13(18)-Oleanen-3-oneCAS# 20248-08-2 |
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| Cas No. | 20248-08-2 | SDF | Download SDF |
| PubChem ID | 14079468 | Appearance | Cryst. |
| Formula | C30H48O | M.Wt | 424.7 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (4aR,6aR,6bS,8aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,13,14,14a-dodecahydro-1H-picen-3-one | ||
| SMILES | CC1(CCC2(CCC3(C(=C2C1)CCC4C3(CCC5C4(CCC(=O)C5(C)C)C)C)C)C)C | ||
| Standard InChIKey | KPUDOJPVQQJLGI-CKARLABJSA-N | ||
| Standard InChI | InChI=1S/C30H48O/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6)13-12-24(31)26(3,4)22(28)11-14-30(23,29)8/h22-23H,9-19H2,1-8H3/t22-,23+,27+,28-,29+,30+/m0/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. δ-Amyrone(13(18)-Oleanen-3-one), a specific inhibitor of cyclooxygenase-2, possesses anti-inflammatory effects, which may be relevant to the regulation of COX-2. 2. δ-Amyrone has protective activity on LPS-induced endotoxic shock, which is attributed to reducing NO production and mediating the pro-inflammatory cytokines, inhibited NF-κB expression. 3. δ-Amyrone exerts its protective effect on experimental gastric ulcer by inhibiting NF-κB signaling pathways, which subsequently reduces overproduction of the inducible enzymes iNOS and suppresses the release of the inflammatory factors TNF-α, IL-6 and NO. |
| Targets | NO | PGE | IL Receptor | TNF-α | COX | p65 | NF-kB | NOS |
13(18)-Oleanen-3-one Dilution Calculator
13(18)-Oleanen-3-one Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.3546 mL | 11.773 mL | 23.546 mL | 47.0921 mL | 58.8651 mL |
| 5 mM | 0.4709 mL | 2.3546 mL | 4.7092 mL | 9.4184 mL | 11.773 mL |
| 10 mM | 0.2355 mL | 1.1773 mL | 2.3546 mL | 4.7092 mL | 5.8865 mL |
| 50 mM | 0.0471 mL | 0.2355 mL | 0.4709 mL | 0.9418 mL | 1.1773 mL |
| 100 mM | 0.0235 mL | 0.1177 mL | 0.2355 mL | 0.4709 mL | 0.5887 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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delta-Amyrone inhibits lipopolysaccharide-induced inflammatory cytokines and protects against endotoxic shock in mice.[Pubmed:26271896]
Chem Biol Interact. 2015 Oct 5;240:354-61.
delta-Amyrone (13(18)-Oleanen-3-one), which is an active constituent extracted and separated from Sedum lineare Thunb., has been found to possess a potent anti-inflammatory effect in different inflammation model animals. But its effects on lipopolysaccharide (LPS)-induced endotoxic shock have not been previous explored. The aim of this study is to evaluate the effect of delta-Amyrone on LPS-induced inflammatory cytokines and the protective effect on endotoxic shock mice. Experimental animals received delta-amyrone (4 and 8 mg/kg, i.p.) and dexamethasone (DEX) (5 mg/kg, i.p.) at 24 and 1 h before LPS injection. delta-Amyrone treatment significantly decreased mortality rate, tissues myeloperoxodase (MPO) activity, p65 NF-kappaB protein expression when compared with the LPS groups. The levels of tumor nectosis factor-alphagene (TNF-alpha) and interleukin-6 (IL-6) both in serum and lung, liver, kidney tissues, as well as the accumulation of nitric oxide (NO) in serum were decreased by delta-amyrone in response to p65 nuclear factors-kappa B (NF-kappaB). These results suggest that the protective activity of delta-amyrone on LPS-induced endotoxic shock is attributed to reducing NO production and mediating the pro-inflammatory cytokines, inhibited NF-kappaB expression.
Protective effect of delta-amyrone against ethanol-induced gastric ulcer in mice.[Pubmed:25572867]
Immunobiology. 2015 Jun;220(6):798-806.
The purpose of this study is to examine the protective effect of delta-amyrone on ethanol-induced gastric ulcer in mice. The mice intragastric administration 75% (0.5 mL/100g) ethanol was pretreated with delta-amyrone (4 and 8 mg/kg) and cimetidine (100 mg/kg) or vehicles in different experimental groups for a continuous three-day, and animals were euthanized 3h after ethanol ingestion. The gastric lesions were significantly attenuated by delta-amyrone (4 and 8 mg/kg) as compared to the ulcer control group. Pre-treatment with delta-amyrone prevented the myeloperoxidase (MPO) activity, production of nitric oxide (NO) in serum, expression of inducible nitric oxide synthase (iNOS) and nuclear factor kappa B (NF-kappaB) p65 protein expression. Analysis of cytokines in gastric tissue and serum of ethanol-induced mice showed the levels of tumor necrosis factor-alpha (TNF-alpha) and interleukin-6 (IL-6) were decreased by delta-amyrone in response to NF-kappaB p65. These results suggested that delta-amyrone exerts its protective effect on experimental gastric ulcer by inhibiting NF-kappaB signaling pathways, which subsequently reduces overproduction of the inducible enzymes iNOS and suppresses the release of the inflammatory factors TNF-alpha, IL-6 and NO. Thus, delta-amyrone shows promise as a therapeutic agent in experimental gastric ulcer.
delta-Amyrone, a specific inhibitor of cyclooxygenase-2, exhibits anti-inflammatory effects in vitro and in vivo of mice.[Pubmed:24813716]
Int Immunopharmacol. 2014 Jul;21(1):112-8.
The whole plant of Sedum lineare Thunb has been used as traditional folk medicines for the treatment of sore throat, persistent hepatitis, jaundice and dysentery. delta-Amyrone (13(18)-Oleanen-3-one), a pentacyclic triterpene compound from S. lineare Thunb, was found to possess a potent anti-inflammatory effect in different inflammation model animals. Pretreatment with delta-Amyrone (i.p.) inhibited the ear edema in xylene-induced mouse ear edema. delta-Amyrone also decreased the level of nitric oxide (NO), prostaglandin E2 (PGE2), interleukin-6 (IL-6) and leukocyte numbers in acetic acid-induced peritonitis in vivo. To clarify the possible mechanism of delta-Amyrone, we investigated the effect of delta-Amyrone in lipopolysaccharide (LPS) induced peritoneal macrophages. The data indicated that delta-Amyrone notably inhibited IL-6, TNF-alpha and NO production. In addition, the result showed that delta-Amyrone may control the cyclooxygenase-2 (COX-2) regulation and not the cyclooxygenase-1 (COX-1) at protein levels. These results suggest that delta-Amyrone is a bioactive agent which possesses anti-inflammatory effects, which may be relevant to the regulation of COX-2.
