RhapontigeninCAS# 500-65-2 |
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| Cas No. | 500-65-2 | SDF | Download SDF |
| PubChem ID | 5320954 | Appearance | White powder |
| Formula | C15H14O4 | M.Wt | 258.3 |
| Type of Compound | Phenols | Storage | Desiccate at -20°C |
| Synonyms | 4'-Methoxy 3,3',5-stilbenetriol; Pontigenin; Prontigenin; Protigenin; Rhapontin aglycone; Rhapontin genin | ||
| Solubility | Soluble in methanol; slightly soluble in water | ||
| Chemical Name | 5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol | ||
| SMILES | COC1=C(C=C(C=C1)C=CC2=CC(=CC(=C2)O)O)O | ||
| Standard InChIKey | PHMHDRYYFAYWEG-NSCUHMNNSA-N | ||
| Standard InChI | InChI=1S/C15H14O4/c1-19-15-5-4-10(8-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+ | ||
| 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 | Rhapontigenin has antioxidative, antihyperlipidemic, antifungal and anticancer activities. Rhapontigenin inhibits HIF-1α accumulation and angiogenesis in PC-3 prostate cancer cells, suppresses breast cancer cell migration and invasion, which is involved in inhibiting the PI3K-dependent Rac1 signaling pathway. Rhapontigenin exhibits dose-dependent inhibition of tyrosinase activity and melanin synthesis in B16F10 melanoma cells. |
| Targets | ROS | PAK | p21 | PI3K | Akt | Tyrosinase | HIF | VEGFR | Antifection |
Rhapontigenin Dilution Calculator
Rhapontigenin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.8715 mL | 19.3573 mL | 38.7147 mL | 77.4293 mL | 96.7867 mL |
| 5 mM | 0.7743 mL | 3.8715 mL | 7.7429 mL | 15.4859 mL | 19.3573 mL |
| 10 mM | 0.3871 mL | 1.9357 mL | 3.8715 mL | 7.7429 mL | 9.6787 mL |
| 50 mM | 0.0774 mL | 0.3871 mL | 0.7743 mL | 1.5486 mL | 1.9357 mL |
| 100 mM | 0.0387 mL | 0.1936 mL | 0.3871 mL | 0.7743 mL | 0.9679 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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The possible mechanism of rhapontigenin influencing antifungal activity on Candida albicans.[Pubmed:22662760]
Med Mycol. 2013 Jan;51(1):45-52.
Rhapontigenin, an aglycone of rhapontin, was produced by biotransformation and we investigated its antifungal activity against Candida albicans, one of the most important opportunistic fungal pathogens. Rhapontigenin is found to have, in vitro, inhibitory activity with a minimal inhibitory concentration (MIC) value against all test isolates of 128-256 mug/ml. We detected increased reactive oxygen species (ROS) levels in yeast cultures treated with Rhapontigenin at the MIC. Rhapontigenin inhibited DNA, RNA, and protein synthesis, especially RNA synthesis, and induced morphological changes and apoptosis of C. albicans. The apoptotic effect of Rhapontigenin on C. albicans at subinhibitory concentrations was higher in the stationary growth phase than in the exponential phase, while the opposite results were noted with amphotericin B. The mechanism of antifungal activity of Rhapontigenin may be associated with the generation of ROS that might induce apoptosis and it may also involve the inhibition of ergosterol biosynthesis.
Rhapontigenin converted from rhapontin purified from Rheum undulatum enhances the inhibition of melanin synthesis.[Pubmed:23221688]
Biosci Biotechnol Biochem. 2012;76(12):2307-9.
Rhapontigenin was produced from rhapontin isolated from a methanol extract of Rheum undulatum roots by enzymatic transformation. Rhapontin and Rhapontigenin exhibited dose-dependent inhibition of tyrosinase activity and melanin synthesis in B16F10 melanoma cells, but the inhibitory activity of Rhapontigenin was greater than that of rhapontin. Thus the bioconversion of rhapontin enhanced its ability to inhibit cellular tyrosinase activity and melanin synthesis.
Antihyperlipidemic effects of rhapontin and rhapontigenin from rheum undulatum in rats fed a high-cholesterol diet.[Pubmed:25127020]
Planta Med. 2014 Aug;80(13):1067-71.
