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Open Access Green as soon as Postprint is submitted to ZB.
Interaction of 7-alkoxycoumarins with the aryl hydrocarbon receptor.
J. Nat. Prod. 80, 1939-1943 (2017)
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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Publication type
Article: Journal article
Document type
Scientific Article
Keywords
Ah Receptor; Coumarins; Ligand; Cells; Derivatives; Activation; Expression
ISSN (print) / ISBN
0163-3864
e-ISSN
1520-6025
Journal
Journal of natural products
Quellenangaben
Volume: 80,
Issue: 6,
Pages: 1939-1943
Publisher
American Chemical Society (ACS)
Publishing Place
Washington, DC
Reviewing status
Peer reviewed
Institute(s)
Institute for Allergy Research (IAF)