10.1021/acs.jnatprod.7b00175.s001 Salvatore Genovese Salvatore Genovese Vito Alessandro Taddeo Vito Alessandro Taddeo Francesco Epifano Francesco Epifano Serena Fiorito Serena Fiorito Cécile Bize Cécile Bize Arnaud Rives Arnaud Rives Philippe de Medina Philippe de Medina Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a <i>Ferulago</i> Species American Chemical Society 2017 Bioactive Prenylated Coumarin HPLC stability studies drug candidate stress conditions NMR data data support MS antigenotoxic properties Ferulago Species Umbelliprenin degradative products 16- membered macrocycle UV-B filters stability profile information hydrolytic medium umbelliprenin plant metabolite chemopreventive agent storage conditions UV-A filters Degradation Profile light exposure 2017-08-30 16:37:46 Journal contribution https://acs.figshare.com/articles/journal_contribution/Characterization_of_the_Degradation_Profile_of_Umbelliprenin_a_Bioactive_Prenylated_Coumarin_of_a_i_Ferulago_i_Species/5358517 Umbelliprenin is a secondary plant metabolite that displays promising chemopreventive, anti-inflammatory, and antigenotoxic properties. It possesses potential for applications to human welfare notably to prevent the emergence of cancer. For this purpose, stability studies are needed to define proper storage conditions and adapted formulations for this drug candidate. The identification of degradative products is a major concern for the preclinical development of umbelliprenin, providing also interesting information related to potential original phytochemicals formed in plants exposed to stressors. The stability profile of umbelliprenin under various stress conditions including exposure to heat, light, oxidation, and hydrolytic medium was assessed via HPLC/UV data. The data support that umbelliprenin undergoes inter- and intramolecular [2+2] cycloaddition under light exposure, leading respectively to a cyclobutane–umbelliprenin dimer and a 16-membered macrocycle. Their structures were characterized via MS and NMR data. It was shown that UV-A filters prevent this process, whereas UV-B filters and antioxidants are not or weakly effective. The study provides useful information for the preclinical development of umbelliprenin as an original chemopreventive agent.