茶叶中聚酯型儿茶素研究进展

doi:10.13305/j.cnki.jts.2014.04.001

摘要/Abstract

摘要： 聚酯型儿茶素（Theasinensins, TSs）是一类儿茶素的氧化产物,是在茶叶加工过程中由于揉捻等工序使茶叶细胞破碎导致儿茶素与酶接触,进而氧化形成的。近年来,一些研究结果表明TSs具有一定的生理活性功能。本文就从TSs的发现、形成机理、分析方法、分离制备、药理作用方面进行综述。

关键词: 茶叶, 儿茶素, 脱氢聚酯型儿茶素, 聚酯型儿茶素, 茶黄素

Abstract: Theasinensins (TSs) are produced by oxidation of catechins. Catechins, due to tea rolling, come into and contact with enzymes during tea processing, TSs are generated. The research achievements indicated the physiological function, recently, rising concern of TSs. The article summarized the discovery of TSs, mechanism of TSs formation, analytical method, separation and preparation, pharmacological action.

Key words: tea, catechins, dehydrotheasinensins, theasinensins, theaflavins

中图分类号:

徐斌, 薛金金, 江和源, 张建勇, 王岩. 茶叶中聚酯型儿茶素研究进展[J]. 茶叶科学, 2014, 34(4): 315-323. doi: 10.13305/j.cnki.jts.2014.04.001.

XU Bin, XUE Jinjin, JIANG Heyuan, ZHANG Jianyong, WANG Yan. Review on Theasinensins in Tea[J]. Journal of Tea Science, 2014, 34(4): 315-323. doi: 10.13305/j.cnki.jts.2014.04.001.

