Theaflavine-3,3'-digallate

Theaflavine-3,3'-digallate
Product Name Theaflavine-3,3'-digallate
CAS No.: 33377-72-9
Catalog No.: CFN98598
Molecular Formula: C43H32O20
Molecular Weight: 868.7 g/mol
Purity: >=98%
Type of Compound: Flavonoids
Physical Desc.: Powder
Targets: ERK | HSV | PPAR | AMPK | MMP(e.g.TIMP) | VEGFR | Androgen Receptor | PARP | Caspase | NF-kB | IkB | IKK
Source: The leaves of Camellia sinensis (L.) O. Kuntze.
Solvent: DMSO, Pyridine, Methanol, Ethanol, etc.
Price: $328/10mg
Theaflavin-3,3'-digallate is a potent AMP-activated protein kinase (AMPK) activator with anti-adiposity activity in adipocytes, suggesting its potential application in functional foods and nutraceuticals for obesity management. Theaflavin-3,3'-digallate is also an inducer of oxidative stress and apoptosis, it has strong antioxidant and antiangiogenic activities, it inhibits the tube formation of endothelial cells via decreased both MMP-2 and MMP-9 activities in vitro. A combination microbicide containing theaflavin-3,3'-digallate and lactic acid can reduce herpes simplex virus (HSV) transmission. Theaflavin-3,3'-digallate may exert its anti-inflammatory and cancer chemopreventive actions by suppressing the activation of NFkappaB through inhibition of IkappaB kinase (IKK) activity. Theaflavin-3,3'-digallate can repress osteoclastogenesis and prevent wear debris-induced osteolysis via suppression of ERK pathway, it is a promising candidate for the treatment of osteoclast-related osteolytic diseases, such as wear debris-induced peri-implant osteolysis (PIO).
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Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Antimicrob Agents Chemother,2013 Aug,57(8): 3806-14.
    Theaflavin-3,3'-digallate and lactic acid combinations reduce herpes simplex virus infectivity.[Reference: WebLink]
    The present study examined the efficacy of using multiple mechanisms as part of a topical microbicide to inactivate herpes simplex virus (HSV) by combining Theaflavine-3,3'-digallate (TF-3) and lactic acid (LA) over the pH range of 4.0 to 5.7 to mimic conditions in the female reproductive tract.
    METHODS AND RESULTS:
    Six clinical isolates of HSV-2 and two clinical isolates of HSV-1 were almost completely inactivated when Theaflavine-3,3'-digallate (100 μM) was present with LA over the pH range of 4.5 to 5.7, whereas four additional HSV-1 clinical isolates required Theaflavine-3,3'-digallate concentrations of 250 to 500 μM for comparable virus titer reduction. Theaflavine-3,3'-digallate reduced HSV-2 titers by 5 log10 in 20 to 30 min at pH 4.5, whereas HSV-1 required 60 min for comparable inactivation. Mixtures of Theaflavine-3,3'-digallate and LA stored at 37 °C for 1 month at pH 4.0 to 5.7 maintained antiviral activity. Semen, but not cervical vaginal fluid, decreased LA-dependent antiviral activity at pH 4.0, but adding Theaflavine-3,3'-digallate to the mixture reduced HSV titers by 4 to 5 log10.
    CONCLUSIONS:
    These results indicate that a combination microbicide containing Theaflavine-3,3'-digallate and LA could reduce HSV transmission.
    J.Funct.Foods,2015,17:271-82.
    Theaflavin-3,3′-digallate, a black tea polyphenol, stimulates lipolysis associated with the induction of mitochondrial uncoupling proteins and AMPK–FoxO3A–MnSOD pathway in 3T3-L1 adipocytes.[Reference: WebLink]
    Phytochemicals have gained an immense interest in obesity management. Previously, we have shown that theaflavin-3,3′-digallate (Theaflavine-3,3'-digallate,TF3), a black tea polyphenol, prevents adipocyte-triggered metaflammation.
    METHODS AND RESULTS:
    Here, we demonstrate that TF3 attenuates triacylglycerol accumulation in adipocytes, concomitant with promoting gene expression profile that favors lipolysis and β-oxidation, and inducing energy dissipation-related genes, mitochondrial uncoupling protein-1 (UCP-1) and UCP-2. The gene expression is in line with the upregulation of peroxisome proliferator-activated receptor α (PPARα), a primary transactivator for the expression of lipolytic genes. TF3 activates AMP-activated protein kinase (AMPK), which is required for TF3 effects of PPARα upregulation, and the reversal of the inactivation of Forkhead-box-O 3A (FoxO3A) and insulin-induced suppression of manganese superoxide dismutase (MnSOD). The role of MnSOD in adipogenesis is verified in MnSOD-overexpressing adipocytes.
