Research Advances in Thearubigins of Tea

doi:10.11924/j.issn.1000-6850.2013-2780

Abstract

Abstract: Thearubigin, the main component of black tea soup color, is a kind of large molecular weight phenolic substance. Its content and changes play a crucial role in tea quality and human health. This paper reviewed the research progress of thearubigin discovery and development from some aspects of summary, such as formation pathway, preparation and separation. We also discussed its pharmacological function and application, including anti-oxidation, anti-aging, anti-mutation, anti-tumor, anti-cancer, anti-inflammatory, anti- leukemia, anti- toxin, obesity prevention and deodorization activities, further more, especially, its prospects of applying in food pigment and chemical industry. In the review of these findings, the result was confirmed that thearubigin research in the future will be focused on introduction of enzyme- relative engineering into purification technique and monomer compound bioactivity study.

References

[1] 李大祥,王华,白蕊,等.茶红素化学及生物学活性研究进展[J].茶叶科学,2013,33(4):327-335.
[2] Wan Xiaochun, Li Daxiang, Zhang Zhengzhu. Green and Black teas: Manufacturing and consumption[A].// Chi-Tang Ho, Jen-Kun Lin, Fereidoon Shahidi. Tea and Tea Products: Chemistry and Health Promoting Properties[C]. CRC Press, Talyor & Francis Group, 2008:1-8.
[3] 沈丽萍.茶黄素研究进展[J].中国农学通报,2010,26(1):134-139.
[4] 程启坤.红茶制造化学研究进展[J].国外农学-茶叶,1984(2):1-10.
[5] Osima Y S. Bull[J]. Agric Sci Chem Soc Japan,1940,16:l06.
[6] Bradrield A E, Penney M. The chemical composition of tea- the approximate composition of a black tea liquor and its relation to quality[J]. Chem and lnd,1944,22:306-310.
[7] Roberts E A H. The chemistry of tea fermentation[J]. J Sci Food Agric,1952,3:l93-196.
[8] 宛晓春.茶叶生物化学(3版)[M].北京:中国农业出版社,2003:8-11, 30-31,180-199,275-278.
[9] Brown A G, Eyton W B, Holmes A. Identification of the thearubigins as polymeric proanthocyanidins[J]. Phytochemistry, 1969(8):2333-2340.
[10] Ozawa T, Kataoka M, Morikawa K, et al. Elucidation of the partial structure of polymeric thearubigins from black tea by chemical degradation[J]. Biosci Biotechnol Biochem, 1996,60(12): 2023- 2027.
[11] Davies A P, Goodsall C, Cai Y, et al. Black tea dimeric and oligomeric pigments—Structures and formation[A].// Gross GG, Hemingway R W, Yoshida T, et al. Plant polyphenols2—Chemistry, biology, pharmacology, ecology[C]. New York: Kluwer Academic/ Plenum Publishers,1999:697-723.
[12] Edwin Haslam. Thoughts on thearubigins[J]. Phytochemistry,2003, 64:61-73.
[13] Menet M C, Sang S, Yang C S, et al. Analysis of theaflavins and thearubigins from black tea Extract by MALDI- TOF mass spectrometry[J]. J Agric Food Chem, 2004, 52(9): 2455-2461.
[14] Kuhnert N. Unraveling the structure of the black tea thearubigins [J]. Arch Biochem Biophys,2010,501:37-51.
[15] Drynan J W, Clifford M N, Obuchowicz, et al. MALDI-TOF mass spectrometry: avoidance of artifacts and analysis of caffeineprecipitated SII thearubigins from 15 commercial black teas[J]. J Agric Food Chem,2012,60:4514-4525.
[16] Luczaj W, Skrzydlewska E. Antioxidative properties of black tea[J]. Prev Med,2005,40:910-918.
[17] 李大祥,宛晓春,杨昌军,等,茶儿茶素氧化机理[J].天然产物研究与开发,2006,18(1):171-181.
[18] Krishnan R, Maru G B. Isolation and analyses of polymeric polyphenol fractions from black tea[J]. Food Chem,2006,94(3):331- 340.
[19] Cattell- D J, NurSten H E. Fractionation and chemistry of ethyl acetate-soluble thearubigins from black tea[J]. Phytochemistry,1976, 15:1967-1970.
