Inclusion complexes of rosmarinic acid and cyclodextrins: stoichiometry, association constants, and antioxidant potential

Abstract

The interaction between beta-cyclodextrin (beta-CD) and the polyphenol rosmarinic acid (RA) is here reported by H-1 NMR titration experiments. The formation of an aqueous soluble inclusion complex is confirmed and valuable information regarding mode of penetration of guest into beta-CD, stoichiometry, and stability of the complex is obtained. The analysis by the continuous variation method shows the undoubted formation of 1:1 beta-CD/RA complex. Additionally, the estimated apparent association constants reveal the importance of the asymmetry of the RA in the complexation; the incorporation of the catechol moiety closer to the carboxylic group is more favorable (K = 2,028 M-1) than from the other end of the RA molecule (K = 1,184 M-1). Finally, we have also investigated the antioxidant activity and storage stability of the beta-CD/RA complexed system; the presence of beta-CD was found to produce a remarkable enhancement on the antioxidant activity.