| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| Targets |
Cynaropicrin exerts its biological effects primarily through the inhibition of the NF-κB signaling pathway, which plays a central role in inflammation and immune responses. It also activates the Nrf2 pathway, leading to the upregulation of antioxidant and cytoprotective enzymes. Additionally, cynaropicrin has been shown to inhibit the production of pro-inflammatory cytokines such as TNF-α, IL-1β, and IL-6, and to modulate the activity of various enzymes involved in lipid metabolism, including HMG-CoA reductase.
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| ln Vitro |
Cynaropicrin, with IC50 values of 8.24 and 3.18 μM, respectively, potently suppresses lipopolysaccharide-induced TNF-α production from human or murine macrophages in a dose-dependent manner. Cynaropicrin exhibited noteworthy suppression of all mitogenic signals, with IC50 values of 0.90 μM for lipopolysaccharide, 1.02 for phytohemagglutinin, and 1.20 for concanavalin A. The growth of CTLL-2 cells is inhibited by Cynaropicrin in a dose-dependent manner; its 50% inhibitory concentration (IC50) on CTLL-2 cell growth is 0.91 μM [1]. Cynaropicrin also suppressed the TNF-α-induced rise in MMP13 mRNA expression in a concentration-dependent manner. Cynaropicrin reduced the IL-1β-induced rise in HIF-2α mRNA expression in SW1353 in a concentration-dependent manner [2].
Cynaropicrin exhibits potent in vitro anti-inflammatory activity by suppressing the production of pro-inflammatory cytokines and chemokines in various cell types, including macrophages and immune cells. It has been shown to inhibit the activation of NF-κB and MAPK signaling pathways. The compound also demonstrates antioxidant activity by scavenging free radicals and upregulating antioxidant enzymes. In cancer cell lines, cynaropicrin has shown cytotoxic and anti-proliferative effects, inducing cell cycle arrest and apoptosis. |
| ln Vivo |
Cynaropicrin has demonstrated in vivo anti-inflammatory and hepatoprotective effects in animal models. In models of acute and chronic inflammation, cynaropicrin has been shown to reduce edema, inflammatory cell infiltration, and tissue damage. In models of liver injury, the compound has demonstrated hepatoprotective effects by reducing oxidative stress and inflammation. It has also shown anti-hyperlipidemic effects in animal models of hyperlipidemia. The compound's in vivo effects are consistent with its in vitro activities.
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| Enzyme Assay |
Cynaropicrin's activity can be assessed using in vitro enzyme/receptor binding assays. Its ability to inhibit NF-κB activation can be evaluated using reporter gene assays or by measuring the DNA-binding activity of NF-κB using electrophoretic mobility shift assays (EMSA). The compound's antioxidant activity can be assessed using standard assays such as DPPH radical scavenging, ABTS radical scavenging, and FRAP assays. Its ability to inhibit HMG-CoA reductase can be evaluated using enzyme activity assays.
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| Cell Assay |
Cellular assays for cynaropicrin typically involve treating various cell types with the compound and measuring inflammatory cytokine production, NF-κB activation, and oxidative stress markers. In macrophages, the compound's ability to inhibit LPS-induced TNF-α, IL-1β, and IL-6 production can be assessed using ELISA. In cancer cell lines, cell viability, proliferation, and apoptosis can be evaluated using MTT assays, flow cytometry, and Western blotting for apoptosis-related proteins.
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| Animal Protocol |
In vivo animal model protocols for cynaropicrin involve its administration (typically oral or intraperitoneal) to animal models of disease. In models of inflammation (e.g., carrageenan-induced paw edema, cotton pellet granuloma), the compound's anti-inflammatory effects are assessed by measuring edema, granuloma formation, and inflammatory markers. In models of liver injury (e.g., CCl4-induced hepatotoxicity), liver enzyme levels, oxidative stress markers, and histopathology are evaluated. In models of hyperlipidemia, serum lipid profiles are measured.
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| ADME/Pharmacokinetics |
Cynaropicrin is a natural product with limited pharmacokinetic data available. As a sesquiterpene lactone, it is expected to be absorbed after oral administration, but its bioavailability may be limited due to first-pass metabolism and poor aqueous solubility. The compound is metabolized in the liver and excreted primarily in the bile and urine. Further pharmacokinetic studies are needed to fully characterize its absorption, distribution, metabolism, and excretion.
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| Toxicity/Toxicokinetics |
The toxicological profile of cynaropicrin has not been extensively studied. As a natural product from artichoke, which has a long history of safe use as a food and herbal medicine, cynaropicrin is generally considered to have a favorable safety profile. However, high doses may cause gastrointestinal disturbances and allergic reactions in susceptible individuals. Comprehensive toxicology studies are needed for clinical development.
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| References |
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| Additional Infomation |
Cynaropicrin is a sesquiterpene lactone. It has been reported to be found in Saussurea costus, Artemisia scoparia, and other organisms with relevant data. See also: Artemisia leaf (partial).
Cynaropicrin (CAS# 35730-78-0) is a natural sesquiterpene lactone isolated from artichoke (Cynara scolymus) leaves. It is one of the major bioactive constituents responsible for the bitter taste and pharmacological properties of artichoke. Cynaropicrin exhibits a wide range of biological activities, including anti-inflammatory, antioxidant, anti-tumor, anti-hyperlipidemic, and hepatoprotective effects. It exerts its effects primarily through the inhibition of the NF-κB pathway and activation of the Nrf2 pathway. |
| Molecular Formula |
C19H22O6
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|---|---|
| Molecular Weight |
346.3744
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| Exact Mass |
346.142
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| CAS # |
35730-78-0
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| Related CAS # |
Cynaropicrin; 35730-78-0
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| PubChem CID |
119093
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| Appearance |
Off-white to light yellow ointment
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| Density |
1.28g/cm3
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| Boiling Point |
566.2ºC at 760mmHg
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| Flash Point |
203.8ºC
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| Source |
Originated from plants: Compositae Saussurea costus (Falc.) Lipsch.
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| LogP |
1.057
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
25
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| Complexity |
690
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| Defined Atom Stereocenter Count |
6
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| SMILES |
O1C(C(=C([H])[H])[C@]2([H])[C@]([H])(C([H])([H])C(=C([H])[H])[C@]3([H])C([H])([H])[C@@]([H])(C(=C([H])[H])[C@]3([H])[C@@]12[H])O[H])OC(C(=C([H])[H])C([H])([H])O[H])=O)=O
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| InChi Key |
KHSCYOFDKADJDJ-NQLMQOPMSA-N
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| InChi Code |
InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1
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| Chemical Name |
[(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 50 mg/mL (~144.35 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.22 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.22 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.22 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8871 mL | 14.4354 mL | 28.8709 mL | |
| 5 mM | 0.5774 mL | 2.8871 mL | 5.7742 mL | |
| 10 mM | 0.2887 mL | 1.4435 mL | 2.8871 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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