Epitheaflagallin 3-O-gallate
(Synonyms: 表没食子儿茶素没食子酸酯) 目录号 : GC38622
Epitheaflagallin 3-O-gallate 是红茶中的次要多酚。Epitheaflagallin 3-O-gallate 在体内和体外表现出多种生理功能，包括抗氧化活性，胰脂肪酶抑制，山梨糖链球菌糖基转移酶抑制以及对基质金属蛋白酶-1 和-3 的活性以及人牙龈成纤维细胞的合成的抑制作用。
Cas No.:102067-92-5
Sample solution is provided at 25 µL, 10mM.
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- Purity: >95.00%
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Epitheaflagallin 3-O-gallate is a minor polyphenol in black tea. Epitheaflagallin 3-O-gallate exhibits versatile physiological functions in vivo and in vitro, including antioxidative activity, pancreatic lipase inhibition, Streptococcus sorbinusglycosyltransferase inhibition, and an inhibiting effect on the activity of matrix metalloprotease-1 and -3 and their synthesis by human gingival fibroblasts[1].
[1]. Itoh N, et al. Functional Characterization of Epitheaflagallin 3-O-Gallate Generated in Laccase-Treated GreenTea Extracts in the Presence of Gallic Acid. J Agric Food Chem. 2017 Dec 6;65(48):10473-10481.
| Cas No. | 102067-92-5 | SDF | |
| 别名 | 表没食子儿茶素没食子酸酯 | ||
| Canonical SMILES | O=C(O[C@H]1[C@@H](C(C=C2O)=CC3=CC(O)=C(O)C(O)=C3C2=O)OC4=CC(O)=CC(O)=C4C1)C5=CC(O)=C(O)C(O)=C5 | ||
| 分子式 | C27H20O13 | 分子量 | 552.44 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at 2-8°C,protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.8102 mL | 9.0508 mL | 18.1015 mL |
| 5 mM | 0.362 mL | 1.8102 mL | 3.6203 mL |
| 10 mM | 0.181 mL | 0.9051 mL | 1.8102 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Functional Characterization of Epitheaflagallin 3-O-gallate Generated in Laccase-Treated Green Tea Extracts in the Presence of Gallic Acid
J Agric Food Chem 2017 Dec 6;65(48):10473-10481.PMID:29131612DOI:10.1021/acs.jafc.7b04208.
Epitheaflagallin (ETFG) and Epitheaflagallin 3-O-gallate (ETFGg) are minor polyphenols in black tea extract that are enzymatically synthesized from epigallocatechin (EGC) and epigallocatechin gallate (EGCg), respectively, in green tea extract via laccase oxidation in the presence of gallic acid. The constituents of laccase-treated green tea extract in the presence of gallic acid are thus quite different from those of nonlaccase-treated green tea extract: EGC and EGCg are present in lower concentrations, and ETFG and ETFGg are present in higher concentrations. Additionally, laccase-treated green tea extract contains further polymerized catechin derivatives, comparable with naturally fermented teas such as oolong tea and black tea. We found that ETFGg and laccase-treated green tea extracts exhibit versatile physiological functions in vivo and in vitro, including antioxidative activity, pancreatic lipase inhibition, Streptococcus sorbinus glycosyltransferase inhibition, and an inhibiting effect on the activity of matrix metalloprotease-1 and -3 and their synthesis by human gingival fibroblasts. We confirmed that these inhibitory effects of ETFGg in vitro match well with the results obtained by docking simulations of the compounds with their target enzymes or noncatalytic protein. Thus, ETFGg and laccase-treated green tea extracts containing ETFGg are promising functional food materials with potential antiobesity and antiperiodontal disease activities.
Characterization and cloning of laccase gene from Hericium coralloides NBRC 7716 suitable for production of Epitheaflagallin 3-O-gallate
Enzyme Microb Technol 2016 Jan;82:125-132.PMID:26672458DOI:10.1016/j.enzmictec.2015.09.004.
Epitheaflagallin 3-O-gallate (ETFGg) is a minor polyphenol found in black tea extract, which has good physiological functions. It is synthesized from epigallocatechin gallate (EGCg) with gallic acid via laccase oxidation. Various basidiomycetes and fungi were screened to find a suitable laccase for the production of ETFGg. A basidiomycete, Hericium coralloides NBRC 7716, produced an appropriate extracellular laccase. The purified laccase produced twice the level of ETFGg compared with commercially available laccase from Trametes sp. The enzyme, termed Lcc2, is a monomeric protein with an apparent molecular mass of 67.2 kDa. The N-terminal amino acid sequence of Lcc2 is quite different from laccase isolated from the fruiting bodies of Hericium. Lcc2 showed similar substrate specificity to known laccases and could oxidize various phenolic substrates, including pyrogallol, gallic acid, and 2,6-dimethoxyphenol. The full-length lcc2 gene was obtained by PCR using degenerate primers, which were designed based on the N-terminal amino acid sequence of Lcc2 and conserved copper-binding sites of laccases, and 5'-, and 3'-RACE PCR with mRNA. The Lcc2 gene showed homology with Lentinula edodes laccase (sharing 77% amino acid identity with Lcc6). We successfully produced extracellular Lcc2 using a heterologous expression system with Saccharomyces cerevisiae. Moreover, it was confirmed that the recombinant laccase generates similar levels of ETFGg as the native enzyme.
Inhibitory effect of green tea polyphenols on membrane-type 1 matrix metalloproteinase, MT1-MMP
Biol Pharm Bull 2003 Sep;26(9):1235-8.PMID:12951464DOI:10.1248/bpb.26.1235.
Matrix metalloproteinases (MMPs), especially membrane-type 1 matrix metalloproteinase (MT1-MMP), which generates an active form of MMP-2 from proMMP-2, are deeply involved in angiogenesis as well as in tumor cell migration and metastasis. To obtain a specific inhibitor for MT1-MMP, we screened a number of natural and synthetic compounds using recombinant human MMP-2, MMP-7, and soluble MT1-MMP in a fluorogenic peptide cleavage assay. (-)-Epigallocatechin 3-O-gallate (EGCG) followed by (-)-epigallocatechin 3,5-di-O-gallate and Epitheaflagallin 3-O-gallate, was found to have potent and distinct inhibitory activity against MT1-MMP. Therefore, we investigated the effect of EGCG on the suppression of MMP-2 activation as determined by gelatin zymography, and observed that the active form of MMP-2 in the conditioned medium of human umbilical vein endothelial cells was decreased in the presence of EGCG. The results suggest the possibility that tea polyphenols suppress tumor growth through the suppression of angiogenesis.