Bergaptol

CAS# 486-60-2

Bergaptol

Catalog No. BCN5588----Order now to get a substantial discount!

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Quality Control of Bergaptol

Number of papers citing our products

Chemical structure

Bergaptol

3D structure

Chemical Properties of Bergaptol

Cas No. 486-60-2 SDF Download SDF
PubChem ID 5280371 Appearance Yellow powder
Formula C11H6O4 M.Wt 202.2
Type of Compound Coumarins Storage Desiccate at -20°C
Solubility DMSO : ≥ 50 mg/mL (247.33 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
Chemical Name 4-hydroxyfuro[3,2-g]chromen-7-one
SMILES C1=CC(=O)OC2=CC3=C(C=CO3)C(=C21)O
Standard InChIKey GIJHDGJRTUSBJR-UHFFFAOYSA-N
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 Bergaptol

The root of Notopterygium incisum

Biological Activity of Bergaptol

DescriptionBergaptol acts as a potent inhibitor of debenzylation activity of CYP3A4 enzyme with an IC50 value of 24.92 uM.Bergaptol shows very good radical scavenging activity, it induces dose-dependent cytotoxic effect on MCF-7 cell viability.
TargetsCYP3A4
In vitro

Antitumor and apoptotic effects of bergaptol are mediated via mitochondrial death pathway and cell cycle arrest in human breast carcinoma cells.[Reference: WebLink]

Bangl. J. Pharmacol., 2016, 11(2):489.

The aim of the present research work was to investigate the anti-cancer and apoptotic effects of Bergaptol in human breast cancer cells (MCF-7).
METHODS AND RESULTS:
The effects on cell cycle arrest and caspase activation were evaluated. MTT assay was used to evaluate the effect of the compound on cell viability. Cellular morphology was demonstrated by fluorescence microscopy. Flow cytometry was used to analyze effect of Bergaptol on cell cycle and apoptosis. The results revealed that Bergaptol induced dose-dependent cytotoxic effect on MCF-7 cell viability showing IC50 value of 52.2 μM. Bergaptol induced both early and late apoptosis in concentration-dependent manner. After treatment with Bergaptol, an increase in the proportion of cells in the S-phase (37.2, 45.3 and 65.1% as compared to 28.6% in untreated cells) and a reduction in the fraction of cells in the G1 phase (44.1, 41.6 and 35.2% as compared to 51.2% in the untreated cells) was observed.

Protocol of Bergaptol

Kinase Assay

Radical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit.[Pubmed: 17400460]

Bioorg Med Chem. 2007 Jun 1;15(11):3684-91.

Grapefruit juice has been shown to increase the oral bioavailability of several clinically important drugs by inhibiting first pass metabolism. Several compounds in grapefruit juice have shown different biological activities. Unique among them are furocoumarins with potent inhibitory activity against cytochrome P450 enzymes.
METHODS AND RESULTS:
In the present study, two bioactive compounds were isolated from grapefruit juice and grapefruit peel oil. The purity of the isolated compounds has been analyzed by HPLC. Structures of the compounds were elucidated by extensive NMR and mass spectral studies and identified as Bergaptol and geranylcoumarin. The isolated compounds were tested for their radical scavenging activity using 2,2'-azobis (3-ethylbenz-thiazoline-6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazil (DPPH) methods at different concentrations. Bergaptol showed very good radical scavenging activity at all the tested concentrations. Furthermore, these compounds were evaluated for their inhibitory activity against CYP3A4 enzyme.
CONCLUSIONS:
Bergaptol and geranylcoumarin were found to be potent inhibitors of debenzylation activity of CYP3A4 enzyme with an IC(50) value of 24.92 and 42.93 microM, respectively.

Bergaptol Dilution Calculator

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Bergaptol Molarity Calculator

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Preparing Stock Solutions of Bergaptol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.9456 mL 24.728 mL 49.456 mL 98.912 mL 123.64 mL
5 mM 0.9891 mL 4.9456 mL 9.8912 mL 19.7824 mL 24.728 mL
10 mM 0.4946 mL 2.4728 mL 4.9456 mL 9.8912 mL 12.364 mL
50 mM 0.0989 mL 0.4946 mL 0.9891 mL 1.9782 mL 2.4728 mL
100 mM 0.0495 mL 0.2473 mL 0.4946 mL 0.9891 mL 1.2364 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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References on Bergaptol

Radical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit.[Pubmed:17400460]

Bioorg Med Chem. 2007 Jun 1;15(11):3684-91.

Grapefruit juice has been shown to increase the oral bioavailability of several clinically important drugs by inhibiting first pass metabolism. Several compounds in grapefruit juice have shown different biological activities. Unique among them are furocoumarins with potent inhibitory activity against cytochrome P450 enzymes. In the present study, two bioactive compounds were isolated from grapefruit juice and grapefruit peel oil. The purity of the isolated compounds has been analyzed by HPLC. Structures of the compounds were elucidated by extensive NMR and mass spectral studies and identified as Bergaptol and geranylcoumarin. The isolated compounds were tested for their radical scavenging activity using 2,2'-azobis (3-ethylbenz-thiazoline-6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazil (DPPH) methods at different concentrations. Bergaptol showed very good radical scavenging activity at all the tested concentrations. Furthermore, these compounds were evaluated for their inhibitory activity against CYP3A4 enzyme. Bergaptol and geranylcoumarin were found to be potent inhibitors of debenzylation activity of CYP3A4 enzyme with an IC(50) value of 24.92 and 42.93 microM, respectively.

Description

Bergaptol is a hydroxylated psoralen that acts as a potent inhibitors of debenzylation activity of CYP3A4 enzyme with an IC50 value of 24.92 uM.

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