Lipophilicity, expressed quantitatively through the LogP, is the most important physicochemical
property for pharmacodynamic and pharmacokinetic characterization of the tested compound,
as well as the most widely used parameter for quantitative structure-activity relationships
(QSAR) descriptions. For this purpose three analytical techniques: the classical Shake Flask, the innovative
Vortex-Assisted Liquid-Liquid Micro-Extraction (VALLME), and HPLC method, have been
employed for the LogP determination of naturally occurring oxyprenylated secondary metabolites
such as boropinic and geraniloxyferulic (GOFA) acid. These techniques have allowed us to correctly determine the LogP
value for model molecule (ferulic acid) and from the comparison, by means of statistical techniques, of the obtained results
it was possible to determine, not only for the first time, the LogP value of these secondary metabolites with interesting
biological activity, but it was also possible to highlight the potential and limitations of the used techniques respect to
the presence of interfering and / or degradation products.
Keywords: Boropinic acid, lipophilicity evaluation, 3-(4'-geranylxy-3'-methoxyphenyl)-2-trans-propenoic acid, prenyloxyphenylpropanoids,
RP-HPLC method, Shake-flask, VALLME method.
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