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Shengmin Sang - One of the best experts on this subject based on the ideXlab platform.

  • The Microbiota Is Essential for the Generation of Black Tea Theaflavins-Derived Metabolites
    2016
    Co-Authors: Huadong Chen, Javier Rivera Guzman, Nicholas D. Gillitt, Salam A. Ibrahim, Saeed Hayek, Shengmin Sang
    Abstract:

    Background: Theaflavins including theaflavin (TF), Theaflavin-3-Gallate (TF3G), theaflavin-39-gallate (TF39G), and theaflavin-3,39-digallate (TFDG), are the most important bioactive polyphenols in black tea. Because of their poor systemic bioavailability, it is still unclear how these compounds can exert their biological functions. The objective of this study is to identify the microbial metabolites of theaflavins in mice and in humans. Methods and Findings: In the present study, we gavaged specific pathogen free (SPF) mice and germ free (GF) mice with 200 mg/kg TFDG and identified TF, TF3G, TF39G, and gallic acid as the major fecal metabolites of TFDG in SPF mice. These metabolites were absent in TFDG- gavaged GF mice. The microbial bioconversion of TFDG, TF3G, and TF39G was also investigated in vitro using fecal slurries collected from three healthy human subjects. Our results indicate that TFDG is metabolized to TF, TF3G, TF39G, gallic acid, and pyrogallol by human microbiota. Moreover, both TF3G and TF39G are metabolized to TF, gallic acid, and pyrogallol by human microbiota. Importantly, we observed interindividual differences on the metabolism rate of gallic acid to pyrogallol among the three human subjects. In addition, we demonstrated that Lactobacillus plantarum 299v and Bacillus subtilis have the capacity to metabolize TFDG. Conclusions: The microbiota is important for the metabolism of theaflavins in both mice and humans. The in vivo functiona

  • The microbiota is essential for the generation of black tea theaflavins-derived metabolites.
    PloS one, 2012
    Co-Authors: Huadong Chen, Saeed A. Hayek, Javier Rivera Guzman, Nicholas D. Gillitt, Salam A. Ibrahim, Christian Jobin, Shengmin Sang
    Abstract:

    Background Theaflavins including theaflavin (TF), Theaflavin-3-Gallate (TF3G), theaflavin-3′-gallate (TF3′G), and theaflavin-3,3′-digallate (TFDG), are the most important bioactive polyphenols in black tea. Because of their poor systemic bioavailability, it is still unclear how these compounds can exert their biological functions. The objective of this study is to identify the microbial metabolites of theaflavins in mice and in humans.

  • The microbiota is essential for the generation of black tea theaflavins-derived metabolites.
    PloS one, 2012
    Co-Authors: Huadong Chen, Saeed A. Hayek, Javier Rivera Guzman, Nicholas D. Gillitt, Salam A. Ibrahim, Christian Jobin, Shengmin Sang
    Abstract:

    Theaflavins including theaflavin (TF), Theaflavin-3-Gallate (TF3G), theaflavin-3'-gallate (TF3'G), and theaflavin-3,3'-digallate (TFDG), are the most important bioactive polyphenols in black tea. Because of their poor systemic bioavailability, it is still unclear how these compounds can exert their biological functions. The objective of this study is to identify the microbial metabolites of theaflavins in mice and in humans. In the present study, we gavaged specific pathogen free (SPF) mice and germ free (GF) mice with 200 mg/kg TFDG and identified TF, TF3G, TF3'G, and gallic acid as the major fecal metabolites of TFDG in SPF mice. These metabolites were absent in TFDG- gavaged GF mice. The microbial bioconversion of TFDG, TF3G, and TF3'G was also investigated in vitro using fecal slurries collected from three healthy human subjects. Our results indicate that TFDG is metabolized to TF, TF3G, TF3'G, gallic acid, and pyrogallol by human microbiota. Moreover, both TF3G and TF3'G are metabolized to TF, gallic acid, and pyrogallol by human microbiota. Importantly, we observed interindividual differences on the metabolism rate of gallic acid to pyrogallol among the three human subjects. In addition, we demonstrated that Lactobacillus plantarum 299v and Bacillus subtilis have the capacity to metabolize TFDG. The microbiota is important for the metabolism of theaflavins in both mice and humans. The in vivo functional impact of microbiota-generated theaflavins-derived metabolites is worthwhile of further study.

