Skimmianine
(Synonyms: 茵芋碱) 目录号 : GC39014
A furoquinoline alkaloid with diverse biological activities
Cas No.:83-95-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Skimmianine is a furoquinoline alkaloid that has been found in Z. nitidum and has diverse biological activities.1,2,3,4 It inhibits acetylcholinesterase (AChE; IC50 = 8.6 ?g/ml for the human enzyme).1 Skimmianine is active against P. falciparum (IC50 = 48.2 ?g/ml), as well as L. gongylophorus, a symbiotic fungus of the agricultural pest A. sexdens (leaf-cutting ant).2,3 It reduces ear edema induced by phorbol 12-myristate 13-acetate in mice (ED45 = 0.75 mg/ear).4
1.Yang, Z.-d., Zhang, D.-b., Ren, J., et al.Skimmianine, a furoquinoline alkaloid from Zanthoxylum nitidum as a potential acetylcholinesterase inhibitorMed. Chem. Res.21722-725(2011) 2.Khalid, S.A., Farouk, A., Geary, T.G., et al.Potential antimalarial candidates from African plants: And in vitro approach using Plasmodium falciparumJ. Ethnopharmacol.15(2)201-209(1986) 3.Biavatti, M.W., Vieira, P.C., da Silva, F.d.G.F., et al.Biological activity of quinoline alkaloids from Raulinoa echinata and x-ray structure of flindersiamineJ. Braz. Chem. Soc.13(1)66-70(2002) 4.García-Argáez, A.N., Ramírez Apan, T.O., Parra Delgado, H., et al.Anti-inflammatory activity of coumarins from Decatropis bicolor on TPA ear mice modelPlanta Med.66(3)279-281(2000)
| Cas No. | 83-95-4 | SDF | |
| 别名 | 茵芋碱 | ||
| Canonical SMILES | COC1=C2N=C(OC=C3)C3=C(OC)C2=CC=C1OC | ||
| 分子式 | C14H13NO4 | 分子量 | 259.26 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.8571 mL | 19.2857 mL | 38.5713 mL |
| 5 mM | 0.7714 mL | 3.8571 mL | 7.7143 mL |
| 10 mM | 0.3857 mL | 1.9286 mL | 3.8571 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Skimmianine: Natural Occurrence, Biosynthesis, Synthesis, Pharmacology and Pharmacokinetics
Med Chem 2022 Dec 13.PMID:36518041DOI:10.2174/1573406419666221213124847.
Back ground: For years, plant materials collected from members of the family Rutaceae have been the subject of various phytochemical and pharmacological studies. In such works, Skimmianine (SM) is a secondary metabolite type furoquinoline alkaloid, which can be seen as a major component available in medicinal plants of the family Rutaceae. Although there have been numerous phytochemical and biological experiments, a brief review of this compound is insufficient. Objective: The current review with the most aim is to provide information on its natural occurrence, structural features, biosynthesis, synthesis, pharmacological values, and pharmacokinetic action Methods: The list of references was gathered from the following databases: Google Scholar, PubMed, Scopus, Web of Science, Science Direct, and Medline. In the meantime, "Skimmianine" either alone, or combined "phytochemistry", "biosynthesis", "synthesis", "pharmacology", and "pharmacokinetics" was taken into consideration, to search for references. Results: Accumulative evidence indicated that many Rutaceae plants, such as genus Zanthoxylum, were associated with the presence of alkaloid SM. Biosynthesis of organic hetero-tricyclic compound SM started from anthranilic acid, whereas its short synthetic steps were initially derived from 2,4,7,8-tetramethoxyquinoline. SM established a great role in pharmaceutical aspect since it possessed antimicrobial, antiparasitic, antiinsect, antiplatelet, antidiabetic, antiviral, cholinesterase inhibitory, analgesic, cardiovascular, and estrogenic activities, especially cytotoxicity and anti-inflammatory activity. Pharmacokinetic progress of SM in rats mostly involved the changes of double bond C2-C3, and methoxy groups. Conclusion: Pharmacological properties justify its usage in drug developments. However, some aspects, such as the extensive mechanism of action, structure-activity relationship, toxicological, and clinical studies, demand more research.
Neuroprotection by Skimmianine in Lipopolysaccharide-Activated BV-2 Microglia
Molecules 2023 Jan 30;28(3):1317.PMID:36770987DOI:10.3390/molecules28031317.
