Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H8O4 |
| Molecular Weight | 216.1895 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C2C=CC(=O)OC2=CC3=C1C=CO3
InChI
InChIKey=BGEBZHIAGXMEMV-UHFFFAOYSA-N
InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3
Bergapten, known as 5-methoxypsoralen, a cumarine-derivate compound, presents in many fruits and vegetables. It has shown antitumor effects in a variety of cell types. The key target of bergapten action in breast cancer cells was identified the oncosuppressor gene PTEN (phosphatase tensin homolog deleted from chromosome 10); bergapten by inducing PTEN expression, produces autophagy in breast cancer cells. Besides, bergapten is under investigation in clinical trial phase III for patients with severe generalized atopic dermatitis.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Plasma and skin concentration of 5-methoxypsoralen in psoriatic patients after oral administration. | 2001 Aug |
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| Photosensitization and mutation induced in Escherichia coli and Saccharomyces cerevisiae strains by dorstenin, a psoralen analog isolated from Dorstenia bahiensis. | 2001 Dec |
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| Seville orange juice-felodipine interaction: comparison with dilute grapefruit juice and involvement of furocoumarins. | 2001 Jan |
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| [Heracl'eum mantegazzi'anum: photosensitization]. | 2001 Jan 18 |
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| Furanocoumarins in celery and parsnips: method and multiyear Canadian survey. | 2001 Jul-Aug |
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| Inhibition of itch-scratch response by fruits of Cnidium monnieri in mice. | 2001 Sep |
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| Inhibition of human CYP3A4 activity by grapefruit flavonoids, furanocoumarins and related compounds. | 2001 Sep-Dec |
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| Evaluation of synergism in the feeding deterrence of some furanocoumarins on Spodoptera littoralis. | 2002 Jan |
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| Genotoxicity of Brosimum gaudichaudii measured by the Salmonella/microsome assay and chromosomal aberrations in CHO cells. | 2002 Jul |
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| Zabon phytophotodermatitis: first case reports due to Citrus maxima. | 2002 May |
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| Determination of 5-methoxypsoralen in human serum. | 2002 Oct 15 |
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| Effect of psoralens on Fenton-like reaction generating reactive oxygen species. | 2003 |
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| Assessing the separation of neutral plant secondary metabolites by micellar electrokinetic chromatography. | 2003 Jul 4 |
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| Effect of 5-methoxypsoralen (5-MOP) on cell apoptosis and cell cycle in human hepatocellular carcinoma cell line. | 2003 Jun |
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| Reproductive toxicity of the psoralens. | 2003 May-Jun |
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| [Study on coumarin compounds from Exocarpium Citri Grandis]. | 2004 Aug |
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| Preparative isolation and purification of bergapten and imperatorin from the medicinal plant Cnidium monnieri using high-speed counter-current chromatography by stepwise increasing the flow-rate of the mobile phase. | 2004 Dec 17 |
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| Chemical and biological diversity of Bergamot (Citrus bergamia) in relation to environmental factors. | 2004 Mar |
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| Furanocoumarin biosynthesis in Ammi majus L. Cloning of bergaptol O-methyltransferase. | 2004 Mar |
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| Phototoxicity of protoporphyrin IX, diarginine diprotoporphyrinate and N,N-diphenylalanyl protoporphyrin toward human fibroblasts and keratinocytes in vitro: effect of 5-methoxypsoralen. | 2004 Nov-Dec |
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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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| Accumulation of biologically active furanocoumarins in Ruta graveolens ssp. divaricata (Tenore) Gams in vitro culture. | 2005 Jan |
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| 5-(3-Phenylpropoxy)psoralen and 5-(4-phenylbutoxy)psoralen: mechanistic studies on phototoxicity. | 2005 Mar |
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| Secondary metabolites of Peucedanum tauricum fruits. | 2005 Mar |
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| Effects of 5-methoxypsoralen (5-MOP) on arylamine N-acetyltransferase activity in the stomach and colon of rats and human stomach and colon tumor cell lines. | 2005 Nov-Dec |
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| Remarkable substrate-specificity of CYP6AB3 in Depressaria pastinacella, a highly specialized caterpillar. | 2006 Apr |
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| [Studies on chemical constituents from roots of Peucedanum praeruptorum II]. | 2006 Aug |
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| Solar simulator-induced phototoxicity of the furoquinoline alkaloid dictamnine compared to 8-methoxypsoralen and 5-methoxypsoralen. | 2006 Aug |
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| [Studies on chemical constituents from fruits of Paliurus ramosissimus]. | 2006 Dec |
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| Parsnip webworms and host plants at home and abroad: trophic complexity in a geographic mosaic. | 2006 Dec |
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| Cytochrome P450-mediated metabolism of xanthotoxin by Papilio multicaudatus. | 2006 Mar |
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| Efficacy of 8-methoxypsoralen vs. 5-methoxypsoralen plus ultraviolet A therapy in patients with mycosis fungoides. | 2006 Mar |
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| Inhibition on human liver cytochrome P450 3A4 by constituents of fennel (Foeniculum vulgare): identification and characterization of a mechanism-based inactivator. | 2007 Dec 12 |
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| Ethnoveterinary medicines used for ruminants in British Columbia, Canada. | 2007 Feb 26 |
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| Coumarins from Cnidium monnieri and their antiosteoporotic activity. | 2007 Jan |
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| Esterase inhibition by grapefruit juice flavonoids leading to a new drug interaction. | 2007 Jul |
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| Antimicrobial activity of the methanolic extracts and compounds from Treculia obovoidea (Moraceae). | 2007 Jul 25 |
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| Quality assessment of Rhizoma et Radix Notopterygii by HPTLC and HPLC fingerprinting and HPLC quantitative analysis. | 2007 Jul 27 |
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| German evidence-based guidelines for the treatment of Psoriasis vulgaris (short version). | 2007 Jun |
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| Burns caused by accidental overdose of photochemotherapy (PUVA). | 2007 May |
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| Herbal medicine today: clinical and research issues. | 2007 Sep |
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| Coumarins from Peucedanum luxurians. | 2007 Sep |
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| Central role of mitochondria and p53 in PUVA-induced apoptosis in human keratinocytes cell line NCTC-2544. | 2008 Feb 15 |
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| In vivo methods for the assessment of topical drug bioavailability. | 2008 Jan |
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| Effective biotic elicitation of Ruta graveolens L. shoot cultures by lysates from Pectobacterium atrosepticum and Bacillus sp. | 2008 Mar |
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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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| Application of chitin and chitosan as elicitors of coumarins and fluoroquinolone alkaloids in Ruta graveolens L. (common rue). | 2008 Oct |
Patents
Sample Use Guides
1,2 mg/kg 2 hours before UVA irradiation p.o. 3 times weekly for 5 weeks
Route of Administration:
Oral
Bone marrow stromal cells (BMSCs) were cultured in osteogenic induction medium with the addition of bergapten for 2 weeks. The concentrations of bergapten used were 0.1, 1, and 10 μmol/L in vitro. Bergapten promotes the expression of alkaline phosphatase (ALP) by BMSCs in vitro in a dose-dependent manner, as revealed by ALP staining.
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D05BA03
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QD05BA03
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C022909
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m2430
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BERGAPTEN
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ACTIVE MOIETY
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