European Journal of Medicinal Chemistry p. 274 - 282 (2018)
Update date:2022-07-29
Topics:
Fiorito, Serena
Epifano, Francesco
Preziuso, Francesca
Cacciatore, Ivana
di Stefano, Antonio
Taddeo, Vito Alessandro
de Medina, Philippe
Genovese, Salvatore
Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor β and aryl hydrocarbon receptor. Such a modulation strictly depends on the individual structure of the coumarin: the presence of a 3,3-dimethylallyloxy side chain is a structural determinant for tanning activation whereas a farnesyl one leads to the opposite effect. The parent compound with a free OH group, umbelliferone, did not provide any interaction. Other coumarins assayed, having shorter chains and/or being substituted in other positions, and prenyloxypsoralens, were not active or not further investigated in this context being cytotoxic at low doses.
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