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| Targets |
Tokinolide B targets the orphan nuclear receptor Nur77 (also known as NR4A1), a transcription factor involved in the regulation of inflammation, apoptosis, and cell proliferation. Among 27 phthalide compounds isolated from A. sinensis, Tokinolide B showed the best Nur77 binding capacity and the best anti-inflammatory activity, which was induced without apoptosis. The compound modulates NF-κB and MAPK signaling pathways to suppress inflammation.
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| ln Vitro |
In vitro, Tokinolide B exhibits significant anti-inflammatory activity by binding to Nur77, demonstrating the best Nur77 binding capacity among 27 phthalide compounds tested. It inhibits nitric oxide and pro-inflammatory cytokine production by modulating NF-κB and MAPK signaling pathways. The compound shows antimicrobial and cytoprotective properties without inducing apoptosis. Its anti-inflammatory effects are mediated through Nur77-dependent mechanisms, making it a unique natural anti-inflammatory agent.
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| ln Vivo |
In vivo, Tokinolide B has been studied for its anti-inflammatory effects, demonstrating the ability to suppress inflammation and oxidative stress. The compound is isolated from Angelica sinensis, a plant used in traditional Chinese medicine, and contributes to the anti-inflammatory properties of the herb. Its in vivo activity is associated with modulation of immune responses and reduction of inflammatory markers. The compound shows potential for treating inflammatory conditions.
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| Enzyme Assay |
For non-cell enzyme/receptor binding assays, Tokinolide B binding to Nur77 is assessed using surface plasmon resonance (SPR) or fluorescence polarization assays. The compound is incubated with recombinant Nur77 protein or Nur77 ligand-binding domain, and binding affinity is measured. Competition binding assays using labeled Nur77 ligands can also be employed to determine the binding affinity and specificity. The compound's ability to modulate Nur77 transcriptional activity can be assessed in cell-free transcription assays.
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| Cell Assay |
For in vitro cell-based assays, Tokinolide B activity is assessed in macrophage or immune cell cultures. Cells are treated with the compound, and pro-inflammatory cytokine production (e.g., TNF-α, IL-6, IL-1β) is measured by ELISA. Nitric oxide production is assessed using the Griess assay. NF-κB and MAPK pathway activation is evaluated by Western blotting for phosphorylated proteins. Cell viability is assessed to ensure the anti-inflammatory effects are not due to cytotoxicity.
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| Animal Protocol |
For in vivo animal experiments, Tokinolide B can be administered orally or intraperitoneally to rodent models of inflammation. Inflammatory markers in blood and tissues are measured following compound administration. Carrageenan-induced paw edema or other inflammation models can be used to assess anti-inflammatory efficacy. The compound's effects on cytokine levels in serum and tissue homogenates are evaluated. Dose-response studies are conducted to determine the optimal therapeutic dose.
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| ADME/Pharmacokinetics |
Tokinolide B has a molecular weight of 380.48 g/mol and molecular formula C₂₄H₂₈O₄. It is a phthalide dimer with complex stereochemistry. The compound appears as a solid and should be stored at 2-8°C for up to 24 months when kept tightly sealed, or at -20°C for long-term storage. It is a natural product isolated from plant sources with purity of ≥98% available for research purposes.
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| Toxicity/Toxicokinetics |
Tokinolide B is considered a natural compound with low toxicity based on its traditional use in herbal medicine. No significant toxicity has been reported at therapeutic concentrations. The compound is for research use only and is not approved for human therapeutic use. Standard safety precautions for handling natural products should be followed. The compound's safety profile in humans has not been fully established through clinical trials.
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| References | |
| Additional Infomation |
Tokinolide B has been reported to be found in ligusticum, angelica, and other organisms with available data.
Tokinolide B is a naturally occurring phthalide dimer found in Angelica sinensis and Ligusticum porteri, plants used in traditional Chinese medicine. It is the most potent anti-inflammatory phthalide among 27 compounds isolated from these plants, acting through Nur77 binding. The compound has been studied for its potential in treating inflammation-related diseases without inducing apoptosis. No clinical trials have been conducted for this compound as a therapeutic agent. It is available for research purposes only. |
| Molecular Formula |
C24H28O4
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|---|---|
| Molecular Weight |
380.4767
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| Exact Mass |
380.198
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| CAS # |
112966-16-2
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| PubChem CID |
11090206
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
644.2±55.0 °C at 760 mmHg
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| Flash Point |
338.5±29.9 °C
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| Vapour Pressure |
0.0±1.9 mmHg at 25°C
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| Index of Refraction |
1.597
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| LogP |
5.22
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
28
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| Complexity |
873
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| Defined Atom Stereocenter Count |
4
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| SMILES |
CCC/C=C\1/[C@]23CC[C@H](C=C2C(=O)O1)[C@H]([C@]34C5=C(C=CCC5)C(=O)O4)CCC
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| InChi Key |
DZMFTLLDUYBHLI-MUSNRYMWSA-N
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| InChi Code |
InChI=1S/C24H28O4/c1-3-5-11-20-23-13-12-15(14-19(23)22(26)27-20)17(8-4-2)24(23)18-10-7-6-9-16(18)21(25)28-24/h6,9,11,14-15,17H,3-5,7-8,10,12-13H2,1-2H3/b20-11-/t15-,17-,23+,24+/m1/s1
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| Chemical Name |
(1S,2Z,7R,8R,9S)-2-butylidene-8-propylspiro[3-oxatricyclo[5.2.2.01,5]undec-5-ene-9,3'-4,5-dihydro-2-benzofuran]-1',4-dione
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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 : ~100 mg/mL (~262.83 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.57 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 (6.57 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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 (6.57 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 | 2.6283 mL | 13.1413 mL | 26.2826 mL | |
| 5 mM | 0.5257 mL | 2.6283 mL | 5.2565 mL | |
| 10 mM | 0.2628 mL | 1.3141 mL | 2.6283 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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