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J Nat Prod. 2017 Jun 23;80(6):1939-1943. doi: 10.1021/acs.jnatprod.7b00173. Epub 2017 May 19.

Interaction of 7-Alkoxycoumarins with the Aryl Hydrocarbon Receptor.

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Department of Experimental Medicine, University of Perugia , Polo Unico Sant'Andrea delle Fratte, Piazzale Gambuli, 06132, Perugia, Italy.
Department of Pharmacy, University "G. D'Annunzio" of Chieti-Pescara , Via dei Vestini 31, 66100 Chieti Scalo (CH), Italy.
Department of Medicine, Piazzale Gambuli, University of Perugia , Perugia, Italy.
Zentrum für Allergie und Umwelt (ZAUM), Technische Universität und Helmholtz Zentrum , München, Germany.


The aryl hydrocarbon receptor (AhR) is a transcription factor activated by a vast array of natural and synthetic ligands. It plays a pivotal role in numerous physiological and pathological responses, such as cell proliferation and differentiation, induction of xenobiotic metabolizing enzymes, response to environmental toxins, and several others. In this study, we investigated the ability of some natural compounds (oxyprenylated ferulic acid and umbelliferone derivatives) and their semisynthetic analogues (e.g., differently substituted 7-alkoxycoumarins) to activate AhR, using a reporter luciferase assay. Among them, we found that 7-isopentenyloxycoumarin was the best AhR activator. Boropinic acid, 7-but-2'-enyloxycoumarin, 7-(2',2'-dimethyl-n-propyloxy)coumarin, 7-benzyloxycoumarin, and 7-(3'-hydroxymethyl-3'-methylallyloxy)coumarin were also active, although to a lesser extent. All the compounds were also analyzed for their ability to inhibit AhR activation, using a reference ligand, 6-formylindolo[3,2-b]carbazole. Data recorded in the present investigation pointed out the importance of a 3,3-dimethylallyloxy side chain attached to the coumarin ring core as a key moiety for AhR activation.

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