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Theaflavin-3-gallate

CAS# 30462-34-1

Theaflavin-3-gallate

Catalog No. BCN2316----Order now to get a substantial discount!

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Chemical structure

Theaflavin-3-gallate

3D structure

Chemical Properties of Theaflavin-3-gallate

Cas No. 30462-34-1 SDF Download SDF
PubChem ID 169167 Appearance Orange-red powder
Formula C36H28O16 M.Wt 716.60
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Theaflavin 2; Theaflavin 2A; Theaflavin monogallate A
Solubility Soluble in ethanol and methan
Chemical Name [(2R,3R)-5,7-dihydroxy-2-[3,4,5-trihydroxy-6-oxo-1-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]benzo[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(=C(C4=C(C(=O)C=C(C=C34)C5C(CC6=C(C=C(C=C6O5)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)O)O)O
Standard InChIKey KMJPKUVSXFVQGZ-WQLSNUALSA-N
Standard InChI InChI=1S/C36H28O16/c37-14-5-20(39)18-10-26(45)35(51-27(18)7-14)17-9-25(44)33(48)30-16(17)1-12(2-24(43)32(30)47)34-29(11-19-21(40)6-15(38)8-28(19)50-34)52-36(49)13-3-22(41)31(46)23(42)4-13/h1-9,26,29,34-35,37-42,44-46,48H,10-11H2,(H,43,47)/t26-,29-,34-,35-/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.
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 Theaflavin-3-gallate

The leaves of Black tea.

Biological Activity of Theaflavin-3-gallate

DescriptionTheaflavin-3-gallate has anticancer and apoptotic effects in non-small cell lung carcinoma, it acts as prooxidants and induce oxidative stress, with carcinoma cells more sensitive than normal fibroblasts. Theaflavin-3-gallate can play a role in decreased intestinal cholesterol absorption via inhibition of micelle formation.
In vitro

Theaflavin-3-gallate and theaflavin-3'-gallate, polyphenols in black tea with prooxidant properties.[Pubmed: 18346048]

Basic Clin Pharmacol Toxicol. 2008 Jul;103(1):66-74.

This study compared the in vitro responses of human gingival fibroblasts and of carcinoma cells derived from the tongue to Theaflavin-3-gallate (TF-2A) and theaflavin-3'-gallate (TF-2B), polyphenols in black tea.
METHODS AND RESULTS:
The antiproliferative and cytotoxic effects of the theaflavin monomers were more pronounced to the carcinoma, than to the normal, cells. In phosphate buffer at pH 7.4, the theaflavins generated hydrogen peroxide and the superoxide anion, suggesting that their mode of toxicity may be due, in part, to the induction of oxidative stress. In a cell-free assay, Theaflavin-3-gallate and TF-2B reacted directly with reduced glutathione (GSH), in a time- and concentration-dependent manner. Intracellular storages of GSH were depleted on treatment of the cells with the theaflavin monomers. Depletion of intracellular GSH was more extensive with Theaflavin-3-gallate than with TF-2B and was more pronounced in the carcinoma, than in the normal, cells. The toxicities of the theaflavins were potentiated when the cells were cotreated with the GSH depleter, d,l-buthionine-[S,R]-sulfoximine. In the presence of catalase, pyruvate and divalent cobalt, all scavengers of reactive oxygen species, the cytotoxicities of the theaflavins were lessened. Theaflavin-3-gallate and TF-2B induced lipid peroxidation in the carcinoma cells, whereas in the fibroblasts, peroxidation was evident upon exposure to Theaflavin-3-gallate, but not to TF-2B.
CONCLUSIONS:
These studies demonstrated that the black tea theaflavin monomers, Theaflavin-3-gallate and TF-2B, act as prooxidants and induce oxidative stress, with carcinoma cells more sensitive than normal fibroblasts.

Anticancer and apoptotic effects of theaflavin-3-gallate in non-small cell lung carcinoma.[Reference: WebLink]

Bangl. J. Pharmacol., 2015, 10(4):3047-53.

The objective was to determine the antiproliferative and apoptotic effects of Theaflavin-3-gallate in human non-small cell lung cancer cells (A-549) along with determining the effect on cell cycle phase distribution, cell migration and invasion.
METHODS AND RESULTS:
Cell viability was determined by MTT assay while as phase contrast and fluorescence microscopies were involved to study apoptotic morphologi-cal features in these cells. Flow cytometry investigated the effect of Theaflavin-3-gallate on cell cycle phase distribution. Theaflavin-3-gallate treatment led to a substantial cytotoxic effect in A-549 cancer cells with IC50 values of 42.1 μM and 27.9 μM at 24 and 48 hours respectively. Further, 80 and 160 μM dose of Theaflavin-3-gallate induced apoptotic features including chromatin margina-tion and micronuclei presence. The population of cells in G2/M phase increased from 2.7% (control) to 6.8%, 17.2% and finally to 46.5% after treatment with 20, 80 and 160 μM concentration of Theaflavin-3-gallate respectively indicating G2/M phase cell cycle arrest.

Protocol of Theaflavin-3-gallate

Structure Identification
J Agric Food Chem. 2008 Dec 24;56(24):12031-6.

