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    Isoimperatorin
    Information
    CAS No. 482-45-1 Price $40 / 20mg
    Catalog No.CFN99107Purity>=98%
    Molecular Weight270.28Type of CompoundCoumarins
    FormulaC16H14O4Physical DescriptionPowder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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    Biological Activity
    Description: Isoimperatorin has analgesic, hepatoprotective, antimicrobial, anti-inflammatory, vascular relaxing and anticancer activities. It inhibited the expression of COX, TNF-α, PPAR-γ,ERK1/2, PI3K, and PKC. It showed significant inhibitory effects on acetylcholinesterase (AChE) with the IC50 of 74.6 uM, it also showed different inhibitory effects on all of the six CYP isoenzymes(human CYP1A2, 2B6, 2C9, 2C19, 2D6 and 3A4 enzymes).
    Targets: P450 (e.g. CYP17) | Nrf2 | COX | TNF-α | ERK | Akt | PI3K | PKC | PPAR | AChR
    In vitro:
    Lett Appl Microbiol. 2014 Apr;58(4):344-9.
    In vitro activity of isoimperatorin, alone and in combination, against Mycobacterium tuberculosis.[Pubmed: 24330002]
    Previous studies have shown that Isoimperatorin (IO), a furanocoumarin isolated from several medicinal plants, has antimycobacterial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294).
    METHODS AND RESULTS:
    This study demonstrated that IO has antimycobacterial activity against 2 drug-sensitive and 6 drug-resistant isolates, with minimum inhibitory concentrations (MICs) of 50-100 μg ml(-1) and 100-200 μg ml(-1), respectively. IO exhibited synergistic antimycobacterial effects with rifampin (RMP), isoniazid (INH) and ethambutol (EMB) against 6 drug-resistant strains, with fractional inhibitory concentration index (FICI) values of 0·133-0·472, 0·123-0·475 and 0·124-0·25, respectively. The IO/RMP, IO/INH and IO/EMB combination treatments had synergistic effects or no interaction in the 2 drug-sensitive strains and the standard strain ATCC 27294. The synergism of combined drugs against drug-resistant strains was better than drug-sensitive strains. No antagonism was observed in with the aforementioned combinations against all strains tested. IO exhibited relatively low cytotoxicity to Vero cells. Our results indicate that IO may serve as promising a template for future antimycobacterial drug development.
    CONCLUSIONS:
    This is the first report on the in vitro synergistic antimycobacterial effects of Isoimperatorin (IO) in combination with three first-line drugs: rifampin (RMP), isoniazid (INH) and ethambutol (EMB). The results indicated that the antimycobacterial activity of IO was modest; however, IO was a useful and effective agent against Myco. tuberculosis when it was combined with first-line antimycobacterial drugs and is worthy of further development as a lead compound for the development of novel antimycobacterial therapeutic agents.
    Arch Pharm Res. 2008 Feb;31(2):210-5.
    The effects of isoimperatorin isolated from Angelicae dahuricae on cyclooxygenase-2 and 5-lipoxygenase in mouse bone marrow-derived mast cells.[Pubmed: 18365692]
    Isoimperatorin (4-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one) is a medicinal herbal product that is isolated from the dried roots of Angelicae dahuricae.
    METHODS AND RESULTS:
    Isoimperatorin inhibits the cyclooxygenase-2 (COX-2) and COX-1-dependent phases of prostaglandin D2 (PGD2) generation in bone marrow-derived mast cells (BMMC) in a concentration-dependent manner, with IC50 values of 10.7 microM and 24 microM, respectively. However, this compound was not able to inhibit COX-1 and 2 protein expression in BMMC that were treated with concentrations of up to 50 microM, which indicates that Isoimperatorin directly inhibits COX-2 activity. Furthermore, this compound consistently inhibited the production of leukotriene C4 (LTC4), as well as the degranulation reaction in BMMC, with an IC50 value of 5.7 microM and 9 microM, respectively, and these effects occurred in a dose dependent fashion.
    CONCLUSIONS:
    These results demonstrate that Isoimperatorin has a dual cyclooxygenase-2 selective/5-lipoxygenase inhibitory activity, and therefore may provide the basis for novel anti-inflammatory drugs.
    J Ethnopharmacol. 2011 Jan 27;133(2):336-44.
    Isoimperatorin, cimiside E and 23-O-acetylshengmanol-3-xyloside from Cimicifugae rhizome inhibit TNF-α-induced VCAM-1 expression in human endothelial cells: involvement of PPAR-γ upregulation and PI3K, ERK1/2, and PKC signal pathways.[Pubmed: 20937376 ]
    Pretreatment of test compounds significantly reduced reactive oxygen species (ROS) production and expression of vascular cell adhesion molecule-1 (VCAM-1), but not intercellular cell adhesion molecule-1 (ICAM-1). Three compounds all dose-dependently increased not only PPAR-γ expression in EA.hy926 cells but inhibited TNF-α-induced phosphorylation of Akt, extracellular-signal-regulated kinase (ERK) and protein kinase C (PKC) with different specificity. Finally, they prevented TNF-α-induced adhesion of U937 monocytic cells to EA.hy926 cells. CONCLUSIONS: The present results show that cimiside E, 23-O-actylshengmanol-3-xyloside, Isoimperatorin isolated from Cimicifugae Rhizome selectively inhibits TNF-α-induced expression of VCAM-1 at least by upregulation of PPAR-γ, and signals for ERK1/2, PI3K, and PKC are involved in this effect.
