SkimmianinCAS# 83-95-4 |
Quality Control & MSDS
3D structure
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Number of papers citing our products
| Cas No. | 83-95-4 | SDF | Download SDF |
| PubChem ID | 6760 | Appearance | White powder |
| Formula | C14H13NO4 | M.Wt | 259.3 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Synonyms | Chloroxylonine; β-Fagarine | ||
| Solubility | Soluble in chloroform | ||
| Chemical Name | 4,7,8-trimethoxyfuro[2,3-b]quinoline | ||
| SMILES | COC1=C(C2=C(C=C1)C(=C3C=COC3=N2)OC)OC | ||
| Standard InChIKey | SLSIBLKBHNKZTB-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C14H13NO4/c1-16-10-5-4-8-11(13(10)18-3)15-14-9(6-7-19-14)12(8)17-2/h4-7H,1-3H3 | ||
| 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. Skimmianine is a new inhibitor against the Leishmania APRT enzyme. 2. Skimmianine has a selective inhibitory effect on the 5-hydroxytryptamine-induced vasopressor responses of rats. 3, Skimmianine is a strong acetylcholinesterase (AChE) inhibitor. 4. Skimmianine has anti-inflammatory properties. 5. Skimmianine has leishmanicidal effect , it is thus a promising drug candidate for L. braziliensis due to its potent immunomodulatory activity. |
| Targets | IL Receptor | NO | NOS | TNF-α | PGE | COX | LOX | SOD | AChR | 5-HT Receptor |
Skimmianin Dilution Calculator
Skimmianin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.8565 mL | 19.2827 mL | 38.5654 mL | 77.1307 mL | 96.4134 mL |
| 5 mM | 0.7713 mL | 3.8565 mL | 7.7131 mL | 15.4261 mL | 19.2827 mL |
| 10 mM | 0.3857 mL | 1.9283 mL | 3.8565 mL | 7.7131 mL | 9.6413 mL |
| 50 mM | 0.0771 mL | 0.3857 mL | 0.7713 mL | 1.5426 mL | 1.9283 mL |
| 100 mM | 0.0386 mL | 0.1928 mL | 0.3857 mL | 0.7713 mL | 0.9641 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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A new quinoline epoxide from the Australian plant Drummondita calida.[Pubmed:21472648]
Planta Med. 2011 Sep;77(14):1644-7.
A drug discovery program aimed at identifying new antimalarial leads from a prefractionated natural product library has resulted in the purification of a new quinoline alkaloid, (2' R)-2',3'-epoxy- N-methylatanine (1), along with eight known natural products, Skimmianin, gamma-fagarine, maculosidine, evolitrine, dictamnine, pteleine, N-methylatanine, and werneria chromene. Compound 1 displayed 74 % inhibition at 80 microM against a chloroquine -resistant Plasmodium falciparum strain (Dd2).
Skimmianine and related furoquinolines function as antagonists of 5-hydroxytryptamine receptors in animals.[Pubmed:7829541]
J Auton Pharmacol. 1994 Oct;14(5):365-74.
1. Skimmianine, kokusaginine and confusameline, three furoquinolines extracted from the leaves of Evodia merrillii (Rutaceae), were investigated to characterize their selective effects on subtypes of 5-hydroxytryptamine (5-HT) receptors. 2. In the isolated membranes of rat cerebrocortex, using [3H]-5-HT and [3H]-ketanserin as radioligands, Skimmianine and the two other furoquinolines displaced radioligand bindings in a concentration-dependent manner. Lower concentrations were required to affect [3H]-ketanserin binding than [3H]-5-HT binding in the order Skimmianine > kokusaginine > confusameline. 3. Furoquinolines inhibited 5-HT-induced contraction mediated by 5-HT2 receptors in the presence of methiothepin in rat isolated aorta. Also, the combination of furoquinolines with ketanserin showed an additive antagonism. 4. These furoquinolines were inactive on the 5-carboxamidotryptamine-induced relaxation of guinea-pig ileum, a 5-HT1-mediated event. However, 5-HT-induced contraction via 5-HT2 receptors was reduced by these furoquinolines in a way similar to that in blood vessels. 5. The failure of these compounds to affect the 5-HT-induced Bezold-Jarisch-like reflex in anaesthetized rats, the major 5-HT3-mediated action, ruled out an action on 5-HT3 receptors. 6. The results obtained suggest that three furoquinoline alkaloids may act on 5-HT receptors in animals, more selectively to the 5-HT2 subtype, in the order of Skimmianine > kokusaginine > confusameline.
Leishmanicidal effect of Spiranthera odoratissima (Rutaceae) and its isolated alkaloid skimmianine occurs by a nitric oxide dependent mechanism.[Pubmed:21810308]
Parasitology. 2011 Sep;138(10):1224-33.
Leishmaniasis is one of the neglected diseases. High cost, systemic toxicity, and diminished efficacy due to development of resistance by the parasites has a negative impact on the current treatment options. Thus, the search for a new, effective and safer anti-leishmanial drug becomes of paramount importance. Compounds derived from natural products may be a better and cheaper source in this regard. This study evaluated the in vitro anti-leishmanial activity of Spiranthera odoratissima (Rutaceae) fractions and isolated compounds, using promastigote and amastigote forms of different Leishmania species. J774 A.1 macrophage was used as the parasite host cell for the in vitro assays. Evaluations of cytoxicity, nitric oxide (NO), interleukin-10 and in silico analysis were carried out. In vitro experiments showed that the fruit hexanic fraction (Fhf) and its alkaloid Skimmianine (Skm) have a significant (P<0.001) effect against L. braziliensis. This anti-L. braziliensis activity of Fhf and Skm was due to increased production of NO and attenuation of IL-10 production in the macrophages at concentrations ranging from 1.6 to 40.0 mug/ml. The in silico assay demonstrated significant interaction between Skm and amino acid residues of NOS2. Skm is thus a promising drug candidate for L. braziliensis due to its potent immunomodulatory activity.
Anti-inflammatory effect of quinoline alkaloid skimmianine isolated from Ruta graveolens L.[Pubmed:23344232]
Inflamm Res. 2013 Apr;62(4):367-76.
OBJECTIVE: The present study evaluates the anti-inflammatory effect of the quinoline alkaloid Skimmianine (SKM), isolated from Ruta graveolens L., against carrageenan-induced acute inflammation. METHODS: SKM at a dose of 5.0 mg/kg body weight was found to be the minimal concentration for maximal edema inhibition. Carrageenan suspension was administered into the sub-plantar tissue of the right hind paw 1 h after SKM and diclofenac (20 mg/kg) administration (i.p.). Paw edema was determined 3 h after carrageenan administration. The rats were then killed and mRNA expressions of TNF-alpha and IL-6, levels of PGE2 and TBARS, activities of COX-2, 5-LOX, SOD, catalase, glutathione peroxidase (GPx) and myeloperoxidase (MPO) and the level of nitrite were measured. RESULTS: SKM treatment resulted in a decrease in the mRNA levels of TNF-alpha and IL-6, which are upstream events of the inflammatory cascade. The levels of PGE2 and NO and the activities of COX-2 and 5-LOX were also significantly reduced after SKM treatment. Neutrophil infiltration, lipid peroxidation and associated oxidative stress in the paw tissue were reduced following SKM treatment. CONCLUSION: These results support the anti-inflammatory properties of Skimmianine and its multi-targeted mechanism of action, suggesting its potential therapeutic efficacy in various inflammatory diseases.
