Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C16H14O4 |
| Molecular Weight | 270.28 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)=CCOC1=C2OC=CC2=CC3=C1OC(=O)C=C3
InChI
InChIKey=OLOOJGVNMBJLLR-UHFFFAOYSA-N
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
| Molecular Formula | C16H14O4 |
| Molecular Weight | 270.28 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22222157 | https://www.ncbi.nlm.nih.gov/pubmed/29332340 | https://www.ncbi.nlm.nih.gov/pubmed/28990061 | https://www.ncbi.nlm.nih.gov/pubmed/29128276
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22222157 | https://www.ncbi.nlm.nih.gov/pubmed/29332340 | https://www.ncbi.nlm.nih.gov/pubmed/28990061 | https://www.ncbi.nlm.nih.gov/pubmed/29128276
Pentosalen (Imperatorin) is a bioactive furanocoumarin and a phytochemical that has been isolated from Urena lobata L. (Malvaceae), Angelica archangelica, etc. Pentosalen has a wide range of potent pharmacological activities, including antibacterial, antitumor, anticonvulsant, acute neurotoxic effects and abirritation. Pentosalen possesses notable anti-inflammatory activity by inhibiting the production of nitric oxide (NO) and prostaglandin E2 (PGE2), and decreasing the expression of inducible nitric oxide synthase (iNOS), cyclooxygenase (COX) 2 and microsomal prostaglandin E synthase. Pentosalen selectively targets gastric cancer cells without causing much damage to normal cells. Pentosalen was identified from a Bioactive Molecules library in a high throughput screening experiment for inhibitors of the phosphodiesterase PDE4. It displays a significant preference for PDE4Bover PDE4A.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Separation and determination of coumarins in Fructus cnidii extracts by pressurized capillary electrochromatography using a packed column with a monolithic outlet frit. | 2009-12-05 |
|
| A vascular smooth muscle/cell membrane chromatography-offline-gas chromatography/mass spectrometry method for recognition, separation and identification of active components from traditional Chinese medicines. | 2009-10-16 |
|
| Simultaneous determination of five coumarins in Angelicae dahuricae Radix by HPLC/UV and LC-ESI-MS/MS. | 2009-10 |
|
| Anticonvulsant and acute neurotoxic effects of imperatorin, osthole and valproate in the maximal electroshock seizure and chimney tests in mice: a comparative study. | 2009-08 |
|
| Citrus auraptene suppresses cyclin D1 and significantly delays N-methyl nitrosourea induced mammary carcinogenesis in female Sprague-Dawley rats. | 2009-07-29 |
|
| Coumarins from Angelica lucida L.--antibacterial activities. | 2009-07-27 |
|
| Development and validation of a gas chromatography-mass spectrometry method for the determination of imperatorin in rat plasma and tissue: application to study its pharmacokinetics. | 2009-07 |
|
| [Effect of Chuanxiong Fangfeng Baizhi prescription on isolated rabbit basilar artery]. | 2009-06 |
|
| Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice. | 2009-03-28 |
|
| Pharmacological properties of the extract and some isolated compounds of Clausena lansium stem bark: anti-trichomonal, antidiabetic, anti-inflammatory, hepatoprotective and antioxidant effects. | 2009-02-25 |
|
| Identification and quantification of the volatile constituents in Cnidium monnieri using supercritical fluid extraction followed by GC-MS. | 2009-01 |
|
| Osthole and imperatorin, the active constituents of Cnidium monnieri (L.) Cusson, facilitate glutamate release from rat hippocampal nerve terminals. | 2008-12 |
|
| Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice. | 2008-10-15 |
|
| Supercritical fluid extraction for identification and determination of volatile metabolites from Angelica dahurica by GC-MS. | 2008-10 |
|
| Lead compounds for anti-inflammatory drugs isolated from the plants of the traditional oriental medicine in Korea. | 2008-09 |
|
| Identification of natural coumarin compounds that rescue defective DeltaF508-CFTR chloride channel gating. | 2008-08 |
|
| Micelle-mediated extraction and cloud-point preconcentration of osthole and imperatorin from Cnidium monnieri with analysis by high performance liquid chromatography. | 2008-07-25 |
|
| Simultaneous determination of 10 active components in traditional Chinese medicine "YIGONG" capsule by RP-HPLC-DAD. | 2008-06-09 |
|
| Metabolism of myristicin by Depressaria pastinacella CYP6AB3v2 and inhibition by its metabolite. | 2008-06 |
|
| Nematicidal coumarins from Heracleum candicans Wall. | 2008-05-20 |
|
| Real-time fluorescence-based detection of furanocoumarin photoadducts of DNA. | 2008-04-11 |
|
| Enhancement of bone morphogenetic protein-2 expression and bone formation by coumarin derivatives via p38 and ERK-dependent pathway in osteoblasts. | 2008-01-28 |
|
| Influence of imperatorin on the anticonvulsant activity and acute adverse-effect profile of lamotrigine in maximal electroshock-induced seizures and chimney test in mice. | 2007-12-18 |
|
