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Journal of Zhejiang University SCIENCE B 2011 Vol.12 No.9 P.744-751


Evaluation of the antioxidant effects of four main theaflavin derivatives through chemiluminescence and DNA damage analyses

Author(s):  Yuan-yuan Wu, Wei Li, Yi Xu, En-hui Jin, You-ying Tu

Affiliation(s):  Department of Tea Science, Zhejiang University, Hangzhou 310058, China, Key Laboratory of Horticultural Plants Growth, Development and Quality Improvement, Ministry of Agriculture, Zhejiang University, Hangzhou 310058, China, Department of Tea Culture, Zhejiang Shuren University, Hangzhou 310015, China

Corresponding email(s):   youytu@zju.edu.cn

Key Words:  Theaflavin derivatives, Black tea, Antioxidant capacity, DNA oxidative damage

Yuan-yuan Wu, Wei Li, Yi Xu, En-hui Jin, You-ying Tu. Evaluation of the antioxidant effects of four main theaflavin derivatives through chemiluminescence and DNA damage analyses[J]. Journal of Zhejiang University Science B, 2011, 12(9): 744-751.

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author="Yuan-yuan Wu, Wei Li, Yi Xu, En-hui Jin, You-ying Tu",
journal="Journal of Zhejiang University Science B",
publisher="Zhejiang University Press & Springer",

%0 Journal Article
%T Evaluation of the antioxidant effects of four main theaflavin derivatives through chemiluminescence and DNA damage analyses
%A Yuan-yuan Wu
%A Wei Li
%A Yi Xu
%A En-hui Jin
%A You-ying Tu
%J Journal of Zhejiang University SCIENCE B
%V 12
%N 9
%P 744-751
%@ 1673-1581
%D 2011
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.B1100041

T1 - Evaluation of the antioxidant effects of four main theaflavin derivatives through chemiluminescence and DNA damage analyses
A1 - Yuan-yuan Wu
A1 - Wei Li
A1 - Yi Xu
A1 - En-hui Jin
A1 - You-ying Tu
J0 - Journal of Zhejiang University Science B
VL - 12
IS - 9
SP - 744
EP - 751
%@ 1673-1581
Y1 - 2011
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.B1100041

Theaflavins (TFs) are the dimers of a couple of epimerized catechins, which are specially formed during black tea fermentation. To explore the differences among four main TF derivatives (theaflavin (TF1), theaflavin-3-gallate (TF2A), theaflavin-3′-gallate (TF2B), and theaflavin-3,3′-digallate (TF3)) in scavenging reactive oxygen species (ROS) in vitro, their properties of inhibiting superoxide, singlet oxygen, hydrogen peroxide, and the hydroxyl radical, and their effects on hydroxyl radical-induced DNA oxidative damage were systematically analyzed in the present study. The results show that, compared with (−)-epigallocatechin gallate (EGCG), TF derivatives were good antioxidants for scavenging ROS and preventing the hydroxyl radical-induced DNA damage in vitro. TF3 was the most positive in scavenging hydrogen peroxide and hydroxyl radical, and TF1 suppressed superoxide. Positive antioxidant capacities of TF2B on singlet oxygen, hydrogen peroxide, hydroxyl radical, and the hydroxyl radical-induced DNA damage in vitro were found. The differences between the antioxidant capacities of four main TF derivatives in relation to their chemical structures were also discussed. We suggest that these activity differences among TF derivatives would be beneficial to scavenge different ROS with therapeutic potential.

Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article


[1]Anderson, R.F., Fisher, L.J., Hara, Y., Harris, T., Mak, W.B., Melton, L.D., Packer, J.E., 2001. Green tea catechins partially protect DNA from ·OH radical-induced strand breaks and base damage through fast chemical repair of DNA radicals. Carcinogenesis, 22(8):1189-1193.

[2]Balentine, D.A., Wiseman, S.A., Bouwens, L.C.M., 1997. The chemistry of tea flavonoids. Crit. Rev. Food Sci. Nutr., 37(8):693-704.

[3]Blumberg, J., 2003. Introduction to the proceedings of the third international scientific symposium on tea and human health: role of flavonoids in the diet. J. Nutr., 133(10):3244S-3246S.

[4]Bushman, J.L., 1998. Green tea and cancer in humans: a review of the literature. Nutr. Cancer, 31(3):151-159.

[5]Cooke, M.S., Evans, M.D., Dizdaroglu, M., Lunec, J., 2003. Oxidative DNA damage: mechanism, mutation, and disease. Faseb. J., 17(10):1195-1214.

[6]Deby-Dupont, G., Deby, C., Mouithys-Mickalad, A., Hoebeke, M., Mathy-Hartert, M., Jadoul, L., Vandenberghe, A., Lamy, M., 1998. The antibiotic ceftazidime is a singlet oxygen quencher as demonstrated by ultra-weak chemiluminescence and by inhibition of AAP consumption. Biochim. Biophys. Acta, 1379(1):61-68.

[7]Finkel, T., Holbrook, N.J., 2000. Oxidants, oxidative stress and the biology of ageing. Nature, 408(6809):239-247.

[8]Hussain, S.P., Hofseth, L.J., Harris, C.C., 2003. Radical causes of cancer. Nat. Rev. Cancer, 3(4):276-285.

[9]Jhoo, J.W., Lo, C.Y., Li, S.M., Sang, S.M., Ang, C.Y.W., Heinze, T.M., Ho, C.T., 2005. Stability of black tea polyphenol, theaflavin, and identification of theanaphthoquinone as its major radical reaction product. J. Agric. Food Chem., 53(15):6146-6150.