参考文献 45

[1]	Tanaka T, Matsuo Y, Kouno I.A novel black tea pigment and two new oxidation products of epigallocatechin-3-O-gallate[J]. J Agric Food Chem, 2005, 53(19): 7571-7578.
[2]	Roberts E A H, Cartwright R A, Oldschool M. The phenolic substance of manufactured tea. Ⅰ[J]. J sci Food Agric, 1957, 8(2): 72-80.
[3]	Roberts E A H. The phenolic substance of manufactured tea. Ⅱ[J]. J sci Food Agric, 1958, 9(4): 212-216.
[4]	Owuor P O, Reeves S G, Wanyoko J K.Correlation of theaflavins content and valuations of kenyan black teas[J]. J Agric Food Chem, 1986, 37(5): 507-513.
[5]	Roberts E A H, Williams D M. The phenolic substance of manufactured tea. Ⅲ[J]. J Sci Food Agric, 1958, 9(4): 217-223.
[6]	Roberts E A H, Williams D M. The phenolic substance of manufactured tea. Ⅳ[J]. J Sci Food Agric, 1959, 10(3): 167-172.
[7]	Ferretti A, Flanagan I V P, Bondarovich H A, et al. The chemistry of tea structures of compounds A and B of roberts and reactions of some model compounds[J]. J Agric Food chem, 1968, 16(5): 756-761.
[8]	Roberts E A H, Williams D M. The phenolic substance of manufactured tea. Ⅴ[J]. J Sci Food Agric, 1959, 10(3): 172-176.
[9]	Nonaka G, kawahara O, Nishioka I. Tannins and related compounds XV. A new class of dimeric flavan-3-ol gallates, theasinensin A and theasinensinB, and proanthocyanidin gallates from green tea leaf[J]. Chem Pharm bull, 1983, 31(11): 3906-3914.
[10]	Hashimoto F, Nonaka G, nishioka I. Tannins and related compounds. LXIX. Isolation and structure elucidation of B,B’-linked bisflavanoids, theasinensin D-G and oolongtheanin from oolong tea[J]. Chem Pharm Bull, 1988, 36(5): 1676-1684.
[11]	Shii T, Tanaka T, Watarumi S, et al. Polyphenol composition of a functional fermented tea obtained by Tea-Rolling processing of green tea and loquat leaves[J]. J Agric Food Chem, 2011, 59(13): 7253-7260.
[12]	Hashimoto F, Nonaka G, Nishioka I.Tannins and related compounds. CXIV. Structures of novel fermentation products, theogallinin, theaflavonin and desgalloyl theaflavonin from black tea, and changes of tea leaf polyphenols during fermentation[J]. Chem Pharm Bull, 1992, 40(6): 1383-1389.
[13]	Parliament T H, Ho C T, Schieberle P, et al. Caffeinated beverages: Health Benefits, Physiological Effects and Chemistry[M]. Wasgington: American Chemical Society, 2000: 316-326.
[14]	Tanaka T, Watarumi S, Matsuo Y, et al. Production of theasinensins A and D, epigallocatechin gallate dimers of black tea, by oxidation-reduction dismutation of dehydrotheasinensin A[J]. Tetrahedron, 2003, 59(40): 7939-7947.
[15]	Tanaka T, Mine C, Watarumi S, et al. Accumulation of epigallocatechin quinone dimers during Tea fermentation and formation of theasinensins[J]. J Nat Prod, 2002, 65(11): 1582-1587.
[16]	Hashimoto F, Nonaka G, Nishioka I.Tannins and related compounds.LXXVII. Novel chalcan-flavan d imers,assamicains A,B and C, and a new flavan-3-ol and proanthocyanidins from the fresh leaves of Camellia sinensin L. var. assamoca kitamura[J]. Chem Pharm Bull, 1989, 37(1): 77-85.
[17]	Ho C T, Shahidi F.Phenolic compounds in foods and natural health products[M]. Washington: American Chemical Society, 2005: 188-196.
[18]	Li Y, Tanaka T, Kouno I.Oxidative coupling of the pyrogallol B-ring with a galloyl group during enzymatic oxidation of epigallocatechin 3-O-gallate[J]. Phytochemistry, 2007, 68(7): 1081-1088.
[19]	Sanga S, Yang I, Buckley B, et al. Autoxidative quinone formation in vitro and metabolite formation in vivo from tea polyphenol (-)-epigallocatechin-3-gallate: Studied by real-time mass spectrometry combined with tandem mass ion mapping[J]. Free Radical Biology and Medicine, 2007, 43(3): 362-371.
[20]	Matsuo Y, Tanaka T, Kouno I.A new mechanism for oxidation of epigallocatechin and production of benzotropolone pigments[J]. Tetrahedron, 2006, 62(20): 4774-4783.
[21]	Roberts E A H, Myers M. The phenolic substance of manufactured tea. Ⅵ. The preparation of theaflavin and of theaflavin gallate[J]. J Sci Food Agric, 1959, 10(4): 176-179.
[22]	宛晓春, 黄继轸, 沈生荣, 等. 茶叶生物化学[M]. 北京: 中国农业出版社, 2007: 180-184.
[23]	Yoshino K, Suzuki M, Sasaki K, et al. Formation of antioxidants from (2)-epigallocatechin gallate in mild alkaline fluids, such as authentic intestinal juice and mouse plasma[J]. J Nutr Biochem, 1999, 10(4): 223-229.
[24]	Kusano R, Andou K, 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.
[25]	Shii T, Miyamoto M, Matsuo Y, et al. Biomimetic one-pot preparation of a black tea polyphenol theasinensin A from epigallocatechin gallate by treatment with copper(II) chloride and ascorbic acid[J]. J Chem Pharm Bull, 2011, 59(9): 1183-1185.
