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Abstract
Caffeic acid phenethyl ester (CAPE) is a bioactive component isolated from propolis. A series of CAPE analogues was synthesized and their antiradical/antioxidant effects analyzed. The effect of the presence of the double bond and of the conjugated system on the antioxidant effect is evaluated with the analogues obtained from 3-(3,4-dihydroxyphenyl) propanoic acid. Those obtained from 2-(3,4-dihydroxyphenyl) acetic acid and 3,4-dihydroxybenzoic acid allow the evaluation of the effect of the presence of two carbons between the carbonyl and aromatic system.
Highlights
From ancient times to nowadays, whether on an empirical or rational basis, natural-based molecules have long been used as drugs or drug leads
Metal ion chelation and inhibition of specific enzymes that induce free radical or lipid peroxidation are acknowledged as the diverse mechanisms used by Caffeic acid phenethyl ester (CAPE) in its antioxidant activity [12,13]
Owing to the biological significance of caffeic acid analogues, we report the synthesis of phenethyl and phenpropyl esters of caffeic acid, 3-(3,4-dihydroxyphenyl) propanoic acid
Summary
From ancient times to nowadays, whether on an empirical or rational basis, natural-based molecules have long been used as drugs or drug leads. Metal ion chelation and inhibition of specific enzymes that induce free radical or lipid peroxidation are acknowledged as the diverse mechanisms used by CAPE in its antioxidant activity [12,13] Based on these promising results, several groups have started to explore strategies for the synthesis of caffeic acid or CAPE analogues with improved biological activities. Caffeic acid is prone to oxidative dimerization [19] In natural compounds such as caffeoylquininic acid, where two or three caffeoyl moieties might be present, such dimerization could influence the antioxidant activity of the molecules. To address this issue, Saito and co-workers synthesized 6 regio- and stereoisomers of dicaffeoyloxycyclohexanes and. The lengthening of the linker from phenethyl to phenpropyl is investigated
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