Imperatorin

CAS# 482-44-0

Imperatorin

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Quality Control of Imperatorin

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Chemical structure

Imperatorin

3D structure

Chemical Properties of Imperatorin

Cas No. 482-44-0 SDF Download SDF
PubChem ID 10212 Appearance White powder
Formula C16H14O4 M.Wt 270.3
Type of Compound Coumarins Storage Desiccate at -20°C
Synonyms Ammidin
Solubility Soluble in DMSO; sparingly soluble in methanol and water
Chemical Name 9-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one
SMILES CC(=CCOC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)C
Standard InChIKey OLOOJGVNMBJLLR-UHFFFAOYSA-N
Standard InChI InChI=1S/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Imperatorin

1 Angelica sp. 2 Apium sp. 3 Foeniculum sp. 4 Heracleum sp. 5 Levisticum sp. 6 Pastinaca sp. 7 Petroselinum sp. 8 Ruta sp. 9 Zanthoxylum sp.

Biological Activity of Imperatorin

DescriptionImperatorin is an effective of NO synthesis inhibitor (IC50=9.2 μmol), which also is a BChE inhibitor (IC50=31.4 μmol); it is a weak agonist of TRPV1 with EC50 of 12.6±3.2 μM. Imperatorin is a potent myorelaxant agent and acts as a calcium antagonist on vascular smooth muscle. Imperatorin has anticonvulsant, anti-inflammatory, anti-oxidant, neuroprotection, and anti-cancer effects, it also has been used in herbal formulations for the treatment of hypertension and cardiovascular diseases. Imperatorin dampens neuronal excitability by inhibiting voltage-gated Na + channels (VGSC), and blocks the HSP27 and HSP72 gene expression.
TargetsCOX | Caspase | HSP (e.g. HSP90) | Sodium Channel | Potassium Channel | Bcl-2/Bax | PPAR | NOS | BChE | TRPV1
In vitro

Imperatorin Suppresses Degranulation and Eicosanoid Generation in Activated Bone Marrow-Derived Mast Cells.[Pubmed: 26336581]

Biomol Ther (Seoul). 2015 Sep; 23(5): 421–427.

Imperatorin has been known to exert many biological functions including anti-inflammatory activity.
METHODS AND RESULTS:
In this study, we investigated the inhibitory effects of Imperatorin on the production of inflammatory mediators in mouse bone marrow-derived mast cells (BMMC). Imperatorin inhibited degranulation and the generation of eicosanoids (leukotriene C4 (LTC4) and prostaglandin D2 (PGD2)) in IgE/antigen (Ag)-stimulated BMMC. To elucidate the molecular mechanism involved in this process, we investigated the effect of Imperatorin on intracellular signaling in BMMC. Biochemical analyses of the IgE/Ag-mediated signaling pathway demonstrated that Imperatorin dramatically attenuated degranulation and the production of 5-lipoxygenase-dependent LTC4 and cyclooxygenase-2-dependent PGD2 through the inhibition of intracellular calcium influx/phospholipase Cγ1, cytosolic phospholipase A2/mitogen-activated protein kinases and/or nuclear factor-κB pathways in BMMC.
CONCLUSIONS:
These results suggest that the effects of Imperatorin on inhibition of degranulation and eicosanoid generation through the suppression of multiple steps of IgE/Ag-mediated signaling pathways would be beneficial for the prevention of allergic inflammation.

Imperatorin exhibits anticancer activities in human colon cancer cells via the caspase cascade.[Pubmed: 26794238 ]

Oncol Rep. 2016 Apr;35(4):1995-2002.

Despite advances in medical treatments for colon cancer, it remains one of the leading causes of cancer-related mortality among men. Thus, more efficacious treatment strategies for colon cancer are needed. Imperatorin is one of the major ingredients present in the root of Angelica dahurica, and has been used in herbal formulations for the treatment of hypertension and cardiovascular diseases. However, the medical properties of Imperatorin remain unclear.
METHODS AND RESULTS:
In the present study, the anti‑proliferative activities of Imperatorin were investigated in the HT‑29 colon cancer cell line. The results showed that Imperatorin significantly inhibited HT‑29 colon cancer cell growth with an IC50 value of 78 μM. Imperatorin induced the apoptosis of colon cancer cells through upregulation of p53 and the caspase cascade. Our findings revealed that Imperatorin induced cell cycle arrest in the G1 phase. The apoptotic index showed a steady increment when the Imperatorin concentration was increased.
CONCLUSIONS:
The results suggest that Imperatorin exerts considerable anti‑proliferative activities in HT‑29 colon cancer cells and highlight the potential of Imperatorin as an anticancer agent for colon cancer.

