A furanocoumarin with diverse biological activities
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Enantiomer(s)
27801Xanthotoxol
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Bergaptol

Item No. 38742

Technical Information
Formal Name
4-hydroxy-7H-furo[3,2-g][1]benzopyran-7-one
CAS Number
486-60-2
Synonyms
  • 4-Hydroxybergapten
  • 5-Hydroxyfuranocoumarin
  • 5-Hydroxypsoralen
  • NSC 341958
Molecular Formula
C11H6O4
Formula Weight
Purity
≥95%
A solid
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 2 mg/ml
λmax
222, 251, 270, 315 nm
SMILES
O=C1OC2=C(C=C1)C(O)=C3C=COC3=C2
InChi Code
InChI=1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H
InChi Key
GIJHDGJRTUSBJR-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Bergaptol is a furanocoumarin that has been found in A. dahurica and has diverse biological activities.1,2,3,4 It inhibits the cytochrome P450 (CYP) isoform CYP3A4 (IC50 = 24.92 µM).2 It scavenges DPPH (Item No. 14805) and ABTS (Item No. 27317) radicals in cell-free assays (EC50s = 26.66 and 13.55 µg/ml, respectively).1 Bergaptol reduces the replication of L. donovani, T. b. brucei, and T. cruzi in L6 myoblasts (IC50s = 2.5, 22.1, and 68 µg/ml, respectively).3 It induces cell cycle arrest at the S phase and apoptosis in MCF-7 breast cancer cells in a concentration-dependent manner.4 Bergaptol also decreases the proliferation of HeLa cervical carcinoma and HepG2 liver cancer cells (IC50s = 58.57 and 68.42 µM, respectively).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bai, Y., Li, D., Zhou, T., et alCoumarins from the roots of Angelica dahurica with antioxidant and antiproliferative activities. J. Funct. Foods 20, 453-462 (2016).

    2. Girennavar, B., Jayaprakasha, G.K., Jadegoud, Y., et alRadical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit. Bioorg. Med. Chem. 15(11), 3684-3691 (2007).

    3. Tasdemir, D., Kaiser, M., Brun, R., et alAntitrypanosomal and antileishmanial activities of flavonoids and their analogues: In vitro, in vivo, structure-activity relationship, and quantitative structure-activity relationship studies. Antimicrob. Agents Chemother. 50(4), 1352-1364 (2006).

    4. Ge, Z.-C., Qu, X., Yu, H.-F., et alAntitumor and apoptotic effects of bergaptol are mediated via mitochondrial death pathway and cell cycle arrest in human breast carcinoma cells. Bangladesh J. Pharmacol. 11(2), 489-494 (2016).