28587-44-2Relevant academic research and scientific papers
Natural oxyprenylated coumarins are modulators of melanogenesis
Fiorito, Serena,Epifano, Francesco,Preziuso, Francesca,Cacciatore, Ivana,di Stefano, Antonio,Taddeo, Vito Alessandro,de Medina, Philippe,Genovese, Salvatore
, p. 274 - 282 (2018)
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.
