E3893
(−)-Epicatechin gallate
≥98% (HPLC), from green tea
동의어(들):
(−)-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-Galloylepicatechin
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크기 선택
제품정보 (DICE 배송 시 비용 별도)
실험식(Hill 표기법):
C22H18O10
CAS 번호:
Molecular Weight:
442.37
NACRES:
NA.21
PubChem Substance ID:
UNSPSC Code:
12352205
MDL number:
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
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 key
LSHVYAFMTMFKBA-TZIWHRDSSA-N
biological source
green tea
assay
≥98% (HPLC)
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
storage temp.
2-8°C
Quality Level
Gene Information
human ... CYP1A2(1544)
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General description
(−)-Epicatechin gallate is one of the major polyphenols present in green tea. It belongs to the catechin gallates group of organic compounds. ECG has a chemical structure like that of (−)-epigallocatechin gallate (EGCG), the other major polyphenol found in green tea.
Application
(−)-Epicatechin gallate has been used:
- in cell proliferation assays on the human brain microvascular endothelial cells (HBMVECs) to understand its effectiveness against anti-ischemic/reperfusion injury
- as an inhibitor in Human Salivary α-Amylase (HAS) and α-Glucosidase (AGH) in inhibition assays
- may be used as a cancer chemopreventive polyphenol in two human colorectal cell lines HCT-116 and SW-480
- as an inhibitor to in vitro collagenase and elastase enzymes
- as a supplement in spermatozoa incubation to check its effectiveness against oxidative stress
Biochem/physiol Actions
(−)-Epicatechin gallate (ECG), a potent free-radical scavenger has an inhibitory effect on collagenase and elastase enzymes making it an anti-aging agent. It displays antiproliferative effects on human colorectal cells and hence is a chemo-preventative agent. It influences cell survival, preventing apoptosis or autophagy by promoting cell proliferation in oxygen-glucose deprived human brain microvascular endothelial cells. Being structurally and functionally similar to EGCG, ECG might be involved in balancing the mammalian target of rapamycin (mTOR)-AMP-activated protein kinase (AMPK) pathways in endoplasmic reticulum stress. It prevents cell death in this scenario by showing resistance against oxygen-deprived cells. ECG may contribute in preventing oxidative stress. It effectively inhibits secretory sphingomyelinase in many disease states and provides protection for human spermatozoa in Assisted reproductive technology (ART).
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
저장 등급
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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
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
Wanda C Reygaert
BioMed research international, 2018, 9105261-9105261 (2018-08-15)
Green tea is one of the most popular drinks consumed worldwide. Produced mainly in Asian countries from the leaves of the Camellia sinensis plant, the potential health benefits have been widely studied. Recently, researchers have studied the ability of green
Sven Stadlbauer et al.
Chemical communications (Cambridge, England), 48(67), 8425-8427 (2012-07-14)
Concise synthesis of (-)-epicatechin and its 3-O-gallate is described, illustrating efficacy of the new strategy for catechin-class polyphenols based on assembly of lithiated fluorobenzene and epoxy alcohol followed by a pyran cyclization. 1,3,5-Trifluorobenzene serves as the A-ring equivalent for functionalization
Kusum Rathore et al.
Carcinogenesis, 33(1), 174-183 (2011-11-03)
Long-term exposure to low doses of environmental carcinogens contributes to sporadic human breast cancers. Epidemiologic and experimental studies indicate that green tea catechins (GTCs) may intervene with breast cancer development. We have been developing a chronically induced breast cell carcinogenesis
문서
Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.
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