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Chemical Compound Review

Theaflavin     6,8,9-trihydroxy-3,11- bis[(2S,3R)-3,5,7...

Synonyms: Theaflavine, Theaflavin 1, SPECTRUM200111, SureCN19551, CHEMBL346119, ...
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Disease relevance of AIDS-051702

  • Our objective was to study the impact of a theaflavin-enriched green tea extract on the lipids and lipoproteins of subjects with mild to moderate hypercholesterolemia [1].
  • Here, we demonstrated the effects of theanaphthoquinone (TNQ), a member of the thearubigins generated by the oxidation of theaflavin (TF-1), on the expression of FAS in human breast cancer cells [2].
  • Study by electron microscope revealed that EGCg and TF3 (1 mM) agglutinated influenza viruses as well as did antibody, and that they prevented the viruses from adsorbing to MDCK cells [3].
  • The exposure of human stomach cancer KATO III cells to black tea theaflavin extract, free theaflavin, and theaflavin digallate that are main components of the extract, led to both growth inhibition and the induction of programmed cell death (apoptosis) [4].
  • These results indicate that tea, especially black tea, may be used as a source of anti-HIV agents and theaflavin derivatives may be applied as lead compounds for developing HIV-1 entry inhibitors targeting gp41 [5].

High impact information on AIDS-051702


Biological context of AIDS-051702


Anatomical context of AIDS-051702

  • Although theaflavin inhibited ovine COX-2, its activity in the formation of PGE(2) was stimulated by theaflavin when ovine COX-2 was mixed with microsomes, suggesting that theaflavin affects the interaction of COX-2 with other microsomal factors (e.g. PGE synthase) [14].
  • The theaflavin fraction is responsible for the facilitatory effect of black tea at the skeletal myoneural junction [15].
  • The theaflavin fraction (Tfs) produced a concentration- dependent facilitation of indirect twitch responses of the rat phrenic nerve diaphragm preparation and the facilitation was dependent on the amount of calcium present in the bathing fluid [15].
  • The stability of theaflavin was studied in varying pH solutions: simulated gastric juice and buffer solutions of pH 5.5, pH 7.4, and pH 8 [16].
  • The growth inhibitory effects of a theaflavin mixture from black tea were more pronounced to malignant (CAL27; HSC-2; HSG1) and immortalized (S-G; GT1) cells than to normal (HGF-2) cells from the human oral cavity [17].

Associations of AIDS-051702 with other chemical compounds


Gene context of AIDS-051702

  • Catechins and all other low-molecular-weight polyphenols except theaflavin derived from balck tea did not show significant GTase-inhibitory activities [21].
  • Theaflavin also significantly reduced tumor necrosis factor-alpha-mediated DNA binding of activator protein-1 [9].
  • RT-PCR analysis also showed theaflavin to be the most important constituent in down-regulating synthesis of iNOS [22].
  • From the estimation of five major catechins, PPO activities in young shoots, and theaflavin and thearubigin contents of crushed, torn, and curled (CTC) black teas, the superior variety and flavorful flush characteristics were refined [23].
  • This result indicated that the benzotropolone moiety in theaflavin may play an important role in its antioxidant properties [16].

