Cynaropicrin
(Synonyms: 菜蓟苦素) 目录号 : GC33330
A sesquiterpene lactone
Cas No.:35730-78-0
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
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Cell experiment: |
Human U937 cells are cultured in RPMI1640 supplemented with 10% fetal bovine serum. To differentiate U937 cells, 2×106 cells/mL are treated with phorbol 12-myristate 13-acetate (PMA) of 20 ng/mL for 24 h. The PMA is removed by washing and adherent cells are then allowed to recuperate for 40 h. The recuperated cells are subsequently incubated with lipopolysaccharide of 1 μg/mL for 6 h with Cynaropicrin and positive control drugs. Supernatants are harvested and assayed by ELISA kit for human TNF-α[1]. |
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Animal experiment: |
Male Swiss mice are used in this study. Mice are housed at a maximum of 8 per cage and kept in a conventional room at 20 to 24°C under a 12 h to 12 h light-dark cycle. The animals are provided with sterilized water and chow ad libitum. Infection is performed by i.p. injection of 104 or 5×103 bloodstream trypomastigotes. The animals (18 to 21 g) are divided into the following groups (at least five mice per group): uninfected (noninfected and untreated), untreated (infected with T. cruzi but treated only with vehicle), and treated (infected and treated i.p. with 0.5 to 50 mg/kg/day compound (including Cynaropicrin) or 100 mg/kg/day benznidazole). Mice receive 0.1 mL (i.p.) at 5 and 8 days postinfection (dpi), or at 11, 12, and 13 dpi for the dose of 25 mg/kg, twice a day (b.i.d.)[3]. |
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References: [1]. Cho JY, et al. In vitro anti-inflammatory effects of cynaropicrin, a sesquiterpene lactone, from Saussurea lappa. Eur J Pharmacol. 2000 Jun 23;398(3):399-407. |
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Cynaropicrin is a sesquiterpene lactone originally isolated from artichoke (C. scolymus) that has diverse biological activities.1,2,3,4,5 It inhibits the growth of SKOV3, LOX-IMVI, A549, MCF-7, HCT15, and PC-3 cancer cells (IC50s = 1.1-8.7 μg/ml).1 Cynaropicrin inhibits hepatitis C virus (HCV) replication in Huh7.5 cells with EC50 values ranging from 0.4 to 1.4 μM for genotypes 1a, 1b, 2b, 3a, 4a, 5a, 6a, and 7a.2 It inhibits release of TNF-α and nitric oxide (NO) from LPS-stimulated RAW264.7 cells (IC50s = 8.24 and 1.1 μM, respectively) as well as LPS-induced lymphocyte proliferation (IC50 = 0.9 μM).3 Cynaropicrin inhibits the growth of T. cruzi bloodstream trypomastigotes isolated from infected mice (EC50 = 1 μg/ml).4 It also exhibits antifeedant activity against S. granarius beetles, T. confusum larvae, and T. granarium larvae.5
1.Elsebai, M.F., Mocan, A., and Atanasov, A.G.Cynaropicrin: A comprehensive research review and therapeutic potential as an anti-hepatitis C virus agentFront. Pharmacol.7:472(2016) 2.Elsebai, M.F., Koutsoudakis, G., Saludes, V., et al.Pan-genotypic hepatitis C virus inhibition by natural products derived from the wild egyptian artichokeJ. Virol.90(4)1918-1930(2015) 3.Cho, J.Y., Baik, K.U., Jung, J.H., et al.In vitro anti-inflammatory effects of cynaropicrin, a sesquiterpene lactone, from Saussurea lappaEur. J. Pharmacol.398(3)399-407(2000) 4.da Silva, C.F., Batista Dda, G., De Araújo, J.S., et al.Activities of psilostachyin A and cynaropicrin against Trypanosoma cruzi in vitro and in vivoAntimicrob. Agents Chemother.57(11)5307-5314(2013) 5.Cis, J., Nowark, G., and Kisiel, W.Antifeedant properties and chemotaxonomic implications of sesquiterpene lactones and syringin from Rhaponticum pulchrumBiochem. System. Ecol.34(12)862-867(2006)
| Cas No. | 35730-78-0 | SDF | |
| 别名 | 菜蓟苦素 | ||
| Canonical SMILES | C=C([C@H]1O)[C@]([C@@]2([H])C1)([H])[C@](OC3=O)([H])[C@@](C3=C)([H])[C@@H](OC(C(CO)=C)=O)CC2=C | ||
| 分子式 | C19H22O6 | 分子量 | 346.37 |
| 溶解度 | DMSO: ≥ 50 mg/mL (144.35 mM) | 储存条件 | -20°C, protect from light |
| 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 | 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 |
| 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。
Cynaropicrin: A Comprehensive Research Review and Therapeutic Potential As an Anti-Hepatitis C Virus Agent
Front Pharmacol 2016 Dec 8;7:472.PMID:28008316DOI:10.3389/fphar.2016.00472.
The different pharmacologic properties of plants-containing Cynaropicrin, especially artichokes, have been known for many centuries. More recently, Cynaropicrin exhibited a potential activity against all genotypes of hepatitis C virus (HCV). Cynaropicrin has also shown a wide range of other pharmacologic properties such as anti-hyperlipidemic, anti-trypanosomal, anti-malarial, antifeedant, antispasmodic, anti-photoaging, and anti-tumor action, as well as activation of bitter sensory receptors, and anti-inflammatory properties (e.g., associated with the suppression of the key pro-inflammatory NF-κB pathway). These pharmacological effects are very supportive factors to its outstanding activity against HCV. Structurally, Cynaropicrin might be considered as a potential drug candidate, since it has no violations for the rule of five and its water-solubility could allow formulation as therapeutic injections. Moreover, Cynaropicrin is a small molecule that can be easily synthesized and as the major constituent of the edible plant artichoke, which has a history of safe dietary use. In summary, Cynaropicrin is a promising bioactive natural product that, with minor hit-to-lead optimization, might be developed as a drug for HCV.
