Okanin
(Synonyms: 奥卡宁) 目录号 : GC36794
Okanin 是 Coreopsis tinctoria 的有效成分。Okanin 通过抑制 TLR4/NF-κB 信号通路减弱 LPS 诱导的小胶质细胞活化。
Cas No.:484-76-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Okanin, effective constituent of the flower tea Coreopsis tinctoria, attenuates LPS-induced microglial activation through inhibition of the TLR4/NF-κB signaling pathways[1]. TLR4 p65
Okanin significantly inhibits LPS-induced TLR4 expression in BV-2 cells. Okanin inhibits the translocation of the NF-κB p65 subunit from the cytosol to the nucleus. Okanin significantly suppresses LPS-induced iNOS expression and also inhibites IL-6 and TNF-α production and mRNA expression in LPS-stimulated BV-2 cells[1].
[1]. Hou Y, et al. Okanin, effective constituent of the flower tea Coreopsis tinctoria, attenuates LPS-induced microglial activation through inhibition of the TLR4/NF-κB signaling pathways. Sci Rep. 2017 Apr 3;7:45705.
| Cas No. | 484-76-4 | SDF | |
| 别名 | 奥卡宁 | ||
| Canonical SMILES | O=C(C1=CC=C(O)C(O)=C1O)/C=C/C2=CC=C(O)C(O)=C2 | ||
| 分子式 | C15H12O6 | 分子量 | 288.25 |
| 溶解度 | Soluble in DMSO | 储存条件 | 4°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 | 3.4692 mL | 17.3461 mL | 34.6921 mL |
| 5 mM | 0.6938 mL | 3.4692 mL | 6.9384 mL |
| 10 mM | 0.3469 mL | 1.7346 mL | 3.4692 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。
Study on the antithrombotic effect and physiological mechanism of Okanin
Biomed Pharmacother 2022 Sep;153:113358.PMID:35785699DOI:10.1016/j.biopha.2022.113358.
The objectives of this study were to investigate the antithrombotic effect and physiological mechanism of Okanin, a flavonoid monomer in Coreopsis tinctoria Nutt. The antithrombotic effects of Okanin were determined by the anticoagulant activity test in vitro and in vivo, the venous thrombosis and arterial thrombosis test in rats. To study the antithrombotic physiological mechanisms of Okanin, UV spectrophotometer and enzyme-linked immunosorbent assay (ELISA) were used to determine the effects of three concentrations of Okanin on the contents of 6-keto-prostaglandin F1α (6-Keto-PGF1α), thromboxane B2 (TXB2), endothelin-1 (ET-1), antithrombin III (AT-Ⅲ), protein C (PC) and von willebrand factor (vWF) in the plasma of rats with arterial thrombosis; ELISA was used to detect the effects of Okanin on the contents of plasminogen (PLG), tissue plasminogen activator (t-PA) and type-1 plasminogen activator inhibitor (PAI-1) in the plasma of mice and Chinese white rabbits. The results showed that Okanin could prolong the coagulation time in vitro and in vivo of animals (P < 0.01 in the high dose group) and the activated partial thromboplastin time (APTT), prothrombin time (PT), and thrombin time (TT) of human venous blood (ATPP of medium dose group P < 0.01; PT, TT P < 0.05. P < 0.01 in the high dose group); inhibit the maximum platelet aggregation rate of rabbits (P < 0.05 in the low dose group; P < 0.01 in the medium and high dose groups), decrease the dry and wet weight of venous thrombosis and the wet weight of common carotid artery thrombosis in rats (low dose group, P < 0.05; medium and high dose groups, P < 0.01); increase the levels of 6-Keto-PGF1α, AT-Ⅲ, PLG and t-PA in animal plasma; decrease the levels of TXB2, ET-1, vWF and PAI-1 in animal plasma. It is concluded that Okanin can significantly inhibit thrombosis, and its physiological mechanisms were related to affecting the activation of related coagulation factors in endogenous and exogenous coagulation pathways, affecting the physiological characteristics of platelets, repairing damaged vascular endothelial cells and enhancing the activity of the fibrinolytic system.