  • structural identification of theaflavin trigallate and tetragallate from black tea using liquid chromatography electrospray ionization tandem mass spectrometry
    Journal of Agricultural and Food Chemistry, 2012
    Co-Authors: Huadong Chen, Kelly L Shurlknight, Tinchung Leung, Shengmin Sang
    Abstract:

    Black tea contains two major pigments, theaflavins and thearubigins. These polyphenols have been associated with certain health benefits including prevention of heart disease and cancer. Elucidating and characterizing the structural aspects of thearubigins, the most abundant pigment in black tea, has been a challenge for many years. Therefore further studies of black tea polyphenols must be conducted in effort to solve this thearubigin dispute. In the present study, black tea extract was found to possess theaflavin trigallate and tetragallate by means of liquid chromatography/electrospray ionization mass spectrometry. These structures were confirmed by analysis of the MS(n) (n = 1-4) spectra and comparison of the MS/MS spectra of the product ions to the MS/MS spectra of authentic (-)-epigallocatechin-3-gallate, (-)-epicatechin-3-gallate and theaflavin-3,3'-digallate. To our knowledge, this is the first report to confirm the presence of theaflavin trigallate and tetragallate in black tea.

  • structural identification of mouse fecal metabolites of theaflavin 3 3 digallate using liquid chromatography tandem mass spectrometry
    Journal of Chromatography A, 2011
    Co-Authors: Huadong Chen, Nicholas D. Gillitt, Christian Jobin, Tiffany A Parks, Xiaoxin Chen, Shengmin Sang
    Abstract:

    Black tea consumption has been associated with many health benefits including the prevention of cancer and heart disease. Theaflavins are the major bioactive polyphenols present in black tea. Unfortunately, limited information is available on their biotransformation. In the present study, we investigated the metabolic fate of theaflavin 3,3′-digallate (TFDG), one of the most abundant and bioactive theaflavins, in mouse fecal samples using liquid chromatography/electrospray ionization tandem mass spectrometry by analyzing the MSn (n = 1–3) spectra. Four metabolites theaflavin, theaflavin 3-gallate, theaflavin 3′-gallate, and gallic acid were identified as the major mouse fecal metabolites of TFDG. Glucuronidated and sulfated, instead of methylated metabolites of theaflavin 3-gallate, theaflavin 3′-gallate, and TFDG were detected and identified as the minor mouse fecal metabolites of TFDG. Our results indicate that TFDG can be degraded in mice. Further studies on the formation of those metabolites in TFDG-treated mice in germ-free conditions are warranted. To our knowledge, this is the first report on the biotransformation of TFDG in mice.

Jenkun Lin - One of the best experts on this subject based on the ideXlab platform.

  • Inhibition of breast cancer cell proliferation by theaflavins from black tea through suppressing proteasomal activities
    Cancer Research, 2006
    Co-Authors: Jenkun Lin, Yu-wen Chen, Shoei-yn Lin-shiau
    Abstract:

    2279 Inhibitors of proteasome are currently emerging as novel cancer preventing and therapeutic agents. To determine whether the black tea polyphenols, including theaflavin, Theaflavin-3-Gallate, theaflavin-3’-gallate, theaflavin-3,3’-digallate (TF3), and (-)-epigallocatechin-3-gallate (EGCG) were potential proteasome inhibitors, we treated purified 20S or 26S proteasome and 26S proteasome in leukemia and cancer cell lines with these compounds. TF3 displayed a potent inhibitory effect on the growth of U937 cells with an estimated IC50 value of 6μM. Furthermore, TF3 had more efficient inhibition on the proteasomal chymotrypsin-like activity of purified proteasome derived from different sources and 26S proteasome in four kinds of cancer cell extracts as compared to those of EGCG. In addition, the theaflavins, especially TF3, inhibited the proteasomal chymotrypsin-like and peptidyl glutamyl peptide hydrolase (PGPH) activities of 26S proteasome in a concentration-dependent manner in human breast cancer MCF7 cells which have been described to be resistant to apoptosis induced by proteasome inhibitors. These results illustrated that proteasome inhibition by theaflavins lead to anti-proliferation of MCF7 cells. Furthermore, comparing well-characterized polyphenols on proteasome inhibition, the ester bond-bearing compounds, with some exceptions, exhibited more potently inhibitory effects on the proteasomal chymotrypsin-like activity than those without ester bond(s). Interestingly, the gallic acid and n-propyl gallate also had slightly inhibition on proteasome activities. Therefore, we suggest that the galloyl moiety might be the other important structure of polyphenols that contributes to the proteasome inhibition.

  • inhibition of 12 o tetradecanoylphorbol 13 acetate induced inflammatory skin edema and ornithine decarboxylase activity by theaflavin 3 3 digallate in mouse
    Nutrition and Cancer, 2002
    Co-Authors: Yu Chih Liang, De Cheng Tsai, Shoeiyn Linshiau, Chieh Fu Chen, Jenkun Lin
    Abstract:

    Among black tea polyphenols, theaflavins were generally considered to be the most effective in cancer chemoprevention. In this study, we examined the inhibitory effects of black tea polyphenols, including theaflavin (TF-1), a mixture (TF-2) of Theaflavin-3-Gallate and theaflavin-3′-gallate, theaflavin-3,3′-digallate (TF-3), and the green tea polyphenol (-)-epigallocatechin-3-gallate (EGCG) on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced edema and ornithine decarboxylase (ODC) activity. Topical application of these polyphenols onto the mouse resulted in inhibition of TPA-induced ear edema and skin epidermal ODC activity. The inhibitory order was as follows: TF-3 > TF-2 ≃ EGCG > TF-1. Western and Northern blots indicated that TF-3 significantly reduced the protein and mRNA levels of ODC in TPA-treated mouse skin and NIH 3T3 cells, whereas EGCG showed less activity. EGCG and TF-3 were able to inhibit the ODC enzyme activity in vitro. Furthermore, TF-3 also significantly reduced the basal promoter activ...

