6’,7’-Epoxybergamottin

6'7'-Epoxybergamottin is a furanocoumarin found in grapefruit.¹ It is a potent inhibitor of the cytochrome P450 (CYP) isoform CYP3A4 with an IC₅₀ value of 0.30 ppm in a cell-free assay, 0.33 µM in HL7 human liver cells, and 0.22 µM in S9 human intestine cells.² It has been studied in the context of drug interactions with grapefruit constituents. It is found in grapefruit juice at concentrations of 0.1-7.4 µM and inhibits the transport of talinolol (Item No. 16116), a permeability glycoprotein (P-gp/ABCB1) transporter substrate, across Caco-2 cell monolayers (IC₅₀ = 0.7 µM).³

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1. Manthey, J.A., Myung, K., Mertens-Talcott, S., et al. The isolation of minor-occurring furano coumarins in grapefruit and analysis of their inhibition of CUP 2A4 and P-Glycoprotein transport of talinolol from caco-2 cells. Proc. Fla. State Hort. Soc. 119, 361-366 (2006).

2. Row, E.C., Brown, S.A., Stachulski, A.V., et al. Design, synthesis and evaluation of furanocoumarin monomers as inhibitors of CYP3A4. Org. Biomol. Chem. 4(8), 1604-1610 (2006).

3. de Castro, W.V., Mertens-Talcott, S., Derendorf, H., et al. Grapefruit juice-drug interactions: Grapefruit juice and its components inhibit P-glycoprotein (ABCB1) mediated transport of talinolol in Caco-2 cells. J. Pharm. Sci. 96(10), 2808-2817 (2007).