ProtostemonineCAS# 27495-40-5 |
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| Cas No. | 27495-40-5 | SDF | Download SDF |
| PubChem ID | 25256772 | Appearance | Powder |
| Formula | C23H31NO6 | M.Wt | 417.5 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| SMILES | CC1CC(OC1=O)C2CCC3N2CCCC4C3C(C(=C5C(=C(C(=O)O5)C)OC)O4)C | ||
| Standard InChIKey | JDGNFRYDHRYXNL-ROHJGGRPSA-N | ||
| Standard InChI | InChI=1S/C23H31NO6/c1-11-10-17(29-22(11)25)14-7-8-15-18-12(2)20(28-16(18)6-5-9-24(14)15)21-19(27-4)13(3)23(26)30-21/h11-12,14-18H,5-10H2,1-4H3/b21-20-/t11-,12-,14-,15-,16+,17-,18+/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. Protostemonine has anti-inflammatory activity, it effectively attenuates LPS-induced inflammatory responses in vitro and in vivo; the beneficial effects are associated with the decreased phosphorylation of MAPK and AKT and the reduced expression of pro-inflammatory mediators, such as iNOS, NO and cytokines. 2. Protostemonine shows strong nematicidal activity against Panagrellus redivevus, with the IC50 value of 0.10 uM. 3. Protostemonine attenuates LPS/GalN-induced acute liver failure and upregulating HO-1 expression is implicated in its hepatoprotective activity. 4. Protostemonine shows significant antitussive activity in a citric acid-induced guinea pig cough model following peripheral administration. |
| Targets | p38MAPK | Akt | NOS | NO | TNF-α | IL Receptor | HO-1 | Nrf2 |
Protostemonine Dilution Calculator
Protostemonine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.3952 mL | 11.976 mL | 23.9521 mL | 47.9042 mL | 59.8802 mL |
| 5 mM | 0.479 mL | 2.3952 mL | 4.7904 mL | 9.5808 mL | 11.976 mL |
| 10 mM | 0.2395 mL | 1.1976 mL | 2.3952 mL | 4.7904 mL | 5.988 mL |
| 50 mM | 0.0479 mL | 0.2395 mL | 0.479 mL | 0.9581 mL | 1.1976 mL |
| 100 mM | 0.024 mL | 0.1198 mL | 0.2395 mL | 0.479 mL | 0.5988 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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Alkaloids from roots of Stemona sessilifolia and their antitussive activities.[Pubmed:19031364]
Planta Med. 2009 Feb;75(2):174-7.
Protostemonamide ( 1), a new Protostemonine-type alkaloid, and 12 known compounds were isolated from the roots of Stemona sessilifolia. Their structures were elucidated by 1 D and 2 D NMR spectral and other spectroscopic studies. The main alkaloidal constituents, Protostemonine ( 2), stemospironine ( 4), and maistemonine ( 7), showed significant antitussive activity in a citric acid-induced guinea pig cough model following peripheral administration; stemonamine ( 11) had antitussive activity following i. c. v. administration.
Protective effects of protostemonine on LPS/GalN-induced acute liver failure: Roles of increased hepatic expression of heme oxygenase-1.[Pubmed:26363973]
Int Immunopharmacol. 2015 Dec;29(2):798-807.
Here, we explored protective effects of Protostemonine (PSN), on mouse acute liver failure induced by lipopolysaccharide/d-galactosamine (LPS/GalN). PSN dose-dependently declined LPS/GalN-induced lethality of mice as well as increase of ALT/AST activities in their serum. Hepatoprotective effects of PSN were also supported by liver histopathological examinations. After LPS/GalN treatment, severe oxidative stresses in the liver could be detected by boosted MDA and ROS as well as decreased GSH. Moreover, hepatic expression of pro-inflammatory cytokines, including TNF-alpha, IL-1beta and IL-6, were sharply elevated. These symptoms were dose-dependently ameliorated by PSN. Mechanistically, PSN promoted the transcription and translation of heme oxygenase-1 (HO-1) in hepatocytes and liver Kupffer cells. Nrf2 is a master transcription factor contributing to the expression of HO-1. PSN elevated Nrf2 nuclear accumulation and enhanced Nrf2/HO-1 promoter interaction. Suppressing enzyme activity of HO-1 by co-treating mice with HO-1 inhibitor ZnPP abolished protective effects of PSN. ZnPP also abrogated alleviative impacts of PSN on LPS/GalN-mediated hepatic oxidative stresses and inflammatory responses. Finally, we showed that PSN exhibited undetectable toxic effects on vital organs of mice. Our findings suggested that PSN is able to attenuate LPS/GalN-induced acute liver failure and upregulating HO-1 expression is implicated in its hepatoprotective activity.
Nematicidal Stemona Alkaloids from Stemona parviflora.[Pubmed:27684288]
J Nat Prod. 2016 Oct 28;79(10):2599-2605.
Eight new alkaloids, 3beta-n-butylstemonamine (1), 8-oxo-3beta-n-butylstemonamine (2), 3-n-butylneostemonine (3), 10-epi-3-n-butylneostemonine (4), 8-oxo-oxymaistemonine (5) Protostemonine N4-oxide (6), (19S)-hydroxy-21-methoxystemofoline (7), and parvistemonine A (8), were isolated from the roots of Stemona parviflora, together with 17 known alkaloids. The structures of the new alkaloids were elucidated based on a comprehensive spectroscopic data analysis. The absolute configurations of 1-4 were determined by the ECD exciton chirality method and quantum ECD calculations. Protostemonine (10) and stemofoline (12) showed strong nematicidal activity against Panagrellus redivevus, with IC50 values of 0.10 and 0.46 muM, respectively.
Protostemonine effectively attenuates lipopolysaccharide-induced acute lung injury in mice.[Pubmed:29047459]
Acta Pharmacol Sin. 2018 Jan;39(1):85-96.
Protostemonine (PSN) is the main anti-inflammatory alkaloid extracted from the roots of Stemona sessilifolia (known as "Baibu" in traditional Chinese medicine). Here, we reported the inhibitory effects of PSN on lipopolysaccharide (LPS)-induced macrophage activation in vitro and LPS-induced acute lung injury in mice. Macrophage cell line RAW264.7 cells and mouse bone marrow-derived macrophages (BMDMs) were treated with PSN (1, 3, 10, 30 and 100 mumol/L) for 0.5 h and then challenged with LPS (0.1 mug/mL) for 24 h. Pretreatment with PSN significantly inhibited LPS-induced phosphorylation of MAPKs and AKT, iNOS expression and NO production in the macrophages. C57BL/6 mice were intratracheally injected with LPS (5 mg/kg) to induce acute lung injury (ALI). The mice were subsequently treated with PSN (10 mg/kg, ip) at 4 and 24 h after LPS challenge. PSN administration significantly attenuated LPS-induced inflammatory cell infiltration, reduced pro-inflammatory cytokine (TNF-alpha, IL-1beta and IL-6) production and eliminated LPS-mediated lung edema. Furthermore, PSN administration significantly inhibited LPS-induced pulmonary MPO activity. Meanwhile, LPS-induced phosphorylation of p38 MAPK, iNOS expression and NO production in the lungs were also suppressed. The results demonstrate that PSN effectively attenuates LPS-induced inflammatory responses in vitro and in vivo; the beneficial effects are associated with the decreased phosphorylation of MAPK and AKT and the reduced expression of pro-inflammatory mediators, such as iNOS, NO and cytokines. These data suggest that PSN may be a potential therapeutic agent in the treatment of ALI.