Okanin in Coreopsis tinctoria Nutt is a major quorum-sensing inhibitor against Chromobacterium violaceum
J Ethnopharmacol 2020 Oct 5;260:113017.PMID:32464313DOI:10.1016/j.jep.2020.113017.
Ethnopharmacological relevance: Coreopsis tinctoria Nutt has various medical and functional properties and its flower is widely used as health-care tea to decrease blood glucose and to lower blood lipids. However, the quorum sensing (QS) inhibition activity of Coreopsis tinctoria Nutt flower remains unclear. Aim of the study: To assess inhibitory activity against quorum sensing by Chromobacterium violaceum, to identify the chemical composition of the extracts and to disclose the action mechanism of separated compound. Material and methods: Violacein inhibition assays were performed in 96-wells microplates. The compounds extracted from Coreopsis tinctoria Nutt flower were separated and purified by various chromatography techniques. Respectively, thin layer chromatography (TLC, GF254), mass spectrometer (Agilent 1100 Series LC/MSD Trap SL), Medium-pressure automatic purification system (Buscisepacore C 620, Switzerland), High performance liquid chromatography (HPLC, Shimadzu LC-20AD, Japan), Liquid preparation Chromatography (Waters2545, USA). The chemical structures were identified by nuclear magnetic resonance (NMR, Bruker AV-500, Germany) technique. The inhibitory mechanism of Okanin against C. violaceum quorum sensing was detected by quantitative real-time PCR (qRT-PCR). Results: Quorum sensing regulates production of bacterial virulence factors, thereby making it an intriguing target for attenuating bacterial pathogenicity. In this study, anti-QS activity of Coreopsis tinctoria Nutt methanol fraction (CTM) was investigated against C. violaceum ATCC12472. CTM showed an inhibitory effect on the QS-mediated virulence factors production such as violacein in C. violaceum without effect on growth rate. Also, Okanin was isolated from CTM and its potential of anti-QS was confirmed after observing a significant reduction of violacein production in C. violaceum. An attempt was made to assess the effect of Okanin on vioABCDE expression in C. violaceum to disclose acting mechanisms. Conclusions: The results of this study contribute to validate an inhibitory effect of Coreopsis tinctoria Nutt flower on quorum sensing by Chromobacterium violaceum and to determine the compound responsible for inhibition. Also, the inhibitory effect was achieved in tandem with the down-regulation of vio operon.
Okanin, effective constituent of the flower tea Coreopsis tinctoria, attenuates LPS-induced microglial activation through inhibition of the TLR4/NF-κB signaling pathways
Sci Rep 2017 Apr 3;7:45705.PMID:28367982DOI:10.1038/srep45705.
The EtOAc extract of Coreopsis tinctoria Nutt. significantly inhibited LPS-induced nitric oxide (NO) production, as judged by the Griess reaction, and attenuated the LPS-induced elevation in iNOS, COX-2, IL-1β, IL-6 and TNF-α mRNA levels, as determined by quantitative real-time PCR, when incubated with BV-2 microglial cells. Immunohistochemical results showed that the EtOAc extract significantly decreased the number of Iba-1-positive cells in the hippocampal region of LPS-treated mouse brains. The major effective constituent of the EtOAc extract, Okanin, was further investigated. Okanin significantly suppressed LPS-induced iNOS expression and also inhibited IL-6 and TNF-α production and mRNA expression in LPS-stimulated BV-2 cells. Western blot analysis indicated that Okanin suppressed LPS-induced activation of the NF-κB signaling pathway by inhibiting the phosphorylation of IκBα and decreasing the level of nuclear NF-κB p65 after LPS treatment. Immunofluorescence staining results showed that Okanin inhibited the translocation of the NF-κB p65 subunit from the cytosol to the nucleus. Moreover, Okanin significantly inhibited LPS-induced TLR4 expression in BV-2 cells. In summary, Okanin attenuates LPS-induced activation of microglia. This effect may be associated with its capacity to inhibit the TLR4/NF-κB signaling pathways. These results suggest that Okanin may have potential as a nutritional preventive strategy for neurodegenerative disorders.
