alpha-CyperoneCAS# 473-08-5 |
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| Cas No. | 473-08-5 | SDF | Download SDF |
| PubChem ID | 6452086 | Appearance | Oil |
| Formula | C15H22O | M.Wt | 218.33 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Synonyms | α-Cyperone; (+)-α-Cyperone | ||
| Solubility | DMSO : < 1 mg/mL (insoluble or slightly soluble) | ||
| Chemical Name | (4aS,7R)-1,4a-dimethyl-7-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one | ||
| SMILES | CC1=C2CC(CCC2(CCC1=O)C)C(=C)C | ||
| Standard InChIKey | KUFXJZXMWHNCEH-DOMZBBRYSA-N | ||
| Standard InChI | InChI=1S/C15H22O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h12H,1,5-9H2,2-4H3/t12-,15+/m1/s1 | ||
| 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 | Alpha-cyperone is associated with the down-regulation of COX-2,IL-6,Nck-2,Cdc42 and Rac1, resulting in reduction of inflammation. which would be highly beneficial for treatment of inflammatory diseases such as AD. Alpha-cyperone is a promising inhibitor of Hla production by S. aureus and protects lung cells from this bacterium, it also shows inhibitory effects on adherence and invasion of avian pathogenic Escherichia coli O78 to chicken type II pneumocytes. |
| Targets | PGE | COX | NO | NOS | NF-kB | p65 | NF-kB | IL Receptor | ERK | TNF-α | JNK | p38MAPK |
| In vitro | Inhibitory effects of α-cyperone on adherence and invasion of avian pathogenic Escherichia coli O78 to chicken type II pneumocytes.[Pubmed: 24629766]Vet Immunol Immunopathol. 2014 May 15;159(1-2):50-7.
α-cyperone alleviates lung cell injury caused by Staphylococcus aureus via attenuation of α-hemolysin expression.[Pubmed: 22713997]J Microbiol Biotechnol. 2012 Aug;22(8):1170-6.
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| Cell Research | Xiang-Qi-Tang and its active components exhibit anti-inflammatory and anticoagulant properties by inhibiting MAPK and NF-κB signaling pathways in LPS-treated rat cardiac microvascular endothelial cells.[Pubmed: 23171279 ]α-Cyperone, isolated from the rhizomes of Cyperus rotundus, inhibits LPS-induced COX-2 expression and PGE2 production through the negative regulation of NFκB signalling in RAW 264.7 cells.[Pubmed: 23500883]J Ethnopharmacol. 2013 May 2;147(1):208-14.The rhizomes of Cyperus rotundus (Cyperaceae) have been used in Asian traditional medicine for the treatment of several inflammatory diseases. However, the anti-inflammatory effects of α-cyperone, a major active compound of Cyperus rotundus, are poorly understood.
Immunopharmacol Immunotoxicol. 2013 Apr;35(2):215-24.Xiang-Qi-Tang (XQT) is a Chinese herbal formula containing Cyperus rotundus, Astragalus membranaceus and Andrographis paniculata. alpha-Cyperone (CYP), astragaloside IV (AS-IV) and andrographolide (AND) are the three major active components in this formula. XQT may modulate the inflammatory or coagulant responses. We therefore assessed the effects of XQT on lipopolysaccharide (LPS)-induced inflammatory model of rat cardiac microvascular endothelial cells (RCMECs).
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alpha-Cyperone Dilution Calculator
alpha-Cyperone Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.5802 mL | 22.9011 mL | 45.8022 mL | 91.6045 mL | 114.5056 mL |
| 5 mM | 0.916 mL | 4.5802 mL | 9.1604 mL | 18.3209 mL | 22.9011 mL |
| 10 mM | 0.458 mL | 2.2901 mL | 4.5802 mL | 9.1604 mL | 11.4506 mL |
| 50 mM | 0.0916 mL | 0.458 mL | 0.916 mL | 1.8321 mL | 2.2901 mL |
| 100 mM | 0.0458 mL | 0.229 mL | 0.458 mL | 0.916 mL | 1.1451 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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Alpha-cyperone is associated with the down-regulation of COX-2,IL-6,Nck-2,Cdc42 and Rac1, resulting in reduction of inflammation. which would be highly beneficial for treatment of inflammatory diseases such as AD. In vitro: The anti-inflammatory activity of alpha-cyperone is associated with the down-regulation of COX-2 and IL-6 via the negative regulation of the NFκB pathway in LPS-stimulated RAW 264.7 cells.[1] Alpha-Cyperone binds and interacts with tubulin and is capable of distinctly destabilizing microtubule polymerization. The effect of this interaction could result in reduction of inflammation which would be highly beneficial for treatment of inflammatory diseases such as AD. One microliter of alpha-Cyperone was dissolved in DMSO (1:1 v/v) and it was further diluted in double distilled water (ddH2O) to a final volume of 20 microliter. [2]
References:
[1]. Jung, S. H. et al. alpha-Cyperone, isolated from the rhizomes of Cyperus rotundus, inhibits LPS-induced COX-2 expression and PGE2 production through the negative regulation of NFkappaB signalling in RAW 264.7 cells. Journal of ethnopharmacology 147, 208-2
[2]. Azimi, A. et al. alpha-Cyperone of Cyperus rotundus is an effective candidate for reduction of inflammation by destabilization of microtubule fibers in brain. Journal of ethnopharmacology, doi:10.1016/j.jep.2016.06.058 (2016).
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alpha-Cyperone, isolated from the rhizomes of Cyperus rotundus, inhibits LPS-induced COX-2 expression and PGE2 production through the negative regulation of NFkappaB signalling in RAW 264.7 cells.[Pubmed:23500883]
J Ethnopharmacol. 2013 May 2;147(1):208-14.
