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Theaflavin-3-gallate Sale

(Synonyms: 茶黄素-3-没食子酸酯) 目录号 : GC37779

A polyphenolic flavonoid with diverse biological activities

Theaflavin-3-gallate Chemical Structure

Cas No.:30462-34-1

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1 mg
¥720.00
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5 mg
¥1,800.00
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10 mg
¥2,880.00
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产品描述

Theaflavin-3-gallate is a polyphenolic flavonoid that has been found in black tea (C. sinensis) and has diverse biological activities.1,2,3 It scavenges singlet oxygen and hydrogen peroxide, as well as superoxide and hydroxide radicals (IC50s = 0.86, 0.45, 21.7, and 32.49 ?M, respectively), in cell-free assays.1 Theaflavin-3-gallate is cytotoxic to, and induces apoptosis in, OVCAR-3 and A2780/CP70 ovarian cancer, but not non-cancerous IOSE 364 ovarian epithelial, cells when used at concentrations of 20 and 40 ?M.2 It reduces oxazolone-induced ear edema and serum and ear levels of TNF-α, IFN-γ, and IL-12 in an oxazolone-sensitized mouse model of delayed-type hypersensitivity when administered at a dose of 50 mg/kg.3

1.Wu, Y.-y., Li, W., Xu, Y., et al.Evaluation of the antioxidant effects of four main theaflavin derivatives through chemiluminescence and DNA damage analysesJ. Zhejiang. Univ. Sci. B.12(9)744-751(2011) 2.Gao, Y., Rankin, G.O., Tu, Y., et al.Inhibitory effects of the four main theaflavin derivatives found in black tea on ovarian cancer cellsAnticancer Res.36(2)643-651(2016) 3.Yoshino, K., Yamazaki, K., and Sano, M.Preventive effects of black tea theaflavins against mouse type IV allergyJ. Sci. Food Agric.90(12)1983-1987(2010)

Chemical Properties

Cas No. 30462-34-1 SDF
别名 茶黄素-3-没食子酸酯
Canonical SMILES O=C(O[C@H]1[C@@H](C(C=C2O)=CC3=C([C@@H]4[C@H](O)CC5=C(O)C=C(O)C=C5O4)C=C(O)C(O)=C3C2=O)OC6=CC(O)=CC(O)=C6C1)C7=CC(O)=C(O)C(O)=C7
分子式 C36H28O16 分子量 716.6
溶解度 DMF: 25 mg/ml,DMF:PBS (pH 7.2) (1:6): 0.1 mg/ml,DMSO: 10 mg/ml,Ethanol: 10 mg/ml 储存条件 -20°C, protect from light
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1 mM 1.3955 mL 6.9774 mL 13.9548 mL
5 mM 0.2791 mL 1.3955 mL 2.791 mL
10 mM 0.1395 mL 0.6977 mL 1.3955 mL
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Research Update

Theaflavin-3-gallate, a natural antagonist for Hsp90: In-silico and in-vitro approach

Chem Biol Interact 2022 Feb 1;353:109774.PMID:34958756DOI:10.1016/j.cbi.2021.109774.

Poor prognosis and metastasis have been recognized as the major cause of breast cancer related deaths worldwide. Recent experimental evidence has shown that Hsp90, the prime chaperone, is overexpressed in many cancers and is responsible if reducing the 5-year survival rate of cancer patients. Therefore, targeted inhibition of Hsp90 may be a new and effective way to target cancer as well as enhancing therapeutic outcomes. In the present study, screening and simulation of potential natural compounds result in the identification of Theaflavin-3-gallate as a promising inhibitory compound of Hsp90. Further in-vitro validation of the cytotoxic effect of Theaflavin-3-gallate in human breast carcinoma cell line MCF7 and normal cell line MCF10A revealed that Theaflavin-3-gallate significantly inhibited the cell proliferation of MCF7 cells whereas no cytotoxic effect was observed on MCF10A cells. We also found that Theaflavin-3-gallate significantly induced programmed cell death by arresting cells in the G2/M phase of the cell cycle. A significant decrease in cell migration and colony formation by Theaflavin-3-gallate treatment was also observed in MCF7 cells. Furthermore, Theaflavin-3-gallate significantly downregulated the mRNA expression patterns of the HSP90, MMP9, VEGFA, and SPP1 genes. Collectively, our results demonstrated Theaflavin-3-gallate as a potential natural Hsp90 inhibitor that can be used to enhance the therapeutic efficacy of existing breast cancer therapies and improve overall survival of breast cancer patients.