Proportional coexistence of Okanin chalcone glycoside and Okanin flavanone glycoside in Bidens pilosa leaves and theoretical investigation on the antioxidant properties of their aglycones
Free Radic Res 2021 Jan;55(1):53-70.PMID:33267705DOI:10.1080/10715762.2020.1859107.
Bidens pilosa plant has been shown to produce Okanin flavanone glycoside and its chalcone derivative. In most other plants, due to chalcone isomerase enzyme, the flavanone tends to exist in higher proportions than their chalcone precursors. Herein we have utilized liquid chromatography-mass spectrometry approach and shown that within the leaves of Bidens pilosa plant the two Okanin glycosides exist in unusual equal proportional distribution, which indicates that Bidens pilosa plant is an alternative rich source of these highly sought-after antioxidant molecules. The aglycone Okanin chalcone (ONC) and Okanin flavanone (ONF) have experimentally been shown to exhibit antioxidant activity. However, experimental findings have not conclusively determined which of the two compounds is a more potent antiradical than the other. Herein, the density functional theory (DFT) method is utilized to establish, from structural and thermodynamic energetic considerations, the preferred antioxidant molecule between the two aglycone okanins. A theoretical study on the antioxidant properties of ONC and ONF has been performed by considering their radical scavenging and metal cation (Mn+, where M = Cu(II) or Fe (III)) chelation ability. The study has been performed using B3LYP/6-31 + G(d,p) method. In the case of the metal chelation mechanism, the LANL2DZ pseudo-potential was selected to describe the selected Mn+ cations. The results of the study suggest that ONC is a better radical scavenger than ONF because of the extended electron delocalization on its neutral radical, which is due to the presence of conjugation within the ONC neutral radical after hydrogen atom abstraction. In the metal chelation mechanism, it is noted that the binding energies depend on the media, the nature of the ligand and the cation and the cation coordination site on the ligand. The charge and the spin density on Mn+ decrease on coordination to the ligand. The ability of the ligands to reduce Mn+ cations, coupled with the strong Mn+ binding properties, has significant implication on the antioxidant ability of both okanins. However, since ONC⋅⋅⋅M+n interaction results in higher binding energy than ONF⋅⋅⋅M+n interaction, the implication is that ONC is a preferred free metal ion chelator than ONF.
Okanin from Coreopsis tinctoria Nutt. alleviates cognitive impairment in bilateral common carotid artery occlusion mice by regulating the miR-7/NLRP3 axis in microglia
Food Funct 2023 Jan 3;14(1):369-387.PMID:36511396DOI:10.1039/d2fo01476a.
Cognitive impairment is the main clinical feature following stroke, and microglia-mediated inflammatory response is a major contributor to it. Coreopsis tinctoria Nutt., an edible chrysanthemum, is commonly used as a functional ingredient in healthcare beverages and food. Okanin, the main active ingredient of Coreopsis tinctoria Nutt. flower, inhibits microglial activation. However, the role of Okanin in cognitive impairment following ischemic stroke is still unknown. In this study, we investigated the effect of Okanin on ischemic stroke and its underlying mechanism both in vivo and in vitro. Okanin was found to attenuate cognitive impairment in bilateral common carotid artery occlusion (BCCAO) mice, inhibit neuronal loss and microglial activation, decrease NOD-like receptor family pyrin domain containing 3 (NLRP3) inflammasome activation, and increase miR-7 expression. Okanin suppressed NLRP3 inflammasome activation in oxygen-glucose deprivation (OGD) and lipopolysaccharide (LPS)-stimulated microglia by increasing miR-7 expression and inhibited microglia-induced neuronal injury. This study provides new insights into the role of Okanin in ischemic stroke and shows that the miR-7/NLRP3 axis plays an important role in mediating the beneficial effects of Okanin on cerebral ischemia. These findings suggest that Okanin has great potential as a functional food for stroke recovery.