[20] Cattell D J, Nursten H E. Separation of thearubigins On Sephadex LH-20[J]. Phytochemistry,1977,16:1269-1272.
[21] Hazarika M, Chakravarty K C, Mahanta P K. Studies on thearubigin pigments in black tea manufacturing systems[J]. J Sci Food Agric,1984,35:1208-1218.
[22] McDowell I, Taylor S, Cay C . The phenolic pigment composition of black tea liquors-Part I: Predicting quality[J]. J Sci Food Agric, 1995,69:467-474.
[23] 萧伟祥,钟瑾,萧慧,等,茶红色素形成机理与制取[J].茶叶科学, 1997,17(1):1-8.
[24] Deugernhardt A, Engelhardt U H, Wendt A S, et a1. Isolation of black tea pigments using high- speed countercurrent chromatography and studies on properties of black tea polymers[J]. J Sci Food Agric,2000,48:5200-5205.
[25] 王华.茶红素分离制备及清除自由基活性的初步研究[D].合肥:安徽农业大学,2007.
[26] Chen N, Bezzina R, Hinch E, et al. Green tea, black tea, and epigallocatechin modify body composition, improve glucose tolerance, and differentially alter metabolic gene expression in rats fed a high-fat diet[J]. Nutr Res,2009,29(11):784-793.
[27] Lorenz M, Urban J, Engelhardt U, et al. Green and black tea are equally potent stimuli of NO production and vasodilation: new insights into tea ingredients involved[J]. Basic Res Cardiol,2009,104 (1):100-110.
[28] Sharma V, Rao L J M. A thought on the biological activities of black tea[J]. Critical Reviews in Food Science and Nutrition,2009, 49(5):379-404.
[29] 宛晓春,李大祥,夏涛.茶色素及其药理学功能[J].天然产物研究与开发, 2001,13(4): 65-70.
[30] Hamada S, Konatani M, Hosono H, et al. Peroxidase- catalyzed generation of catechin oligomers that inhibit glucosyltrasferase from Streptococcus sorbinus[J].FEMS Microbiology Letters,1996, 143:35-40.
[31] Yoshino K, Suzuki M, Sasaki K, et al. Formation of antioxidants from (- )- epigallocatechin gallate in mild alkaline fluids, such as authentic intestinal juice and mouse plasma[J]. J Nutri Boichem, 1999(10): 223-229.
[32] Yang Z Y, Tu Y Y, Xia H L, et al. Suppression of free-radicals and protection against H2O2-induced oxidative damage in HPF-1 cell by oxidized phenolic compounds present in black tea[J]. Food chemistry, 2007,105:1349-1356.
[33] Frippiat C, Dewdle J, Remacle J, et al. Signal transduction in H2O2- induced senescence-like phenotype in human diploid fibroblasts[J]. Free Radic Biol Med,2002,33:1334-1346.
[34] ?uczaj W, Skrzydlewska E. Antioxidative properties of black tea[J]. Preventive Medicine,2005,40:910-918.
[35] Toussaint O, Medrano E E, von Zglinicki, T. Cellular and molecular mechanisms of stress- induced premature senescence(SIPS) of human diploid fibroblasts and melanocytes[J]. Exp Gerontol,2000, 35:927-945.
[36] Holder J, Bhaduri A N. Protective role of black tea against oxidative damage of human red blood cell[J]. Boichem Biophys Res Commun,1998,244: 903-907.
[37] Giovannelli L, Testa G, De- filippo C, et al. Effect of complex polyphenols and tannins from red wine on DNA oxidative damage of rat colon mucosa in vivo[J]. Eur J Nutr,2000,39:207-212.
[38] Lodovici M, Casalini C, De- filippo C, et al. Inhibition of 1,2- dimethylhydrazine- induced oxidative DNA damage in rat colon mucosa by black tea complex polyphenols[J]. Food Chem. Toxicol, 2000,38:1085-1088.
[39] Catterall F, Copeland E, Clifford M N, et al. Contribution of theafulvins to the antimutagenicity of black tea: their mechanism of action[J]. Mutagenesis,1998,13(6):631-636.
[40] Gupta S, Chaudhuri T, Ganguly D K, et al. Anticlastogenic effects of black tea (World blend) and its two active polyphenols theaflavins and thearubigins in vivo in Swiss albino mice[J]. Life Sci,2001,69(23):2735-2744.
