Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H10O5 |
| Molecular Weight | 246.2155 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C2OC=CC2=C(OC)C3=C1OC(=O)C=C3
InChI
InChIKey=DFMAXQKDIGCMTL-UHFFFAOYSA-N
InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12376476 | https://www.ncbi.nlm.nih.gov/pubmed/28556437 | https://www.ncbi.nlm.nih.gov/pubmed/25240925
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12376476 | https://www.ncbi.nlm.nih.gov/pubmed/28556437 | https://www.ncbi.nlm.nih.gov/pubmed/25240925
Isopimpinellin is a natural product synthesized by Umbelliferae (or Apiaceae), also known as the carrot or parsley family. It can be found in celery, garden angelica, parsnip, fruits and in the rind and pulp of limes. There have been several studies looking into the effects of Isopimpinellin and other so-called naturally occurring coumarins (such as bergamottin and Imperatorin) as anticarcinogens.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Vasorelaxing effect of coumarins from Cnidium monnieri on rabbit corpus cavernosum. | 2001 Apr |
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| Oral administration of naturally occurring coumarins leads to altered phase I and II enzyme activities and reduced DNA adduct formation by polycyclic aromatic hydrocarbons in various tissues of SENCAR mice. | 2001 Jan |
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| Inhibition of itch-scratch response by fruits of Cnidium monnieri in mice. | 2001 Sep |
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| Amino acids in SRS1 and SRS6 are critical for furanocoumarin metabolism by CYP6B1v1, a cytochrome P450 monooxygenase. | 2002 Apr |
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| Effects of storage conditions on furocoumarin levels in intact, chopped, or homogenized parsnips. | 2002 Apr 24 |
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| Constituents of the fruits and leaves of Euodia daniellii. | 2002 Dec |
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| Antipruritic effect of Cnidii Monnieri Fructus (fruits of Cnidium monnieri CUSSON). | 2002 Feb |
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| Role of cytochrome P450 1a1 and 1b1 in the metabolic activation of 7,12-dimethylbenz[a]anthracene and the effects of naturally occurring furanocoumarins on skin tumor initiation. | 2002 Feb |
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| Bullous phytophotodermatitis associated with high natural concentrations of furanocoumarins in limes. | 2002 Mar |
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| Simultaneous determination of furanocoumarins in infusions and decoctions from "Carapiá" (dorstenia species) by high-performance liquid chromatography. | 2002 Mar 13 |
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| Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice. | 2002 Oct |
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| [Studies on the coumarins in the root of Zanthoxylum dimorphophyllum]. | 2003 Apr |
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| Constituents of Peucedanum zenkeri seeds and their antimicrobial effects. | 2003 Aug |
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| Cytotoxic activity of coumarins from the fruits of Cnidium monnieri on leukemia cell lines. | 2003 Dec |
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| A new dicoumarinyl ether and two rare furocoumarins from Ruta montana. | 2003 Feb |
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| HPLC-NMR/HPLC-MS analysis of the bark extract of Stauranthus perforatus. | 2003 Jan-Feb |
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| Naturally occurring coumarins inhibit human cytochromes P450 and block benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene DNA adduct formation in MCF-7 cells. | 2003 Mar |
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| LC determination of impurities in methoxsalen drug substance: isolation and identification of isopimpinellin as a major impurity by atmospheric pressure chemical ionization LC/MS and NMR. | 2003 Nov 24 |
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| The furanocoumarins in the roots of Heracleum sibiricum L. | 2003 Sep-Oct |
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| [Quantification of isopimpinellin in root of Toddalia asiatica by HPLC]. | 2004 Aug |
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| Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster. | 2004 Jul 14 |
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| Computer-assisted, high-performance liquid chromatography with mass spectrometric detection for the analysis of coumarins in Peucedanum palustre and Angelica archangelica. | 2004 May-Jun |
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| Accumulation of biologically active furanocoumarins in agitated cultures of Ruta graveolens L. and Ruta graveolens ssp. divaricata (Tenore) Gams. | 2005 Aug |
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| Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes. | 2005 Feb 15 |
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| Accumulation of biologically active furanocoumarins in Ruta graveolens ssp. divaricata (Tenore) Gams in vitro culture. | 2005 Jan |
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| Melanogenesis stimulation in murine b16 melanoma cells by umberiferae plant extracts and their coumarin constituents. | 2005 Jul |
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| Coumarins are competitive inhibitors of cytochrome P450 1B1, with equal potency for allelic variants. | 2005 Mar |
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| [Studies on chemical constituents from fruits of Paliurus ramosissimus]. | 2006 Dec |
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| [Studies on chemical constituents in roots of Heracleum rapula]. | 2006 Feb |
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| Naturally occurring coumarins inhibit 7,12-dimethylbenz[a]anthracene DNA adduct formation in mouse mammary gland. | 2006 Jun |
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| Cytochrome P450-mediated metabolism of xanthotoxin by Papilio multicaudatus. | 2006 Mar |
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| [Studies on the chemical constituents of the aerial parts of Seseli mairei]. | 2007 Jan |
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| [Inhibitory effects of 11 coumarin compounds against growth of human bladder carcinoma cell line E-J in vitro]. | 2007 Jan |
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| [Simultaneous determination of 5 active components in Fructus Cnidii by HPLC]. | 2007 Sep |
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| Identification of Ruta graveolens L. metabolites accumulated in the presence of abiotic elicitors. | 2008 Jan-Feb |
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| In vitro antiplasmodial activity of extract and constituents from Esenbeckia febrifuga, a plant traditionally used to treat malaria in the Brazilian Amazon. | 2008 May |
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| Osthol and isopimpinellin from Fructus cnidii for the control of Dactylogyrus intermedius in Carassius auratus. | 2008 Nov 25 |
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| Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice. | 2008 Oct 15 |
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| Botanical origin of Indian celery seed (fruit). | 2009 Jul |
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| Citrus auraptene suppresses cyclin D1 and significantly delays N-methyl nitrosourea induced mammary carcinogenesis in female Sprague-Dawley rats. | 2009 Jul 29 |
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| [Chemical constituents of fresh celery]. | 2009 Jun |
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| Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice. | 2009 Mar 28 |
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| Simultaneous and sensitive determination of xanthotoxin, psoralen, isoimpinellin and bergapten in rat plasma by liquid chromatography-electrospray ionization mass spectrometry. | 2010 Feb 15 |
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| Application of the concept of relative photomutagenic potencies to selected furocoumarins in V79 cells. | 2010 Mar |
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| Aggressive mammary carcinoma progression in Nrf2 knockout mice treated with 7,12-dimethylbenz[a]anthracene. | 2010 Oct 8 |
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| Naturally occurring food toxins. | 2010 Sep |
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| The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins. | 2013 May 2 |
Patents
Sample Use Guides
RAW264.7 cells were seeded in 96-well plates and maintained in DMEM supplemented with 5% FBS, 100 U/ml penicillin, and 100 mg/ml streptomycin. After incubation at 37 °C for 24 h, compounds were added into the media and incubated for 4 h. Then LPS (1 mg/ml) was added and co-incubated for another 24 h. After that, the supernatant of the media was mixed with an equal volume of Griess reagent. Nitrite production was determined by measuring the optical density at 540 nm.
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C45597
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28853
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Isopimpinellin
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C63673
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SUBSTANCE RECORD
