MicheliolideCAS# 68370-47-8 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 68370-47-8 | SDF | Download SDF |
PubChem ID | 442279 | Appearance | Powder |
Formula | C15H20O3 | M.Wt | 248.3 |
Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
Solubility | DMSO : 100 mg/mL (402.71 mM; Need ultrasonic) | ||
Chemical Name | (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one | ||
SMILES | CC1=C2CCC(C2C3C(CC1)C(=C)C(=O)O3)(C)O | ||
Standard InChIKey | RDJAFOWISVMOJY-PWNZVWSESA-N | ||
Standard InChI | InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3/t11-,12-,13-,15+/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. Micheliolide has potential as a candidate drug for the treatment of diabetic nephropathy, it can effectively attenuate the high glucose-stimulated activation of NF-κB, the degradation of IκBα, and the expression of MCP-1, TGF-β1 and FN in rat mesangial cells (MCs). 2. Micheliolide ameliorates liver steatosis by upregulating PPAR-γ expression, thereby inhibiting NF-κB-mediated inflammation and activating AMPK/mTOR-dependent autophagy. 3. Micheliolide may serve as a neuroprotective agent in neuroinflammation-related neurodegenerative disorders. it can suppress LPS-induced neuroinflammatory responses. 4. Micheliolide plays anti-inflammatory and immunomodulatory roles in Mycobacterium tuberculosis-induced immune response by inhibiting NF-κB and NLRP3 inflammasome activation. 5. Micheliolide exerts its antineoplastic effects via inhibition of NF-κB expression and activity, and by generating intracellular reactive oxygen species (ROS). |
Targets | PPAR | p65 | NF-kB | IkB | AMPK | mTOR | COX | TNF-α | IL Receptor | NO | NOS | Akt | JNK | p38MAPK | ERK | HO-1 | Nrf2 | PI3K | ROS | TGF-β/Smad | IKK |
Micheliolide Dilution Calculator
Micheliolide Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 4.0274 mL | 20.1369 mL | 40.2739 mL | 80.5477 mL | 100.6847 mL |
5 mM | 0.8055 mL | 4.0274 mL | 8.0548 mL | 16.1095 mL | 20.1369 mL |
10 mM | 0.4027 mL | 2.0137 mL | 4.0274 mL | 8.0548 mL | 10.0685 mL |
50 mM | 0.0805 mL | 0.4027 mL | 0.8055 mL | 1.611 mL | 2.0137 mL |
100 mM | 0.0403 mL | 0.2014 mL | 0.4027 mL | 0.8055 mL | 1.0068 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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Micheliolide could effectively attenuate the high glucose-stimulated activation of NF-κB, the degradation of IκBα, and the expression of MCP-1, TGF-β1 and FN in rat mesangial cells (MCs).
References:
[1]. Jia QQ, et al. Sesquiterpene lactones and their derivatives inhibit high glucose-induced NF-κB activation and MCP-1 and TGF-β1 expression in rat mesangial cells. Molecules. 2013 Oct 21;18(10):13061-77.
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Antineoplastic effects and mechanisms of micheliolide in acute myelogenous leukemia stem cells.[Pubmed:27542251]
Oncotarget. 2016 Oct 4;7(40):65012-65023.
Leukemic stem cells (LSCs) greatly contribute to the initiation, relapse, and multidrug resistance of leukemia. Current therapies targeting the cell cycle and rapidly growing leukemic cells, including conventional chemotherapy, have little effect due to the self-renewal and differentiated malignant cells replenishment ability of LSCs despite their scarce supply in the bone marrow. Micheliolide (MCL) is a natural guaianolide sesquiterpene lactone (GSL) which was discovered in michelia compressa and michelia champaca plants, and has been shown to exert selective cytotoxic effects on CD34+CD38- LSCs. In this study, we demonstrate that DMAMCL significantly prolongs the lifespan of a mouse model of human acute myelogenous leukemia (AML). Mechanistic investigations further revealed that MCL exerted its cytotoxic effects via inhibition of NF-kappaB expression and activity, and by generating intracellular reactive oxygen species (ROS). These results provide valuable insight into the mechanisms underlying MCL-induced cytotoxicity of LSCs, and support further preclinical investigations of MCL-related therapies for the treatment of AML.
