A naturally occurring furanocoumarin with diverse biological activities
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Isomer(s)
351678-Geranyloxypsoralen
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Bergamottin

Item No. 10009439

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one
CAS Number
7380-40-7
Synonyms
  • 5-Geranoxypsoralen
Molecular Formula
C21H22O4
Formula Weight
338.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 10 mg/ml
λmax
250, 308 nm
SMILES
O=C1C=CC2=C(OC/C=C(C)/CC/C=C(C)/C)C3=C(OC=C3)C=C2O1
InChi Code
InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+
InChi Key
DBMJZOMNXBSRED-OQLLNIDSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Bergamottin is a furanocoumarin found in grapefruit juice and lemon, lime, and bergamot oils that has diverse biological activities.1 In vitro, bergamottin inhibits migration and invasion of HT-1080 fibrosarcoma cells at sub-cytotoxic concentrations via inhibition of matrix metalloproteinase-9 (MMP-9) expression.2 It shows antiproliferative activity against HepG2 liver, HL-60 leukemia, and BGC-823 gastric cancer cell lines in a dose-dependent manner and induces cell death of CHO cells following near ultraviolet irradiation.1,3 Bergamottin inhibits the cytochrome P450 isoform 3A4 (CYP3A4; Ki = 7.7 μM) and is a mixed inhibitor of simvastatin (Item No. 10010344) drug metabolism (Ki = 174 μM).4,5 It also increases glucose consumption in HepG2 cells in a dose-dependent manner.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ashwood-Smith, M.J., Ceska, O., Warrington, P.J., et al. The photobiological activity of 5-geranoxypsoralen and its photoproducts. Photochem. Photobiol. 55(4), 529-532 (1992).

    2. Hwang, Y.P., Yun, H.J., Choi, J.H., et al. Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by bergamottin via the inhibition of protein kinase Cdelta/p38 mitogen-activated protein kinase and JNK/nuclear factor-kappaB-dependent matrix metalloproteinase-9 expression. Mol. Nutr. Food Res. 54(7), 977-990 (2010).

    3. Liu, Y., Ren, C., Cao, Y., et al. Characterization and purification of bergamottin from Citrus grandis (L.) Osbeck cv. Yongjiazaoxiangyou and its antiproliferative activity and effect on glucose consumption in HepG2 cells. Molecules 22(7), (2017).

    4. He, K., Iyer, K.R., Hayes, R.N., et al. Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chem. Res. Toxicol. 11(4), 252-259 (1998).

    5. Le Goff-Klein, N., Koffel, J.C., Jung, L., et al. In vitro inhibition of simvastatin metabolism, a HMG-CoA reductase inhibitor in human and rat liver by bergamottin, a component of grapefruit juice. Eur. J. Pharm. Sci. 18(1), 31-35 (2003).