    CONCLUSIONS:
    Thus, our results demonstrate TF3 as a potent AMPK activator with anti-adiposity activity in adipocytes, suggesting its potential application in functional foods and nutraceuticals for obesity management.
    Showa Univ. J. Med. Sci.,2007,19(2):59-72.
    Theaflavin-3, 3'-digallate Inhibits Tube Formation in Cocultured Endothelial Cells with Fibroblasts[Reference: WebLink]
    Several tea polyphenols, particularly those containing galloyl, have antitumor affects via strong antioxidant and antiangiogenic activi-ties. Theaflavin-3, 3'-digallate (Theaflavine-3,3'-digallate,TF3), a theaflavin derivative in black tea, has 2 galloyl groups. Matrix metalloproteinases (MMPs) are associated with extracellular matrix degradation, cellular migration, and angiogenesis, and (-) -epigallocatechin-3-gallate (EGCG) is an inhibitor of MMP activity and secretion; thus one of its major actions is the inhibition of angiogenesis. However, there are few studies of angiogenesis in theaflavin derivatives.
    METHODS AND RESULTS:
    We investigated the effects of TF3 on angiogenesis in vitro. Angiogenesis was assayed using cocultured human umbilical vein endothelial cells with fibroblasts. Cells were cultivated in various concentrations of TF3 and EGCG in the presence or absence of vascular endothelial growth factor-A. After 11 days, MMP-2 and MMP-9 activities and the pro-MMP-2 protein in the medium were measured by gelatin zymography and immunoassay, respectively. Tube formation was markedly inhibited by 100 μmol/L TF3 or EGCG. Even at 10 iumolIL, TF3 or EGCG inhibited tube formation. The MMP-2 and MMP-9 activities were inhibited and pro-MMP-2 protein concentrations were reduced by TF3 or EGCG in a concentration-dependent manner, regardless of the presence of vascular endothelial growth factor. The effect of TF3 was similar to that of EGCG, indicating that the tube formation of endothelial cells was suppressed via decreased both MMP-2 and MMP-9 activities in vitro.
    CONCLUSIONS:
    Our results demonstrate antiangiogenic activity of TF3 in vitro, and suggest possible anti-tumor effects of TF3.
    Acta Biomater. 2017 Jan 15;48:479-488.
    Theaflavin-3,3'-digallate represses osteoclastogenesis and prevents wear debris-induced osteolysis via suppression of ERK pathway.[Pubmed: 27838465 ]
    Peri-implant osteolysis (PIO) and the following aseptic loosening is the leading cause of implant failure. Emerging evidence suggests that receptor activator of nuclear factor kappa-B ligand (RANKL)-induced osteoclast formation and osteoclastic bone resorption are responsible for particle-stimulated PIO.
    METHODS AND RESULTS:
    Here, we explored the effect of theaflavin-3,3'-digallate (Theaflavine-3,3'-digallate,TF3) on titanium particle-induced osteolysis in vivo and in vitro. Twenty-eight male C57BL/6 mice were randomly separated into four groups: sham control (sham), titanium particles only (titanium), titanium particles with low TF3 concentration (low-TF3, 1mg/kg TF3), and titanium particles with high TF3 concentration (high-TF3, 10mg/kg TF3). Two weeks later, micro-computed tomography and histological analysis were performed. Bone-marrow-derived macrophages and RAW264.7 murine macrophages were applied to examine osteoclast formation and differentiation. TF3 significantly inhibited titanium particle-induced osteolysis and prevented bone destruction compared with titanium group. Interestingly, the number of mature osteoclasts reduced after treatment with TF3 in vivo, suggesting osteoclast formation might be inhibited by TF3. In vitro, TF3 suppressed osteoclast formation, polarization and osteoclastic bone resorption by specifically targeting the RANKL-induced ERK signal pathway.
    CONCLUSIONS:
    Collectively, these results suggest that TF3, a natural active compound derived from black tea, is a promising candidate for the treatment of osteoclast-related osteolytic diseases, such as wear debris-induced PIO.
    Carcinogenesis. 2004 Jul;25(7):1109-18.
    NCBINCBI Logo Skip to main content Skip to navigation Resources How To About NCBI Accesskeys Sign in to NCBI PubMed US National Library of Medicine National Institutes of Health Search databaseSearch term Search AdvancedHelp Result Filters Format: Abstrac[Pubmed: 14963012 ]
    Androgens play a critical role in regulating the growth, differentiation and survival of epithelial cells in many androgen-responsive organs, such as prostate and skin. The enzyme steroid 5alpha-reductase (EC 1.3.99.5) catalyzes the conversion of testosterone (T) to a more active androgen, dihydrotestosterone (DHT). DHT then binds to androgen receptors (AR) and functions in the nucleus to regulate specific gene expression. Androgens via their cognate receptor may be involved in the development and progression of benign prostate hyperplasia, prostate cancer, hirsutism, male pattern alopecia and acne.