New cytotoxic sesquiterpene lactones from Anthemis scrobicularis.[Pubmed:25227949]
J Asian Nat Prod Res. 2014;16(9):922-9.
Four new sesquiterpene lactones, 4alpha-hydroxy-guaia-10(14),11(13)-diene-12,6alpha-olide (1), 4alpha-hydroxy-9alpha-acetoxy-guaia-1(10),2-diene-12,6alpha-olide (4), 4alpha-hydroxy-9beta-acetoxy-guaia-1(10),2-diene-12,6alpha-olide (5), and 1alpha,4alpha-dihydroxy-9alpha-acetoxy-guaia-10(14),2-diene-12,6alpha-olide (6), were isolated from the aerial parts of Anthemis scrobicularis. Their structures were elucidated on the basis of their IR, NMR, and MS spectroscopic data. In addition, two known sesquiterpene lactones Micheliolide (2) and achillin (3) were also isolated. The cytotoxicity of some of the isolated compounds was tested against HCT 116, HepG-2, and MCF-7 cell lines. Micheliolide and 4alpha-hydroxy-guaia-10(14),11(13)-diene-12,6alpha-olide showed pronounced inhibitory activity while 4alpha-hydroxy-9alpha-acetoxy-guaia-1(10),2-diene-12,6alpha-olide showed weak activity.
Micheliolide suppresses LPS-induced neuroinflammatory responses.[Pubmed:29040306]
PLoS One. 2017 Oct 17;12(10):e0186592.
Microglia-involved neuroinflammation is thought to promote brain damage in various neurodegenerative disorders. Thus, inhibition of microglial over-activation may have a therapeutic benefit for the treatment of neurodegenerative disorders. Micheliolide (MCL) is a sesquiterpene lactone which inhibits various inflammatory response. However, whether MCL can inhibit neuroinflammation caused by LPS-activated BV2 microglia has not yet been explored. In this study, we demonstrated that treatment of BV2 cells with MCL significantly repressed LPS-stimulated nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression, as well as tumor necrosis factor-alpha (TNF-alpha), interleukin-6 (IL-6) and nitric oxide (NO) induction. MCL also attenuated mRNA levels of multiple pro-inflammatory cytokines and mediators such as iNOS, COX-2, TNF-alpha, IL-6 and IL-1beta. Mechanistic studies revealed that MCL suppressed LPS-stimulated the activation of IkappaBalpha/NF-kappaB pathway and Akt pathway. Moreover, MCL inhibited LPS-induced the activition of c-Jun N-terminal kinase (JNK), p38 MAPK kinase, and extracellular signal-regulated kinases 1/2 (ERK1/2). Meanwhile, MCL markedly promoted antioxidant protein heme oxygenase-1 (HO-1) expression by enhancing NF-E2-related factor 2 (Nrf2) activity. Together, our results imply that MCL may serve as a neuroprotective agent in neuroinflammation-related neurodegenerative disorders.
Micheliolide alleviates hepatic steatosis in db/db mice by inhibiting inflammation and promoting autophagy via PPAR-gamma-mediated NF-small ka, CyrillicB and AMPK/mTOR signaling.[Pubmed:29656210]
Int Immunopharmacol. 2018 Jun;59:197-208.
