儿茶素酰基化修饰研究进展

doi:10.13305/j.cnki.jts.2009.1.001

摘要/Abstract

摘要： 儿茶素因其独特和广泛的生物活性引起了研究者和公众的极大关注,但由于其脂溶性差、体内不稳定和生物利用度低等使其应用受到了限制。本文就提高其应用特性的酰基化修饰及修饰后的生理活性研究进展进行了综述,并对其发展作了展望。

Abstract: Researchers and the general public have been paid more and more attention to catechins due to their distinctive and extensive bioactivities, but the further applications are restricted because its liposoluble is not high, unstability and low bioavailability in vivo. This paper reviewed the research progress of acylation modificated catechins and their physiological activities as well as the prospects of development．

Key words: catechins, molecule modification, acylation, bioactivity, research progress

中图分类号:

TS272

刘晓辉, 江和源, 张建勇, 袁新跃, 崔宏春. 儿茶素酰基化修饰研究进展[J]. 茶叶科学, 2009, 29(1): 1-8. doi: 10.13305/j.cnki.jts.2009.1.001.

LIU Xiao-hui, JIANG He-yuan, ZHANG Jian-yong, YUAN Xin-yue, CUI Hong-chun. Advances in Researches on Catechins Acylation Modification[J]. Journal of Tea Science, 2009, 29(1): 1-8. doi: 10.13305/j.cnki.jts.2009.1.001.

