Journal of Tea Science ›› 2016, Vol. 36 ›› Issue (2): 119-130.doi: 10.13305/j.cnki.jts.2016.02.002
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LIU Min, RAO Guowu, HUA Yunfen*
Received:
2015-09-29
Online:
2016-04-15
Published:
2019-08-23
CLC Number:
LIU Min, RAO Guowu, HUA Yunfen. Research Advance in Synthesis and Pharmacological Effects of EGCG Derivatives[J]. Journal of Tea Science, 2016, 36(2): 119-130.
[1] Osanai K, Huo C, Landis-Piwowar K R, et al. Synthesis of (2R, 3R)-epigallocatechin-3- [2] Karori S, Wachira F, Wanyoko J, et al.Antioxidant capacity of different types of tea products[J]. African Journal of Biotechnology, 2007, 6(19): 2287-2296. [3] Zheng R, Chen TS, Lu TA comparative reverse docking strategy to identify potential antineoplastic targets of tea functional components and binding mode[J]. International journal of molecular sciences, 2011, 12(8): 5200-5212. [4] Cichello S, Liu P, Jois M.The anti-obesity effects of EGCG in relation to oxidative stress and air-pollution in China[J]. Natural products and bioprospecting, 2013, 3(6): 256-266. [5] Zhang Y, Wang SX, Ma JW, et al.EGCG inhibits properties of glioma stem-like cells and synergizes with temozolomide through downregulation of p-glycoprotein inhibition[J]. Journal of Neuro-Oncology, 2014, 121(1): 1-12. [6] An Z, Qi Y, Huang D, et al.EGCG inhibits Cd2+-induced apoptosis through scavenging ROS rather than chelating Cd2+ in HL-7702 cells[J]. Toxicology mechanisms and methods, 2014, 24(4): 259-267. [7] Landis-Piwowar K, Bazzi S, Dou QP.Discovery of green tea polyphenol-based proteasome inhibitors—A successful collaboration with Tak-Hang (Bill) Chan[J]. Canadian Journal of Chemistry, 2011, 90(1): 17-22. [8] Yanase E, Matsumoto E, Shinoda Y.Synthesis of methyl derivatives of epigallocatechin gallate (EGCg) and their stabilities[J]. ITE Letters on Batteries New Technologies & Medicine (with News), 2005, 6(1): 34-37. [9] Mori S, Miyake S, Kobe T, et al.Enhanced anti-influenza a virus activity of (-)-epigallocatechin-3- [10] Moon Y-H, Lee J-H, Ahn J-S, et al.Synthesis, structure analyses, and characterization of novel epigallocatechin gallate (EGCG) glycosides using the glucansucrase from Leuconostoc mesenteroides B-1299CB[J]. Journal of agricultural and food chemistry, 2006, 54(4): 1230-1237. [11] Lin S F, Lin Y-H, Lin M, et al.Synthesis and structure-activity relationship of 3- [12] Fudouji R, Tanaka T, Taguri T, et al.Coupling reactions of catechins with natural aldehydes and allyl alcohols and radical scavenging activities of the triglyceride-soluble products[J]. Journal of Agricultural and Food Chemistry, 2009, 57(14): 6417-6424. [13] Lam W H, Kazi A, Kuhn D J, et al.A potential prodrug for a green tea polyphenol proteasome inhibitor: evaluation of the peracetate ester of (-)-epigallocatechin gallate [(-)-EGCG][J]. Bioorganic & Medicinal Chemistry, 2004, 12(21): 5587-5593. [14] Saijo R.Isolation and chemical structures of two new catechins from fresh tea leaf[J]. Agricultural and Biological Chemistry, 1982, 46(7): 1969-1970. [15] Forester SC, Lambert JD.The catechol- [16] 赵新. 甲基化EGCG对SGC7901细胞Cyclin E、Bcl-2、Bcl-xL表达影响与抑癌作用研究[J]. 现代肿瘤医学, 2012, 20(1): 51-55. [17] MIYASE T, SANO M. Preparation of catechin derivatives with increased stability: JP2001253879 [P].2001-09-18. [18] 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]. Chemical Research in Toxicology, 2002, 15(8): 1042-1050. [19] 吕海鹏, 孙业良, 林智, 等. 表没食子儿茶素没食子酸酯的甲基化分子修饰[J]. 食品科学, 2010(15): 139-142. [20] 伍妍俊, 汪小钢, 宛晓春. 甲基化EGCG的合成及其在人工模拟胃肠液中的稳定性[J]. 安徽农业大学学报, 2010, 37(4): 688-691. [21] Utenova BT, Malterud KE, Rise F.Antioxidant activity of [22] 王保超. 甲基化EGCG类似物的设计合成及抗肿瘤MDR活性研究[D]. 