  • Cancer chemoprevention by tea polyphenols through modulating signal transduction pathways.
    Archives of pharmacal research, 2002
    Co-Authors: Jenkun Lin
    Abstract:

    The action mechanisms of several chemopreventive agents derived from herbal medicine and edible plants have become attractive issues in cancer research. Tea is the most widely consumed beverage worldwide. Recently, the cancer chemopreventive actions of tea have been intensively investigated. It have been demonstrated that the active principles of tea were attributed to their tea polyphenols. Recently, tremendous progress has been made in elucidating the molecular mechanisms of cancer chemoprevention by tea and tea polyphenols. The suppression of various tumor biomarkers including growth factor receptor tyrosine kinases, cytokine receptor kinases, PI3K, phosphatases, ras, raf, MAPK cascades, N x FB, I x B kinase, PKA, PKB, PKC, c-jun, c-fos, c-myc, cdks, cyclins, and related transducing proteins by tea polyphenols has been studied in our laboratory and others. The I x B kinase (IKK) activity in LPS-activated murine macrophages (RAW 264.7 cells) was found to be inhibited by various tea polyphenols including (-) epigallocatechin-3-gallate (EGCG), theaflavin (TF-1), Theaflavin-3-Gallate (TF-2) and theaflavin-3,3'-digallate (TF-3). TF-3 inhibited IKK activity in activated macrophages more strongly than did the other tea polyphenols. TF-3 inhibited both IKK1 and IKK2 activity and prevented the degradation of I x B x and I x B x in activated macrophage cells. The results suggested that the inhibition of IKK activity by TF-3 and other tea polyphenols could occur by a direct effect on IKKs or on upstream events in the signal transduction pathway. TF-3 and other tea polyphenols blocked phosphorylation of IB from the cytosolic fraction, inhibited NFB activity and inhibited increases in inducible nitric oxide synthase levels in activated macrophage. TF-3 and other tea polyphenols also inhibited strongly the activities of xanthine oxidase, cyclooxygenase, EGF-receptor tyrosine kinase and protein kinase C. These results suggest that TF-3 and other tea polyphenols may exert their cancer chemoprevention through suppressing tumor promotion and inflammation by blocking signal transduction. The mechanisms of this inhibition may be due to the blockade of the mitogenic and differentiating signals through modulating EGFR function, MAPK cascades, NFkappaB activation as well as c-myc, c-jun and c-fos expression.

  • Suppression of lipopolysaccharide-induced nuclear factor-κB activity by theaflavin-3,3′-digallate from black tea and other polyphenols through down-regulation of IκB kinase activity in macrophages
    Biochemical pharmacology, 2000
    Co-Authors: Min-hsiung Pan, Shoei-yn Lin-shiau, Jer Huei Lin, Jenkun Lin
    Abstract:

    We investigated the inhibition of IkappaB kinase (IKK) activity in lipopolysaccharide (LPS)-activated murine macrophages (RAW 264.7 cell line) by various polyphenols including (-)-epigallocatechin-3-gallate, theaflavin, a mixture of theaflavin-3 gallate and theaflavin-3'-gallate, theaflavin-3,3'-digallate (TF-3), pyrocyanidin B-3, casuarinin, geraniin, and penta-O-galloyl-beta-D-glucose (5GG). TF-3 inhibited IKK activity in activated macrophages more strongly than did the other polyphenols. TF-3 strongly inhibited both IKK1 and IKK2 activity and prevented the degradation of IkappaBalpha and IkappaBbeta in activated macrophage cells. The results suggested that the inhibition of IKK activity by TF-3 could occur by a direct effect on IKKs or on upstream events in the signal transduction pathway. Furthermore, geraniin, 5GG, and TF-3 all blocked phosphorylation of IKB from the cytosolic fraction, inhibited nuclear factor-kappaB (NFkappaB) activity, and inhibited increases in inducible nitric oxide synthase levels in activated macrophages. These results suggest that TF-3 may exert its anti-inflammatory and cancer chemopreventive actions by suppressing the activation of NFkappaB through inhibition of IKK activity.

