Flavokawain BCAS# 1775-97-9 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 1775-97-9 | SDF | Download SDF |
| PubChem ID | 5356121 | Appearance | Orange powder |
| Formula | C17H16O4 | M.Wt | 284.3 |
| Type of Compound | Chalcones | Storage | Desiccate at -20°C |
| Synonyms | Flavokavain B; Flavokavin B; 2'-Hydroxy 4',6'-dimethoxychalcone; Persicochalcone | ||
| Solubility | DMSO : 5 mg/mL (17.59 mM; ultrasonic and warming and heat to 60°C) | ||
| Chemical Name | (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one | ||
| SMILES | COC1=CC(=C(C(=C1)OC)C(=O)C=CC2=CC=CC=C2)O | ||
| Standard InChIKey | QKQLSQLKXBHUSO-CMDGGOBGSA-N | ||
| Standard InChI | InChI=1S/C17H16O4/c1-20-13-10-15(19)17(16(11-13)21-2)14(18)9-8-12-6-4-3-5-7-12/h3-11,19H,1-2H3/b9-8+ | ||
| 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 | Flavokawain B, the hepatotoxic constituent from kava root, induces GSH-sensitive oxidative stress through modulation of IKK/NF-κB and MAPK signaling pathways. Flavokawain B has potent anti-inflammatory, and anti-cancer activities, it can significantly inhibit production of NO and PGE2 in LPS-induced RAW 264.7 cells. Flavokawain B acts through ROS generation and GADD153 up-regulation to regulate the expression of Bcl-2 family members, thereby inducing mitochondrial dysfunction and apoptosis in HCT116 cells. |
| Targets | PPAR | ERK | TNF-α | PARP | p53 | Bcl-2/Bax | Caspase | IL Receptor | p21 | P450 (e.g. CYP17) | NO | PGE | ROS |
| In vitro | The chalcones cardamonin and flavokawain B inhibit the differentiation of preadipocytes to adipocytes by activating ERK.[Pubmed: 24845100]Arch Biochem Biophys. 2014 Jul 15;554:44-54.We treated 3T3-L1 cells with a panel of 46 polyphenols and measured intracellular lipid accumulation by Sudan II staining. Four of them, including cardamonin and Flavokawain B, inhibited lipid We searched for polyphenols capable of inhibiting the lipid accumulation in 3T3-L1 cells, and investigated the mechanisms of two effective chalcones cardamonin and Flavokawain B on differentiation of preadipocytes.
In vivo antitumor and antimetastatic effects of flavokawain B in 4T1 breast cancer cell-challenged mice.[Pubmed: 25834398]Drug Des Devel Ther. 2015 Mar 6;9:1401-17.Flavokawain B (FKB) is a naturally occurring chalcone that can be isolated through the root extracts of the kava-kava plant (Piper methysticum). It can also be synthesized chemically to increase the yield. Flavokawain B is a promising candidate as a biological agent, as it is reported to be involved in a wide range of biological activities. Furthermore, Flavokawain B was reported to have antitumorigenic effects in several cancer cell lines in vitro. However, the in vivo antitumor effects of Flavokawain B have not been reported on yet. |
| Kinase Assay | Flavokawain B inhibits growth of human squamous carcinoma cells: Involvement of apoptosis and cell cycle dysregulation in vitro and in vivo.[Pubmed: 21543203 ]J Nutr Biochem. 2012 Apr;23(4):368-78.Flavokawain B is a natural chalcone isolated from the rhizomes of Alpenia pricei Hayata. |
| Cell Research | Flavokawain B inhibits the growth of acute lymphoblastic leukemia cells via p53 and caspase-dependent mechanisms.[Pubmed: 25641429]Leuk Lymphoma. 2015 Feb 23:1-10.The anti-leukemic effect and the potential molecular mechanisms of action of Flavokawain B on ALL were investigated. |
Flavokawain B Dilution Calculator
Flavokawain B Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.5174 mL | 17.5871 mL | 35.1741 mL | 70.3482 mL | 87.9353 mL |
| 5 mM | 0.7035 mL | 3.5174 mL | 7.0348 mL | 14.0696 mL | 17.5871 mL |
| 10 mM | 0.3517 mL | 1.7587 mL | 3.5174 mL | 7.0348 mL | 8.7935 mL |
| 50 mM | 0.0703 mL | 0.3517 mL | 0.7035 mL | 1.407 mL | 1.7587 mL |
| 100 mM | 0.0352 mL | 0.1759 mL | 0.3517 mL | 0.7035 mL | 0.8794 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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Flavokawain B inhibits growth of human squamous carcinoma cells: Involvement of apoptosis and cell cycle dysregulation in vitro and in vivo.[Pubmed:21543203]
J Nutr Biochem. 2012 Apr;23(4):368-78.
