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Peer-reviewedCC BYFood Chemistry: X

Unraveling the formation mechanism of 3-methylindole from tryptophan in the glucose-mediated Maillard reaction: a combined ReaxFF MD, DFT, and experimental study

  • Yuan-Yuan Yang1
  • Chao-Kun Wei
  • Xin Pan2
  • An-Ran Zheng3
  • Wen-Li Wang4
  • Chun-Mei Yang5
  • Yuan Liu6
6 affiliations
  1. 1School of Food Science and Engineering, Ningxia University, Yinchuan 750021, People's Republic of China; School of Biological Science and Engineering, North Minzu University, Yinchuan 750021, People's Republic of China
  2. 2School of Food Science and Engineering, Ningxia University, Yinchuan 750021, People's Republic of China
  3. 3School of Biological Science and Engineering, North Minzu University, Yinchuan 750021, People's Republic of China
  4. 4School of Agriculture & Biology, Shanghai Jiao Tong University, Shanghai 200240, People's Republic of China
  5. 5Ningxia Ningyang Food Co., Ltd., Wuzhong 751100, People's Republic of China
  6. 6School of Food Science and Engineering, Ningxia University, Yinchuan 750021, People's Republic of China; School of Agriculture & Biology, Shanghai Jiao Tong University, Shanghai 200240, People's Republic of China
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Abstract

3-Methylindole is a concentration-dependent aroma compound, and its formation mechanism in the tryptophan-glucose Maillard reaction is crucial for flavor regulation but remains incompletely elucidated. Using gas chromatography-olfactometry-mass spectrometry (GC-O-MS), 3-methylindole was identified as a key odor-active compound (OAV > 1). Reactive molecular dynamics (ReaxFF MD) and density functional theory (DFT) revealed a sequential pathway involving nucleophilic addition, Amadori rearrangement, dehydration, decarboxylation, and Strecker degradation, and characterized 16 transition states and their activation energies, indicating a net endothermic reaction. Pyrolysis-gas chromatography–mass spectrometry (Py-GC–MS) detected methylglyoxal and indole-3-acetaldehyde as key intermediates, whose temperature-dependent concentration trends supported the proposed pathway. Differential scanning calorimetry (DSC) further confirmed the multi-stage endothermic behavior, consistent with the DFT results. This study proposes a complete formation mechanism of 3-methylindole, providing a theoretical basis for indole-type flavor generation and a methodological framework for studying volatile compounds in complex thermally processed food systems.

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Cite

BibTeXRIS
BibTeX
@article{yang2026unraveling,
  title = {{Unraveling the formation mechanism of 3-methylindole from tryptophan in the glucose-mediated Maillard reaction: a combined ReaxFF MD, DFT, and experimental study}},
  author = {Yuan-Yuan Yang and Chao-Kun Wei and Xin Pan and An-Ran Zheng and Wen-Li Wang and Chun-Mei Yang and Yuan Liu},
  journal = {Food Chemistry: X},
  year = {2026},
  month = nov,
  doi = {10.1016/j.fochx.2026.104719},
  url = {https://doi.org/10.1016/j.fochx.2026.104719},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Unraveling the formation mechanism of 3-methylindole from tryptophan in the glucose-mediated Maillard reaction: a combined ReaxFF MD, DFT, and experimental study
AU  - Yuan-Yuan Yang
AU  - Chao-Kun Wei
AU  - Xin Pan
AU  - An-Ran Zheng
AU  - Wen-Li Wang
AU  - Chun-Mei Yang
AU  - Yuan Liu
PY  - 2026
DA  - 2026/11/06
JO  - Food Chemistry: X
DO  - 10.1016/j.fochx.2026.104719
UR  - https://doi.org/10.1016/j.fochx.2026.104719
AB  - 3-Methylindole is a concentration-dependent aroma compound, and its formation mechanism in the tryptophan-glucose Maillard reaction is crucial for flavor regulation but remains incompletely elucidated. Using gas chromatography-olfactometry-mass spectrometry (GC-O-MS), 3-methylindole was identified as a key odor-active compound (OAV > 1). Reactive molecular dynamics (ReaxFF MD) and density functional theory (DFT) revealed a sequential pathway involving nucleophilic addition, Amadori rearrangement, dehydration, decarboxylation, and Strecker degradation, and characterized 16 transition states and their activation energies, indicating a net endothermic reaction. Pyrolysis-gas chromatography–mass spectrometry (Py-GC–MS) detected methylglyoxal and indole-3-acetaldehyde as key intermediates, whose temperature-dependent concentration trends supported the proposed pathway. Differential scanning calorimetry (DSC) further confirmed the multi-stage endothermic behavior, consistent with the DFT results. This study proposes a complete formation mechanism of 3-methylindole, providing a theoretical basis for indole-type flavor generation and a methodological framework for studying volatile compounds in complex thermally processed food systems.
SN  - 2590-1575
ER  -