  • Induction of apoptosis by the oolong tea polyphenol theasinensin A through cytochrome c release and activation of caspase-9 and caspase-3 in human U937 cells.
    Journal of agricultural and food chemistry, 2000
    Co-Authors: Min-hsiung Pan, Yu Chih Liang, Shoei-yn Lin-shiau, Nan Qun Zhu, Jenkun Lin
    Abstract:

    This study examined the growth inhibitory effects of theasinensin A (from oolong tea) and black tea polyphenols, including theaflavin (TF-1), a mixture (TF-2) of Theaflavin-3-Gallate (TF-2a) and theaflavin-3'-gallate (TF-2b), and theaflavin-3,3'-digallate (TF-3) in human cancer cells. Theasinensin A, TF-1, and TF-2 displayed strong growth inhibitory effects against human histolytic lymphoma U937, with estimated IC50 values of 12 microM, but were less effective against human acute T cell leukemia Jurkat, whereas TF-3 and (-)-epigallocatechin-3-gallate (EGCG) had lower activities. The molecular mechanisms of tea polyphenol-induced apoptosis as determined by annexin V apoptosis assay, DNA fragmentation, and caspase activation were further investigated. Loss of membrane potential and reactive oxygen species (ROS) generation were also detected by flow cytometry. Treatment with tea polyphenols caused rapid induction of caspase-3, but not caspase-1, activity and stimulated proteolytic cleavage of poly(ADP-ribose) polymerase (PARP). Pretreatment with a potent caspase-3 inhibitor, Z-Asp-Glu-Val-Asp-fluoromethyl ketone, inhibited theasinensin A induced DNA fragmentation. Furthermore, it was found that theasinensin A induced loss of mitochondrial transmembrane potential, elevation of ROS production, release of mitochondrial cytochrome c into the cytosol, and subsequent induction of caspase-9 activity. These results indicate that theasinensin A allows caspase-activated deoxyribonuclease to enter the nucleus and degrade chromosomal DNA and induces DFF-45 (DNA fragmentation factor) degradation. The results suggest that induction of apoptosis by theasinensin A may provide a pivotal mechanism for their cancer chemopreventive function.

Tsutomu Nakayama - One of the best experts on this subject based on the ideXlab platform.

  • Efficient Synthesis of Theaflavin 3-Gallate by a Tyrosinase-Catalyzed Reaction with (−)-Epicatechin and (−)-Epigallocatechin Gallate in a 1-Octanol/Buffer Biphasic System
    Journal of Agricultural and Food Chemistry, 2018
    Co-Authors: Asako Narai-kanayama, Yoshinori Uekusa, Fumiyuki Kiuchi, Tsutomu Nakayama
    Abstract:

    Theaflavins, the orange–red pigments contained in black tea, have attracted attention as a result of their health-promoting effects. However, their synthetic preparation, in which the enzymatic oxidation of catechol-type catechin is followed by the quinone-induced oxidative dimerization of selectively combined catechol- and pyrogallol-type catechins, provides only a low yield. In the present study, we found that a 1-octanol/buffer biphasic system improved the yield of theaflavin 3-gallate in a tyrosinase-catalyzed synthetic reaction with (−)-epicatechin and (−)-epigallocatechin gallate. When the enzymatic reaction proceeded in a buffer solution, oxidized (−)-epigallocatechin gallate was preferentially used for self-dimerization. However, self-dimerization was suppressed in the octanol phase, allowing oxidized (−)-epigallocatechin gallate to participate in coupling with (−)-epicatechin quinone, leading to effective production of theaflavin 3-gallate. Furthermore, the preferential localization of theaflavin...

  • Efficient Synthesis of Theaflavin 3-Gallate by a Tyrosinase-Catalyzed Reaction with (−)-Epicatechin and (−)-Epigallocatechin Gallate in a 1-Octanol/Buffer Biphasic System
    Journal of agricultural and food chemistry, 2018
    Co-Authors: Asako Narai-kanayama, Yoshinori Uekusa, Fumiyuki Kiuchi, Tsutomu Nakayama
    Abstract:

    Theaflavins, the orange-red pigments contained in black tea, have attracted attention as a result of their health-promoting effects. However, their synthetic preparation, in which the enzymatic oxidation of catechol-type catechin is followed by the quinone-induced oxidative dimerization of selectively combined catechol- and pyrogallol-type catechins, provides only a low yield. In the present study, we found that a 1-octanol/buffer biphasic system improved the yield of theaflavin 3-gallate in a tyrosinase-catalyzed synthetic reaction with (-)-epicatechin and (-)-epigallocatechin gallate. When the enzymatic reaction proceeded in a buffer solution, oxidized (-)-epigallocatechin gallate was preferentially used for self-dimerization. However, self-dimerization was suppressed in the octanol phase, allowing oxidized (-)-epigallocatechin gallate to participate in coupling with (-)-epicatechin quinone, leading to effective production of theaflavin 3-gallate. Furthermore, the preferential localization of theaflavin 3-gallate in the octanol phase prevented (-)-epicatechin-quinone-induced degradation.