ETHNOPHARMACOLOGICAL RELEVANCE: The rhizomes of Cyperus rotundus (Cyperaceae) have been used in Asian traditional medicine for the treatment of several inflammatory diseases. However, the anti-inflammatory effects of alpha-Cyperone, a major active compound of Cyperus rotundus, are poorly understood. MATERIALS AND METHODS: PGE2 and cytokines released from cells were measured using an EIA assay kit. The expression of iNOS, COX-2, TNF-alpha, and IL-6 was measured by real-time RT-PCR and/or Western blot analysis. A luciferase assay was performed to measure the effect of alpha-Cyperone on NFkappaB activity. RESULTS: The n-hexane fraction of the 80% EtOH extract from the rhizomes of Cyperus rotundus was found to inhibit both NO and PGE2 production in RAW 264.7 cells. alpha-Cyperone isolated from the n-hexane fraction significantly inhibited PGE2 production by suppressing the LPS-induced expression of inducible COX-2 at both the mRNA and the protein levels. In contrast, alpha-Cyperone had little effect on NO production and iNOS expression. Additionally, alpha-Cyperone downregulated the production and mRNA expression of the inflammatory cytokine IL-6. Moreover, treatment with alpha-Cyperone suppressed the transcriptional activity of NFkappaB and the nuclear translocation of the p65 NFkappaB subunit in LPS-induced RAW 264.7 cells. CONCLUSION: The anti-inflammatory activity of alpha-Cyperone is associated with the down-regulation of COX-2 and IL-6 via the negative regulation of the NFkappaB pathway in LPS-stimulated RAW 264.7 cells.
Xiang-Qi-Tang and its active components exhibit anti-inflammatory and anticoagulant properties by inhibiting MAPK and NF-kappaB signaling pathways in LPS-treated rat cardiac microvascular endothelial cells.[Pubmed:23171279]
Immunopharmacol Immunotoxicol. 2013 Apr;35(2):215-24.
Xiang-Qi-Tang (XQT) is a Chinese herbal formula containing Cyperus rotundus, Astragalus membranaceus and Andrographis paniculata. alpha-Cyperone (CYP), astragaloside IV (AS-IV) and andrographolide (AND) are the three major active components in this formula. XQT may modulate the inflammatory or coagulant responses. We therefore assessed the effects of XQT on lipopolysaccharide (LPS)-induced inflammatory model of rat cardiac microvascular endothelial cells (RCMECs). XQT, CYP, AS-IV and AND inhibited the production of tumor necrosis factor alpha (TNF-alpha), intercellular cell adhesion molecule-1 (ICAM-1) and plasminogen activator inhibitor-1 (PAI-1), and up-regulated the mRNA expression of Kruppel-like factor 2 (KLF2). XQT and CYP inhibited the secretion of tissue factor (TF). To further explore the mechanism, we found that XQT, or its active components CYP, AS-IV and AND significantly inhibited extracellular signal-regulated kinase (ERK), c-jun NH2-terminal kinase (JNK) and p38 phosphorylation protein expression as well as decreased the phosphorylation levels of nuclear factor kappaB (NF-kappaB) p65 proteins in LPS-stimulated RCMECs. These results suggested that XQT and its active components inhibited the expression of inflammatory and coagulant mediators via mitogen-activated protein kinase (MAPKs) and NF-kappaB signaling pathways. These findings may contribute to future research on the action mechanisms of this formula, as well as therapy for inflammation- or coagulation-related diseases.
alpha-cyperone alleviates lung cell injury caused by Staphylococcus aureus via attenuation of alpha-hemolysin expression.[Pubmed:22713997]
J Microbiol Biotechnol. 2012 Aug;22(8):1170-6.
In this study, we aimed to evaluate the effect of alpha- cyperone on S. aureus. We used a hemolysin test to examine the hemolytic activity in supernatants of S. aureus cultured with increasing concentrations of alpha- cyperone. In addition, we evaluated the production of alpha- hemolysin (Hla) by Western blotting. Real-time RT-PCR was performed to test the expression of hla (the gene encoding Hla) and agr (accessory gene regulator). Furthermore, we investigated the protective effect of alpha- cyperone on Hla-induced injury of A549 lung cells by live/ dead and cytotoxicity assays. We showed that in the presence of subinhibitory concentrations of alpha-Cyperone, Hla production was markedly inhibited. Moreover, alpha- cyperone protected lung cells from Hla-induced injury. These findings indicate that alpha-Cyperone is a promising inhibitor of Hla production by S. aureus and protects lung cells from this bacterium. Thus, alpha-Cyperone may provide the basis for a new strategy to combat S. aureus pneumonia.
Inhibitory effects of alpha-cyperone on adherence and invasion of avian pathogenic Escherichia coli O78 to chicken type II pneumocytes.[Pubmed:24629766]
Vet Immunol Immunopathol. 2014 May 15;159(1-2):50-7.
Avian pathogenic Escherichia coli (APEC) are extra-intestinal pathogenic E. coli, and usually cause avian septicemia through breaching the blood-gas barrier. Type II pneumocytes play an important role of maintaining the function of the blood-gas barrier. However, the mechanism of APEC injuring type II pneumocytes remains unclear. alpha-Cyperone can inhibit lung cell injury induced by Staphylococcus aureus. In order to explore whether alpha-Cyperone regulates the adherence and invasion of APEC-O78 to chicken type II pneumocytes, we successfully cultured chicken type II pneumocytes. The results showed that alpha-Cyperone significantly decreased the adherence of APEC-O78 to chicken type II pneumocytes. In addition, alpha-Cyperone inhibited actin cytoskeleton polymerization induced by APEC-O78 through down regulating the expression of Nck-2, Cdc42 and Rac1. These results provide new evidence for the prevention of colibacillosis in chicken.
