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1,2,3,6-Tetragalloylglucose

CAS# 79886-50-3

1,2,3,6-Tetragalloylglucose

Catalog No. BCN2159----Order now to get a substantial discount!

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1,2,3,6-Tetragalloylglucose: 5mg $161 In Stock
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Quality Control of 1,2,3,6-Tetragalloylglucose

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Chemical structure

1,2,3,6-Tetragalloylglucose

3D structure

Chemical Properties of 1,2,3,6-Tetragalloylglucose

Cas No. 79886-50-3 SDF Download SDF
PubChem ID 73178 Appearance Powder
Formula C34H28O22 M.Wt 788.57
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(2R,3R,4S,5R,6S)-3-hydroxy-4,5,6-tris[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
SMILES C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)O
Standard InChIKey RATQVALKDAUZBW-XPMKZLBQSA-N
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.
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.
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.

Source of 1,2,3,6-Tetragalloylglucose

The peel of Punica granatum L.

Biological Activity of 1,2,3,6-Tetragalloylglucose

Description1. 1,2,3,6-Tetragalloylglucose has antioxidative activity. 2. 1,2,3,6-Tetragalloylglucose shows the most potent anticomplement activity (IC(50), 34 microM).
TargetsLDL

1,2,3,6-Tetragalloylglucose Dilution Calculator

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1,2,3,6-Tetragalloylglucose Molarity Calculator

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Preparing Stock Solutions of 1,2,3,6-Tetragalloylglucose

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.2681 mL 6.3406 mL 12.6812 mL 25.3624 mL 31.703 mL
5 mM 0.2536 mL 1.2681 mL 2.5362 mL 5.0725 mL 6.3406 mL
10 mM 0.1268 mL 0.6341 mL 1.2681 mL 2.5362 mL 3.1703 mL
50 mM 0.0254 mL 0.1268 mL 0.2536 mL 0.5072 mL 0.6341 mL
100 mM 0.0127 mL 0.0634 mL 0.1268 mL 0.2536 mL 0.317 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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References on 1,2,3,6-Tetragalloylglucose

Anti-complement activity of constituents from the stem-bark of Juglans mandshurica.[Pubmed:12843637]

Biol Pharm Bull. 2003 Jul;26(7):1042-4.

Four known flavonoids and two galloyl glucoses isolated from the stem-bark of Juglans mandshurica (Juglandaceae), namely taxifolin (1), afzelin (2), quercitrin (3), myricitrin (4), 1,2,6-trigalloylglucose (5), and 1,2,3,6-Tetragalloylglucose (6), were evaluated for their anti-complement activity against complement system. Afzelin (2) and quercitrin (3) showed inhibitory activity against complement system with 50% inhibitory concentrations (IC(50)) values of 258 and 440 microM. 1,2,6-Trigalloylglucose (5) and 1,2,3,6-Tetragalloylglucose (6) exhibited anti-complement activity with IC(50) values of 136 and 34 microM. In terms of the evaluation of the structure-activity relationship of 3,5,7-trihydroxyflavone, compounds 2, 3, and 4 were hydrolyzed with naringinase to give kaempferol (2a), quercetin (3a), and myricetin (4a) as their aglycones, and these were also tested for their anti-complement activity. Of the three aglycones, kaempferol (2a) exhibited weak anti-complement activity with an IC(50) value of 730 microM, while quercetin (3a) and myricetin (4a) were inactive in this assay system. Among the compounds tested, 1,2,3,6-Tetragalloylglucose (6) showed the most potent anticomplement activity (IC(50), 34 microM).

Inhibition effects of the classical pathway complement of isolated compounds from Quercus glauca.[Pubmed:21078772]

Hum Exp Toxicol. 2011 Sep;30(9):1415-9.

Species of the Quercus species is an evergreen broadleaf tree found not only in Korea but also in China, Taiwan, and Japan. Quercus species is the most commonly occurring plant among the 50 native species of the family Fagaceae in Korea, China, and Taiwan. Quercus species have been used for diarrhea, dysentery, dermatitis, and hemorrhagia in Korean folk medicine. The present study evaluated the anticomplement effect of constituents from Quercus species (Fagaceae) in classical pathway complement system. We have evaluated leaves of five species of the Quercus genus with regard to its anticomplement activity and have identified its active principles following activity-guided isolation. Bioactivity-guided fractionation of the 80% methanol extracts of the stem barks of Quercus glauca Thunberg has led to the isolation of galloyl derivatives, displaying high anticomplement activity. Four galloyl derivatives isolated from the leaves of Q. glauca, namely 6'-O-galloyl salidroside (1), methyl gallate (2), 1,2,3,6-Tetragalloylglucose (3), and 1,2,6-trigalloylglucose (4). 1, 2, 3 and 4 showed inhibitory activity against complement system with 50% inhibitory concentrations (IC(50)) values of 224 muM, 362.4 muM, 32.3 muM, and 138.3 muM. Among the compounds tested, 3 showed the most potent anticomplement activity (IC(50), 32.3 muM). This is the first report of the isolation and anticomplement activity from Q. glauca.

Antioxidative activities of galloyl glucopyranosides from the stem-bark of Juglans mandshurica.[Pubmed:18685223]

Biosci Biotechnol Biochem. 2008 Aug;72(8):2158-63.

Two phenolics, 1,2,6-trigalloylglucose (1) and 1,2,3,6-Tetragalloylglucose (2), isolated from the stem-bark of Juglans mandshurica were evaluated for their antioxidative activities. The results showed that compounds 1 and 2 exhibited strong scavenging activities against 1,1'-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis-(3-ethylbenzenthiazoline-6-sulphonic) acid (ABTS(*+)), and superoxide radicals (O(2)(*-)), and also had a significant inhibitory effect on lipid peroxidation and low-density lipoprotein (LDL) oxidation. The strong superoxide radical scavenging of 1 and 2 resulted from the potential competitive inhibition with xanthine at the active site of xanthine oxidase (OX). In addition, compounds 1 and 2 displayed significant lipoxygenase inhibitory activity, the mode of inhibition also being identified as competitive. In comparison, the antioxidative activities of compounds 1 and 2, together with gallic acid, indicated that the number of galloyl moieties could play an important role in the antioxidative activity.

Description

1,2,3,6-Tetragalloylglucose is a potent UDP glucuronosyltransferase 1 family, polypeptide A1 (UGT1A1) inhibitor, with a Ki of 1.68 μM.

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