  • efficient synthesis of theaflavin 3 gallate by a tyrosinase catalyzed reaction with epicatechin and epigallocatechin gallate in a 1 octanol buffer biphasic system
    Journal of Agricultural and Food Chemistry, 2018
    Co-Authors: Asako Naraikanayama, Yoshinori Uekusa, Fumiyuki Kiuchi, Tsutomu Nakayama
    Abstract:

    Theaflavins, the orange-red pigments contained in black tea, have attracted attention as a result of their health-promoting effects. However, their synthetic preparation, in which the enzymatic oxidation of catechol-type catechin is followed by the quinone-induced oxidative dimerization of selectively combined catechol- and pyrogallol-type catechins, provides only a low yield. In the present study, we found that a 1-octanol/buffer biphasic system improved the yield of theaflavin 3-gallate in a tyrosinase-catalyzed synthetic reaction with (-)-epicatechin and (-)-epigallocatechin gallate. When the enzymatic reaction proceeded in a buffer solution, oxidized (-)-epigallocatechin gallate was preferentially used for self-dimerization. However, self-dimerization was suppressed in the octanol phase, allowing oxidized (-)-epigallocatechin gallate to participate in coupling with (-)-epicatechin quinone, leading to effective production of theaflavin 3-gallate. Furthermore, the preferential localization of theaflavin 3-gallate in the octanol phase prevented (-)-epicatechin-quinone-induced degradation.

  • Theaflavin-3-Gallate specifically interacts with phosphatidylcholine, forming a precipitate resistant against the detergent action of bile salt.
    Bioscience biotechnology and biochemistry, 2018
    Co-Authors: Asako Narai-kanayama, Kosuke Saruwatari, Natsumi Mori, Tsutomu Nakayama
    Abstract:

    Black tea is a highly popular beverage, and its pigments, polymerized catechins such as theaflavins (TFs), are attracting attention due to their beneficial health effects. In this study, to test the inhibitory activities of TFs on the intestinal absorption of cholesterol, we investigated their effects on phosphatidylcholine (PC) vesicles in the absence or presence of a bile salt. (-)-Epicatechin gallate, (-)-epigallocatechin gallate, and TFs formed insoluble complexes with PC vesicles. Galloylated TFs such as TF2A, TF2B, and TF3 precipitated far more than other polyphenols. The subsequent addition of taurocholate redispersed the polyphenol-PC complexes, except that a large amount of TF2A remained insoluble. After incubation with taurocholate-PC micelles, TF2A elevated the turbidity of the micelle solution, providing red sediments. The TF2A-specific effect was dependent on the PC concentration. These results suggest that TF2A interacts with PC and aggregates in a specific manner different from catechins and other TFs.

  • Efficient Synthesis of Theaflavin 3‑Gallate by a Tyrosinase-Catalyzed Reaction with (−)-Epicatechin and (−)-Epigallocatechin Gallate in a 1‑Octanol/Buffer Biphasic System
    2018
    Co-Authors: Asako Narai-kanayama, Yoshinori Uekusa, Fumiyuki Kiuchi, Tsutomu Nakayama
    Abstract:

    Theaflavins, the orange–red pigments contained in black tea, have attracted attention as a result of their health-promoting effects. However, their synthetic preparation, in which the enzymatic oxidation of catechol-type catechin is followed by the quinone-induced oxidative dimerization of selectively combined catechol- and pyrogallol-type catechins, provides only a low yield. In the present study, we found that a 1-octanol/buffer biphasic system improved the yield of theaflavin 3-gallate in a tyrosinase-catalyzed synthetic reaction with (−)-epicatechin and (−)-epigallocatechin gallate. When the enzymatic reaction proceeded in a buffer solution, oxidized (−)-epigallocatechin gallate was preferentially used for self-dimerization. However, self-dimerization was suppressed in the octanol phase, allowing oxidized (−)-epigallocatechin gallate to participate in coupling with (−)-epicatechin quinone, leading to effective production of theaflavin 3-gallate. Furthermore, the preferential localization of theaflavin 3-gallate in the octanol phase prevented (−)-epicatechin-quinone-induced degradation

Chung S Yang - One of the best experts on this subject based on the ideXlab platform.

