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Purity: ≥98%
(+)-Praeruptorin A [(9S,10S) isomer] is a naturally occurring coumarin derivative isolated from P. praeruptorum (a Chinese herbal medicine) with potential anticancer and anti-inflammatory effects. It downregulated IL-1β and TNF-α in LPS-induced cells.
| Targets |
Natural product; anti-inflammatory; NF-κB
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|---|---|
| ln Vitro |
Praeruptorin A and praeruptorin C, racemic to each other, are main bioactive constituents of the species Peucedanum praeruptorum, traditionally used as a Chinese herbal medicine (also known as Bai-Hua Qian Hu). In the present study, the ability of praeruptorins A and C to activate the constitutive androstane receptor and induce human multidrug resistance-associated protein 2 expressions in HepG2 cells was investigated. The changes in mRNA level, protein expression, and transport activity of multidrug resistance-associated protein 2 were determined by quantitative real-time PCR, Western blot, and the CDF uptake assay, respectively. The effects of constitutive androstane receptor knockdown on multidrug resistance-associated protein 2 mRNA and protein expression were also measured by transient transfection of a specific constitutive androstane receptor siRNA. The results showed that praeruptorin A and praeruptorin C significantly induced the multidrug resistance-associated protein 2 mRNA and protein expression, and enhanced the transport activity of multidrug resistance-associated protein 2. A further study showed that mRNA and protein upregulation were attenuated by transient transfection of a specific constitutive androstane receptor siRNA, suggesting that the upregulation of multidrug resistance-associated protein 2 was mediated by the constitutive androstane receptor. Taken together, our findings indicate that praeruptorin A and praeruptorin C can significantly upregulate multidrug resistance-associated protein 2 expression via the constitutive androstane receptor-mediated pathway in vitro, and this should be taken as an herb-drug interaction[1].
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| References | |
| Additional Infomation |
Praeruptorin A is a member of coumarins.
(+)-Praeruptorin A has been reported in Peucedanum japonicum, Prionosciadium thapsoides, and Ligusticum lucidum with data available. |
| Molecular Formula |
C21H22O7
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|---|---|
| Molecular Weight |
386.3952
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| Exact Mass |
386.136
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| CAS # |
73069-27-9
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| Related CAS # |
73069-27-9
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| PubChem CID |
38347607
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| Appearance |
White to off-white solid
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
486.8±45.0 °C at 760 mmHg
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| Flash Point |
211.5±28.8 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.574
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| LogP |
4.18
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
28
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| Complexity |
720
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| Defined Atom Stereocenter Count |
2
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| SMILES |
O1C2C([H])=C([H])C3C([H])=C([H])C(=O)OC=3C=2C([H])(C([H])(C1(C([H])([H])[H])C([H])([H])[H])OC(C(=C([H])C([H])([H])[H])C([H])([H])[H])=O)OC(C([H])([H])[H])=O
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| InChi Key |
XGPBRZDOJDLKOT-NXIDYTHLSA-N
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| InChi Code |
InChI=1S/C21H22O7/c1-6-11(2)20(24)27-19-18(25-12(3)22)16-14(28-21(19,4)5)9-7-13-8-10-15(23)26-17(13)16/h6-10,18-19H,1-5H3/b11-6-/t18-,19-/m0/s1
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| Chemical Name |
[(9S,10S)-10-acetyloxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-9-yl] (Z)-2-methylbut-2-enoate
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| Synonyms |
(+)-Praeruptorin A; Praeruptorin A; 73069-27-9; 73069-25-7; (+-)-Praeruptorin A; 2-Butenoic acid, 2-methyl-,(9S,10S)-10-(acetyloxy)-9,10-dihydro-8,8-dimethyl-2-oxo-2H,8H-benzo[1,2-b:3,4-b']dipyran-9-yl ester, (2Z)-; CCRIS 7247; ( inverted exclamation markA)-Praeruptorin A;
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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: ~33.3 mg/mL (~86.3 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.47 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 (6.47 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 (6.47 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 | 2.5880 mL | 12.9400 mL | 25.8799 mL | |
| 5 mM | 0.5176 mL | 2.5880 mL | 5.1760 mL | |
| 10 mM | 0.2588 mL | 1.2940 mL | 2.5880 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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