Addition of Malonyl Groups Enhances Intestinal Absorption of Anthocyanins Derived from Edible Red Chrysanthemum (Dendranthema grandiflorum) in Rats

Abstract

Petals of red chrysanthemum (Dendranthema grandiflorum) are habitually eaten in Japan. In the present study, plasma concentration profiles of two major acylated anthocyanins derived from the petals of red chrysanthemum were evaluated in rats after oral administration of an anthocyanin-rich fraction obtained from red chrysanthemum. The structures of the two major anthocyanins in the petals of red chrysanthemum were determined to be cyanidin 3-O-β-D-(3″, 6″-di-O-malonyl)-glucopyranoside and cyanidin 3-O-β-D-(6″-mono-O-malonyl)-glucopyranoside. Both malonyl anthocyanins were quickly absorbed from the gastrointestinal tract and were detected in rat blood plasma in their original acylated forms 15 min after the oral administration of the anthocyanin fraction obtained from the petals of red chrysanthemum. The absorption amounts of anthocyanins evaluated from the area under the plasma concentration curves during 8 h normalized to the orally administered dose were in the following order: cyanidin 3-O-β-D-(3″, 6″-di-O-malonyl)-glucopyranoside > cyanidin 3-O-β-D-(6″-mono-O-malonyl)-glucopyranoside > cyanidin 3-O-β-D-glucopyranoside. The present results demonstrated that the additional malonylation of the glucopyranosyl moiety of position 3″ and 6″ of cyanidin 3-O-β-D-glucopyranoside enhanced the intestinal absorption of anthocyanins.