  • theaflavin 3 3 digallate induces epidermal growth factor receptor downregulation
    Molecular Carcinogenesis, 2006
    Co-Authors: Hideya Mizuno, Chung S Yang, Yong Yeon Cho, Feng Zhu, Ann M Bode, Zigang Dong
    Abstract:

    Black tea is one of the most popular beverages worldwide and especially in Western nations. Theaflavins, a mixture of theaflavin (TF-1), Theaflavin-3-Gallate (TF-2a), theaflavin-3'-gallate (TF-2b), and theaflavin-3,3'-digallate (TF-3) are the major components of black tea. Among these black tea components, theaflavin is generally considered to be the more effective component for the inhibition of carcinogenesis. Recently, TF-3 has been shown to have an antiproliferative effect on tumor cells, but the mechanism is not clear. In this study, we showed that TF-3-induced internalization and downregulation of the epidermal growth factor receptor (EGFR). These results suggested that TF-3 induces EGFR endocytosis and degradation. We further showed that TF-3 stimulated EGFR ubiquitination and tyrosine kinase activation. Interestingly, TF-3-induced EGFR downregulation is inhibited by the proteasome inhibitor, MG132, but not by the EGFR-specific receptor tyrosine kinase inhibitor, AG1478. Furthermore, pretreatment with TF-3 inhibited EGF-induced EGFR autophosphorylation, ERKs phosphorylation and AP-1 activation in JB6 Cl41 cells. In addition, TF-3 inhibited EGF-induced anchorage-independent cell transformation. Overall, our results indicate that TF-3 might exert chemopreventive effects through the downregulation of the EGFR.

  • delivery of tea polyphenols to the oral cavity by green tea leaves and black tea extract
    Cancer Epidemiology Biomarkers & Prevention, 2004
    Co-Authors: Joshua D Lambert, Pius Maliakal, Saileta Prabhu, Xiaofeng Meng, Chitang Ho, Hong Lu, Chung S Yang
    Abstract:

    Catechins and theaflavins, polyphenolic compounds derived from tea ( Camellia sinensis , fam. Theaceae), have been reported to have a wide range of biological activities including prevention of tooth decay and oral cancer. The present study was undertaken to determine the usefulness of green tea leaves and black tea extract for the delivery of catechins and theaflavins to the oral cavity. After holding either green tea leaves (2 g) or brewed black tea (2 g of black tea leaves in 100 ml) in the mouth for 2–5 min and thoroughly rinsing the mouth, high concentrations of catechins ( C max = 131.0–2.2 μm) and theaflavins ( C max = 1.8–0.6 μm) were observed in saliva in the 1st hour. Whereas there was significant interindividual variation in the peak levels of catechins and theaflavins, the overall kinetic profile was similar, with t 1/2 = 25–44 min and 49–76 min for catechins and theaflavins, respectively (average coefficient of variation in t 1/2 was 23.4%). In addition to the parent catechin and theaflavin peaks, five unidentified peaks were also observed in saliva after black tea treatment. Hydrolysis of theaflavin gallates, apparently by salivary esterases, was observed in vitro and in vivo . These results indicate that tea leaves can be used as a convenient, slow-release source of catechins and theaflavins and provide information for the possible use of tea in the prevention of oral cancer and dental caries.

  • theadibenzotropolone a a new type pigment from enzymatic oxidation of epicatechin and epigallocatechin gallate and characterized from black tea using lc ms ms
    Tetrahedron Letters, 2002
    Co-Authors: Shengmin Sang, Chung S Yang, Xiaofeng Meng, Robert T. Rosen, Shiying Tian, Ruth E Stark, Chitang Ho
    Abstract:

    Abstract Theaflavins and thearubigins are major pigments of black tea. In the course of studies on the oxidation mechanism of tea polyphenols, a new type of tea pigment, theadibenzotropolone A, together with theaflavin 3-gallate were formed by the reaction of (−)-epicatechin (EC) and (−)-epigallocatechin gallate (EGCG) with horseradish peroxidase in the presence of H 2 O 2 . The structure of theadibenzotropolone A was elucidated on the basis of MS and 2D NMR spectroscopic analyses. The observation that galloyl ester groups of theaflavins can be oxidized to form dibenzotropolone skeletons strongly implied that this type of oxidation as an important pathway to extend the molecular size of thearubigins. The existence of this compound in black tea was characterized by LC/ESI-MS/MS. Theadibenzotropolone A is the first theaflavin type trimer of catechins in black tea.

  • Theadibenzotropolone A, a new type pigment from enzymatic oxidation of (−)-epicatechin and (−)-epigallocatechin gallate and characterized from black tea using LC/MS/MS
    Tetrahedron Letters, 2002
    Co-Authors: Shengmin Sang, Xiaofeng Meng, Robert T. Rosen, Shiying Tian, Ruth E Stark, Chung S Yang
    Abstract:

    Abstract Theaflavins and thearubigins are major pigments of black tea. In the course of studies on the oxidation mechanism of tea polyphenols, a new type of tea pigment, theadibenzotropolone A, together with theaflavin 3-gallate were formed by the reaction of (−)-epicatechin (EC) and (−)-epigallocatechin gallate (EGCG) with horseradish peroxidase in the presence of H 2 O 2 . The structure of theadibenzotropolone A was elucidated on the basis of MS and 2D NMR spectroscopic analyses. The observation that galloyl ester groups of theaflavins can be oxidized to form dibenzotropolone skeletons strongly implied that this type of oxidation as an important pathway to extend the molecular size of thearubigins. The existence of this compound in black tea was characterized by LC/ESI-MS/MS. Theadibenzotropolone A is the first theaflavin type trimer of catechins in black tea.

