ZeylenoneCAS# 193410-84-3 |
Quality Control & MSDS
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| Cas No. | 193410-84-3 | SDF | Download SDF |
| PubChem ID | 10571940 | Appearance | Powder |
| Formula | C21H18O7 | M.Wt | 382.4 |
| Type of Compound | Miscellaneous | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | [(1S,5R,6S)-5-benzoyloxy-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl]methyl benzoate | ||
| SMILES | C1=CC=C(C=C1)C(=O)OCC2(C(C(C=CC2=O)OC(=O)C3=CC=CC=C3)O)O | ||
| Standard InChIKey | UUNZIGRBVXAOSR-PLMTUMEDSA-N | ||
| Standard InChI | InChI=1S/C21H18O7/c22-17-12-11-16(28-20(25)15-9-5-2-6-10-15)18(23)21(17,26)13-27-19(24)14-7-3-1-4-8-14/h1-12,16,18,23,26H,13H2/t16-,18+,21-/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 | 1. Zeylenone has good antitumor efficacy, it inhibits proliferation and induces apoptosis in cervical carcinoma cells via PI3K/AKT/mTOR and MAPK/ERK pathways. 2. Zeylenone shows inhibitory activity toward the root growth of Lactuca sativa. |
| Targets | PI3K | mTOR | Akt | MAPK | ERK |
Zeylenone Dilution Calculator
Zeylenone Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.6151 mL | 13.0753 mL | 26.1506 mL | 52.3013 mL | 65.3766 mL |
| 5 mM | 0.523 mL | 2.6151 mL | 5.2301 mL | 10.4603 mL | 13.0753 mL |
| 10 mM | 0.2615 mL | 1.3075 mL | 2.6151 mL | 5.2301 mL | 6.5377 mL |
| 50 mM | 0.0523 mL | 0.2615 mL | 0.523 mL | 1.046 mL | 1.3075 mL |
| 100 mM | 0.0262 mL | 0.1308 mL | 0.2615 mL | 0.523 mL | 0.6538 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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Quantitative analysis of differential protein expression in cervical carcinoma cells after zeylenone treatment by stable isotope labeling with amino acids in cell culture.[Pubmed:26130516]
J Proteomics. 2015 Aug 3;126:279-87.
Cervical carcinoma is a malignant tumor that poses a serious threat to women's health and survival. Approximately 10-25% of cervical cancers are adenocarcinomas (ACs). AC has high rates of recurrence and mortality, while there is no effective treatment for now. Zeylenone (Zey), which is isolated from an ethanol extract of the leaves of Uvaria grandiflora Roxb. of the family Annonaceae, has shown potent inhibitory activity against various tumor cells, including cervical carcinoma cells. To gain insight into the molecular mechanism underlying the effect of Zey on AC, we quantified protein expression changes in AC cells treated with Zey. We used stable isotope labeling with amino acids in cell culture (SILAC) in combination with high-performance liquid chromatography-electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) and bioinformatics analysis to compare protein expression profiles in HeLa cells before and after Zey treatment. Of 1805 differentially expressed proteins identified, 229 were screened as key protein molecules and classified into nine categories. Profiling of differentially-expressed proteins contributed to our understanding of the molecular mechanism by which Zey induces HeLa cell apoptosis. Using this method, candidate targets can be identified for developing new drugs against cervical carcinoma.
Zeylenone, a naturally occurring cyclohexene oxide, inhibits proliferation and induces apoptosis in cervical carcinoma cells via PI3K/AKT/mTOR and MAPK/ERK pathways.[Pubmed:28490807]
Sci Rep. 2017 May 10;7(1):1669.
There is a strong rationale to therapeutically target the PI3K/Akt/mTOR and MAPK/ERK pathways in cervical carcinoma since they are highly deregulated in this disease. Previous study by our group have demonstrated that Zeylenone (Zey) exhibited strong suppressive activity on PI3K/AKT/mTOR and MAPK/ERK signaling, providing a foundation to investigate its antitumor activity in cervical carcinoma. Herein, the present study aimed to investigate suppressive effect of Zey on HeLa and CaSki cells, and further explore the underlying mechanisms. Cells were treated with Zey for indicated time, followed by measuring its effects on cell viability, colony formation, cell cycle, cell apoptosis, and signal pathways. In vivo antitumor activity of Zey was then assessed with nude xenografts. We found that Zey substantially suppressed cell proliferation, induced cell cycle arrest, and increased cell apoptosis, accompanied by increased production of ROS, decreased mitochondrial membrane potential, activated caspase apoptotic cascade, and attenuated PI3K/Akt/mTOR and MAPK/ERK pathways. Additionally, in vivo experiments showed that Zey exerted good antitumor efficacy against HeLa bearing mice models via decreasing levels of p-PI3K and p-ERK. Collectively, these data clearly demonstrated the antitumor activity of Zey in cervical carcinoma cells, which is most likely via the regulation of PI3K/Akt/mTOR and MAPK/ERK pathways.
Zeylenone inhibits proliferation and promotes apoptosis in ovarian carcinoma cells via Janus kinase 2 / signal transducers and activators of transcription 3 pathways.[Pubmed:29974554]
J Obstet Gynaecol Res. 2018 Aug;44(8):1451-1457.
AIM: Ovarian cancer is the fifth common cancer in females. The aim of our study was to determine function of Zeylenone on cell viability and apoptosis of ovarian carcinoma SKOV3 cells. METHODS: Cell viability was measured by Cell counting kit-8 (CCK8) assay; Mitochondrial membrane potential (MMP) and apoptosis were detected by flow cytometry. The mRNA and protein levels of related factors were determined by Real-time quantitative polymerase chain reaction (RT-qPCR) and Western blot, respectively. RESULTS: Cell viability was decreased by Zeylenone in a dose-dependent manner. Zeylenone with concentrations of 2.5, 5 and 10 mumol/L was used to treat ovarian carcinoma SKOV3 cells for 24 h in the following study. The loss of MMP and apoptosis were both significantly increased by Zeylenone. The mRNA and protein levels of cytochrome c (cyto c) and apoptosis inducing factor (AIF) in cytosol were increased by Zeylenone. The mRNA and protein levels of Caspase-3, Fas, Fasl and Bax were increased; while the expression of Bcl-2 was decreased by Zeylenone. The expression of (Janus family of tyrosine kinase) p-JAK and signal transducer and activator of transcription (p-STAT) was decreased significantly by Zeylenone. CONCLUSION: Zeylenone inhibited cell proliferation and promoted apoptosis in ovarian carcinoma cells. The JAK-STAT pathway was involved in this progress.