Protocol of Imperatorin

Kinase Assay

Suppression of voltage-gated Na(+) channels and neuronal excitability by imperatorin.[Pubmed: 24113522]

Eur J Pharmacol. 2013 Dec 5;721(1-3):49-55.

Imperatorin is a naturally occurring furocoumarin compound isolated from plants such as Angelica archangelica and Cnidium monnieri. It has multiple pharmacological effects including anticonvulsant effects.
METHODS AND RESULTS:
Here we determined the effects of Imperatorin on voltage-gated Na(+) channels (VGSC) using whole-cell patch clamp techniques in differentiated neuronal NG108-15 cells. We showed that Imperatorin inhibited VGSC; such inhibition did not show state-dependence. Imperatorin caused a left shift in the steady-state inactivation curve without affecting activation gating. The inhibition of VGSC by Imperatorin displayed a mild frequency-dependence. Imperatorin was also shown to inhibit VGSC and action potential amplitude without affecting voltage-gated K(+) channels in rat hippocampal CA1 neurons.
CONCLUSIONS:
In conclusion, our results suggest that Imperatorin dampens neuronal excitability by inhibiting VGSC.

Cell Research

Imperatorin, a furanocoumarin from Angelica dahurica (Umbelliferae), induces cytochrome c-dependent apoptosis in human promyelocytic leukaemia, HL-60 Cells.[Pubmed: 12193260]

The effect of quercetin and imperatorin on programmed cell death induction in T98G cells in vitro.[Pubmed: 24911084]

Pharmacol Rep. 2014 Apr;66(2):292-300.

High expression of HSP27 and HSP72 in glioma cells has been closely associated with chemoresistance and decreased sensitivity to programmed cell death induction. Therefore, it is important to devise therapies that effectively target invasive cancer cells by inducing cell death. The aim of our study was to assess the effect of quercetin and Imperatorin applied separately and in combinations on the apoptosis and autophagy induction in human T98G cells cultured in vitro.
METHODS AND RESULTS:
Cell death induction was analyzed by the staining method. The Western blotting technique and fluorimetric measurements of activity were used to assess the expression of marker proteins of apoptosis and autophagy. The specific siRNA transfected method was used for blocking of the expression of HSP27 and HSP72 genes. The experiments revealed the highest percentage of apoptotic cells after using a 50?M concentration of both compounds. Simultaneous quercetin and Imperatorin administration induced apoptosis more effectively than incubation with single drugs. These results were accompanied with decreased HSP27 and HSP72 expression, and a high level of caspase-3 and caspase-9 activity. Autophagy was not observed. Additional experiments were performed on a cell line with blocked Hsp27 and Hsp72 expression and significant increase the sensitivity to apoptosis induction upon quercetin and Imperatorin treatment was noticed.
CONCLUSIONS:
The present study indicates that quercetin and Imperatorin are potent apoptosis inducers, especially when they act synergistically, which may be a promising combination useful in glioma therapy. Our results also demonstrated that blocking the HSP27 and HSP72 gene expression might serve as a therapeutic target for the human brain cancer.

Pharmacol Toxicol. 2002 Jul;91(1):40-8.

