Siegeskaurolic acidCAS# 52645-97-3 |
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| Cas No. | 52645-97-3 | SDF | Download SDF |
| PubChem ID | 260658 | Appearance | Powder |
| Formula | C20H32O3 | M.Wt | 320.47 |
| Type of Compound | Diterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| SMILES | CC12CCCC(C1CCC34C2CCC(C3)C(C4)CO)(C)C(=O)O | ||
| Standard InChIKey | HHAMKMUMKLXDFQ-UMTOMPLCSA-N | ||
| Standard InChI | InChI=1S/C20H32O3/c1-18-7-3-8-19(2,17(22)23)15(18)6-9-20-10-13(4-5-16(18)20)14(11-20)12-21/h13-16,21H,3-12H2,1-2H3,(H,22,23)/t13-,14-,15-,16-,18+,19+,20-/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. Siegeskaurolic acid exhibits anti-inflammatory and antinociceptive effects, which due to the inhibition of iNOS and COX-2 expression in RAW 264.7 macrophages via NF-kappaB inactivation. |
| Targets | NO | PGE | TNF-α | COX | p65 | NOS | NF-kB |
Siegeskaurolic acid Dilution Calculator
Siegeskaurolic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.1204 mL | 15.6021 mL | 31.2042 mL | 62.4083 mL | 78.0104 mL |
| 5 mM | 0.6241 mL | 3.1204 mL | 6.2408 mL | 12.4817 mL | 15.6021 mL |
| 10 mM | 0.312 mL | 1.5602 mL | 3.1204 mL | 6.2408 mL | 7.801 mL |
| 50 mM | 0.0624 mL | 0.312 mL | 0.6241 mL | 1.2482 mL | 1.5602 mL |
| 100 mM | 0.0312 mL | 0.156 mL | 0.312 mL | 0.6241 mL | 0.7801 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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Anti-inflammatory activities of ent-16alphaH,17-hydroxy-kauran-19-oic acid isolated from the roots of Siegesbeckia pubescens are due to the inhibition of iNOS and COX-2 expression in RAW 264.7 macrophages via NF-kappaB inactivation.[Pubmed:17207792]
Eur J Pharmacol. 2007 Mar 8;558(1-3):185-93.
To isolate the anti-inflammatory components in Siegesbeckia pubescens root, we performed activity-guided fractionation using a carrageenan-induced edema rat model. Antinociceptive effects were followed using acetic acid-induced abdominal constriction and hot plate tests in mice. Chloroform extract was subjected to silica gel and octadesyl silane (ODS) column chromatography, and a diterpene was isolated which was identified as ent-16alphaH,17-hydroxy-kauran-19-oic acid (Siegeskaurolic acid). Pretreatment with Siegeskaurolic acid (20 or 30 mg/kg/day, p.o.) exhibited anti-inflammatory and antinociceptive effects in these animal models. To investigate the mechanisms underlying this anti-inflammatory action, we investigated the effect of Siegeskaurolic acid on lipopolysaccharide (LPS)-induced responses in a murine macrophage cell line, RAW 264.7. Siegeskaurolic acid was found to significantly inhibit the productions of nitric oxide (NO), prostaglandin E(2) (PGE(2)), and tumor necrosis factor-alpha (TNF-alpha). Consistent with these findings, inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins, and iNOS, COX-2, and TNF-alpha mRNAs were found to be inhibited by Siegeskaurolic acid. Furthermore, Siegeskaurolic acid inhibited the nuclear factor-kappaB (NF-kappaB) activation induced by LPS, and this was associated with the prevention of inhibitor kappaB degradation (I kappaB), and subsequently with decreased nuclear p65 and p50 protein levels. Taken together, our data indicate that the anti-inflammatory and antinociceptive properties of Siegeskaurolic acid may be due to iNOS, COX-2 and TNF-alpha inhibition via the down-regulation of NF-kappaB binding activity.