| Inhibition of acetylcholinesterase by extracts and constituents from Angelica archangelica and Geranium sylvaticum. | 2007-12-12 |
|
| Imperatorin enhances the protective activity of conventional antiepileptic drugs against maximal electroshock-induced seizures in mice. | 2007-11-28 |
|
| Imperatorin induces vasodilatation possibly via inhibiting voltage dependent calcium channel and receptor-mediated Ca2+ influx and release. | 2007-11-14 |
|
| [Simultaneous determination of 5 active components in Fructus Cnidii by HPLC]. | 2007-09 |
|
| Time-course and dose-response relationships of imperatorin in the mouse maximal electroshock seizure threshold model. | 2007-09 |
|
| Effect of chrysin and natural coumarins on UGT1A1 and 1A6 activities in rat and human hepatocytes in primary culture. | 2007-07 |
|
| [Studies on chemical constituents in fruit of Gardenia jasminoides]. | 2007-06 |
|
| High-performance liquid chromatographic method for the determination and pharmacokinetic study of oxypeucedanin hydrate and byak-angelicin after oral administration of Angelica dahurica extracts in mongrel dog plasma. | 2007-05-09 |
|
| Allelic variation in the Depressaria pastinacella CYP6AB3 protein enhances metabolism of plant allelochemicals by altering a proximal surface residue and potential interactions with cytochrome P450 reductase. | 2007-04-06 |
|
| Ethyl acetate extract from Angelica Dahuricae Radix inhibits lipopolysaccharide-induced production of nitric oxide, prostaglandin E2 and tumor necrosis factor-alphavia mitogen-activated protein kinases and nuclear factor-kappaB in macrophages. | 2007-04 |
|
| Antitumor effects of Osthol from Cnidium monnieri: an in vitro and in vivo study. | 2007-03 |
|
| Antiproliferative effect of furanocoumarins from the root of Angelica dahurica on cultured human tumor cell lines. | 2007-03 |
|
| Ethnoveterinary medicines used for ruminants in British Columbia, Canada. | 2007-02-26 |
|
| Antibacterial and anticoagulant activities of coumarins isolated from the flowers of Magydaris tomentosa. | 2007-02 |
|
| Coumarins from Cnidium monnieri and their antiosteoporotic activity. | 2007-01 |
|
| Determination of liquiritin, naringin, hesperidin, thymol, imperatorin, honokiol, isoimperatorin, and magnolol in the traditional Chinese medicinal preparation Huoxiang-zhengqi liquid using high-performance liquid chromatography. | 2006-11 |
|
| [Analysis of coumarins in Fructus Cnidii by HPLC-ESI-MS]. | 2006-10 |
|
| [Studies on chemical constituents from roots of Peucedanum praeruptorum II]. | 2006-08 |
|
| Naturally occurring coumarins inhibit 7,12-dimethylbenz[a]anthracene DNA adduct formation in mouse mammary gland. | 2006-06 |
|
| Preparative isolation of imperatorin, oxypeucedanin and isoimperatorin from traditional Chinese herb "bai zhi"Angelica dahurica (Fisch. ex Hoffm) Benth. et Hook using multidimensional high-speed counter-current chromatography. | 2006-05-19 |
|
| Serotonergic activity-guided phytochemical investigation of the roots of Angelica sinensis. | 2006-04 |
|
| Remarkable substrate-specificity of CYP6AB3 in Depressaria pastinacella, a highly specialized caterpillar. | 2006-04 |
|
| Cytochrome P450-mediated metabolism of xanthotoxin by Papilio multicaudatus. | 2006-03 |
|
| [Studies on chemical constituents in roots of Heracleum rapula]. | 2006-02 |
|
| [Progress in study of chemical constituents and anti-tumor activities of Cnidium monnieri]. | 2005-09 |
|
| New cosmetic agents for skin whitening from Angelica dahurica. | 2005-08-09 |
|
| Identification and determination of active components in Angelica dahurica Benth and its medicinal preparation by capillary electrophoresis. | 2001-05-30 |
Patents
Sample Use Guides
The effect of imperatorin on cell viability was evaluated by 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide (MTT) assay. In brief, SGC-7901 gastric cancer cells and 3T3 normal cells were seeded in a 96-well plate at a density of 2x106 cells/well. The cells were incubated for 48 hrs and then treated with various concentrations (0, 10, 50, 75, 100, 125 and 175 μM) of imperatorin and incubated for 24, 48 and 72 hrs. In the control group, the cells were treated with the solvent only (DMSO) and not the drug. Following incu¬bation, the cells were washed with PBS three times and a 200 μl solution of MTT dye was added and the whole cell sample was again incubated for 40 min. After this, the absorbance was measured at 490 nm using ELISA plate reader (ELX 800; Bio-Τek Instruments, USA).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:20:56 GMT 2025
by
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on
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| Record UNII |
K713N25C78
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| Record Status |
Validated (UNII)
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| Record Version |
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C45597
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C63672
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IMPERATORIN
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