Skimmianine is a furoquinoline alkaloid which is found in the Zanthoxylum genus and also in other plants of the Rutaceae family. This study evaluated the effects of Skimmianine on the production of pro-inflammatory mediators in LPS-activated BV-2 microglia. Cultured BV-2 cells were treated with Skimmianine (10, 20 and 30 μM), followed by stimulation with LPS (100 ng/mL). Levels of TNFα and IL-6 in cell supernatants were measured using ELISA, while NO and PGE2 levels were evaluated with Griess assay and EIA, respectively. Western blotting was used to determine the protein expression of iNOS, COX-2, phospho-p65 and phospho-IκBα. Results showed that Skimmianine reduced LPS-induced elevated the secretion of TNFα, IL-6, NO, and PGE2, as well as the increased protein expression of iNOS and COX-2. Experiments to elucidate the mechanisms of the anti-neuroinflammatory activity of Skimmianine revealed the significant inhibition of LPS-induced increased NF-κB-mediated luciferase activity. Pre-treatment with Skimmianine also reduced LPS-induced the increased phosphorylation of NF-κB/p65 and IκBα proteins. Furthermore, Skimmianine interfered with the binding capacity of NF-κB to consensus sites. Skimmianine pre-treatment protected HT-22 cells from toxicity induced by microglia-conditioned media, as well as increasing MAP-2 expression. The results of this study suggest that Skimmianine inhibits neuroinflammation in LPS-activated microglia by targeting the NF-κB activation pathway. Skimmianine also produced neuroprotection against neurotoxicity induced by microglia-conditioned media.
Skimmianine as a novel therapeutic agent suppresses proliferation and migration of human esophageal squamous cell carcinoma via blocking the activation of ERK1/2
Neoplasma 2022 May;69(3):571-582.PMID:35144474DOI:10.4149/neo_2022_211118N1640.
Esophageal squamous cell carcinoma (ESCC), one of the main histopathological subtypes of esophageal cancer (EC), is characterized by high morbidity and mortality. Clinical treatment for ESCC lacks specific molecular targets and effective therapeutic drugs. Skimmianine (SK), one of the natural fluroquinolone alkaloids, is widely present in Rutaceae family plants. Here, we mainly used CCK-8 assay, clone formation, flow cytometry analysis, wound-healing assay, Transwell assay, western blot, quantitative real-time PCR (qRT-PCR), molecular docking analysis, tumor xenograft assay, and immunohistochemistry (IHC) staining to investigate the potential anti-tumor effect of SK on ESCC. We demonstrated that SK inhibited the proliferation of TE-1 and Eca109 cells via inducing the G0/G1 phase cell cycle arrest, prevented the migration and invasion of tumor cells via regulating epithelial-mesenchymal transition (EMT) in vitro. In addition, SK obviously suppressed the growth of xenografted Eca109 tumors in nude mice. The anti-tumor mechanism of SK could be blocking the activation of extracellular signal-regulated kinases 1/2 (ERK1/2) in the mitogen-activated protein kinase (MAPK)/ERK signaling pathway. Our basic research suggests that SK can be a potential therapeutic agent for ESCC.
Skimmianine and related furoquinolines function as antagonists of 5-hydroxytryptamine receptors in animals
J Auton Pharmacol 1994 Oct;14(5):365-74.PMID:7829541DOI:10.1111/j.1474-8673.1994.tb00617.x.
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.
Metabolic Profile of Skimmianine in Rats Determined by Ultra-Performance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Tandem Mass Spectrometry
Molecules 2017 Mar 23;22(4):489.PMID:28333075DOI:10.3390/molecules22040489.
Skimmianine is a furoquinoline alkaloid present mainly in the Rutaceae family. It has been reported to have analgesic, antispastic, sedative, anti-inflammatory, and other pharmacologic activities. Despite its critical pharmacological function, its metabolite profiling is still unclear. In this study, the in vivo metabolite profiling of Skimmianine in rats was investigated using ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UPLC/Q-TOF-MS). The metabolites were predicted using MetabolitePilotTM software. These predicted metabolites were further analyzed by MS² spectra, and compared with the detailed fragmentation pathway of the Skimmianine standard and literature data. A total of 16 metabolites were identified for the first time in rat plasma, urine, and feces samples after oral administration of Skimmianine. Skimmianine underwent extensive Phase I and Phase II metabolism in rats. The Phase I biotransformations of Skimmianine consist of epoxidation of olefin on its furan ring (M1) followed by the hydrolysis of the epoxide ring (M4), hydroxylation (M2, M3), O-demethylation (M5-M7), didemethylation (M14-M16). The Phase II biotransformations include glucuronide conjugation (M8-M10) and sulfate conjugation (M11-M13). The epoxidation of 2,3-olefinic bond followed by the hydrolysis of the epoxide ring and O-demethylation were the major metabolic pathways of Skimmianine. The results provide key information for understanding the biotransformation processes of Skimmianine and the related furoquinoline alkaloids.