Epitheaflagallin 3-O-gallateCAS# 102067-92-5 |
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| Cas No. | 102067-92-5 | SDF | Download SDF |
| PubChem ID | 467319 | Appearance | Powder |
| Formula | C27H20O13 | M.Wt | 552.44 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | [(2R,3R)-5,7-dihydroxy-2-(2,3,4,5-tetrahydroxy-6-oxobenzo[7]annulen-8-yl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate | ||
| SMILES | C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C=C(C(=C4O)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O | ||
| Standard InChIKey | CMGRMMSVGCHWOK-FQRUVTKNSA-N | ||
| Standard InChI | InChI=1S/C27H20O13/c28-12-6-14(29)13-8-20(40-27(38)11-4-15(30)22(34)16(31)5-11)26(39-19(13)7-12)10-1-9-2-18(33)24(36)25(37)21(9)23(35)17(32)3-10/h1-7,20,26,28-31,33-34,36-37H,8H2,(H,32,35)/t20-,26-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Epitheaflagallin 3-O-gallate shows antioxidative activity, pancreatic lipase inhibition, Streptococcus sorbinus glycosyltransferase inhibition, and an inhibiting effect on the activity of matrix metalloprotease-1 and -3. 2. Epitheaflagallin 3-O-gallate is a promising functional food material with potential antiobesity and antiperiodontal disease activities. 3. Epitheaflagallin 3-O-gallate suppresses tumor growth through the suppression of angiogenesis. |
| Targets | MMP(e.g.TIMP) |
Epitheaflagallin 3-O-gallate Dilution Calculator
Epitheaflagallin 3-O-gallate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.8102 mL | 9.0508 mL | 18.1015 mL | 36.203 mL | 45.2538 mL |
| 5 mM | 0.362 mL | 1.8102 mL | 3.6203 mL | 7.2406 mL | 9.0508 mL |
| 10 mM | 0.181 mL | 0.9051 mL | 1.8102 mL | 3.6203 mL | 4.5254 mL |
| 50 mM | 0.0362 mL | 0.181 mL | 0.362 mL | 0.7241 mL | 0.9051 mL |
| 100 mM | 0.0181 mL | 0.0905 mL | 0.181 mL | 0.362 mL | 0.4525 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Functional Characterization of Epitheaflagallin 3-O-Gallate Generated in Laccase-Treated Green Tea Extracts in the Presence of Gallic Acid.[Pubmed:29131612]
J Agric Food Chem. 2017 Dec 6;65(48):10473-10481.
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.[Pubmed:26672458]
Enzyme Microb Technol. 2016 Jan;82:125-132.
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.