    METHODS AND RESULTS:
    The aim of this study was to determine whether theaflavin-3,3'-digallate (Theaflavine-3,3'-digallate,TF3) and penta-O-galloyl-beta-D-glucose (5GG) have inhibitory effects on androgen production and action. We found that TF3 and 5GG inhibit rat liver microsomal 5alpha-reductase activity. Furthermore, TF3 and 5GG significantly reduced androgen-responsive LNCaP prostate cancer cell growth, suppressed expression of the AR and lowered androgen-induced prostate-specific antigen secretion and fatty acid synthase protein level.
    CONCLUSIONS:
    In conclusion, our result suggests that TF3 and 5GG might be useful chemoprevention agents for prostate cancer through suppressing the function of androgen and its receptor.
    Biochem Pharmacol. 2000 Feb 15;59(4):357-67.
    Suppression of lipopolysaccharide-induced nuclear factor-kappaB activity by theaflavin-3,3'-digallate from black tea and other polyphenols through down-regulation of IkappaB kinase activity in macrophages.[Pubmed: 10644043]

    METHODS AND RESULTS:
    We investigated the inhibition of IkappaB kinase (IKK) activity in lipopolysaccharide (LPS)-activated murine macrophages (RAW 264.7 cell line) by various polyphenols including (-)-epigallocatechin-3-gallate, theaflavin, a mixture of theaflavin-3 gallate and theaflavin-3'-gallate, theaflavin-3,3'-digallate (Theaflavine-3,3'-digallate,TF-3), pyrocyanidin B-3, casuarinin, geraniin, and penta-O-galloyl-beta-D-glucose (5GG). TF-3 inhibited IKK activity in activated macrophages more strongly than did the other polyphenols. TF-3 strongly inhibited both IKK1 and IKK2 activity and prevented the degradation of IkappaBalpha and IkappaBbeta in activated macrophage cells. The results suggested that the inhibition of IKK activity by TF-3 could occur by a direct effect on IKKs or on upstream events in the signal transduction pathway. Furthermore, geraniin, 5GG, and TF-3 all blocked phosphorylation of IKB from the cytosolic fraction, inhibited nuclear factor-kappaB (NFkappaB) activity, and inhibited increases in inducible nitric oxide synthase levels in activated macrophages.
    CONCLUSIONS:
    These results suggest that TF-3 may exert its anti-inflammatory and cancer chemopreventive actions by suppressing the activation of NFkappaB through inhibition of IKK activity.
    Toxicol In Vitro. 2008 Apr;22(3):598-609.
    Theaflavin-3,3'-digallate, a component of black tea: an inducer of oxidative stress and apoptosis.[Pubmed: 18248951 ]

    METHODS AND RESULTS:
    Treatment of human oral squamous carcinoma HSC-2 cells and normal GN46 fibroblasts with theaflavin-3,3'-digallate (Theaflavine-3,3'-digallate,TF-3), a polyphenol in black tea, showed a concentration and time dependent inhibition of growth, with the tumor cells more sensitive than the fibroblasts. In buffer and in cell culture medium, TF-3 generated reactive oxygen species, with lower levels detected in buffer amended with catalase and superoxide dismutase, indicating the generation of hydrogen peroxide and superoxide, respectively, and suggesting that TF-3 may be an inducer of oxidative stress. The toxicity of TF-3 was decreased in the presence of catalase, pyruvate, and divalent cobalt, all scavengers of reactive oxygen species, but was potentiated in the presence of diethyldithiocarbamate, an inhibitor of superoxide dismutase. The intracellular level of glutathione in HSC-2 cells was lessened after a 4-h exposure to 250 and 500 microM TF-3. However, for GN46 fibroblasts, a 4-h exposure to 250 microM TF-3 stimulated, but to 500 microM TF-3 lessened, intracellular glutathione. Treatment of the cells with the glutathione depleters, 1,3-bis(2-chloroethyl)-N-nitrosourea, 1-chloro-2,4-dinitrobenzene, and d,l-buthionine-[S,R]-sulfoximine potentiated the toxicity of TF-3.
    CONCLUSIONS:
    Induction of apoptotic cell death in HSC-2 cells treated with TF-3 was noted by apoptotic cell morphologies, by TUNEL staining, by PARP cleavage, and by elevated activity of caspase-3. Apoptosis was not noted in GN46 fibroblasts treated with TF-3.
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