Inclusion complex formation between high amylose corn starch and alkylresorcinols from rye bran

•Alkylresorcinols (ARs) consisting of 13 homologs were extracted from rye bran.•ARs were shown to form inclusion complex with high amylose corn starch.•Inclusion complex was extracted by two steps to determine complexed AR components.•Saturated ARs with longer alkyl chains form more stable complex.•The AR inclusion complex may have potential use as anti-staling agent. The formation of high amylose corn starch (HACS)-alkylresorcinol (AR) inclusion complexes was demonstrated using HACS and a crude AR extract from rye bran, and was confirmed by complementary characterization techniques. Inclusion complex was extracted using hot 2-propanol/water (3:1), and thirteen different AR homologs were identified in the 2-propanol/water extract. However, this extraction regime was insufficient to remove all guests from the inclusion complexes, but did result in annealing of the V-type crystallinity, yielding an endotherm with higher onset and peak temperatures and dissociation enthalpy. The remaining guest compounds were recovered by disruption of the inclusion complexes with DMSO followed by liquid-liquid extraction. A total of nine AR homologs were recovered and two saturated long alkyl chain AR homologs (C21:0 and C19:0) were obviously enriched in the complexes compared to the crude AR extract. The formation of HACS-AR inclusion complexes may have the potential to inhibit staling in baked goods.