[41] Halder B, Pramanick S, Mukhopadhyay S, et al. Inhibition of benzo [a]pyrene induced mutagenicity and genotoxicity by black tea polyphenols theaflavins and thearubigins in multiple test systems [J]. Food Chem Toxicol,2005,43(4):591-597.
[42] Halder B, Pramanick S, Mukhopadhyay S, et al. Anticlastogenic effects of black tea polyphenols theaflavins and thearubigins in human lymphocytes in vitro[J]. Toxicology in Vitro,2006,20(5):608- 613.
[43] Gupta S, Chowdhuri T, Seth P, et al. Antimutagenic effects of black tea (World blend) and its two active polyphenols theaflavins and thearubigins in Salmonella assays[J] .Phytother Res,2002,16(7):655- 661.
[44] 陈虎,胡英,周睿,等,茶黄素的抗氧化机理的研究进展[J].茶叶科学, 2005,25(4):237-241.
[45] Liang Y, Chen Y, Lin Y, et al. Suppression of extracellular signals and cell proliferation by the black tea polyphenol, theaflavin- 3,3'- digallate[J]. Carcinogenesis,1999,20(4):733-736.
[46] Sakamoto K. Synergistic effects of thearubigin and genistein On human prostate tumor cell(PC- 3) Growth via cell cycle arrest[J]. Cancer Lett., 2000,151:103-109.
[47] Lodovicim M, Casalini C, Filippo D E, et al. Inhibition of 1,2- dimethylhydrazine- induced oxidative DNA damage in rat colon mucosa by black tea complex polyphenols[J]. Food Chem Toxicol, 2000,38(12):1085-1088.
[48] Patela R, Maru G. Polymeric black tea polyphenols induce phase II enzymes via Nrf2 in mouse liver and lungs[J]. Free Radic Biol Med, 2008,44(11):1897-1911.
[49] Patela R, Ingle A, Maru G. Polymeric black tea polyphenols inhibit 1,2- dimethylhydrazine induced colorectal carcinogenesis by inhibiting cell proliferation via Wnt/β- catenin pathway[J]. Toxicol Appl Pharm,2008,227(1):136-146.
[50] Kumar G, Dange P, Kailaje V, et al. Polymeric black tea polyphenols modulate the localization and activity of 12- Otetradecanoylphorbol- 13- acetate- mediated kinases in mouse skin: Mechanisms of their anti-tumor-promoting action[J]. Free Radical Biology and Medicine,2012,53(6):1358-1370.
[51] Halder B, Bhattacharya U, Mukhopadhyay S, et al. Molecular mechanism of black tea polyphenols induced apoptosis in human skin cancer cells: involvement of Bax translocation and mitochondria mediated death cascade[J]. Carcinogenesis,2008,29(1): 129-138.
[52] Krishnan R, Maru G B. Inhibitory effect(s) of polymeric black tea polyphenols on the formation of B(a)P- derived DNA adducts in mouse skin[J]. J Environ Pathol Toxicol Oncol,2005,24(2):79-90.
[53] Osawa T, Kato Y. Protective role of antioxidative food factors in oxidative stress caused by hyperglycemia. Ann N Y Acad Sci, 2005, 1043:440.
[54] Maity S, Ukil A, Karmakar S, et al. Thearubigin, the major polyphenol of black tea, ameliorates mucosal injury in trinitrobenzene sulfonic acid- induced colitis[J]. Eur J Pharmacol, 2003,470(1/2):103-112.
[55] Das M, Chaudhuri T, Goswami S K, et a1. Studies with black tea and its constituents on leukemic cells and cell lines[J]. J Exp Clin Cancer Res,2002,21(4):563-568.
[56] Halder B, Gupta S D, Gomes A. Black tea polyphenols induce human leukemic cell cycle arrest by inhibiting Akt signaling[j]. FEBS J, 2012,279(16):2876-2891.
[57] Cameron AR, Anton S, Melville L, et al. Black tea polyphenols mimic insulin/insulin- like growth factor- 1 signalling to the longevity factor FOXO1a[J]. Aging cell,2008,7:69-77.
[58] Miki, Ui Hideyuki Yasaki Shibatda. M, et al. Effect of Tea catechins for halitosis and their application to chewing gum[J]. Nippon Shokuhin Kogyo Gakkaishi,1991,38(12):1098-1102.