  • inhibition of activator protein 1 activity and cell growth by purified green tea and black tea polyphenols in h ras transformed cells structure activity relationship and mechanisms involved
    Cancer Research, 1999
    Co-Authors: Jee Y Chung, Zigang Dong, Xiaofeng Meng, Chuanshu Huang, Chung S Yang
    Abstract:

    ras gene mutation, which perpetually turns on the growth signal transduction pathway, occurs frequently in many cancer types. The mouse epidermal JB6 cell line has been transfected with a mutant H-ras gene to mimic carcinogenesis in vitro. These transformed cells (30.7b Ras 12) are able to grow in soft agar, exhibiting anchorage independence and high endogenous activator protein 1 (AP-1) activity, which can be detected by a stable AP-1 luciferase reporter. The present study investigated the ability of different pure green and black tea polyphenols to inhibit this ras signaling pathway. The major green tea polyphenols (catechins), (−)-epigallocatechin-3-gallate (EGCG), (−)-epigallocatechin, (−)-epicatechin-3-gallate, (−)-epicatechin, and their epimers, and black tea polyphenols, theaflavin, Theaflavin-3-Gallate, theaflavin-3′-gallate, and theaflavin-3,3′-digallate (TFdiG), were compared with respect to their ability to inhibit the growth of 30.7b Ras 12 cells and AP-1 activity. All of the tea polyphenols except (−)-epicatechin showed strong inhibition of cell growth and AP-1 activity. Among the catechins, both the galloyl structure on the B ring and the gallate moiety contributed to the growth inhibition and AP-1 activity; the galloyl structure appeared to have a stronger effect on the inhibitory action than the gallate moiety. The epimers of the catechins showed similar inhibitory effects on AP-1 activity. The addition of catalase to the incubation of the cells with EGCG or TFdiG did not prevent the inhibitory effect on AP-1 activity, suggesting that H2O2 does not play a significant role in the inhibition by tea polyphenols. Both EGCG and TFdiG inhibited the phosphorylation of p44/42 (extracellular signal-regulated kinase 1 and 2) and c-jun without affecting the levels of phosphorylated-c-jun-NH2-terminal kinase. TFdiG inhibited the phosphorylation of p38, but EGCG did not. EGCG lowered the level of c-jun, whereas TFdiG decreased the level of fra-1. These results suggest that tea polyphenols inhibited AP-1 activity and the mitogen-activated protein kinase pathway, which contributed to the growth inhibition; however, different mechanisms may be involved in the inhibition by catechins and theaflavins.

Huadong Chen - One of the best experts on this subject based on the ideXlab platform.

  • The Microbiota Is Essential for the Generation of Black Tea Theaflavins-Derived Metabolites
    2016
    Co-Authors: Huadong Chen, Javier Rivera Guzman, Nicholas D. Gillitt, Salam A. Ibrahim, Saeed Hayek, Shengmin Sang
    Abstract:

    Background: Theaflavins including theaflavin (TF), Theaflavin-3-Gallate (TF3G), theaflavin-39-gallate (TF39G), and theaflavin-3,39-digallate (TFDG), are the most important bioactive polyphenols in black tea. Because of their poor systemic bioavailability, it is still unclear how these compounds can exert their biological functions. The objective of this study is to identify the microbial metabolites of theaflavins in mice and in humans. Methods and Findings: In the present study, we gavaged specific pathogen free (SPF) mice and germ free (GF) mice with 200 mg/kg TFDG and identified TF, TF3G, TF39G, and gallic acid as the major fecal metabolites of TFDG in SPF mice. These metabolites were absent in TFDG- gavaged GF mice. The microbial bioconversion of TFDG, TF3G, and TF39G was also investigated in vitro using fecal slurries collected from three healthy human subjects. Our results indicate that TFDG is metabolized to TF, TF3G, TF39G, gallic acid, and pyrogallol by human microbiota. Moreover, both TF3G and TF39G are metabolized to TF, gallic acid, and pyrogallol by human microbiota. Importantly, we observed interindividual differences on the metabolism rate of gallic acid to pyrogallol among the three human subjects. In addition, we demonstrated that Lactobacillus plantarum 299v and Bacillus subtilis have the capacity to metabolize TFDG. Conclusions: The microbiota is important for the metabolism of theaflavins in both mice and humans. The in vivo functiona

  • The microbiota is essential for the generation of black tea theaflavins-derived metabolites.
    PloS one, 2012
    Co-Authors: Huadong Chen, Saeed A. Hayek, Javier Rivera Guzman, Nicholas D. Gillitt, Salam A. Ibrahim, Christian Jobin, Shengmin Sang
    Abstract:

    Background Theaflavins including theaflavin (TF), Theaflavin-3-Gallate (TF3G), theaflavin-3′-gallate (TF3′G), and theaflavin-3,3′-digallate (TFDG), are the most important bioactive polyphenols in black tea. Because of their poor systemic bioavailability, it is still unclear how these compounds can exert their biological functions. The objective of this study is to identify the microbial metabolites of theaflavins in mice and in humans.