Imperatorin, a biologically active furanocoumarin from the roots of Angelica dahurica (Umbelliferae), was found to induce apoptosis in human promyelocytic leukaemia, HL-60 cells.
METHODS AND RESULTS:
DNA fragmentation assay, morphology-based evaluation, and flow cytometric analysis demonstrated that Imperatorin at micromolar concentrations was able to trigger apoptosis of HL-60 cells. Neither necrosis nor differentiation was observed at cytotoxic micromolar concentrations of Imperatorin. Further studies showed that the cytochrome c/caspase-9 pathway was responsible for Imperatorin-induced apoptosis; i.e., mitochondrial membrane was depolarized, Bcl-2 was down-regulated, cytochrome c was released from mitochondria, caspase-9 and caspase-3 were activated, and poly(ADP-ribose) polymerase was cleaved. Furthermore, Imperatorin-induced apoptosis was significantly blocked by Z-VAD-FMK (a broad spectrum caspase inhibitor), Z-LEHD-FMK (a caspase-9 inhibitor) and Ac-DMQD-CHO (a caspase-3 inhibitor), but not by Z-IEDT-FMK (a caspase-8 inhibitor).

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Preparing Stock Solutions of Imperatorin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.6996 mL 18.498 mL 36.9959 mL 73.9919 mL 92.4898 mL
5 mM 0.7399 mL 3.6996 mL 7.3992 mL 14.7984 mL 18.498 mL
10 mM 0.37 mL 1.8498 mL 3.6996 mL 7.3992 mL 9.249 mL
50 mM 0.074 mL 0.37 mL 0.7399 mL 1.4798 mL 1.8498 mL
100 mM 0.037 mL 0.185 mL 0.37 mL 0.7399 mL 0.9249 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Imperatorin

Imperatorin is an effective of NO synthesis inhibitor (IC50=9.2 μmol), which also is a BChE inhibitor (IC50=31.4 μmol). Imperatorin is a weak agonist of TRPV1 with EC50 of 12.6±3.2 μM.

In Vitro:Imperatorin is a plant secondary metabolite belonging to the coumarins-specifically the furanocoumarins. Imperatorin enhances the GABA-induced chloride ion current (IGABA) through the α1β2γ2S receptors. Imperatorin potentiates IGABA at 100 μmol by 50.5±16.3 % and at 300 μmol by 109.8±37.7 %, respectively. Imperatorin, together with Phellopterin, found in the roots of A. dahurica, inhibit [3H]diazepam binding to the benzodiazepine site of the rat brain GABAA receptor in vitro with an IC50 of 12.3 μmol for Imperatorin and 400 nmol for Phellopterin. Imperatorin, in a concentration ranging from 3.5 to 14 mmol, significantly and irreversibly inhibits GABA-T in a time-dependent and concentration-dependent manner, by irreversibly binding with the active site of GABA-T.Imperatorin is a reversible acetylcholinesterase (AChE) inhibitor, and acts in dose-dependent manner. The AChE and BChE inhibitory activities of Imperatorin and a crude extract from the fruits of Angelica archangelica L. is tested by the spectrophotometric method at concentrations of 12.5, 25, 50, and 100 μg/mL. Imperatorin displays low inhibition towards AChE (13.75-46.11 %), whereas it has remarkable inhibitory effect against BChE (37.46-83.98 %). Imperatorin shows selectivity toward BChE rather than AChE, with an IC50 for BChE of 31.4 μmol. Imperatorin, together with (+)-Byakangelicol, are found to be the most effective BACE-1 inhibitors, with IC50s of 91.8 and 104.9 μmol, respectively. Imperatorin (IC50=9.2 μmol) is also effective as an inhibitor of NO synthesis[1]. Imperatorin is a weak agonist of TRPV1, a channel implicated in detecting several noxious stimuli, exhibiting EC50 of 12.6±3.2 μM[2].

