欢迎访问《茶叶科学》,今天是

EGCG4"Me的选择性合成

  • 赖榕辉 ,
  • 赵文芳 ,
  • 黄亚辉 ,
  • 周文 ,
  • 吴春兰 ,
  • 赖幸菲 ,
  • 赵文霞 ,
  • 张敏
展开
  • 1 华南农业大学园艺学院,广东 广州 510642;
    2 上海交通大学药学院,上海 200240;
    3 华南园艺作物种质创新与利用广东省普通高校重点实验室,广东 广州 510642;
    4. 福建省三明市茶叶技术推广站,福建 三明 365000
赖榕辉(1987— ),男,福建龙岩人,硕士,主要从事茶叶加工与生化方面的研究。

收稿日期: 2013-03-04

  修回日期: 2013-03-25

  网络出版日期: 2019-09-04

基金资助

广东省茶叶产业推进关键技术研究与示范(2009B020201013)

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
Expand
  • 1. College of Horticultur, South China Agricultural University, Guangzhou 510642, China;
    2. School of Pharmacy, Shanghai Jiaotong University, Shanghai 200240, China;
    3. Key Laboratory of Innovation and Utilization for Germplasm Resources in Horticultural Crops in Southern China of Guangdong Higher Education Institutes, Guangzhou 510642, China;
    4. Tea technology promotion station, Sanming 365000, China

Received date: 2013-03-04

  Revised date: 2013-03-25

  Online published: 2019-09-04

摘要

以EGCG和没食子酸丙酯(PG)为起始化合物,以碘甲烷作为甲基化试剂,通过化学合成的方法选择性地合成了EGCG的甲基化衍生物EGCG4"Me,通过核磁共振鉴定其结构。

关键词: EGCG; EGCG4"Me; 化学合成

本文引用格式

赖榕辉 , 赵文芳 , 黄亚辉 , 周文 , 吴春兰 , 赖幸菲 , 赵文霞 , 张敏 . EGCG4"Me的选择性合成[J]. 茶叶科学, 2013 , 33(6) : 550 -555 . DOI: 10.13305/j.cnki.jts.2013.06.001

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.

参考文献

[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.
文章导航

/