[10]Jovanovic, S.V., Hara, Y., Steenken, S., Simic, M.G., 1997. Antioxidant potential of theaflavins. A pulse radiolysis study. J. Am. Chem. Soc., 119(23):5337-5343.

[11]Leung, L.K., Su, Y.L., Chen, R.Y., Zhang, Z.H., Huang, Y., Chen, Z.Y., 2001. Theaflavins in black tea and catechins in green tea are equally effective antioxidants. J. Nutr., 131(9):2248-2251.

[12]Lewis, J.G., Stewart, W., Adams, D.O., 1988. Role of oxygen radicals in induction of DNA damage by metabolite of benzene. Cancer Res., 48(17):4762-4765.

[13]Li, W., Wu, J.X., Tu, Y.Y., 2010. Synergistic effects of tea polyphenols and ascorbic acid on human lung adenocarcinoma SPC-A-1 cells. J. Zhejiang Univ.-Sci. B, 11(6):458-464.

[14]Lin, J.K., Chen, P.C., Ho, C.T., Lin-Shiau, S.Y., 2000. Inhibition of xanthine oxidase and suppression of intracellular reactive oxygen species in HL-60 cells by theaflavin-3, 3′-digallate, (−)-epigallocatechin-3-gallate, and propyl gallate. J. Agric. Food. Chem., 48(7):2736-2743.

[15]Lin, Y.L., Tsai, S.H., Lin-Shiau, S.Y., Ho, C.T., Lin, J.K., 1999. Theaflavin-3,3′-digallate from black tea blocks the nitric oxide synthase by downregulating the activation of NF-kappaB in macrophages. Eur. J. Pharmacol., 367(2-3):379-388.

[16]Miller, N.J., Castelluccio, C., Tijburg, L., Rice-Evans, C.A., 1996. The antioxidant properties of theaflavins and their gallate esters-free radical scavengers or metal chelators. FEBS Lett., 392(1):40-44.

[17]Miyamoto, S., Martinez, G.R., Medeiros, M.H.G., Di-Mascio, P., 2003. Singlet molecular oxygen generated from lipid hydroperoxides by the Russell mechanism: studies using 18O-labeled linoleic acid hydroperoxide and monomol light emission measurements. J. Am. Chem. Soc., 125(20):6172-6179.

[18]Rice-Evans, C.A., Miller, N.J., Paganga, G., 1997. Antioxidant properties of phenolic compounds. Trends Plant Sci., 2(4):152-159.

[19]Roberts, E.A.H., 1958. The phenolic substances of manufactured tea. J. Sci. Food Agric., 9(4):212-216.

[20]Tian, B., Hua, Y.J., 2005. Concentration dependence of prooxidant and antioxidant effects of aloin and aloe-emodin on DNA. Food Chem., 91(3):413-418.

[21]Tian, B., Wu, Y.Y., Sheng, D.H., Zheng, Z.G., Gao, G.J., Hua, Y.J., 2004. Chemiluminescence assay for reactive oxygen species scavenging activities and inhibition on oxidative damage of DNA in Deinococcus radiodurans. Luminescence, 19(2):78-84.

[22]Trevisanato, S.I., Kim, Y.I., 2000. Tea and health. Nutr. Rev., 58(1):1-10.

[23]Tu, Y.Y., Xia, H.L., 2004. Immobilized Polyphenol Oxidase Catalyze Purified Tea Polyphenols into High Quality Theaflavins. China Patent 02136982.8 ZL.

[24]Tu, Y.Y., Xu, X.Q., Xia, H.L., Watanabe, N., 2005. Optimization of theaflavins biosynthesis from tea polyphenols using an immobilized enzyme system and response surface methodology. Biotechnol. Lett., 27(4):269-274.

[25]Wang, J., Xing, D., 2002. Detection of vitamin C-induced singlet oxygen formation in oxidized LDL using MCLA as a chemiluminescence probe. Acta Biochim. Biophys. Sin., 34(1):11-15.

[26]Xu, Y., Jin, Y.X., Wu, Y.Y., Tu, Y.Y., 2010. Isolation and purification of four individual theaflavins using semi-preparative high performance liquid chromatography. J. Liq. Chromatogr. R. T., 33(20):1791-1801.

[27]Yang, C.S., Wang, X., Lu, G., Picinich, S.C., 2009. Cancer prevention by tea: animal studies, molecular mechanisms and human relevance. Nat. Rev. Cancer, 9(6):429-439.

[28]Yang, Z.Y., Tu, Y.Y., Xia, H.L., Jie, G.L., Chen, X.M., He, P.M., 2007. Suppression of free-radicals and protection against H2O2-induced oxidative damage in HPF-1 cell by oxidized phenolic compounds present in black tea. Food Chem., 105(4):1349-1356.

[29]Yang, Z.Y., Jie, G.L., Dong, F., Xu, Y., Watanabe, N., Tu, Y.Y., 2008. Radical-scavenging abilities and antioxidant properties of theaflavins and their gallate esters in H2O2-mediated oxidative damage system in the HPF-1 cells. Toxicol. in Vitro, 22(5):1250-1256.

[30]Yu, W.L., Zhao, Y.P., 2005. Chemiluminescence evaluation of oxidative damage to biomolecules induced by singlet oxygen and the protective effects of antioxidants. Biochim. Biophys. Acta, 1725(1):30-34.

[31]Zhu, Y.X., Huang, H., Tu, Y.Y., 2006. A review of recent studies in China on the possible beneficial health effects of tea. Int. J. Food Sci. Tech., 41(4):333-340.

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