  • The microbiota is essential for the generation of black tea theaflavins-derived metabolites.
    PloS one, 2012
    Co-Authors: Huadong Chen, Saeed A. Hayek, Javier Rivera Guzman, Nicholas D. Gillitt, Salam A. Ibrahim, Christian Jobin, Shengmin Sang
    Abstract:

    Theaflavins including theaflavin (TF), Theaflavin-3-Gallate (TF3G), theaflavin-3'-gallate (TF3'G), and theaflavin-3,3'-digallate (TFDG), are the most important bioactive polyphenols in black tea. Because of their poor systemic bioavailability, it is still unclear how these compounds can exert their biological functions. The objective of this study is to identify the microbial metabolites of theaflavins in mice and in humans. In the present study, we gavaged specific pathogen free (SPF) mice and germ free (GF) mice with 200 mg/kg TFDG and identified TF, TF3G, TF3'G, and gallic acid as the major fecal metabolites of TFDG in SPF mice. These metabolites were absent in TFDG- gavaged GF mice. The microbial bioconversion of TFDG, TF3G, and TF3'G was also investigated in vitro using fecal slurries collected from three healthy human subjects. Our results indicate that TFDG is metabolized to TF, TF3G, TF3'G, gallic acid, and pyrogallol by human microbiota. Moreover, both TF3G and TF3'G are metabolized to TF, gallic acid, and pyrogallol by human microbiota. Importantly, we observed interindividual differences on the metabolism rate of gallic acid to pyrogallol among the three human subjects. In addition, we demonstrated that Lactobacillus plantarum 299v and Bacillus subtilis have the capacity to metabolize TFDG. The microbiota is important for the metabolism of theaflavins in both mice and humans. The in vivo functional impact of microbiota-generated theaflavins-derived metabolites is worthwhile of further study.

  • structural identification of theaflavin trigallate and tetragallate from black tea using liquid chromatography electrospray ionization tandem mass spectrometry
    Journal of Agricultural and Food Chemistry, 2012
    Co-Authors: Huadong Chen, Kelly L Shurlknight, Tinchung Leung, Shengmin Sang
    Abstract:

    Black tea contains two major pigments, theaflavins and thearubigins. These polyphenols have been associated with certain health benefits including prevention of heart disease and cancer. Elucidating and characterizing the structural aspects of thearubigins, the most abundant pigment in black tea, has been a challenge for many years. Therefore further studies of black tea polyphenols must be conducted in effort to solve this thearubigin dispute. In the present study, black tea extract was found to possess theaflavin trigallate and tetragallate by means of liquid chromatography/electrospray ionization mass spectrometry. These structures were confirmed by analysis of the MS(n) (n = 1-4) spectra and comparison of the MS/MS spectra of the product ions to the MS/MS spectra of authentic (-)-epigallocatechin-3-gallate, (-)-epicatechin-3-gallate and theaflavin-3,3'-digallate. To our knowledge, this is the first report to confirm the presence of theaflavin trigallate and tetragallate in black tea.

  • structural identification of mouse fecal metabolites of theaflavin 3 3 digallate using liquid chromatography tandem mass spectrometry
    Journal of Chromatography A, 2011
    Co-Authors: Huadong Chen, Nicholas D. Gillitt, Christian Jobin, Tiffany A Parks, Xiaoxin Chen, Shengmin Sang
    Abstract:

    Black tea consumption has been associated with many health benefits including the prevention of cancer and heart disease. Theaflavins are the major bioactive polyphenols present in black tea. Unfortunately, limited information is available on their biotransformation. In the present study, we investigated the metabolic fate of theaflavin 3,3′-digallate (TFDG), one of the most abundant and bioactive theaflavins, in mouse fecal samples using liquid chromatography/electrospray ionization tandem mass spectrometry by analyzing the MSn (n = 1–3) spectra. Four metabolites theaflavin, theaflavin 3-gallate, theaflavin 3′-gallate, and gallic acid were identified as the major mouse fecal metabolites of TFDG. Glucuronidated and sulfated, instead of methylated metabolites of theaflavin 3-gallate, theaflavin 3′-gallate, and TFDG were detected and identified as the minor mouse fecal metabolites of TFDG. Our results indicate that TFDG can be degraded in mice. Further studies on the formation of those metabolites in TFDG-treated mice in germ-free conditions are warranted. To our knowledge, this is the first report on the biotransformation of TFDG in mice.