1,3,5-Trihydroxy-4-prenylxanthoneCAS# 53377-61-0 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 53377-61-0 | SDF | Download SDF |
| PubChem ID | 10335672 | Appearance | Yellow powder |
| Formula | C18H16O5 | M.Wt | 312.3 |
| Type of Compound | Xanthones | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 1,3,5-trihydroxy-4-(3-methylbut-2-enyl)xanthen-9-one | ||
| SMILES | CC(=CCC1=C(C=C(C2=C1OC3=C(C2=O)C=CC=C3O)O)O)C | ||
| Standard InChIKey | JCHQJCJKSHNCBA-UHFFFAOYSA-N | ||
| 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 | 1. 1,3,5-Trihydroxy-4-prenylxanthone is a relatively potent inhibitor of phosphodiesterase type 5 (PDE5), with an IC50 value of 3.0 μM. 2. 1,3,5-Trihydroxy-4-prenylxanthone inhibits LPS-induced NF-κB and AP-1 activations by interfering with the posttranslational modification (phosphorylation and/or ubiquitinylation) of IRAK-1 in the cell membrane to impede TAK1-mediated activation of IKK and MAPKs signal transduction. 3. 1,3,5-Trihydroxy-4-prenylxanthone shows in vitro inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), with IC50 values of 56.3plusmn;0.4 and 46.0plusmn;0.3 M, respectively. |
| Targets | NF-kB | IkB | AP-1 | JNK | ERK | TGF-β/Smad | AChR | IKK |
1,3,5-Trihydroxy-4-prenylxanthone Dilution Calculator
1,3,5-Trihydroxy-4-prenylxanthone Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.202 mL | 16.0102 mL | 32.0205 mL | 64.041 mL | 80.0512 mL |
| 5 mM | 0.6404 mL | 3.202 mL | 6.4041 mL | 12.8082 mL | 16.0102 mL |
| 10 mM | 0.3202 mL | 1.601 mL | 3.202 mL | 6.4041 mL | 8.0051 mL |
| 50 mM | 0.064 mL | 0.3202 mL | 0.6404 mL | 1.2808 mL | 1.601 mL |
| 100 mM | 0.032 mL | 0.1601 mL | 0.3202 mL | 0.6404 mL | 0.8005 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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1,3,5-trihydroxy-4-prenylxanthone represses lipopolysaccharide-induced iNOS expression via impeding posttranslational modification of IRAK-1.[Pubmed:21232528]
Biochem Pharmacol. 2011 Mar 15;81(6):752-60.
Both high level of nitric oxide (NO) and its generating enzyme, inducible NO synthase (iNOS), play important roles in pathophysiological conditions such as inflammatory processes. We previously found that 1,3,5-Trihydroxy-4-prenylxanthone (TH-4-PX) isolated from Cudrania cochinchinensis repressed lipopolysaccharide (LPS)-induced NO production in RAW264.7 macrophages. Here we further examined the underlying mechanisms using RT-PCR and Western blot analyses. Consistent with NO inhibition, suppression of LPS-induced iNOS expression by TH-4-PX through abolishing IkappaB kinase (IKK) phosphorylation, IkappaB degradation and nuclear factor-kappaB (NF-kappaB) nuclear translocation was observed. After LPS stimulation, the increased nuclear level of c-Fos and c-Jun (major components of activator protein-1, AP-1) and the phosphorylated level of upstream signal molecules, such as c-Jun NH2-terminal kinase (JNK) and extracellular signal-regulated kinase, (ERK) were all significantly suppressed by TH-4-PX, while p38 remained unaffected. A further experiment revealed that TH-4-PX inhibited the phosphorylation of transforming growth factor-beta (TGF-beta)-activated kinase 1 (TAK1), an upstream signaling molecule required for IKK and mitogen-activated protein kinases (MAPKs) activation. Stimulation with LPS also triggered the modification (phosphorylation and ubiquitination) and eventually the proteasomal degradation of membrane-associated interleukin (IL)-1 receptor-associated serine/threonine kinase 1 (IRAK-1), an essential signaling component to toll-like receptor (TLR)-mediated TAK-1 activation. Interestingly, the modified pattern of IRAK-1 in the presence LPS was significantly attenuated by TH-4-PX treatment. In conclusion, TH-4-PX inhibited LPS-induced NF-kappaB and AP-1 activations by interfering with the posttranslational modification (phosphorylation and/or ubiquitinylation) of IRAK-1 in the cell membrane to impede TAK1-mediated activation of IKK and MAPKs signal transduction.
Phosphodiesterase inhibitory activity of the flavonoids and xanthones from Anaxagorea luzonensis.[Pubmed:25920267]
Nat Prod Commun. 2015 Feb;10(2):301-3.
Five flavonoids, one isoflavone and five xanthones were isolated from Anaxagorea luzonensis. Of these eleven isolated compounds, 1,3,5-Trihydroxy-4-prenylxanthone (3) was a relatively potent inhibitor of phosphodiesterase type 5 (PDE5), with an IC50 value of 3.0 muM. This is the first report showing that natural xanthones can exhibit promising PDE5 inhibitory activity. Moreover, this study revealed that the presence of the C-4 prenyl residue attached to the xanthone core is correlated with the significant PDE5 inhibitory activity.