参考文献

[1] 宛晓春. 茶叶生物化学(第三版)[M]. 北京: 中国农业出版社, 2003, 9~15.
[2] 唐传核. 植物功能性食品[M]. 北京: 化学工业出版社, 2004, 324~364.
[3] 沈生荣, 杨贤强, 贾春友. 油溶性茶多酚对色拉油的抗氧化作用[J]. 茶叶, 1998, 24(3): 134~137.
[4] 陈理, 孙东. EGCG棕榈酸酯对人卵巢癌HO-8910细胞株的体外抑制活性实验研究[J]. 医学研究杂志, 2006, 35(3): 39~40.
[5] Sang S, Lambert JD, Yang CS.Bioavailability and stability issues in understanding the cancer preventive effects of tea polyphenols[J]. J Sci Food Agric, 2006, 86(14): 2256~2265.
[6] Chen ZY, Zhu QY, Tsang D, et al. Degradation of green tea catechins in tea drinks[J]. J Agric Food Chem, 2001, 49(1): 477~482.
[7] Zhu QY, Zhang A, Tsang D, et al. Stability of green tea catechins[J]. J Agric Food Chem, 1997, 45(12): 4624~4628.
[8] Henning SM, Niu Y, Lee NH, et al. Bioavailability and antioxidant activity of tea flavanols after consumption of green tea, black tea, or a green tea extract supplement[J]. Am J Clin Nutr, 2004, 80(6): 1558~1564.
[9] 陈平, 孙东, 郑小明. EGCG肉豆蔻酸酯的制备、结构及其抗氧化活性[J]. 浙江大学学报(理学版), 2003, 30(4): 422~425.
[10] Tanaka T, Kusano R, Kouno I.Synthesis and antioxidant activity of novel amphipathic derivatives of tea polyphenol[J]. Bioorga&Med Chem Lett, 1998, 8(6): 1801~1806.
[11] Yano S, Fujimura Y, Umeda D, et al. Relationship between the biological activities of methylated derivatives of (-)-epigallocatechin-3-O-gallate(EGCG) and their cell surface binding activities[J]. J Agric Food Chem, 2007, 55(17): 7144~7148.
[12] Meng X, Sang S, Zhu N, et al. Identification and characterization of methylated and ring-fission metabolites of tea catechins formed in humans, mice, and rats[J]. Chem Res Toxicol, 2002, 15: 1042~1050.
[13] Sakai M, Suzuki M, Nanjo F, ,et al. 3-O-acylated catechins. 3-O-acylated catechins and method of producing same. European Patent, 0618203A1.1994-10-05.
[14] Moon YH, Lee JH, Ahn JS, et al. Synthesis, structure analyses, and characterization of novel epigallocatechin gallate (EGCG) glycosides using the glucansucrase from leuconostoc mesenteroides B-1299CB[J]. J Agric Food Chem, 2006, 54(4): 1230~1237.
[15] Sato T, Nakagawa H, Kurosu J, et al. α-Anomer-selective glucosylation of (+)-catechin by the crude enzyme, showing glucosyl transfer activity, of Xanthomonas campestris WU-9701[J]. J Biosci Bioeng, 2000, 90(6): 625~630.
[16] 石碧, 狄荧. 植物多酚[M]. 北京: 科学出版社, 2000.
[17] 李卫, 宁正祥. 黄酮类化合物的分子修饰[J]. 食品科学, 2005, 26(8): 505~507.
[18] 杨贤强, 王岳飞, 陈留记, 等. 茶多酚化学[M]. 上海科学技术出版社, 2003, 454~455.
[19] 高永贵, 王岳飞, 杨贤强, 等. 脂溶性茶多酚抗油脂氧化及其增效剂的研究[J]. 中国粮油学报, 2000, 15(3): 54~58.
[20] 沈生荣, 金超芳, 杨贤强. 儿茶素的分子修饰[J]. 茶叶, 1999, 25(2): 76~79.
[21] 王巧娥, 唐安斌, 石碧, 等. 脂溶性茶多酚的合成及其抗油脂自动氧化特性的研究[J]. 开然产物研究与开发, 2001, 13(4): 12~15.
[22] 丁玲, 屠幼英, 陈晓敏. 分子修饰后的儿茶素生物活性研究现状[J]. 茶叶科学技术, 2005(1): 1~3.
[23] 张怡, 房诗宏. 茶多酚类抗氧化剂的改性[J]. 食品科学, 2001, 22(2): 88~92.
[24] Tobiason FL.MNDO and AMI molecular orbital and molecular mechanics analyses of (+)-catechin, (-)-epicatechin and their 3-O-acetyl derivatives[J]. Basic Life Sci, Plant Polyphenols, 1992, 59: 459~478.
[25] Patti A, Piattelli M, Nicolosi G.Use of Mucor miehei lipase in the preparation of long chain 3-O-acylcatechins[J]. J Mol Catal B: Enzym, 2000, 10: 577~582.
[26] Uesato S, Kitagawa Y, Hara Y, et al. Antitumor promoting activities of 3-O-acyl-(-)epigallocatechins[J]. Bioorg Med Chem Lett, 2000, 10(15): 1673~1675.
[27] Matsubara K, Saito A, Tanaka A, et al. Catechin conjugated with fatty acid inhibits DNA polymerase and angiogenesis[J]. DNA Cell Biol, 2006, 25(2): 95~103.
[28] Chen L, Lee MJ, Li H, et al. Absorption, distribution, elimination of tea polyphenols in rats[J]. Drug Metab Dispos, 1997, 25(9): 1045~1050.
[29] Lambert JD, Lee MJ, Lu H, et al. Epigallocatechin-3-gallate is absorbed but extensively glucuronidated following oral administration to mice[J]. J Nutr, 2003, 133: 4172~4177.
[30] Bravo L.Polyphenols: chemistry, dietary sources, metabolism and nutritional significance[J]. Nutr Rev, 1998, 56(11): 317~333.
[31] Kohri T, Matsumoto N, Yamakawa M, et al. Metabolic fate of (-)-[4-³H]epigallocatechin gallate in rats after oral administration[J]. J Agric Food Chem, 2001, 49(8): 4102~4112.
[32] Hong J, Lambert JD, Lee SH, et al. Involvement of multidrug resistance-associated proteins in regulating cellular levels of (-)-epigallocatechin-3-gallate and its methyl metabolites[J]. Biochem Biophys Res Commun, 2003, 310: 222~227.