In Vivo:At doses of 10 and 20 mg/kg and 30 min after injection, Imperatorin shows an anxiolytic effect and improved different stages of memory and learning processes-both acquisition and consolidation. It is also shown that acute administration Imperatorin at doses of 10 and 20 mg/kg reduced the anxiogenic effect of nicotine (0.1 mg/kg, subcutaneous, s.c.). At 30 and 40 mg/kg, i.p. Imperatorin significantly potentiates the anticonvulsant activity of carbamazepine against maximal electroshock-induced seizures expressed by lowering the ED50 from 10.8 to 6.8 mg/kg (by 34 %) and 6 mg/kg (by 42 %), respectively. Moreover, Imperatorin at 30 mg/kg and carbamazepine at 6.8 mg/kg shows increases the total brain concentration of carbamazepine from 1.260 to 2.328 μg/mL (by 85%), which may be caused by modifying the blood-barrier permeability or acting like an inhibitor of multi-drug resistance proteins[1]. Imperatorin, a naturally occurring furanocoumarin, inactivates gamma-aminobutyric acid transaminase and inhibits acetylcholinesterase activity. Imperatorin administered acutely at the doses of 5 and 10 mg/kg prior to the injection of scopolamine (1 mg/kg) improves memory acquisition and consolidation impaired by scopolamine. Furthermore, repeatable (7 days, twice daily) administration of the highest dose of Imperatorin (10 mg/kg) significantly attenuates the effects of scopolamine on memory acquisition, whereas the doses of 5 and 10 mg/kg of this furanocoumarin are effective when memory consolidation is measured [3].

References:
[1]. Kozioł E, et al. Imperatorin-pharmacological meaning and analytical clues: profound investigation. Phytochem Rev. 2016;15:627-649. [2]. Chen X, et al. Furanocoumarins are a novel class of modulators for the transient receptor potential vanilloid type 1 (TRPV1) channel. J Biol Chem. 2014 Apr 4;289(14):9600-10. [3]. Budzynska B, et al. Effects of imperatorin on scopolamine-induced cognitive impairment and oxidative stress in mice. Psychopharmacology (Berl). 2015 Mar;232(5):931-42.

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References on Imperatorin

Imperatorin, a furanocoumarin from Angelica dahurica (Umbelliferae), induces cytochrome c-dependent apoptosis in human promyelocytic leukaemia, HL-60 Cells.[Pubmed:12193260]

Pharmacol Toxicol. 2002 Jul;91(1):40-8.

Imperatorin, a biologically active furanocoumarin from the roots of Angelica dahurica (Umbelliferae), was found to induce apoptosis in human promyelocytic leukaemia, HL-60 cells. DNA fragmentation assay, morphology-based evaluation, and flow cytometric analysis demonstrated that Imperatorin at micromolar concentrations was able to trigger apoptosis of HL-60 cells. Neither necrosis nor differentiation was observed at cytotoxic micromolar concentrations of Imperatorin. Further studies showed that the cytochrome c/caspase-9 pathway was responsible for Imperatorin-induced apoptosis; i.e., mitochondrial membrane was depolarized, Bcl-2 was down-regulated, cytochrome c was released from mitochondria, caspase-9 and caspase-3 were activated, and poly(ADP-ribose) polymerase was cleaved. Furthermore, Imperatorin-induced apoptosis was significantly blocked by Z-VAD-FMK (a broad spectrum caspase inhibitor), Z-LEHD-FMK (a caspase-9 inhibitor) and Ac-DMQD-CHO (a caspase-3 inhibitor), but not by Z-IEDT-FMK (a caspase-8 inhibitor).

Suppression of voltage-gated Na(+) channels and neuronal excitability by imperatorin.[Pubmed:24113522]

Eur J Pharmacol. 2013 Dec 5;721(1-3):49-55.

Imperatorin is a naturally occurring furocoumarin compound isolated from plants such as Angelica archangelica and Cnidium monnieri. It has multiple pharmacological effects including anticonvulsant effects. Here we determined the effects of Imperatorin on voltage-gated Na(+) channels (VGSC) using whole-cell patch clamp techniques in differentiated neuronal NG108-15 cells. We showed that Imperatorin inhibited VGSC; such inhibition did not show state-dependence. Imperatorin caused a left shift in the steady-state inactivation curve without affecting activation gating. The inhibition of VGSC by Imperatorin displayed a mild frequency-dependence. Imperatorin was also shown to inhibit VGSC and action potential amplitude without affecting voltage-gated K(+) channels in rat hippocampal CA1 neurons. In conclusion, our results suggest that Imperatorin dampens neuronal excitability by inhibiting VGSC.

Imperatorin Suppresses Degranulation and Eicosanoid Generation in Activated Bone Marrow-Derived Mast Cells.[Pubmed:26336581]

Biomol Ther (Seoul). 2015 Sep;23(5):421-7.

