Tao Wenwen, Li Qingyao, Chen Kexian, Feng Ling, Li Zuguang
School of Food Science and Biotechnology, Zhejiang Gongshang University, Hangzhou, Zhejiang 310018, PR China.
School of Food Science and Biotechnology, Zhejiang Gongshang University, Hangzhou, Zhejiang 310018, PR China.
Food Chem. 2021 Aug 15;353:129429. doi: 10.1016/j.foodchem.2021.129429. Epub 2021 Mar 3.
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.
通过建立具有统计学意义且高度预测性的三维定量结构-性质关系模型，从空间结构角度阐明了辣椒素相关膳食成分的口腔辛辣感的作用机制。我们的研究结果借助药效团模型，直观呈现了与辛辣受体可能存在的有利和不利的空间及静电相互作用，并揭示了辣椒素香草基、酰胺部分、线性烷基链及其相邻结构区域中，产生所需辛辣感所需的合适的电负性/正性或体积较大的取代基，这不仅与我们之前的结构-辛辣度相关性中提出的观点互补，还用于清晰阐明化合物之间的辛辣差异，并通过预测21种辣椒素类似物的辛辣度，尽管其辛辣度实验数据不明确。希望这项工作有助于全面理解辛辣机制，并便于发现/设计具有所需辛辣度的类似物，以扩大其在食品中的应用。
