Molecular mechanisms of caramel-like odorant-olfactory receptor interactions based on a computational chemistry approach

Shitong Zeng; Lili Zhang; Peng Li; Dandan Pu; Yingjie Fu; Ruiyi Zheng; Hui Xi; Kaina Qiao; Dingzhong Wang; Baoguo Sun; Shihao Sun; Yuyu Zhang

doi:10.1016/j.foodres.2023.113063

Molecular mechanisms of caramel-like odorant-olfactory receptor interactions based on a computational chemistry approach

Food Res Int. 2023 Sep:171:113063. doi: 10.1016/j.foodres.2023.113063. Epub 2023 May 29.

Authors

Shitong Zeng¹, Lili Zhang², Peng Li³, Dandan Pu², Yingjie Fu³, Ruiyi Zheng², Hui Xi³, Kaina Qiao², Dingzhong Wang³, Baoguo Sun², Shihao Sun⁴, Yuyu Zhang⁵

Affiliations

¹ Zhengzhou Tobacco Research Institute of CNTC, Zhengzhou 450001, China; Key Laboratory of Flavor Science of China General Chamber of Commerce, Beijing Technology and Business University, Beijing 100048, China.
² Key Laboratory of Flavor Science of China General Chamber of Commerce, Beijing Technology and Business University, Beijing 100048, China; Food Laboratory of Zhongyuan, Beijing Technology and Business University, Beijing 100048, China.
³ Zhengzhou Tobacco Research Institute of CNTC, Zhengzhou 450001, China.
⁴ Zhengzhou Tobacco Research Institute of CNTC, Zhengzhou 450001, China. Electronic address: sunsh@ztri.com.cn.
⁵ Key Laboratory of Flavor Science of China General Chamber of Commerce, Beijing Technology and Business University, Beijing 100048, China; Food Laboratory of Zhongyuan, Beijing Technology and Business University, Beijing 100048, China. Electronic address: zhangyuyu@btbu.edu.cn.

PMID: 37330856
DOI: 10.1016/j.foodres.2023.113063

Abstract

Molecular mechanisms of caramel-like odorant-olfactory receptor interactions were investigated based on molecular docking and molecular dynamics simulations. The transmembrane regions TM-3, TM-5 and TM-6 of receptors were main contributors of amino acid residues in the docking. Molecular docking results showed that hydrogen bonding and pi-pi stacking were the key forces for the stabilization of caramel-like odorants. The binding energies were positively correlated with the molecular weight of caramel-like odorants. Residues Asn155 (84%, OR2W1), Asn206 (86%, OR8D1), Ser155 (77%, OR8D1), Asp179 (87%, OR5M3), Val182 (84%, OR2J2) and Tyr260 (94%, OR2J2) with high frequencies played an important role in the complexes formation. Odorants 4-hydroxy-5-methylfuran-3(2H)-one (16#) and methylglyoxal (128#) were screened by molecular field-based similarity analysis, which tended to bind to the receptors OR1G1 and OR52H1 respectively, resulting a caramel-like aroma perception. The obtained results are useful for better understanding the perception of caramel-like odorants and their high-throughput screening.

Keywords: Caramel; Molecular docking; Molecular dynamics simulations; Molecular field-based similarity analysis; Odor; Olfactory receptor.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Computational Chemistry
Molecular Docking Simulation
Odorants* / analysis
Receptors, Odorant* / chemistry
Receptors, Odorant* / metabolism
Smell

Substances

Receptors, Odorant