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文件

E3893

(−)-表儿茶素没食子酸酯

Name: (−)-表儿茶素没食子酸酯
Brand: SIAL

≥98% (HPLC), from green tea

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别名:

(-)-cis-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate, (-)-cis-3,3′,4′,5,7-Pentahydroxyflavane 3-gallate, 3- O -没食子酰表儿茶精

经验公式（希尔记法）:

C₂₂H₁₈O₁₀

CAS号:

1257-08-5

分子量:

442.37

MDL编号:

MFCD00075936

PubChem化学物质编号:

24894531

NACRES:

NA.21

生物来源

green tea

质量水平

100

检测方案

≥98% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

储存温度

2-8°C

SMILES string

Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c4ccc(O)c(O)c4

InChI

1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1

InChI key

LSHVYAFMTMFKBA-TZIWHRDSSA-N

Gene Information

human ... CYP1A2(1544)

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一般描述

(−)-表儿茶素没食子酸酯是绿茶的主要多酚成分之一，属于儿茶素没食子酸酯类有机化合物。ECG的化学结构与绿茶中的另一种主要多酚(−)-表没食子儿茶素没食子酸酯(EGCG)相似。

应用

(−)-表儿茶素没食子酸酯已用于：

通过人脑微血管内皮细胞(HBMVEC)的增殖检测，了解其抗缺血再灌注损伤的有效性
作为人唾液α-淀粉酶(HAS)和α-葡萄糖苷酶(AGH)抑制检测的抑制剂
可用作人结直肠细胞系HCT-116和SW-480的多酚类癌症化学预防药物
作为胶原酶和弹性蛋白酶的体外抑制剂
作为精子培育的添加剂，验证其抗氧化应激作用的有效性

生化/生理作用

(−)-表儿茶素没食子酸酯(ECG)是强效的自由基清除剂，因对胶原蛋白和弹性蛋白酶具有抑制作用而可用作抗老化剂。它对人结直肠细胞具有抗增殖作用，因而可用作化学预防药物。它影响细胞生存，可通过促进氧糖剥夺的人脑微血管内皮细胞的增殖，防止细胞凋亡或自噬。ECG在结构与功能上都与EGCG类似，可参与内质网应激中哺乳动物雷帕霉素靶蛋白(mTOR)-AMP激活蛋白激酶(AMPK)通路的平衡。它在这种情况下可抵抗氧剥夺造成的细胞损伤，从而防止细胞死亡。ECG可参与防止氧化应激。它可有效抑制多种疾病状态下的分泌性鞘磷脂酶作用，并在辅助生殖技术(ART)中为人类精子提供保护。

象形图

GHS07

警示用语：

Warning

危险声明

H315 - H319 - H335

预防措施声明

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

危险分类

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

靶器官

Respiratory system

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

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Epigallocatechin-3-Gallate (EGCG) Promotes Autophagy-Dependent Survival via Influencing the Balance of mTOR-AMPK Pathways upon Endoplasmic Reticulum Stress.

Marianna Holczer et al.

Oxidative medicine and cellular longevity, 2018, 6721530-6721530 (2018-04-11)

The maintenance of cellular homeostasis is largely dependent on the ability of cells to give an adequate response to various internal and external stimuli. We have recently proposed that the life-and-death decision in endoplasmic reticulum (ER) stress response is defined

Strong Inhibition of Secretory Sphingomyelinase by Catechins, Particularly by (-)-Epicatechin 3-O-Gallate and (-)-3'-O-Methylepigallocatechin 3-O-Gallate.

Keiko Kobayashi et al.

Journal of nutritional science and vitaminology, 62(2), 123-129 (2016-06-07)

Sphingomyelinases (SMases) are key enzymes involved in many diseases which are caused by oxidative stress, such as atherosclerosis, diabetes mellitus, nonalcoholic fatty liver disease, and Alzheimer's disease. SMases hydrolyze sphingomyelin to generate ceramide, a well-known pro-apoptotic lipid. SMases are classified

Evaluation of different teas against starch digestibility by mammalian glycosidases.

Lee Wah Koh et al.

Journal of agricultural and food chemistry, 58(1), 148-154 (2010-01-07)

Current work investigated the ability of different tea (green, oolong and black teas) in inhibiting human salivary alpha-amylase (HSA) and mammalian alpha-glucosidase (AGH). The inhibitory profiles were correlated to their major polyphenol content (theaflavins and catechins). The fully fermented black

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Nutrients, 4(11), 1679-1691 (2012-12-04)

Green tea is a popular drink consumed daily by millions of people around the world. Previous studies have shown that some polyphenol compounds from green tea possess anticancer activities. However, systemic evaluation was limited. In this study, we determined the

Epicatechin Gallate Protects HBMVECs from Ischemia/Reperfusion Injury through Ameliorating Apoptosis and Autophagy and Promoting Neovascularization.

Bing Fu et al.

Oxidative medicine and cellular longevity, 2019, 7824684-7824684 (2019-04-10)

Green tea is one of the most beverages with antioxidants and nutrients. As one of the major components of green tea, (-)-epicatechin gallate (ECG) was evaluated for its antioxidative properties in the present study. Cell proliferation assay, tube formation, cell

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