[33] Lam WH, Kazi A, Kuhn DJ, et al. A potential prodrug for a green tea polyphenol proteasome inhibitor: evaluation of the peracetate ester of (-)-epigallocatechin gallate [(-)-EGCG][J]. Bioorga&Med Chem, 2004, 12(21): 5587~5593.
[34] Lambert DJ, Sang S, Hong J, et al. Peracetylation as a means of enhancing in vitro bioactivity and bioavailability of epigallocatechin-3-gallate[J]. Drug Metab Dispos, 2006, 34(12): 2111~2116.
[35] Landis-Piwowar KR, Huo C, Chen D, et al. A novel prodrug of the green tea polyphenol (-)-epigallocatechin-3-gallate as a potential anticancer agent[J]. Cancer Res, 2007, 67(9): 4303~4310.
[36] Landis-Piwowar KR, Kuhn DJ, Wan SB, et al. Evaluation of proteasome-inhibitory and apoptosis-inducing potencies of novel (-)-EGCG analogs and their prodrugs[J]. Int J Mol Med, 2005, 15(4): 735~742.
[37] Kuhn DJ, Lam WH, Kazi A, et al. Synthetic peracetate tea polyphenols as potent proteasome inhibitors and apoptosis inducers in human cancer cells[J]. Front Biosci, 2005, 10: 1010~1023.
[38] Osanai K, Landis-Piwowar KR, Dou QP, et al. A para-amino substituent on the D-ring of green tea polyphenol epigallocatechin-3-gallate as a novel proteasome inhibitor and cancer cell apoptosis inducer[J]. Bioorga&Med Chem, 2007, 15(15): 5076~5082.
[39] Osanai K, Huo C, Landis-Piwowar KR, et al. Synthesis of (2R,3R)-epigallocatechin-3-O-(4-hydroxybenzoate), a novel catechin from Cistus salvifolius, and evaluation of its proteasome inhibitory activities[J]. Tetraedron, 2007, 63(32): 7565~7570.
[40] Ferreira D, Marais JPJ, Slade D.Heterogeneity of the interflavanyl bond in proanthocyanidins from natural sources lacking C-4 (C-ring) deoxy flavonoid nucleophiles[J]. Phytochemistry, 2005, 66(18): 2216~2237.
[41] Saito A, Mizushina Y, Ikawa H, et al. Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases[J]. Bioorga&Med Chem, 2005, 13(8): 2759~2771.
[42] 刘屏, 穆丽华, 韩亚亮, 等. 鸡血藤活性化合物儿茶素结构修饰及抗辐射作用研究[J]. 解放军药学报, 2007, 23(5): 321~324.
[43] 江和源. 表没食子儿茶素没食子酸酯乙酰化物的制备方法. 中国专利, 101190910A.2008-06-04.
[44] 徐向群, 程启坤, 王华夫. 茶多酚油溶剂型的抗氧化活性研究[J]. 食品科学, 1996, 17(5):7~9.
[45] 熊谷彩子. (-)-表没食儿茶素脂肪酸转导体的抗促癌活性[J]. 国外医学: 中医药分册, 2003, 25(5): 316.
[46] 陈平, 钟建华, 孙东. 脂溶性茶多酚中的主要活性组分及对人卵巢癌HO-8910细胞株的体外抑制活性[J].茶叶科学, 2003, 23(2): 115~118.
[47] Folkman J.Angiogenesis in cancer, vascular, rheumatoid and other diseases[J]. Nature Med, 1995, 1: 27~31.
[48] Matsubara K, Saito A, Tanaka A, et al. Epicatechin conjugated with fatty acid is a potent inhibitor of DNA polymerase and angiogenesis[J]. Life Sci, 2007, 80(17): 1578~1585.
[49] 来伟旗, 陈建国, 梅松, 等.脂溶性茶多酚调节血脂作用实验研究[J]. 职业与健康, 2007, 23(7): 510~511.
[50] Nakagawa K, Fujii S, Ohgi A, et al. Antioxidative activity of 3-O-octanoyl-(+)-catechin, a newly synthesized catechin, in vitro[J]. J Health Sci, 2005, 51(4): 492~496.
[51] 李炎武, 谭卫兵, 邝雪英, 等. 泛素调节的蛋白质降解-2004年诺贝尔化学奖简介[J]. 化学教育, 2004(11): 30~32.
[52] Sun CL, Yuan JM, Koh WP, et al. Green tea, black tea and breast cancer risk: a meta-analysis of epidemiological studies[J]. Carcinogenesis, 2006, 27(7): 1310~1315.
[53] Huo C, Shi G, Lam WH, et al. Semi-synthesis and proteasome inhibition of D-ring deoxy analogs of (-)-epigallocatechin gallate (EGCG), the active ingredient of green tea extract[J]. Can J Chem, 2008, 86(6): 495~502.
[54] Katunuma N, Ohashia A, Sano E, et al. Catechin derivatives: Specific inhibitor for caspases-3, 7 and 2, and the prevention of apoptosis at the cell and animal levels[J]. FEBS Lett, 2006, 580(3): 741~746.
[55] Lee SC, Chan WK, Lee TW, et al. Effect of a prodrug of the green tea polyphenol (-)-epigallocatechin-3-gallate on the growth of androgen-independent prostate cancer in vivo[J]. Nutr Cancer, 2008, 60(4): 483~491.
[56] Utenova BT, Malterud KE, Rise F.Antioxidant activity of O-protected derivatives of (-)-epigallocatechin-3-gallate: inhibition of soybean and rabbit 15-lipoxygenases[J]. ARKIVOC, 2007, (ix): 6~16.
[57] Anderson KM, Seed T, Meng J, et a1. Five-lipoxygenase inhibitors reduce Panc-1 survival: the mode of cell death and synergism of MK886 with gamma linolenic acid[J]. Anticancer Res, 1998, 18(2A): 791~800.
[58] 廖晖, Banbury LK, Leach DN, et al. 12味止血中药对脂多糖诱导小鼠巨噬细胞产生一氧化氮的抑制作用[J]. 中国药房, 2007, 18(9): 649~651.
[59] 张晶, 郑毅男, 刘桂英. 抑制花生四烯酸代谢活性中药研究现状[J]. 天然产物研究与开发, 2001, 13(4): 83~87.