Synthesis of cynaropicrin-d(4)
Bioorg Med Chem Lett 2015 Dec 1;25(23):5504-7.PMID:26520660DOI:10.1016/j.bmcl.2015.10.065.
Cynaropicrin is a guaianolide sesquiterpene lactone, which has potent in vitro and in vivo inhibitory activity against Trypanosoma brucei, the protozoan parasite that causes human African trypanosomiasis (HAT; sleeping sickness). Herein, we describe the synthesis of Cynaropicrin's deuterated derivative, cynaropicrin-d4, by the replacement of the side chain of natural Cynaropicrin. The synthesized cynaropicrin-d4 could be employed as an internal standard for liquid chromatography-mass spectrometry (LC-MS) analysis, in the pharmacokinetic study of Cynaropicrin. This could potentially advance the study of this therapeutic lead.
Total synthesis of Cynaropicrin
Org Biomol Chem 2021 Jul 21;19(27):6038-6044.PMID:33982042DOI:10.1039/d1ob00657f.
Cynaropicrin is found in artichoke (Cynara scolymus) and is the source of its bitter taste and it is a sesquiterpene lactone with a 5-7-5 tricyclic skeleton, six chiral centers, and four exo-olefins. This natural product has numerous attractive biological activities including the inhibition of NF-κB activation, antihepatitis C activity, and antitrypanosomal activity. In this study, the first total synthesis of Cynaropicrin was achieved starting from (S)-α-pinene. The synthesis involved a stereoselective Favorskii rearrangement and an indium-promoted diastereoselective Barbier reaction.
Cynaropicrin Averts the Oxidative Stress and Neuroinflammation in Ischemic/Reperfusion Injury Through the Modulation of NF-kB
Appl Biochem Biotechnol 2022 Jul 15.PMID:35838888DOI:10.1007/s12010-022-04060-x.
Cerebral ischemia and successive reperfusion are the prevailing cause of cerebral stroke. Currently cerebral stroke is considered to be one of the prior causes for high mortality, disability, and morbidity. Cynaropicrin, a sesquiterpene lactone, exhibits various pharmacologic properties and also has an anti-inflammatory property associated with the suppression of the key pro-inflammatory NF-κB pathway. The protective effect of Cynaropicrin against oxidative stress and neuroinflammation during CIR injury through the modulation of NF-κB pathway was studied in the current investigation. The experimental rats split into 5 groups as sham-operated control group (group 1), middle cerebral artery occlusion (MCAO)-induced rats (group 2), MCAO rats treated with Cynaropicrin (diluted in saline) immediately 2 h after MCAO with 5, 10, and 25 mg/kg administration orally were designated as groups 3, 4, and 5, respectively. In MCAO-induced animals, the severity of ischemic was evident by the elevated level nitrate, MDA, MMPs, inflammatory mediators, Bax, caspase-3, and NF-κB. The level of Nrf-2, antioxidant enzymes, Bcl-2, and IL-10 was reduced in the MCAO-induced animals. Treatment with Cynaropicrin in dosage-based manner increased the level of antioxidant enzymes, IL-10, Nrf-2, and Bcl-2 in the animals which indicates the antioxidative effect of Cynaropicrin. The level of nitrate, MDA, MMPs, proinflammatory cytokines, inflammatory mediators, Bax, caspase-3, and NF-κB was reduced in the rats treated with Cynaropicrin in a dosage-based manner. Experimental animals treated with Cynaropicrin in a dosage-dependent way showed a defensive mechanism against oxidative stress and neuroinflammation by inhibiting the NF-κB pathway.
Extraction and recovery processes for Cynaropicrin from Cynara cardunculus L. using aqueous solutions of surface-active ionic liquids
Biophys Rev 2018 Jun;10(3):915-925.PMID:29294260DOI:10.1007/s12551-017-0387-y.
Due to the wide range of relevant biological activities and high commercial value of Cynaropicrin, and aiming at developing cost-effective processes, aqueous solutions of ionic liquids (ILs) were investigated for the extraction and recovery of Cynaropicrin from the leaves of Cynara cardunculus L. Both cationic (1-alkyl-3-methylimidazolium chloride) and anionic (cholinium carboxylate) surface-active ILs were investigated, as well as a wide range of conventional surfactants and molecular organic solvents, allowing us to conclude that aqueous solutions of cationic surface-active ILs display a better performance for the extraction of Cynaropicrin. Operational conditions were optimized, leading to a Cynaropicrin extraction yield of 3.73 wt%. The recycling of both the biomass and the solvent were further investigated to appraise the extraction media saturation and to achieve a higher Cynaropicrin extraction yield (6.47 wt%). Finally, it was demonstrated that 65 wt% of the extracted Cynaropicrin can be efficiently recovered by precipitation from the IL aqueous extract through the addition of water as anti-solvent, allowing us to put forward both the extraction and recovery processes of the target value-added compound from biomass followed by solvent recycling. This approach opens the door to the development of more sustainable processes using aqueous solutions of ILs instead of the volatile organic solvents commonly used in biomass processing.