茶红素化学及生物学活性研究进展

doi:10.13305/j.cnki.jts.2013.04.006

Abstract

Abstract: Thearubigins are mixtures of heterogeneous acidic phenolic pigments, which are condensed oligomers or polymers from catechins and theaflavins. Thearubigins contribute to tea color, the body strength, intensity and liquor color of a black tea brew. Due to their heterogeneity, their solubility and chromatographic behaviors are dissilimar and their structures are still ambiguous. The classic isolation method of the thearubigin subfractions has been developed with organic solvent extraction. So far, no thearubigin monomer has been reported. However, some studies have demonstrated that thearubigins possess antioxidative, anti-tumor, anti-mutagenic, anti-carcinogenic, anti-inflammatory, anti-leukemic, obesity-preventive and even anti-neurotoxin activities in vitro and in animal models since 1990s. As the abundant polyphenolic compounds in black tea, thearubigins may be the potential active compounds contributing to human health.

Key words: black tea, thearubigins, structure, bioactivity

CLC Number:

LI Da-xiang, WANG Hua, BAI Rui, XIAN Shu, WAN Xiao-chun. The Chemistry and Bioactivity of Thearubigins[J]. Journal of Tea Science, 2013, 33(4): 327-335.

References 65

[1]	Xiaochun Wan, Daxiang Li, Zhengzhu Zhang.Green and Black teas: Manufacturing and consumption[C]//Chi-Tang Ho, Jen-Kun Lin, Fereidoon Shahidi. Tea and Tea Products: Chemistry and Health Promoting Properties. CRC Press, Talyor & Francis Group, 2008: 1-8.
[2]	Yang Chung S, Maliakal Pius, Meng Xiaofeng.Inhibition of carcinogenesis by tea[J]. Annu Rev Pharmacol Toxicol, 2002, 42: 42-45.
[3]	Edwin Haslam.Thoughts on thearubigins[J]. Phytochemistry, 2003, 64: 61-73.
[4]	Opie SC, Robertson A, Clifford MN.Black tea thearubigins-their HPLC separation and preparation during in vitro oxidation[J]. J Sci Food Agri, 1990, 50(4): 547-561.
[5]	宛晓春. 茶叶生物化学: [M]. 3版. 北京: 中国农业出版社, 2003: 8-11, 30-31, 180-199, 275-278.
[6]	萧伟祥, 钟瑾, 萧慧, 等. 茶红色素形成机理及制取[J]. 茶叶科学, 1997, 17(1): 1-8.
[7]	Tanaka T, Watarumi S, Fujieda M.New black tea polyphenol having N-ethyl-2-pyrrolidinone moiety derived from tea amino acid theanine: isolation ,characterization and partial synthesis[J]. Food Chem, 2005, 93: 81-87.
[8]	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.
[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[C]//Gross G G, Hemingway R W, Yoshida T, et al. Plant polyphenols 2—Chemistry, biology, pharmacology, ecology. New York: Kluwer Academic/Plenum Publishers, 1999: 697-723.
[12]	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.
[13]	Kuhnert N.Unraveling the structure of the black tea thearubigins[J]. Arch Biochem Biophys, 2010, 501: 37-51.
[14]	Drynan JW, Clifford MN, Obuchowicz, et al. MALDI-TOF mass spectrometry: avoidance of artifacts and analysis of caffeine-precipitated SII thearubigins from 15 commercial black teas[J]. J Agric Food Chem, 2012, 60: 4514-4525.
[15]	Roberts E A H, Catright R A, Oldschool M. Fractionation and paper chromatography of water soluble substances from manufactured tea[J]. J Sci Food Agric, 1957(8): 72-80.
[16]	Roberts E A H. The phenolic substances of manufacture tea.Ⅱ-Their origin as enzymic oxidation products in fermentation[J]. J Sci Food Agric, 1958, 9: 212-216.
[17]	Bailey R G, Nursten H E.Comparative study of the reversed phase high-performance liquid chromatography of black tea liquors with special reference to the thearubigins[J]. J Chromatogr, 1991, 542: 115-128.
[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]	Ozawa T.Separation of the components in black tea infusion by chromatography on Toyopearl[J]. Agric Biol Chem, 1982, 46(4): 1079-1081.
[23]	Degenhardt A, Engelhardt U H, Wendt A S, et al. 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.
[24]	Degenhardt A, Engelhardt U H, Winterhalter P, et al. Centrifugal precipitation chromatography——a novel chromatographic system for fractionation of polymeric pigments from black tea and red wine[J]. J Agric Food Chem, 2001, 49(4): 1730-1736.
[25]	钟萝. 茶叶品质理化分析[M]. 上海: 上海科技出版社, 1989: 291-293.
[26]	Wan XC.Methods to quantitatively measure active components in tea/ tea extracts[J]. Food Science and Nutrition, 2001, 41(5): 400-401.
[27]	ISO 14502-1 (2005). Determination of Substances Characteristic of Green and Black Tea. Content of Total Polyphenols in Tea. Colorimetric Method Using Folin-Ciocalteu Reagent[S]. ISO: Geneva, 2005.