上海: 中国海洋大学, 2014. [23] Aihara Y, Yoshida A, Furuta T, et al.Regioselective synthesis of methylated epigallocatechin gallate via nitrobenzenesulfonyl (Ns) protecting group[J]. Bioorganic & Medicinal Chemistry Letters, 2009, 19(15): 4171-4174. [24] Wan SB, Dou QP, Chan TH.Regiospecific and enantioselective synthesis of methylated metabolites of tea catechins[J]. Tetrahedron, 2006, 62(25): 5897-5904. [25] 费冬梅. 甲基化EGCG 的酶法合成研究[D]. 杭州: 中国农业科学院茶叶研究所, 2011. [26] 朱松. 表没食子儿茶素没食子酸酯(EGCG)酶法乙酰化分子修饰及其产物的抗氧化性能研究[D]. 无锡: 江南大学, 2014. [27] 沈生荣, 金超芳. 儿茶素的分子修饰[J]. 茶叶, 1999, 25(2): 76-79. [28] 陈平, 孙东, 郑小明. EGCG棕榈酸酯的制备, 结构及其抗氧化活性[J]. 浙江大学学报: 理学版, 2003, 30(4): 422-425. [29] 孙东, 陈平. EGCG肉豆蔻酸酯的制备, 结构及其抗氧化活性[J]. 温州医学院学报, 2006, 36(3): 225-227. [30] 陈平. 抗氧化剂的EGCG脂肪酸酯及其制备方法: CN1448395[P].2003-10-15. [31] 朱媛, 张雪松, 黄小忠. 脂溶性茶多酚制备工艺的研究[J]. 中国粮油学报, 2014(6): 74-78. [32] Kuhn D, Lam W H, Kazi A, et al.Synthetic peracetate tea polyphenols as potent proteasome inhibitors and apoptosis inducers in human cancer cells[J]. Front Biosci, 2005, 10(2): 1010-1023. [33] Matsumura K, Kaihatsu K, Mori S, et al.Enhanced antitumor activities of (-)-epigallocatechin-3- [34] Spencer J P.Metabolism of tea flavonoids in the gastrointestinal tract[J]. The Journal of nutrition, 2003, 133(10): 3255S-3261S. [35] 陈义. 表没食子儿茶素没食子酸酯的富集提取、分离与改性[D]. 合肥: 安徽农业大学, 2007. [36] Hyun E K, Park H Y, Kim H J, et al.Production of epigallocatechin gallate 7- [37] Kitao S, Ariga T, Matsudo T, et al.The syntheses of catechin-glucosides by transglycosylation with Leuconostoc mesenteroides sucrose phosphorylase[J]. Bioscience, biotechnology, and biochemistry, 1993, 57(12): 2010-2015. [38] Osanai K, Landis-Piwowar K R, Dou Q P, 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]. Bioorganic & medicinal chemistry, 2007, 15(15): 5076-5082. [39] Yu Z, Qin X L, Gu Y Y, et al.Prodrugs of fluoro-substituted benzoates of EGC as tumor cellular proteasome inhibitors and apoptosis inducers[J]. International journal of molecular sciences, 2008, 9(6): 951-961. [40] M Koizumi,T Akao,L Imamura, et al.Enzymatic sulfation of isoamyl gallate and (-)-epigallocatechin gallate by bacterial arylsulfotransferase[J]. Chemical and pharmaceutical bulletin, 1992, 40(7): 1864-1867. [41] Kumagai A, Nagaoka Y, Obayashi T, et al.Tumor chemopreventive activity of 3- [42] Tobiason F L.Mndo and am1 molecular orbital and molecular mechanics analyses of (+)-catechin, (-)-epicatechin, and their 3- [43] Song J M, Park K D, Lee K H, et al.Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives[J]. Antiviral research, 2007, 76(2): 178-185. [44] Furuta T, Hirooka Y, Abe A, et al.Concise synthesis of dideoxy-epigallocatechin gallate (DO-EGCG) and evaluation of its anti-influenza virus activity[J]. Bioorganic & medicinal chemistry letters, 2007, 17(11): 3095-3098. [45] Uesato S, Taniuchi K, Kumagai A, et al.Inhibitory effects of 3- [46] Sakai M, Suzuki M, Nanjo F, et al. 3- [47] Tanaka T, Kusano R, Kouno I.Synthesis and antioxidant activity of novel amphipathic derivatives of tea polyphenol[J]. Bioorganic & medicinal chemistry letters, 1998, 8(14): 1801-1806. [48] Nakai M, Fukui Y, Asami S. Epigallocatechin dimers or trimers having lipase inhibitory activity and/or antioxidant activity: 20110124887 [P].2011-05-26. [49] Siddiqui I A, Adhami V M, Bharali D J, et al.Introducing nanochemoprevention as a novel approach for cancer control: proof of principle with green tea polyphenol epigallocatechin-3-gallate[J]. Cancer Research, 2009, 69(5): 1712-1716. [50] Folch-Cano C, Guerrero J, Speisky H, et al.NMR and molecular fluorescence spectroscopic study of the structure and thermodynamic parameters of EGCG/β-cyclodextrin inclusion complexes with potential antioxidant activity[J]. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2014, 78(1/4): 287-298. [51] 张润华, 王贤和, 陈萍, 等. 表没食子儿茶素没食子酸酯增强食管癌细胞对阿霉素化疗敏感性[J]. 中华临床医师杂志: 电子版, 2013, 7(22): 10144-10147. |
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