in 13 of 15 green tea varieties; C-1 was most concentrated in tea cultivars classified as Assam hybrids (0. 50-0.82% of dry weight). Quantitative analyses of green tea, oolong tea, and black tea manufactured from same batches of tea leaves showed that neither catechin derivative was produced during the fermentation process. Oral doses of C-1 and C-2 (5-50 mg/kg) significantly inhibited type I allergic (anaphylactic) reactions in mice sensitized with ovalbumin and Freund's incomplete adjuvant. These inhibitory effects exceeded that of the major tea catechin, (-)-epigallocatechin 3-O-gallate, which has known antiallergic properties.