Chlorogenic Acids Mimics - Synthesis, Structure and Antioxidant Activity
Magdalena Szewczyk, Maja Morawiak, Aleksandra Narczyk, Zbigniew Pakulski, Zofia Urbanczyk-Lipkowska

A series of chlorogenic acid analogs involving replacement of quinic moiety by glucuronic acid followed by coupling with ferulic, lipoic or caffeic acid as well as exchange an ester bond between saccharide and natural polyphenol by an amide bond were synthesized. Antioxidant and free radical scavenging properties of such conjugates in comparison to chlorogenic, ferulic, caffeic and lipoic acids were tested by FRAP and ABTS tests, respectively. These results suggest that replacement of quinic by glucuronic moiety yields chlorogenic acid mimics with high antioxidant activity. Experimental evidence was found that antioxidant and scavenging properties are independent properties and are derivative of not only natural type of polyphenol but also sugar moiety. Molecular structure of compounds 10 and stereochemistry of substrate 1 were confirmed on the basis of X-ray analysis of the respective monocrystals.

Full Text: PDF DOI: 10.15640/jcb.v6n1a4