Imperatorin has been known to exert many biological functions including anti-inflammatory activity. In this study, we investigated the inhibitory effects of Imperatorin on the production of inflammatory mediators in mouse bone marrow-derived mast cells (BMMC). Imperatorin inhibited degranulation and the generation of eicosanoids (leukotriene C4 (LTC4) and prostaglandin D2 (PGD2)) in IgE/antigen (Ag)-stimulated BMMC. To elucidate the molecular mechanism involved in this process, we investigated the effect of Imperatorin on intracellular signaling in BMMC. Biochemical analyses of the IgE/Ag-mediated signaling pathway demonstrated that Imperatorin dramatically attenuated degranulation and the production of 5-lipoxygenase-dependent LTC4 and cyclooxygenase-2-dependent PGD2 through the inhibition of intracellular calcium influx/phospholipase Cgamma1, cytosolic phospholipase A2/mitogen-activated protein kinases and/or nuclear factor-kappaB pathways in BMMC. These results suggest that the effects of Imperatorin on inhibition of degranulation and eicosanoid generation through the suppression of multiple steps of IgE/Ag-mediated signaling pathways would be beneficial for the prevention of allergic inflammation.

The effect of quercetin and imperatorin on programmed cell death induction in T98G cells in vitro.[Pubmed:24911084]

Pharmacol Rep. 2014 Apr;66(2):292-300.

BACKGROUND: High expression of HSP27 and HSP72 in glioma cells has been closely associated with chemoresistance and decreased sensitivity to programmed cell death induction. Therefore, it is important to devise therapies that effectively target invasive cancer cells by inducing cell death. The aim of our study was to assess the effect of quercetin and Imperatorin applied separately and in combinations on the apoptosis and autophagy induction in human T98G cells cultured in vitro. METHODS: Cell death induction was analyzed by the staining method. The Western blotting technique and fluorimetric measurements of activity were used to assess the expression of marker proteins of apoptosis and autophagy. The specific siRNA transfected method was used for blocking of the expression of HSP27 and HSP72 genes. RESULTS: The experiments revealed the highest percentage of apoptotic cells after using a 50?M concentration of both compounds. Simultaneous quercetin and Imperatorin administration induced apoptosis more effectively than incubation with single drugs. These results were accompanied with decreased HSP27 and HSP72 expression, and a high level of caspase-3 and caspase-9 activity. Autophagy was not observed. Additional experiments were performed on a cell line with blocked Hsp27 and Hsp72 expression and significant increase the sensitivity to apoptosis induction upon quercetin and Imperatorin treatment was noticed. CONCLUSIONS: The present study indicates that quercetin and Imperatorin are potent apoptosis inducers, especially when they act synergistically, which may be a promising combination useful in glioma therapy. Our results also demonstrated that blocking the HSP27 and HSP72 gene expression might serve as a therapeutic target for the human brain cancer.

Imperatorin exhibits anticancer activities in human colon cancer cells via the caspase cascade.[Pubmed:26794238]

Oncol Rep. 2016 Apr;35(4):1995-2002.

Despite advances in medical treatments for colon cancer, it remains one of the leading causes of cancer-related mortality among men. Thus, more efficacious treatment strategies for colon cancer are needed. Imperatorin is one of the major ingredients present in the root of Angelica dahurica, and has been used in herbal formulations for the treatment of hypertension and cardiovascular diseases. However, the medical properties of Imperatorin remain unclear. In the present study, the antiproliferative activities of Imperatorin were investigated in the HT29 colon cancer cell line. The results showed that Imperatorin significantly inhibited HT29 colon cancer cell growth with an IC50 value of 78 microM. Imperatorin induced the apoptosis of colon cancer cells through upregulation of p53 and the caspase cascade. Our findings revealed that Imperatorin induced cell cycle arrest in the G1 phase. The apoptotic index showed a steady increment when the Imperatorin concentration was increased. The results suggest that Imperatorin exerts considerable antiproliferative activities in HT29 colon cancer cells and highlight the potential of Imperatorin as an anticancer agent for colon cancer.

Description

Imperatorin is an effective of NO synthesis inhibitor (IC50=9.2 μmol), which also is a BChE inhibitor (IC50=31.4 μmol).

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