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Advisor(s)
Abstract(s)
Phenolic acids are ubiquitous antioxidants accounting for approximately one third of the phenolic
compounds in our diet. Their importance was supported by epidemiological studies that suggest an
inverse relationship between dietary intake of phenolic antioxidants and the occurrence of diseases, such
as cancer and neurodegenerative disorders. However, until now, most of natural antioxidants have
limited therapeutic success a fact that could be related with their limited distribution throughout the
body and with the inherent difficulties to attain the target sites.
The development of phenolic antioxidants based on a hybrid concept and structurally based on natural
hydroxybenzoic (gallic acid) and hydroxycinnamic (caffeic acid) scaffolds seems to be a suitable solution
to surpass the mentioned drawbacks. Galloylecinnamic hybrids were synthesized and their antioxidant
activity as well as partition coefficients and redox potentials evaluated. The structureepropertyeactivity
relationship (SPAR) study revealed the existence of a correlation between the redox potentials and
antioxidant activity. The galloylecinnamic acid hybrid stands out as the best antioxidant supplementing
the effect of a blend of gallic acid plus caffeic acid endorsing the hypothesis that the whole is greater than
the sum of the parts. In addition, some hybrid compounds possess an appropriate lipophilicity allowing
their application as chain-breaking antioxidant in biomembranes or other type of lipidic systems. Their
predicted ADME properties are also in accordance with the general requirements for drug-like compounds.
Accordingly, these phenolic hybrids can be seen as potential antioxidants for tackling the oxidative
status linked to the neurodegenerative, inflammatory or cancer processes.
Description
Keywords
Cinnamic acid Gallic acid Hybrid antioxidants Antioxidant activity Redox potential SPAR Drug-like properties
Citation
Publisher
Elsevier