Flavokawain B is a natural chalcone isolated from the rhizomes of Alpenia pricei Hayata. In the present study, we have investigated the antiproliferative and apoptotic effect of Flavokawain B (5-20 mug/ml; 17.6-70.4 muM) against human squamous carcinoma (KB) cells. Exposure of KB cells with Flavokawain B resulted in apoptosis, evidenced by loss of cell viability, profound morphological changes, genomic DNA fragmentation and sub-G1 phase accumulation. Apoptosis induced by Flavokawain B results in activation of caspase-9, -3 and -8, cleavage of poly ADP ribose polymerase (PARP) and Bid in KB cells. Flavokawain B also down-regulate Bcl-2 with concomitant increase in Bax level, which resulted in release of cytochrome c. Taken together, the induction of apoptosis by Flavokawain B involved in both death receptor and mitochondrial pathway. We also observed that Flavokawain B caused the G2/M phase arrest that was mediated through reductions in the levels of cyclin A, cyclin B1, Cdc2 and Cdc25C and increases in p21/WAF1, Wee1 and p53 levels. Moreover, Flavokawain B significantly inhibits matrix metalloproteinase-9 and urokinase plasminogen activator expression, whereas tissue inhibitor of matrix metalloproteinase-1 and plasminogen activator inhibitor-1 were increased, which are playing critical role in tumor metastasis. In addition, Flavokawain B treatment significantly inhibited in vivo growth of human KB cell-derived tumor xenografts in nude mice, which is evidenced by augmentation of apoptotic DNA fragmentation, as detected by in situ terminal deoxynucleotidyl transferase-meditated dUTP nick end-labeling staining. The induction of cell cycle arrest and apoptosis by Flavokawain B may provide a pivotal mechanism for its cancer chemopreventive action.
The chalcones cardamonin and flavokawain B inhibit the differentiation of preadipocytes to adipocytes by activating ERK.[Pubmed:24845100]
Arch Biochem Biophys. 2014 Jul 15;554:44-54.
AIM: We searched for polyphenols capable of inhibiting the lipid accumulation in 3T3-L1 cells, and investigated the mechanisms of two effective chalcones cardamonin and Flavokawain B on differentiation of preadipocytes. METHOD AND RESULTS: We treated 3T3-L1 cells with a panel of 46 polyphenols and measured intracellular lipid accumulation by Sudan II staining. Four of them, including cardamonin and Flavokawain B, inhibited lipid accumulation. In the further study, cardamonin and Flavokawain B inhibited lipid accumulation by downregulating the expression of CCAAT/enhancer binding protein (C/EBP)-beta, C/EBPalpha, and peroxisome proliferator-activated receptor-gamma (PPARgamma) at both mRNA and protein levels. Cardamonin and Flavokawain B also increased phosphorylation of extracellular signal-regulated kinase (ERK) in the early phase of adipocyte differentiation. PD98059, an ERK inhibitor, restored C/EBPbeta, PPARgamma expression and intracellular lipid accumulation in adipocytes. Moreover, cardamonin and Flavokawain B also modulated the secretion of C-reactive protein, dipeptidyl peptidase IV, interleukin-6, tumor necrosis factor-alpha and fibroblast growth factor-21 in mature adipocytes. CONCLUSIONS: These results indicate that ERK activation and consequent downregulation of adipocyte-specific transcription factors are involved in the inhibitory effects of the chalcones cardamonin and Flavokawain B on adipocyte differentiation. Moreover, cardamonin and Flavokawain B are able to modulate secretion of adipokines in mature adipocytes.
In vivo antitumor and antimetastatic effects of flavokawain B in 4T1 breast cancer cell-challenged mice.[Pubmed:25834398]
Drug Des Devel Ther. 2015 Mar 6;9:1401-17.
Flavokawain B (FKB) is a naturally occurring chalcone that can be isolated through the root extracts of the kava-kava plant (Piper methysticum). It can also be synthesized chemically to increase the yield. This compound is a promising candidate as a biological agent, as it is reported to be involved in a wide range of biological activities. Furthermore, FKB was reported to have antitumorigenic effects in several cancer cell lines in vitro. However, the in vivo antitumor effects of FKB have not been reported on yet. Breast cancer is one of the major causes of cancer-related deaths in the world today. Any potential treatment should not only impede the growth of the tumor, but also modulate the immune system efficiently and inhibit the formation of secondary tumors. As presented in our study, FKB induced apoptosis in 4T1 tumors in vivo, as evidenced by the terminal deoxynucleotidyl transferase dUTP nick end labeling and hematoxylin and eosin staining of the tumor. FKB also regulated the immune system by increasing both helper and cytolytic T-cell and natural killer cell populations. In addition, FKB also enhanced the levels of interleukin 2 and interferon gamma but suppressed interleukin 1B. Apart from that, FKB was also found to inhibit metastasis, as evaluated by clonogenic assay, bone marrow smearing assay, real-time polymerase chain reaction, Western blot, and proteome profiler analysis. All in all, FKB may serve as a promising anticancer agent, especially in treating breast cancer.
Flavokawain B inhibits the growth of acute lymphoblastic leukemia cells via p53 and caspase-dependent mechanisms.[Pubmed:25641429]
Leuk Lymphoma. 2015;56(8):2398-407.
The development of novel chemotherapeutic drugs is needed for the treatment of patients with acute lymphoblastic leukemia (ALL). In this study, the anti-leukemic effect and the potential molecular mechanisms of action of Flavokawain B on ALL were investigated. Flavokawain B was found to significantly inhibit the cellular proliferation of B-ALL and T-ALL cell lines in a dose-dependent manner. It also induced cellular apoptosis by increasing the expression of p53, Bax and Puma, and activating the cleavage of caspase-3 and poly ADP-ribose polymerase (PARP). Furthermore, the enhancement of p53-dependent apoptosis by Flavokawain B could be rescued by pifithrin-alpha, a pharmacological inhibitor of p53 transcriptional activity. Moreover, the proliferation of leukemia blast cells from 16 patients with ALL was inhibited by Flavokawain B, and tumor growth in xenograft mice was also suppressed by this drug. In conclusion, our results demonstrate the therapeutic potential of Flavokawain B for the treatment of ALL.