Rhapontin was purified from a methanol extract from the roots of Rheum undulatum, and Rhapontigenin was produced by an enzymatic transformation of rhapontin. Rats were fed a high-cholesterol diet to induce hyperlipidemia, followed by oral treatment with rhapontin or Rhapontigenin (1-5 mg/kg/day). Rhapontin and Rhapontigenin treatment resulted in a significant (p<0.05) dose-dependent decrease in the serum lipid level, while the high-density lipoprotein cholesterol level increased slightly compared with the experimental control. Furthermore, rhapontin and Rhapontigenin treatment improved the pathological characteristics of the degenerating fatty liver in high-cholesterol diet-induced hyperlipidemic rats dose-dependently. Aspartate aminotransferase and alanine aminotransferase levels in rhapontin- and Rhapontigenin-treated hyperlipidemic rats were not significantly different from those in the control. These results indicate that rhapontin and Rhapontigenin can be used as potent antihyperlipidemic agents.
Rhapontigenin suppresses cell migration and invasion by inhibiting the PI3K-dependent Rac1 signaling pathway in MDA-MB-231 human breast cancer cells.[Pubmed:24828286]
J Nat Prod. 2014 May 23;77(5):1135-9.
The invasive behavior of cancer cells resulting in metastasis is the major cause of cancer-related deaths. Rhapontigenin (1) has various biological activities including anticancer activities. However, whether and how 1 affects cancer invasion has never been explored. Here, we examined the anti-invasive effects of 1 and its underlying molecular mechanisms in the highly invasive human breast cancer cell line designated MDA-MB-231. At noncytotoxic concentrations, 1 strongly suppressed serum-induced cell migration and invasion as judged by Boyden chamber analysis and wound-healing assays, respectively. Compound 1 strikingly reduced Rac1 activity as judged by both absorbance-based and pull-down assays. In addition, its downstream effectors such as WASP-family verprolin homologous proteins 2 (WAVE-2) and p21-activated kinase 1 (PAK1) signaling cascades were attenuated after treatment with 1. Immunofluorescence staining showed that 1 diminished lamellipodia formation at the leading edge of cells. Finally, 1 decreased the phosphorylation of phosphoinisitide-3-kinase (PI3K) and AKT. Rac1 activity was inhibited by the PI3K inhibitor wortmannin. Taken together, these results suggest that 1 suppresses breast cancer cell migration and invasion, which is involved in inhibiting the PI3K-dependent Rac1 signaling pathway.
Rhapontigenin inhibited hypoxia inducible factor 1 alpha accumulation and angiogenesis in hypoxic PC-3 prostate cancer cells.[Pubmed:21628883]
Biol Pharm Bull. 2011;34(6):850-5.
Hypoxia inducible factor 1 alpha (HIF-1alpha) is frequently over-expressed in the numerous types of cancer and plays an important role in angiogenesis. In the present study, the inhibitory mechanism of Rhapontigenin isolated from Vitis coignetiae was investigated on HIF-1alpha stability and angiogenesis in human prostate cancer PC-3 cells. Rhapontigenin significantly suppressed HIF-1alpha accumulation at protein level but not at mRNA level in PC-3 cells under hypoxia. Also, Rhapontigenin suppressed hypoxia-induced HIF-1alpha activation in various cancer cells, such as colorectal adenocarcinoma (SW620), breast adenocarcinoma (MCF-7), fibrosarcoma (HT-1080) and prostate carcinoma (LNCaP). Interestingly, Rhapontigenin had more potency in inhibition of hypoxia-induced HIF-1alpha expression than that of resveratrol, a known HIF-1alpha inhibitor. In addition, Rhapontigenin promoted hypoxia-induced HIF-1alpha degradation and cycloheximide (CHX) blocked protein synthesis. A prolyl hydroxylase (PHD) inhibitor dimethyloxalylglycine (DMOG) is usually utilized to examine whether prolyl hydroxylation is involved in inhibition of HIF-1alpha accumulation. Here, DMOG recovered HIF-1alpha accumulation inhibited by Rhapontigenin. Immunoprecipitation assay also revealed that rhapotigenin enhanced the binding of hydroxylated HIF-1alpha to von Hippel-Lindau (VHL) tumor suppressor protein. Furthermore, Rhapontigenin reduced vascular endothelial growth factor (VEGF) secretion in hypoxic PC-3 cells as well as suppressed tube formation in human umbilical vein endothelial cells (HUVECs) treated by the conditioned media of hypoxic PC-3 cells. However, anti-angiogenic effect of Rhapontigenin in hypoxic PC-3 cells was reversed by DMOG. Taken together, these findings suggest that Rhapontigenin inhibits HIF-1alpha accumulation and angiogenesis in PC-3 prostate cancer cells.