[28]	中华人民共和国国家质量监督检验检疫总局,中国国家标准化管理委员会. GB/T 8313—2008. 茶叶中茶多酚和儿茶素类含量的检测方法[S]. 2008.
[29]	李大祥, 宛晓春, 刘莉华, 等. 茶色素中茶黄素类的HPLC定量[J]. 茶叶科学, 2004, 24(2): 124-128.
[30]	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.
[31]	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.
[32]	Sharma V, Rao LJM.A thought on the biological activities of black tea[J]. Critical Reviews in Food Science and Nutrition, 2009, 49(5): 379-404.
[33]	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.
[34]	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.
[35]	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.
[36]	Yoshino K, Hara Y, Sano M, et al. Antioxidative effects of black tea theaflavins and thearubigin on lipid peroxidation of rat liver homogenates induced by tert-butyl hydroperoxide[J]. Biol Pharm Bull, 1994, 17(1): 146-149.
[37]	王华, 李大祥, 宛晓春. 茶红素清除DPPH自由基能力的研究[J]. 中国茶叶加工, 2007(3): 29-31.
[38]	Yang ZY, Tu YY, Xia HL, 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.
[39]	Łuczaj W, Skrzydlewska E.Antioxidative properties of black tea[J]. Preventive Medicine, 2005, 40: 910-918.
[40]	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.
[41]	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.
[42]	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.
[43]	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.
[44]	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.
[45]	Kumar G, Dange P, Kailaje V, et al. Polymeric black tea polyphenols modulate the localization and activity of 12-O-tetradecanoylphorbol-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.
[46]	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.
[47]	Bhattacharya U, Halder B, Mukhopadhyay S, et al. Role of oxidation-triggered activation of JNK and p38 MAPK in black tea polyphenols induced apoptotic death of A375 cells[J]. Cancer Science, 2009, 100(10): 1971-1978.
[48]	Dhawan A, Anderson D, de Pascual-Teresa S, et al. Evaluation of the antigenotoxic potential of monomeric and dimeric flavanols, and black tea polyphenols against heterocyclic amine-induced DNA damage in human lymphocytes using the Comet assay[J]. Mutat Res, 2002, 515(1/2): 39-56.
[49]	Krishnan R, Maru GB.Inhibitory effect(s) of polymeric black tea polyphenol fractions on the formation of [3H]-B(a)P-derived DNA adducts[J]. J Agric Food Chem, 2004, 52(13): 4261-4269.
[50]	Krishnan R, Maru GB.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.
[51]	Catterall F, Copeland E, Clifford MN, et al. Contribution of theafulvins to the antimutagenicity of black tea: their mechanism of action[J]. Mutagenesis, 1998, 13(6): 631-636.
[52]	Gupta S, Chaudhuri T, Ganguly DK, 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.
[53]	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
[54]	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.
[55]	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.
[56]	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.
[57]	Das M, Chaudhuri T, Goswami SK, et al. Studies with black tea and its constituents on leukemic cells and cell lines[J]. J Exp Clin Cancer Res, 2002, 21(4): 563-568.
[58]	Halder B, Gupta SD, Gomes A.Black tea polyphenols induce human leukemic cell cycle arrest by inhibiting Akt signaling[j]. FEBS J, 2012, 279(16): 2876-2891.
[59]	Satoh E, Ishii T, Shimizu Y, et al. Black tea extract, thearubigin fraction, counteract the effects of botulinum neurotoxins in mice[J]. Br J Pharmacol, 2001, 132(4): 797-798.
[60]	Satoh E, Ishii T, Shimizu Y, et al. The mechanism underlying the protective effect of the thearubigin fraction of black tea (Camellia sinensis) extract against the neuromuscular blocking action of botulinum neurotoxins[J]. Pharmacol Toxicol, 2002, 90(4): 199-202.
[61]	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.
[62]	Kusano R, Andou H, Fujieda M, et al. Polymer-like polyphenols of black tea and their lipase and amylase inhibitory activities[J]. Chem Pharm Bull, 2008, 56(3): 266-272.
[63]	Uchiyama S, Taniguchi Y, Saka A, et al. Prevention of diet-induced obesity by dietary black tea polyphenols extract in vitro and in vivo[J]. Nutrition, 2011, 27: 287-292.
[64]	Ruxton CHS.Black tea and health[J]. Nutrition Bulletin, 2008, 33: 91-101.
[65]	Henning SM, Wang PW, Heber D.Chemopreventive effects of tea in prostate cancer: green tea versus black tea[J]. Mol Nutr Food Res, 2011, 55: 905-920.