Analytical, diagnostic and therapeutic context of AIDS-051702


  1. Cholesterol-lowering effect of a theaflavin-enriched green tea extract: a randomized controlled trial. Maron, D.J., Lu, G.P., Cai, N.S., Wu, Z.G., Li, Y.H., Chen, H., Zhu, J.Q., Jin, X.J., Wouters, B.C., Zhao, J. Arch. Intern. Med. (2003) [Pubmed]
  2. Theanaphthoquinone inhibits fatty acid synthase expression in EGF-stimulated human breast cancer cells via the regulation of EGFR/ErbB-2 signaling. Weng, M.S., Ho, C.T., Ho, Y.S., Lin, J.K. Toxicol. Appl. Pharmacol. (2007) [Pubmed]
  3. Inhibition of the infectivity of influenza virus by tea polyphenols. Nakayama, M., Suzuki, K., Toda, M., Okubo, S., Hara, Y., Shimamura, T. Antiviral Res. (1993) [Pubmed]
  4. Black tea theaflavins induce programmed cell death in cultured human stomach cancer cells. Hibasami, H., Komiya, T., Achiwa, Y., Ohnishi, K., Kojima, T., Nakanishi, K., Sugimoto, Y., Hasegawa, M., Akatsuka, R., Hara, Y. Int. J. Mol. Med. (1998) [Pubmed]
  5. Theaflavin derivatives in black tea and catechin derivatives in green tea inhibit HIV-1 entry by targeting gp41. Liu, S., Lu, H., Zhao, Q., He, Y., Niu, J., Debnath, A.K., Wu, S., Jiang, S. Biochim. Biophys. Acta (2005) [Pubmed]
  6. Differential effects of theaflavin monogallates on cell growth, apoptosis, and Cox-2 gene expression in cancerous versus normal cells. Lu, J., Ho, C.T., Ghai, G., Chen, K.Y. Cancer Res. (2000) [Pubmed]
  7. Effect of black and green tea polyphenols on c-jun phosphorylation and H(2)O(2) production in transformed and non-transformed human bronchial cell lines: possible mechanisms of cell growth inhibition and apoptosis induction. Yang, G.Y., Liao, J., Li, C., Chung, J., Yurkow, E.J., Ho, C.T., Yang, C.S. Carcinogenesis (2000) [Pubmed]
  8. Tea polyphenols and theaflavins are present in prostate tissue of humans and mice after green and black tea consumption. Henning, S.M., Aronson, W., Niu, Y., Conde, F., Lee, N.H., Seeram, N.P., Lee, R.P., Lu, J., Harris, D.M., Moro, A., Hong, J., Pak-Shan, L., Barnard, R.J., Ziaee, H.G., Csathy, G., Go, V.L., Wang, H., Heber, D. J. Nutr. (2006) [Pubmed]
  9. Theaflavin, a black tea extract, is a novel anti-inflammatory compound. Aneja, R., Odoms, K., Denenberg, A.G., Wong, H.R. Crit. Care Med. (2004) [Pubmed]
  10. Delivery of tea polyphenols to the oral cavity by green tea leaves and black tea extract. Lee, M.J., Lambert, J.D., Prabhu, S., Meng, X., Lu, H., Maliakal, P., Ho, C.T., Yang, C.S. Cancer Epidemiol. Biomarkers Prev. (2004) [Pubmed]
  11. Tea polyphenols inhibit acetyl-CoA:1-alkyl-sn-glycero-3-phosphocholine acetyltransferase (a key enzyme in platelet-activating factor biosynthesis) and platelet-activating factor-induced platelet aggregation. Sugatani, J., Fukazawa, N., Ujihara, K., Yoshinari, K., Abe, I., Noguchi, H., Miwa, M. Int. Arch. Allergy Immunol. (2004) [Pubmed]
  12. Two types of oxidative dimerization of the black tea polyphenol theaflavin. Tanaka, T., Inoue, K., Betsumiya, Y., Mine, C., Kouno, I. J. Agric. Food Chem. (2001) [Pubmed]
  13. Studies with black tea and its constituents on leukemic cells and cell lines. Das, M., Chaudhuri, T., Goswami, S.K., Murmu, N., Gomes, A., Mitra, S., Besra, S.E., Sur, P., Vedasiromoni, J.R. J. Exp. Clin. Cancer Res. (2002) [Pubmed]
  14. Effects of purified green and black tea polyphenols on cyclooxygenase- and lipoxygenase-dependent metabolism of arachidonic acid in human colon mucosa and colon tumor tissues. Hong, J., Smith, T.J., Ho, C.T., August, D.A., Yang, C.S. Biochem. Pharmacol. (2001) [Pubmed]
  15. The theaflavin fraction is responsible for the facilitatory effect of black tea at the skeletal myoneural junction. Basu, S., Chaudhuri, T., Chauhan, S.P., Das Gupta, A.K., Chaudhury, L., Vedasiromoni, J.R. Life Sci. (2005) [Pubmed]
  16. Stability of black tea polyphenol, theaflavin, and identification of theanaphthoquinone as its major radical reaction product. Jhoo, J.W., Lo, C.Y., Li, S., Sang, S., Ang, C.Y., Heinze, T.M., Ho, C.T. J. Agric. Food Chem. (2005) [Pubmed]
  17. In vitro cytotoxicity of a theaflavin mixture from black tea to malignant, immortalized, and normal cells from the human oral cavity. Babich, H., Pinsky, S.M., Muskin, E.T., Zuckerbraun, H.L. Toxicology in vitro : an international journal published in association with BIBRA. (2006) [Pubmed]
  18. Effects of tea polyphenols on the invasion and matrix metalloproteinases activities of human fibrosarcoma HT1080 cells. Maeda-Yamamoto, M., Kawahara, H., Tahara, N., Tsuji, K., Hara, Y., Isemura, M. J. Agric. Food Chem. (1999) [Pubmed]
  19. Apoptosis-inducing activity of polyphenol compounds derived from tea catechins in human histiolytic lymphoma U937 cells. Saeki, K., Sano, M., Miyase, T., Nakamura, Y., Hara, Y., Aoyagi, Y., Isemura, M. Biosci. Biotechnol. Biochem. (1999) [Pubmed]
  20. Suppression of fatty acid synthase in MCF-7 breast cancer cells by tea and tea polyphenols: a possible mechanism for their hypolipidemic effects. Yeh, C.W., Chen, W.J., Chiang, C.T., Lin-Shiau, S.Y., Lin, J.K. Pharmacogenomics J. (2003) [Pubmed]
  21. Inhibitory effect of oolong tea polyphenols on glycosyltransferases of mutans Streptococci. Nakahara, K., Kawabata, S., Ono, H., Ogura, K., Tanaka, T., Ooshima, T., Hamada, S. Appl. Environ. Microbiol. (1993) [Pubmed]
  22. Black tea is a powerful chemopreventor of reactive oxygen and nitrogen species: comparison with its individual catechin constituents and green tea. Sarkar, A., Bhaduri, A. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  23. Fermentation characteristics of some assamica clones and process optimization of black tea manufacturing. Baruah, A.M., Mahanta, P.K. J. Agric. Food Chem. (2003) [Pubmed]
  24. An in vitro study of theaflavins extracted from black tea to neutralize bovine rotavirus and bovine coronavirus infections. Clark, K.J., Grant, P.G., Sarr, A.B., Belakere, J.R., Swaggerty, C.L., Phillips, T.D., Woode, G.N. Vet. Microbiol. (1998) [Pubmed]
  25. Reaction of iron(III) with theaflavin: complexation and oxidative products. O'Coinceanainn, M., Bonnely, S., Baderschneider, B., Hynes, M.J. J. Inorg. Biochem. (2004) [Pubmed]
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