The Selective Synthesis of (-)-epigallocatechin-3-(4-O-methylgallate)

LAI Rong-hui; ZHAO Wen-fang; HUANG Ya-hui; ZHOU Wen; WU Chun-lan; LAI Xing-fei; ZHAO Wen-xia; ZHANG Min

doi:10.13305/j.cnki.jts.2013.06.001

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Journal of Tea Science ›› 2013, Vol. 33 ›› Issue (6) : 550-555. DOI: 10.13305/j.cnki.jts.2013.06.001

The Selective Synthesis of (-)-epigallocatechin-3-(4-O-methylgallate)

LAI Rong-hui^1,4, ZHAO Wen-fang¹, HUANG Ya-hui^1,3,*, ZHOU Wen², WU Chun-lan¹, LAI Xing-fei¹, ZHAO Wen-xia¹, ZHANG Min¹

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Abstract

(-)-epigallocatechin-3-(4-O-methylgall ate)(EGCG4″Me) was selective synthesized through chemical process from EGCG and propyl gallate (PG), with iodomethane (CH₃I) as methylating reagent, in this paper. The final product was characterized by H¹-NMR.

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chemical modification / EGCG / EGCG4″Me

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LAI Rong-hui, ZHAO Wen-fang, HUANG Ya-hui, ZHOU Wen, WU Chun-lan, LAI Xing-fei, ZHAO Wen-xia, ZHANG Min. The Selective Synthesis of (-)-epigallocatechin-3-(4-O-methylgallate)[J]. Journal of Tea Science. 2013, 33(6): 550-555 https://doi.org/10.13305/j.cnki.jts.2013.06.001

References

[1] Sano M, Suzuki M, Miyase T, et al. Novel Antiallergic Catechin Derivatives Isolated from Oolong Tea[J]. Journal of Agricultural and Food Chemistry, 1999, 47(5): 1906-1910.
[2] Fujimura Y, Tachibana H, Maeda Y M, et al. Antiallergic tea catechin, (-)-epigallocatechin-3-O-(3-O-methyl)-gallate, suppresses Fc∈RI expression in human basophilic KU812 cells[J]. Journal of agricultural and food chemistry, 2002, 50(20): 5729-5734.
[3] MaedaY M, Inagaki N, Kitaura J, et al. O-methylated catechins from tea leaves inhibit multiple protein kinases in mast cells[J]. The Journal of Immunology, 2004, 172(7): 4486.
[4] Suzuki M, Yoshino K, Maeda Y M, et al. Inhibitory effects of tea catechins and O-methylated derivatives of (-)-epigallocatechin-3-O-gallate on mouse type Ⅳ allergy[J]. Journal of agricultural and food chemistry, 2000, 48(11): 5649-5653.
[5] Maeda Y M, Ema K, Shibuichi I.In vitro and in vivo anti-allergic effects of ‘benifuuki’ green tea containing O-methylated catechin and ginger extract enhancement[J]. Cytotechnology, 2007, 55(2): 135-142.
[6] 吕海鹏, 费冬梅, 张悦, 等. EGCG甲基化衍生物酶促反应的反应条件研究[J]. 茶叶科学, 2012, 32(5): 441-447.
[7] Osanai K, Huo C, Landis-Piwowar K R, 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]. Tetrahedron, 2007, 32(63): 7565-7570.
[8] 秦绪龙. 表没食子儿茶素衍生物的半合成及活性评价[D]. 青岛: 中国海洋大学, 2007.
[9] 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.
[10] 吕海鹏, 谭俊峰, 林智. 茶树中质资源EGCG3″Me含量及其变化规律研究[J]. 茶叶科学, 2006, 26(4): 310-314.
[11] 罗正飞, 龚正礼, 汪毅, 等. 茶叶中甲基化EGCG的研究[J]. 西南大学学报: 自然科学版, 2008(3): 56-59.
[12] 周蓓, 王琳, 李伟, 等. 茶叶中甲基化儿茶素的分离, 纯化和高效液相色谱法分析[J]. 分析化学, 2008, 36(4): 494-498.
[13] 罗正飞, 金孝芳, 龚正礼, 等. EGCG3"Me的提取与分离工艺研究[J]. 茶叶科学, 2011, 31(3): 218-224.
[14] 李银花, 张盛, 黄建安, 等. 茶叶中EGCG3"Me和EGCG4”Me的分离制备与鉴定[J]. 茶叶科学, 2012, 32(4): 313-318.
[15] 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.
[16] Yanase E, Matsumtto E, Shinoda Y, et al. Synthesis of Methyl Derivatives of Epigallocatechin Gallate (EGCg) and Their Stabilities[J]. ITE Lett Batter New Technol Med, 2005, 6(1): 34-37.
[17] 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.
[18] 伍妍俊. 甲基化EGCG的合成及其稳定性研究[D]. 合肥: 安徽农业大学, 2010.
[19] Utenovaa B T, Malterudb K E, Risea F.Antioxidant activity of O-protected derivatives of (-)-epigallocatechin-3-gallate: inhibition of soybean and rabbit 15-lipoxygenases[J]. Arkivoc, 2007, 9: 6-16.
[20] Zaveri N T.Synthesis of a 3,4,5-Trimethoxybenzoyl Ester Analogue of Epigallocatechin-3-gallate (EGCG):? A Potential Route to the Natural Product Green Tea Catechin, EGCG[J]. Organic Letters, 2001, 3(6): 843-846.
[21] Wan S B, Qiu P D, Chan T H.Regiospecific and enantioselective synthesis of methylated metabolites of tea catechins[J]. Tetrahedron, 2006, 62(25): 5897-5904.