Theaflavins from black tea, especially theaflavin-3-gallate, reduce the incorporation of cholesterol into mixed micelles.[Pubmed: 19049290]

Tea is one of the most widely consumed beverages in the world and may be associated with reduced heart disease rates. Theaflavins, which are formed in the production of black tea, have been suggested being responsible for the blood-cholesterol-lowering (BCL) effects of tea.
METHODS AND RESULTS:
We hypothesized that the effect of theaflavins on BCL could be through interference in the formation of dietary mixed micelles, which could result in reduced intestinal cholesterol absorption. Micelles were produced by mixing oleic acid, bile acids, lyso-phosphatidylcholine, and cholesterol. Theaflavin-treated micelles/particles were analyzed using electron microscopy (cryo-TEM), high-performance liquid chromatography (HPLC) analysis, and light-scattering particle size measurements. A dose-dependent inhibitory effect of theaflavins on the incorporation of (14)C-labeled cholesterol into micelles and a theaflavin-dependent increase in particle size was found. These particles consisted of insoluble large multilamellar vesicles with onion-like structures. Ultracentrifugation and HPLC analysis revealed that the pellets contained mainly Theaflavin-3-gallate, while the remaining theaflavins were found to be present in the supernatant. Using purified theaflavin subtypes confirmed that mainly Theaflavin-3-gallate is responsible for multilamellar vesicle formation.
CONCLUSIONS:
These results show that theaflavins can play a role in decreased intestinal cholesterol absorption via inhibition of micelle formation.

Theaflavin-3-gallate Dilution Calculator

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Preparing Stock Solutions of Theaflavin-3-gallate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.3955 mL 6.9774 mL 13.9548 mL 27.9096 mL 34.887 mL
5 mM 0.2791 mL 1.3955 mL 2.791 mL 5.5819 mL 6.9774 mL
10 mM 0.1395 mL 0.6977 mL 1.3955 mL 2.791 mL 3.4887 mL
50 mM 0.0279 mL 0.1395 mL 0.2791 mL 0.5582 mL 0.6977 mL
100 mM 0.014 mL 0.0698 mL 0.1395 mL 0.2791 mL 0.3489 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 Theaflavin-3-gallate

Theaflavin-3-gallate and theaflavin-3'-gallate, polyphenols in black tea with prooxidant properties.[Pubmed:18346048]

Basic Clin Pharmacol Toxicol. 2008 Jul;103(1):66-74.

This study compared the in vitro responses of human gingival fibroblasts and of carcinoma cells derived from the tongue to Theaflavin-3-gallate (TF-2A) and theaflavin-3'-gallate (TF-2B), polyphenols in black tea. The antiproliferative and cytotoxic effects of the theaflavin monomers were more pronounced to the carcinoma, than to the normal, cells. In phosphate buffer at pH 7.4, the theaflavins generated hydrogen peroxide and the superoxide anion, suggesting that their mode of toxicity may be due, in part, to the induction of oxidative stress. In a cell-free assay, TF-2A and TF-2B reacted directly with reduced glutathione (GSH), in a time- and concentration-dependent manner. Intracellular storages of GSH were depleted on treatment of the cells with the theaflavin monomers. Depletion of intracellular GSH was more extensive with TF-2A than with TF-2B and was more pronounced in the carcinoma, than in the normal, cells. The toxicities of the theaflavins were potentiated when the cells were cotreated with the GSH depleter, d,l-buthionine-[S,R]-sulfoximine. In the presence of catalase, pyruvate and divalent cobalt, all scavengers of reactive oxygen species, the cytotoxicities of the theaflavins were lessened. TF-2A and TF-2B induced lipid peroxidation in the carcinoma cells, whereas in the fibroblasts, peroxidation was evident upon exposure to TF-2A, but not to TF-2B. These studies demonstrated that the black tea theaflavin monomers, TF-2A and TF-2B, act as prooxidants and induce oxidative stress, with carcinoma cells more sensitive than normal fibroblasts.

Theaflavins from black tea, especially theaflavin-3-gallate, reduce the incorporation of cholesterol into mixed micelles.[Pubmed:19049290]

J Agric Food Chem. 2008 Dec 24;56(24):12031-6.

Tea is one of the most widely consumed beverages in the world and may be associated with reduced heart disease rates. Theaflavins, which are formed in the production of black tea, have been suggested being responsible for the blood-cholesterol-lowering (BCL) effects of tea. We hypothesized that the effect of theaflavins on BCL could be through interference in the formation of dietary mixed micelles, which could result in reduced intestinal cholesterol absorption. Micelles were produced by mixing oleic acid, bile acids, lyso-phosphatidylcholine, and cholesterol. Theaflavin-treated micelles/particles were analyzed using electron microscopy (cryo-TEM), high-performance liquid chromatography (HPLC) analysis, and light-scattering particle size measurements. A dose-dependent inhibitory effect of theaflavins on the incorporation of (14)C-labeled cholesterol into micelles and a theaflavin-dependent increase in particle size was found. These particles consisted of insoluble large multilamellar vesicles with onion-like structures. Ultracentrifugation and HPLC analysis revealed that the pellets contained mainly Theaflavin-3-gallate, while the remaining theaflavins were found to be present in the supernatant. Using purified theaflavin subtypes confirmed that mainly Theaflavin-3-gallate is responsible for multilamellar vesicle formation. These results show that theaflavins can play a role in decreased intestinal cholesterol absorption via inhibition of micelle formation.

Description

Theaflavin-3'-gallate, a black tea theaflavin monomer, is regarded as the biologically important active component of black tea and provides health benefits. Theaflavin-3'-gallate acts as prooxidants and induces oxidative stress in the carcinoma cells. Theaflavin-3'-gallate reacts directly with reduced glutathione (GSH) in a time- and concentration-dependent manner.

Keywords:

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