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Merck
CN
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文件

G6782

Sigma-Aldrich

(−)-没食子儿茶素没食子酸酯

from green tea, ≥98% (HPLC)

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别名:
(2S,3R)-2-（3,4,5-三羟基苯基）-3,4-二氢-1 (2H)-苯并吡喃-3,5,7-三醇 3-（3,4,5-三羟基苯甲酸酯）
经验公式（希尔记法）:
C22H18O11
CAS号:
4233-96-9
分子量:
458.37
MDL编号:
MFCD00214298
UNSPSC代码:
12352200
PubChem化学物质编号:
24895275
NACRES:
NA.77

生物来源

green tea

质量水平

200

检测方案

≥98% (HPLC)

形式

powder

应用

metabolomics
vitamins, nutraceuticals, and natural products

储存温度

2-8°C

SMILES字符串

Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@@H](Oc2c1)c4cc(O)c(O)c(O)c4

InChI

1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21+/m1/s1

InChI key

WMBWREPUVVBILR-NQIIRXRSSA-N

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相关类别

一般描述

(−)-没食子儿茶素没食子酸酯(GCG)是含有一个没食子基元的多酚类化合物。它是常见的儿茶素类物质表没食子儿茶素没食子酸酯的差向异构体。儿茶素在热处理或巴氏灭菌过程中经常发生差向异构化。

应用

(−)-没食子儿茶素没食子酸酯已用于：
  • 进行植物乳杆菌(Lactobacillus plantarum)重组单宁酶的酶活测定
  • 研究其对HIV-1整合酶的抑制作用
  • 研究其在大鼠肝脏胆固醇代谢中的调节机理
  • 分析其作为多酚对人精子的影响以及在辅助生殖技术中的应用
  • 研究其对细胞型朊蛋白(PrPC)压力保护性活性和羊瘙痒病朊蛋白(PrPSc)形成的干扰作用

生化/生理作用

已知(−)-没食子儿茶素没食子酸酯等儿茶素类物质具有抗病毒、抗氧化、抗突变和抗肥胖功效。它具有人免疫缺陷病毒-1(HIV-1)整合酶抑制活性，可干扰人免疫缺陷病毒-1(HIV-1)整合酶和病毒DNA之间的相互作用。GCG还可抑制肠出血型大肠杆菌的Vero毒素(VT)释放。它对胆固醇吸收具有抑制作用，据报道在降低血浆胆固醇方面比儿茶素更具功效，因而可用于防止动脉粥样硬化。

象形图

Exclamation mark
GHS07

警示用语：

Warning

危险声明

H315,H319,H335

危险分类

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

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Angelika S Rambold et al.
Journal of neurochemistry, 107(1), 218-229 (2008-08-12)
A hallmark in prion diseases is the conformational transition of the cellular prion protein (PrP(C)) into a pathogenic conformation, designated scrapie prion protein (PrP(Sc)), which is the essential constituent of infectious prions. Here, we show that epigallocatechin gallate (EGCG) and
Y Sugita-Konishi et al.
Biochimica et biophysica acta, 1472(1-2), 42-50 (1999-11-26)
We studied the effects of six catechin derivatives (catechin, epigallocatechin, epicatechin, epicatechin gallate, epigallocatechin gallate (EGCg) and gallocatechin gallate (GCg)) in green tea on the production and extracellular release of Vero toxins (VTs) from enterohemorrhagic Escherichia coli (EHEC) cultured at
Sang Min Lee et al.
Lipids, 43(5), 419-429 (2008-03-28)
The (-)-gallocatechin gallate (GCG) concentration in some tea beverages can account for as much as 50% of the total catechins, as a result of sterilization. The present study aims to examine the effects of GCG-rich tea catechins on hyperlipidemic rats
Fan Jiang et al.
Clinical immunology (Orlando, Fla.), 137(3), 347-356 (2010-09-14)
Four catechins with the galloyl moiety, including catechin gallate (CG), epigallocatechin gallate (EGCG), gallocatechin gallate (GCG), and epicatechin gallate (ECG), were found to inhibit HIV-1 integrase effectively as determined by our ELISA method. In our docking study, it is proposed
Ikuo Ikeda et al.
Journal of agricultural and food chemistry, 51(25), 7303-7307 (2003-12-04)
It has been known that tea catechins, (-)-epicatechin (1), (-)-epigallocatechin (2), (-)-epicatechin gallate (3), and (-)-epigallocatechin gallate (4) are epimerized to(-)-catechin (5), (-)-gallocatechin (6), (-)-catechin gallate (7), and (-)-gallocatechin gallate (8), respectively, during retort pasteurization. We previously reported that tea
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