Theaflavin Chemistry and Its Health Benefits

Oxid Med Cell Longev 2021 Nov 18;2021:6256618.PMID:34804369DOI:10.1155/2021/6256618.

Huge epidemiological and clinical studies have confirmed that black tea is a rich source of health-promoting ingredients, such as catechins and theaflavins (TFs). Furthermore, TF derivatives mainly include theaflavin (TF1), Theaflavin-3-gallate (TF2A), theaflavin-3'-gallate (TF2B), and theaflavin-3,3'-digallate (TF3). All of these TFs exhibit extensive usages in pharmaceutics, foods, and traditional medication systems. Various indepth studies reported that how TFs modulates health effects in cellular and molecular mechanisms. The available literature regarding the pharmacological activities of TFs has revealed that TF3 has remarkable anti-inflammatory, antioxidant, anticancer, antiobesity, antiosteoporotic, and antimicrobial properties, thus posing significant effects on human health. The current manuscript summarizes both the chemistry and various pharmacological effects of TFs on human health, lifestyle or aging associated diseases, and populations of gut microbiota. Furthermore, the biological potential of TFs has also been focused to provide a deeper understanding of its mechanism of action.

Insight into interaction mechanism between Theaflavin-3-gallate and α-glucosidase using spectroscopy and molecular docking analysis

J Food Biochem 2021 Jan;45(1):e13550.PMID:33150631DOI:10.1111/jfbc.13550.

To elucidate the α-glucosidase (α-GC) inhibitory mechanism of Theaflavin-3-gallate (TF-3-G), their interaction mechanism was investigated using spectroscopy and molecular docking analysis. The inhibition ratio of TF-3-G against α-GC was determined to be 92.3%. Steady fluorescence spectroscopy showed that TF-3-G effectively quenched the intrinsic fluorescence of α-GC through static quenching, forming a stable complex through hydrophobic interactions. Formation of the TF-3-G/α-GC complex was also confirmed by resonance light scattering spectroscopy. Synchronous fluorescence spectroscopy and circular dichroism spectroscopy indicated that the secondary structure of α-GC was changed by TF-3-G. Molecular docking was used to simulate TF-3-G/α-GC complex formation, showing that TF-3-G might be inserted into the hydrophobic region around the active site of ɑ-GC, and bind with the catalytic Asp215 and Asp352 residues. The ɑ-GC inhibitory mechanism of TF-3-G was mainly attributed to the change in ɑ-GC secondary structure caused by the complex formation. PRACTICAL APPLICATIONS: α-Glucosidase (α-GC) can hydrolyze the glycosidic bonds of starch and oligosaccharides in food and release glucose. Therefore, the inhibition of α-GC activity has been used to treat postprandial hyperglycemia and type 2 diabetes mellitus. Theaflavin-3-gallate (TF-3-G), a flavonoid found in the fermentation products of black tea, exhibits strong inhibition of α-GC activity. However, the α-GC inhibitory mechanism of TF-3-G is unclear. This study aids understanding of this mechanism, and proposed a possibly basic theory for improving the medicinal value of TF-3-G in diabetes therapy.

Theaflavin-3-gallate specifically interacts with phosphatidylcholine, forming a precipitate resistant against the detergent action of bile salt

Biosci Biotechnol Biochem 2018 Mar;82(3):466-475.PMID:29488451DOI:10.1080/09168451.2017.1422967.

Black tea is a highly popular beverage, and its pigments, polymerized catechins such as theaflavins (TFs), are attracting attention due to their beneficial health effects. In this study, to test the inhibitory activities of TFs on the intestinal absorption of cholesterol, we investigated their effects on phosphatidylcholine (PC) vesicles in the absence or presence of a bile salt. (-)-Epicatechin gallate, (-)-epigallocatechin gallate, and TFs formed insoluble complexes with PC vesicles. Galloylated TFs such as TF2A, TF2B, and TF3 precipitated far more than other polyphenols. The subsequent addition of taurocholate redispersed the polyphenol-PC complexes, except that a large amount of TF2A remained insoluble. After incubation with taurocholate-PC micelles, TF2A elevated the turbidity of the micelle solution, providing red sediments. The TF2A-specific effect was dependent on the PC concentration. These results suggest that TF2A interacts with PC and aggregates in a specific manner different from catechins and other TFs.

Theaflavin-3-gallate and theaflavin-3'-gallate, polyphenols in black tea with prooxidant properties

Basic Clin Pharmacol Toxicol 2008 Jul;103(1):66-74.PMID:18346048DOI:10.1111/j.1742-7843.2008.00232.x.

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.