Food Chem. 2021 Mar 3;353:129429. doi: 10.1016/j.foodchem.2021.129429. Online ahead of print.
ABSTRACT
The mechanistic insights into the oral pungency of capsaicin-related dietary components have been elucidated from the spatial structural perspectives by establishing statistically significant and highly predictive three-dimensional quantitative structure-property relationship models. Our results visualized the possible favorable and unfavorable steric and electrostatic interactions with the pungent receptors with the assistance of pharmacophore models, and revealed the suitable electronegative/positive or bulky substitutions in the vanillyl group, amide moiety, linear alkyl chain and their adjacent structural area of capsaicin required for the desired pungency, which was not only complementary to the viewpoints proposed in our previous structure-pungency correlations, but also was applied to clearly clarify the pungent differences in compounds, and well predict the pungency of 21 capsaicin analogs though with ambiguous experimental data on pungency. Hopefully, this work would benefit the overall understanding of the pungent mechanism and facile discovery/design of analogs with desired pungency to expand their applications in foods.
PMID:33714121 | DOI:10.1016/j.foodchem.2021.129429
