EupatoriopicrinCAS# 6856-01-5 |
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| Cas No. | 6856-01-5 | SDF | Download SDF |
| PubChem ID | 5281461 | Appearance | Powder |
| Formula | C20H26O6 | M.Wt | 362.42 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | [(3aR,4R,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate | ||
| SMILES | CC1=CC2C(C(CC(=CCC1)C)OC(=O)C(=CCO)CO)C(=C)C(=O)O2 | ||
| Standard InChIKey | VWJYWGYJIDQUEG-DKDOXNMLSA-N | ||
| Standard InChI | InChI=1S/C20H26O6/c1-12-5-4-6-13(2)10-17(26-20(24)15(11-22)7-8-21)18-14(3)19(23)25-16(18)9-12/h6-7,9,16-18,21-22H,3-5,8,10-11H2,1-2H3/b12-9+,13-6+,15-7+/t16-,17-,18+/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. Eupatoriopicrin shows anti-trypanosomal activities and cytotoxicity against Trypanosoma brucei rhodesiense. 2. Eupatoriopicrin shows a weak sensitizing capacity in guinea pigs. 3. Eupatoriopicrin-induced DNA damage may play a role in the observed cytotoxicity. |
| Targets | Antifection |
Eupatoriopicrin Dilution Calculator
Eupatoriopicrin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.7592 mL | 13.7961 mL | 27.5923 mL | 55.1846 mL | 68.9807 mL |
| 5 mM | 0.5518 mL | 2.7592 mL | 5.5185 mL | 11.0369 mL | 13.7961 mL |
| 10 mM | 0.2759 mL | 1.3796 mL | 2.7592 mL | 5.5185 mL | 6.8981 mL |
| 50 mM | 0.0552 mL | 0.2759 mL | 0.5518 mL | 1.1037 mL | 1.3796 mL |
| 100 mM | 0.0276 mL | 0.138 mL | 0.2759 mL | 0.5518 mL | 0.6898 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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Antitrypanosomal sesquiterpene lactones from Saussurea costus.[Pubmed:21624443]
Fitoterapia. 2011 Oct;82(7):955-9.
In the course of a larger screen of 1800 plant and fungal extracts, the ethyl acetate extract of Saussurea costus roots potently inhibited the growth of Trypanosoma brucei rhodesiense. Subsequent HPLC based activity profiling led to the identification of the sesquiterpene lactones arbusculin B (1), alpha-cyclocostunolide (2), costunolide (3), and dehydrocostuslactone (4). They were tested for in vitro antitrypanosomal activities and cytotoxicity alongside the structurally related sesquiterpene lactones parthenolide (5), zaluzanin D (6), and Eupatoriopicrin (7), and had IC(50)s between 0.8 and 22 muM. Cytotoxic IC(50)s were from 1.6 to 19 muM, and selectivity indices from 0.5 to 6.5.
Allergenic sesquiterpene lactones from Eupatorium cannabinum L. and Kaunia rufescens (Lund ex de Candolle).[Pubmed:9615309]
Nat Toxins. 1997;5(6):223-7.
From Eupatorium cannabinum L., a hitherto unknown alpha-methylene-gamma-butyrolactone, 3 beta-peroxyeucannabinolide, was isolated. This compound and Eupatoriopicrin from the same plant showed a weak sensitizing capacity in guinea pigs. 2-oxoludartin and dehydroleucodin, isolated from Kaunia rufescens (syn. Eupatorium rufescens), were strong sensitizers in the same sensitizarian procedure.
Induction of DNA damage in Ehrlich ascites tumour cells by exposure to eupatoriopicrin.[Pubmed:2751694]
Biochem Pharmacol. 1989 Jul 15;38(14):2279-83.
The sesquiterpene lactone Eupatoriopicrin (EUP) from Eupatorium cannabinum L. has been shown to be cytotoxic in a glutathione (GSH)-dependent way. In order to assess possible DNA damage as a cause for cell death, the study reported was initiated. After 2 hr incubation of Ehrlich ascites tumour cells with EUP, the DNA damage, determined by the use of an alkaline DNA unwinding method, followed by hydroxylapatite column chromatography of degraded DNA, was observed at concentrations only slightly higher than those causing cell death in a clonogenic assay. The amount of EUP, requested to demonstrate DNA damage after a 24-hr post-incubation period lay within the concentration range that was effective in the clonogenic assay (1-10 micrograms/ml). Glutathione (GSH) depletion of the cells to about 99%, by use of buthionine sulphoximine (BSO), enhanced the extent of DNA damage. It is concluded that EUP-induced DNA damage may play a role in the observed cytotoxicity.