    Isoimperatorin Description
    Source: The roots of Peucedanum ostruthium L.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 3.6999 mL 18.4993 mL 36.9987 mL 73.9973 mL 92.4967 mL
    5 mM 0.74 mL 3.6999 mL 7.3997 mL 14.7995 mL 18.4993 mL
    10 mM 0.37 mL 1.8499 mL 3.6999 mL 7.3997 mL 9.2497 mL
    50 mM 0.074 mL 0.37 mL 0.74 mL 1.4799 mL 1.8499 mL
    100 mM 0.037 mL 0.185 mL 0.37 mL 0.74 mL 0.925 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Kinase Assay:
    Zhongguo Zhong Yao Za Zhi. 2013 Apr;38(8):1237-41.
    Inhibitory effect of imperatorin and isoimperatorin on activity of cytochrome P450 enzyme in human and rat liver microsomes.[Pubmed: 23944042]
    Imperatorin (IM) and Isoimperatorin (ISOIM) are major active components of common herbal medicines from Umbelliferae plants, and widely used in clinic.
    METHODS AND RESULTS:
    This article studies the inhibitory effect of IM and ISOIM on the activity of cytochrome P450 (CYP) enzyme, and assesses their potential drug-drug interaction. IM and ISOIM were incubated separately with human or rat liver microsomes for 30 min, with phenacetin, bupropion, tolbutamide, S-mephenytoin, dextromethorphan and midazolam as probe substrates. Metabolites of the CYP probe substrates were determined by LC-MS/MS, and IC50 values were calculated to assess the inhibitory effect of the two drugs on human CYP1A2, 2B6, 2C9, 2C19, 2D6 and 3A4 enzymes, as well as on rat CYP1A2, 2B6, 2D2 and 3A1/2, and grade their inhibitory intensity. In human liver microsomes, IM and ISOIM showed different inhibitory effects on all of the six CYP isoenzymes. They were strong inhibitors for 1A2 and 2B6. The IC50 values were 0.05 and 0.20 micromol x L(-1) for 1A2, and 0.18 and 1.07 micromol x L(-1) for 2B6, respectively. They also showed moderate inhibitory effect on 2C19, and weak effect on 2C9, 2D6 and 3A4. In rat liver microsomes, IM and ISOIM were identified as moderate inhibitors for 1A2, with IC50 values of 1.95 and 2.98 micromol x L(-1). They were moderate and weak inhibitors for 2B6, with IC50 values of 6.22 and 21.71 micromol x L(-1), respectively. They also had weaker inhibitory effect on 2D2 and 3A1/2. The results indicated that IM and ISOIM had extensive inhibitory effects on human CYP enzymes.
    CONCLUSIONS:
    They are strong inhibitors of CYP1 A2 and 2B6 enzymes. However, it is worth noting the interaction arising from the inhibitory effect of CYP enzymes in clinic.
    Cell Research:
    Oncol Lett. 2017 Jan; 13(1): 518–524.
    Isoimperatorin induces apoptosis of the SGC-7901 human gastric cancer cell line via the mitochondria-mediated pathway[Pubmed: 28123591]
    Cell lines:SGC-7901 cells
    Concentrations: 5, 10, 15, 20, 25, 30, 35 and 40 μg/ml
    Incubation Time: 48 h
    Method:
    The antiproliferative activity of Isoimperatorin against SGC-7901 cells was evaluated using an MTT reduction assay. The SGC-7901 cells were seeded on 96-well culture plates with RPMI-1640 medium at a density of 5×103 cells/well. After 24 h of incubation at 37°C in 5% CO2/95% air, the cells were treated at different concentrations of Isoimperatorin (5, 10, 15, 20, 25, 30, 35 and 40 μg/ml) and 0.05% DMSO (control) for 48 h to examine dose-dependency; or with Isoimperatorin at a concentration of 20 μg/ml and 0.05% DMSO (control) for 12, 24, 36, 48, 60 and 72 h to examine time-dependent effects. Subsequently, 20 μl MTT (5 mg/ml) was separately added into each well, and the cells were cultured at 37°C in 5% CO2/95% air for another 3 h. Subsequently, 200 μl DMSO was separately added into each well and the optical density (OD) of the DMSO solution was measured at 570 nm using a microplate reader.
    Animal Research:
    Oncol Lett. 2017, 13(1): 518–524.
    Isoimperatorin induces apoptosis of the SGC-7901 human gastric cancer cell line via the mitochondria-mediated pathway[Pubmed: 28123591]
    Animal Models:Sixteen female nude mice (5–6 weeks old) inoculated with SGC-7901 cells (tumor xenograft model)
    Formulation: 0.5% DMSO
    Dosages:10 mg/kg
    Administration: i.p.