The anti-inflammatory, immunomodulatory, and anticancer effects of Micheliolide (MCL) isolated from Michelia champaca were previously reported, but its role and underlying mechanisms in relieving liver steatosis remain unclear. Herein, we investigated the effects of MCL on hepatic steatosis using a db/db mouse model and lipid mixture (LM)-induced AML12 and LO2 cells. The body and liver weights, food consumption, lipid content and liver aminotransferase levels in serum, the lipid content and inflammatory cytokine levels in liver tissue, and the extent of hepatic steatosis in db/db mice were increased compared with those in db/m mice, and these increases were reversed by MCL treatment. Similarly, MCL also attenuated the inflammatory responses and lipid accumulation in LM-treated AML12 and L02 cells by upregulating PPAR-gamma and decreasing p-Ismall ka, CyrillicBalpha and p-NF-kappaB/p65, thereby inhibiting the NF-kappaB pathway and reducing lipotoxicity. Furthermore, MCL administration increased LC3B, Atg7 and Beclin-1 expression and the LC3B-II/I ratio in db/db mouse livers and LM-treated AML12 and L02 cells, and these MCL-induced increases were mediated by the activation of PPAR-gamma and p-AMPK and inhibition of p-mTOR and induce autophagy. These effects were blocked by PPAR-gamma and AMPK inhibitors. Our findings suggest that MCL ameliorates liver steatosis by upregulating PPAR-gamma expression, thereby inhibiting NF-kappaB-mediated inflammation and activating AMPK/mTOR-dependent autophagy.
MCL Plays an Anti-Inflammatory Role in Mycobacterium tuberculosis-Induced Immune Response by Inhibiting NF-kappaB and NLRP3 Inflammasome Activation.[Pubmed:28642632]
Mediators Inflamm. 2017;2017:2432904.
Mycobacterium tuberculosis (Mtb) remains a significant menace to global health as it induces granulomatous lung lesions and systemic inflammatory responses during active tuberculosis (TB). Micheliolide (MCL), a sesquiterpene lactone, was recently reported to have a function of relieving LPS-induced inflammatory response, but the regulative role of MCL on the immunopathology of TB still remains unknown. In this experiment, we examined the inhibitory effect of MCL on Mtb-induced inflammatory response in mouse macrophage-like cell line Raw264.7 by downregulating the activation of nuclear factor kappa B (NF-kappaB) and NLRP3 inflammasome. Evidences showed that MCL decreased the secretion of Mtb-induced inflammatory cytokines (IL-1beta and TNF-alpha) in a dose-dependent manner. Meanwhile, MCL dramatically suppressed Mtb-induced activation of iNOS and COX2 as well as subsequent production of NO. Furthermore, MCL inhibited Mtb-induced phosphorylation of Akt (Ser 473) in Raw264.7. According to our results, MCL plays an important role in modulating Mtb-induced inflammatory response through PI3K/Akt/NF-kappaB pathway and subsequently downregulating the activation of NLRP3 inflammasome. Therefore, MCL may represent as a potential drug candidate in the adjuvant treatment of TB by regulating host immune response.
Sesquiterpene lactones and their derivatives inhibit high glucose-induced NF-kappaB activation and MCP-1 and TGF-beta1 expression in rat mesangial cells.[Pubmed:24152676]
Molecules. 2013 Oct 21;18(10):13061-77.
Diabetic nephropathy (DN) is one of the most common and serious chronic complications of diabetes mellitus, however, no efficient clinical drugs exist for the treatment of DN. We selected and synthesized several sesquiterpene lactones (SLs), and then used the MTT assay to detect rat mesangial cells (MCs) proliferation, ELISA to measure the expression level of monocyte chemoattractant protein-1 (MCP-1), transforming growth factor beta (TGF-beta1) and fibronectin(FN), real-time fluorescent quantitative PCR analysis to measure the MCP-1 and TGF-beta1 gene expression, western blot to detect the level of IkappaBalpha protein and EMSA to measure the activation of nuclear factor kappa B (NF-kappaB). We discovered that SLs, including parthenolide (PTL), Micheliolide (MCL), arglabin, and isoalantolactone (IAL), as well as several synthetic analogs of these molecules, could effectively attenuate the high glucose-stimulated activation of NF-kappaB, the degradation of IkappaBalpha, and the expression of MCP-1, TGF-beta1 and FN in rat mesangial cells (MCs). These findings suggest that SLs and their derivatives have potential as candidate drugs for the treatment of DN.