synthesis and antiradicalantioxidant activities of caffeic acid phenethyl ester and its related propionic, acetic, and benzoic acid analoguesc咖啡酸苯乙基酯的合成和antiradicalantioxidant活动及其相关丙、醋、苯甲酸analoguesc.pdfVIP

Molecules 2012, 17, 14637-14650; doi:10.3390/molecules171214637 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis and Antiradical/Antioxidant Activities of Caffeic Acid Phenethyl Ester and Its Related Propionic, Acetic, and Benzoic Acid Analogues Luc M. LeBlanc, Aurélie F. Paré, Jacques Jean-François, Martin J. G. Hébert, Marc E. Surette and Mohamed Touaibia * Department of Chemistry and Biochemistry, Université de Moncton, Moncton, NB E1A 3E9, Canada; E-Mails: LC280974@dal.ca (L.M.L.); aurelie.pare@usherbrooke.ca (A.F.P.); jacques.jean-francois@umoncton.ca (J.J .-F.); emh3363@umoncton.ca (M.J.G.H.); marc.surette@umoncton.ca (M.E.S.) * Author to whom correspondence should be addressed; E-Mail: mohamed.touaibia@umoncton.ca; Tel.: +1-506-858-4493; Fax: +1-506-858-4541. Received: 25 October 2012; in revised form: 9 November 2012 / Accepted: 5 December 2012 / Published: 10 December 2012 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 a