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Murrayone, a coumarin class of natural product extracted from M. paniculata, isthe most bioactive substance in this species and is a cancer metastasischemopreventive agent based on its unique pharmacological properties.
| Animal Protocol |
- For the pharmacokinetic study: Sprague-Dawley rats (twelve males and twelve females) were randomly divided into four groups. Three groups received murrayone by intragastric administration at doses of 20, 50, and 125 mg/kg, respectively. The last group received murrayone by intravenous bolus injection at 20 mg/kg. Blood samples (approximately 0.2 mL) were collected from the ocular vein into heparinized tubes prior to dosing and at 0.1667, 0.5, 0.75, 1.0, 2.0, 4.0, 6.0, 8.0, 12, and 24 hours post-dosing. After centrifuging whole blood at 4000×g for 10 minutes, the plasma was immediately separated and stored at −80°C until analysis. [1]
- Animals were housed under standard conditions of temperature and humidity, specific pathogen-free, with access to water and food ad libitum for at least one week before the experiment. Before administration, animals were fasted overnight with free access to water. The pharmacokinetic study was approved by the local Ethics Committee of Fuzhou University. [1] |
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| ADME/Pharmacokinetics |
- After intragastric administration at 20, 50, and 125 mg/kg, the mean Tmax values ranged from 0.75 h to 1 h, indicating rapid absorption. [1]
- The mean elimination half-life (t1/2) after oral doses ranged from approximately 5.01 to 5.97 h, and after intravenous administration (20 mg/kg) t1/2 was 3.52 ± 1.22 h, suggesting rapid elimination. [1] - The absolute bioavailability (F) of murrayone in rats was approximately 37.81% at 20 mg/kg, 22.72% at 50 mg/kg, and 23.63% at 125 mg/kg (intragastric vs. intravenous 20 mg/kg). [1] - The apparent volume of distribution (Vd/F) was 293.4 ± 170.5 L/kg (20 mg/kg, i.g.), 855.6 ± 390.6 L/kg (50 mg/kg, i.g.), and 729.5 ± 264.6 L/kg (125 mg/kg, i.g.), indicating wide tissue distribution. [1] - Clearance (Cl/F) values were 39.58 ± 12.75 L/h/kg (20 mg/kg, i.g.), 102.0 ± 19.39 L/h/kg (50 mg/kg, i.g.), and 93.58 ± 23.05 L/h/kg (125 mg/kg, i.g.). Intravenous clearance (Cl) at 20 mg/kg was 5.469 ± 0.983 L/h/kg. [1] - The mean residence time (MRT) after oral administration ranged from 5.12 to 6.35 h, and after intravenous administration was 3.84 ± 0.340 h. [1] - The area under the curve (AUC0-∞) after oral doses: 1.464 ± 0.489 h·μg/mL (20 mg/kg), 2.231 ± 0.474 h·μg/mL (50 mg/kg), 5.933 ± 1.405 h·μg/mL (125 mg/kg); after intravenous 20 mg/kg: 3.761 ± 0.695 h·μg/mL. [1] - The exposure level (Cmax and AUC) was positively related to the administered dose (correlation coefficients r² = 0.8195 for Cmax vs. dose, and 0.8571 for AUC vs. dose). [1] |
| References | |
| Additional Infomation |
It has been reported that Murrayone is present in Murraya paniculata and Murraya exotica, and there is relevant data on this.
- Murrayone is a coumarin extracted from the traditional Chinese medicine Murraya paniculata (L.), which is documented in the Chinese Pharmacopoeia (2015 Edition) and has properties of abortion, anti-inflammation, anticoagulation, antimicrobial, and anticancer. [1] - The authors’ laboratory successfully extracted and isolated murrayone with a purity of >95%. [1] - The developed UPLC/MS/MS method had a lower limit of quantitation (LLOQ) of 4.0 ng/mL for murrayone in rat plasma, with good linearity (r²=0.9987) over a range of 4.0–1600 ng/mL. The average absolute recoveries were 85.9–92.4% at three QC levels. [1] - Murrayone was stable under various storage and processing conditions (short-term at ambient temperature for 4 h, long-term at −20°C for 30 days, three freeze-thaw cycles, and post-preparative at 4°C for 24 h). [1] |
| Molecular Formula |
C15H14O4
|
|---|---|
| Molecular Weight |
258.2693
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| Exact Mass |
258.089
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| Elemental Analysis |
C, 69.76; H, 5.46; O, 24.78
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| CAS # |
19668-69-0
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| PubChem CID |
5319964
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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 |
452.8±45.0 °C at 760 mmHg
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| Melting Point |
130℃
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| Flash Point |
203.4±28.8 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.558
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| LogP |
1.93
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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
|
| Heavy Atom Count |
19
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| Complexity |
424
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O1C(C([H])=C([H])C2C([H])=C([H])C(=C(C([H])([H])C(C(=C([H])[H])C([H])([H])[H])=O)C1=2)OC([H])([H])[H])=O
|
| InChi Key |
IISMOXLSZASLDD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H14O4/c1-9(2)12(16)8-11-13(18-3)6-4-10-5-7-14(17)19-15(10)11/h4-7H,1,8H2,2-3H3
|
| Chemical Name |
7-methoxy-8-(3-methyl-2-oxobut-3-enyl)chromen-2-one
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| Synonyms |
Murrayone
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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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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 (~193.60 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.68 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.8719 mL | 19.3596 mL | 38.7192 mL | |
| 5 mM | 0.7744 mL | 3.8719 mL | 7.7438 mL | |
| 10 mM | 0.3872 mL | 1.9360 mL | 3.8719 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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