Isoscopoletin

Isoscopoletin is a coumarin that has been found in D. fragrans and has diverse biological activities and is an active metabolite of scoparone .^1,2,3,4,5 It is formed from scoparone by the cytochrome P450 (CYP) isoform Cyp2c29 in mouse liver microsomes.⁵ Isoscopoletin is cytotoxic to A549 lung, MCF-7 breast, and HepG2 liver cancer cells (IC₅₀s = 5.25, 8.58, and 4.76 ?M, respectively).¹ It is active against Gram-positive and Gram-negative bacteria, including S. aureus and E. coli, respectively, as well as the plant pathogenic fungus A. niger, in agar diffusion assays.² Isoscopoletin inhibits 15-lipoxygenase (15-LO; IC₅₀ = 15.1 ?M) and reduces paw thickness in a rat model of carrageenan-induced paw edema when administered at a dose of 0.1 mg/kg.^3,4

1.Zhao, D.-D., Zhao, Q.-S., Liu, L., et al.Compounds from Dryopteris fragrans (L.) Schott with cytotoxic activityMolecules19(3)3345-3355(2014) 2.Nazir, S., Li, B., Tahir, K., et al.Antimicrobial activity of five constituents isolated from Ranunculus muricatusJ. Med. Plants Res.7(47)3438-3443(2013) 3.Deng, S., Palu, A.K., West, B.J., et al.Lipoxygenase inhibitory constituents of the fruits of noni (Morinda citrifolia) collected in TahitiJ. Nat. Prod.70(5)859-862(2007) 4.Selim, Y.A., and Ouf, N.H.Anti-inflammatory new coumarin from the Ammi majus LOrg. Med. Chem. Lett.2(1)1(2012) 5.Meyer, R.P., Hagemeyer, C.E., Knoth, R., et al.Oxidative hydrolysis of scoparone by cytochrome P450 CYP2C29 reveals a novel metaboliteBiochem. Biophys. Res. Commun.285(1)32-39(2001)