The Chemistry and Bioactivity of Thearubigins

PDF (PC)

Knowledge

Cited

Abstract

Cite this article

share this article

References 65

Related Articles 15

Metrics

Comments

Recommended 10

[1]	WANG Feng, CHEN Yuzhen, WU Zhidan, YOU Zhiming, YU Wenquan, YU Xiaomin, YANG Zhenbiao. Effects of Organic Management Mode on Soil Fungal Community Structure and Functions in Tea Gardens [J]. Journal of Tea Science, 2022, 42(5): 672-688.
[2]	OUYANG Ke, ZHANG Cheng, LIAO Xueli, KUN Jirui, TONG Huarong. Characterization of the Key Aroma in Corn-scented Congou Black Tea Manufactured from Camellia nanchuanica by Sensory Omics Techniques [J]. Journal of Tea Science, 2022, 42(3): 397-408.
[3]	LI Changle, GE Yue, YAN Meilin, LI Hui, LIN Qingqing, WANG Pu, ZHAO Hua, WANG Mingle, WANG Yu, GUO Fei, NI Dejiang. Analysis of Genetic Diversity and Population Structure of 32 Tea Landraces in China [J]. Journal of Tea Science, 2021, 41(5): 619-630.
[4]	MAO Juan, JIANG Hongjian, YANG Rubing, LI Chongxing, MA Chengying, CHEN Liang, MA Jianqiang. Genetic Diversity and Population Structure of Wild and Cultivated Camellia taliensis Populations [J]. Journal of Tea Science, 2021, 41(4): 454-462.
[5]	ZHAO Yiqing, LIU Zhengjun, ZHANG Tianxin, ZHAO Yanting, XIAO Bin, GAO Yuefang. Cloning of CsCHLI Gene and Its Expression Analysis in Different Albino Tea Cultivars (Camellia sinensis) [J]. Journal of Tea Science, 2021, 41(3): 327-336.
[6]	CUI Lidan, ZHANG Xianglin, XIANG Xi, LI Lanlan, QU Qingyun, XU Yangyang, WANG Jiguo, LIU Feng, GONG Zhihua, XIAO Wenjun. The Effect of Initial Microwave Drying on Black Tea Quality [J]. Journal of Tea Science, 2021, 41(3): 406-418.
[7]	WANG Shenglin, YANG Chongshan, LIU Zhongyuan, LIU Shanjian, DONG Chunwang. Rapid Detection Method of Tea Polyphenol Content in Black Tea Fermentation Based on Electrical Properties [J]. Journal of Tea Science, 2021, 41(2): 251-260.
[8]	LIU Fengjing, RAN Wei, LI Xiwang, WANG Suqin, SUN Xiaoling. The Comparison of Leaf Structures and Empoasca Onukii Matsuda Honeydew Excretion among Five Tea Cultivars (Strains) [J]. Journal of Tea Science, 2020, 40(5): 625-631.
[9]	HE Fei, LI Donghua, BU Fan. Analysis of Arbuscular Mycorrhizal Fungal Community Structure in the Rhizosphere of Different Tea Cultivars [J]. Journal of Tea Science, 2020, 40(3): 319-327.
[10]	LIU Zhen, CHENG Yang, YANG Peidi, ZHAO Yang, NING Jing, YANG Yang. Genetic Diversity and Structure of Chengbudong Tea Population Revealed by nSSR and cpDNA Markers [J]. Journal of Tea Science, 2020, 40(2): 250-258.
[11]	WANG Jiaqin, YAO Yuefeng, YUAN Haibo, JIANG Yongwen, LI Jia. A Quantitative Method for Brightness Evaluation of Congou Black Tea Infusions Based on Color Difference Analysis [J]. Journal of Tea Science, 2020, 40(2): 259-268.
[12]	AN Ting, JIANG Yongwen, LIANG Gaozhen, HU Bin, DONG Chunwang. Optimization of Performance Parameters of Black Tea Withering Machine Based on CFD and RSM [J]. Journal of Tea Science, 2019, 39(5): 547-554.
[13]	XU Yongmei, SHI Yunfeng. An Empirical Analysis of the Trade and Influencing Factors of China's Black Tea Export to Countries along the Belt and Road [J]. Journal of Tea Science, 2019, 39(5): 602-610.
[14]	HOU Aixiang, YAN Daomin, SUN Jingwen, ZHENG Xu, LI Saidan, XIAO Runhua, BEI Shuang. Effects of Green, Black and Fu Brick Tea Aqueous Extracts on the Characteristics of Intestinal Microbiota during in vitro Fermentation [J]. Journal of Tea Science, 2019, 39(4): 403-414.
[15]	ZHOU Yang, XIAO Wenjun, LIN Ling, YUAN Dongyin, PENG Yingqi, TAN Chunbo, ZHANG Qiang, GONG Zhihua. Hypoglycemic Effects of Black Tea and Fungus Fermented Black Brick Tea on Hyperglycemic Model Mice [J]. Journal of Tea Science, 2019, 39(4): 415-424.