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.