[26]	Neilson A P, Song B J, Sapper T N, et al. Tea catechin auto-oxidation dimers are accumulated and retained by Caco-2 human intestinal cells[J]. Nutrition Research, 2010, 30(5): 327-340.
[27]	Tanaka T, Watarumi S, Fujieda M, et al. New black tea polyphenol having N-ethyl-2-pyrrolidinone moiety derived from tea amino acid theanine: isolation, characterization and partial synthesis[J]. Food Chemistry, 2005, 93(1): 81-87.
[28]	Qiu J, Kitamura Y, Miyata Y, et al. Transepithelial transport of theasinensins through Caco-2 cell monolayers and their absorption in sprague-dawley rats after oral administration[J]. J Agric Food Chem, 2012, 60(32): 8036-8043.
[29]	Shibamoto T, Terao J, Osawa T, et al. Functional foods for disease prevention I[M]. Washington: American Chemical Society, 1998: 209-216.
[30]	Morello M J. Shahidi F, Ho C T.Free Radicals in Food[C]. Washington: American Chemical Society, 2002: 213-223.
[31]	Hashimoto F, Ono M, Masuoka C, et al. Evaluation of the anti-oxidative effect (in vitro) of tea polyphenols[J]. Biosci Biotechnol Biochem, 2003, 67(2): 396-401.
[32]	Saeki K, Sano M, Miyase T, et al. Apoptosis-inducing activity of polyphenol compounds derived from tea catechins in human histiolytic lymphoma U937 cell[J]. Biosci Biotechnol Biochem, 1999, 63(3): 585-587.
[33]	Pan M H, Liang Y C, Lin-Shiau S Y, et al. 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[J]. J Agric Food Chem, 2000, 48(12): 6337-6346.
[34]	Shahidi F, Ho C T, Watanabe S, et al. Food factors in health promotion and disease prevention[M]. Washington: American Chemical Society, 2003: 50-71.
[35]	Hou D X, Masuzaki S, Tanigawa S, et al. Oolong Tea Theasinensins Attenuate Cyclooxygenase-2 Expression in Lipopolysaccharide (LPS)-Activated Mouse Macrophages: Structure-Activity Relationship and Molecular Mechanisms[J]. J Agric Food Chem, 2010, 58(24): 12735-12743.
[36]	Chena J H, Qina S, Xiaob J P, et al. A genome-wide microarray highlights the antiinflammatory genes targeted by Oolong tea theasinensin A in macrophages[J]. J Nutrition and Cancer, 2001, 63(7): 1064-1073.
[37]	Hatano T, Kusuda1 M, Hori M, et al. Theasinensin A, a tea polyphenol formed from (-)-epigallocatechin gallate, suppresses antibiotic resistance of methicillin-resistant staphylococcus aureus[J]. Planta Med, 2003, 69(11): 984-989.
[38]	Taylor P W, Hamilton-Miller J, Stapleton P D.Antimicrobial properties of green tea catechins[J]. Food Sci Technol Bull, 2005, 16(2): 71-81.
[39]	Isaacs C E, Xu W M, Merz G, et al. Digallate dimers of (-)-epigallocatechin gallate Inactivate herpes simplex virus[J]. Antimicrob Agents Chemother, 2011, 55(12): 5646-5653.
[40]	Toshima A, Matsui T, Noguchi M, et al. Identification of α-glucosidase inhibitors from a new fermented tea obtained by tea-rolling processing of loquat (Eriobotrya japonica) and green tea leaves[J]. J Sci Food Agric, 2010, 90(9): 1545-1550.
[41]	Miyata Y, Tanaka T, Tamaya K, et al. Cholesterol-Lowering Effect of Black Tea Polyphenols, Theaflavins, Theasinensin A and Thearubigins[J]. Food Science and Technology Research, 2011, 17(6): 585-588.
[42]	Mokdad A H, Ford E S, Bowman B A, et al. Prevalence of Obesity, Diabetes, and Obesity-Related Health Risk Factors[J]. JAMA, 2003, 289(1): 76-79.
[43]	Sturm R.The Effects of Obesity, Smoking, And Drinking on Medical Problems And Costs[J]. Health Affairs, 2002, 21(2): 245-253.
[44]	Nakai M, Fukui Y, Asami S, et al.Inhibitory effects of Oolong tea polyphenols on pancreatic lipase in vitro [J]. J Agric Food Chem, 2005, 53(11): 4593-4598.===Yuko F, Takashi I, Sumio A, et al. Structures and biological activity of oolong tea polymerized polyphenols and quantification by LC-MSMS[C]//The Chemical Society of Japan, The Pharmaceutical Society of Japan, The Japanese Society for Agricultural Chemistry. Symposium on the chemistry of natural products: 50. Tokyo: The Chemical Society of Japan, 2008, 475-480. Inhibitory effects of Oolong tea polyphenols on pancreatic lipase in vitro [J]. J Agric Food Chem, 2005, 53(11): 4593-4598.===Yuko F, Takashi I, Sumio A, et al. Structures and biological activity of oolong tea polymerized polyphenols and quantification by LC-MSMS[C]//The Chemical Society of Japan, The Pharmaceutical Society of Japan, The Japanese Society for Agricultural Chemistry. Symposium on the chemistry of natural products: 50. Tokyo: The Chemical Society of Japan, 2008, 475-480. http://ci.nii.ac.jp/ naid/110007066723/en
[45]	Matsuo Y, Hayashi T, Saito Y, et al. Structures of enzymatic oxidation products of epigallocatechin[J]. Tetrahedron, 2013, 69(42): 8952-8958.