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Updated: Jul 19, 2025

Author Spotlight: Unveiling the Structural and Dynamic Aspects of Glycan Molecular Recognition
Published on: May 17, 2024
Probing covalent and non-covalent interactions between vanillic acid and starch and their effects on digestibility by
Yunxiang Ma1, Ruixi Chen2, Zidi Chen2
1College of Food Science and Engineering, Gansu Agricultural University, Lanzhou 730070, Gansu, China; State Key Laboratory of Arid Land Crop Science, Gansu Agricultural University, Lanzhou 730070, Gansu, China.
Abstract:
Intermolecular interactions play a significant role on the physicochemical properties and digestibility of starchy foods. This study investigated the covalent and non-covalent interactions between vanillic acid (VA) and porous starch (PS) as well as their effects on digestibility using solid-state NMR. VA-PS conjugates and mixtures were synthesized and characterized using 1H NMR, FT-IR, SEM and XRD. 13C NMR peaks at 163 ppm and FT-IR signals at 1737 cm-1 indicated the formation of ester bond in VA-PS conjugates. While differences between covalent and non-covalent interactions were also probed by solid-state NMR. The specific binding sites between VA and PS were subsequently identified by 1H13C HETCOR spectra before assessing the impact of covalent and non-covalent interactions on digestibility through an in vitro digestion test. The results revealed 13C chemical shifts of about 2.0 ppm, indicating stronger intermolecular interactions, and reduced mobility of the VA-PS conjugate due to its covalent bonding. Overall, the results showed that the VA-PS conjugate, characterized by stronger covalent interactions, exhibited superior effects in inhibiting starch digestibility compared with non-covalent interactions.
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