Inhibitory Effect of Cyclodextrins on the Discoloration Reaction of an Anthocyanidin, Pelargonidin Chloride, in Acidic Media

Abstract

An anthocyanidin, pelargonidin (PG), loses its color with time in acidic media. The rate determining step of the discoloration reaction at pH 1–4 is the nucleophilic attack of the OH^- ion on PG to give a hemiacetal, which readily isomerizes to the corresponding α-diketone. Native, branched, and methylated cyclodextrins (CDs) form inclusion complexes with PG to retard the discoloration. The inhibitory effect (copigmentation) of CDs on the PG discoloration is slight in α-CD, significant in β- and γ-CDs, and the largest in heptakis(2,6-dimethyl)-β-CD (DM-β-CD). The β-CD and DM-β-CD include the phenyl moiety of PG, whereas γ-CD includes the benzopyrylium moiety of PG. The CD cavities protect the reaction site of included PG from the attack of the OH^- ion.