Active sites of peptides Asp-Asp-Asp-Tyr and Asp-Tyr-Asp-Asp protect against cellular oxidative stress

Huifan Liu; Jiaxi Liang; Gengsheng Xiao; Celia Vargas-De-La-Cruz; Jesus Simal-Gandara; Jianbo Xiao; Qin Wang

doi:10.1016/j.foodchem.2021.130626

Active sites of peptides Asp-Asp-Asp-Tyr and Asp-Tyr-Asp-Asp protect against cellular oxidative stress

Food Chem. 2022 Jan 1:366:130626. doi: 10.1016/j.foodchem.2021.130626. Epub 2021 Jul 19.

Authors

Huifan Liu¹, Jiaxi Liang¹, Gengsheng Xiao¹, Celia Vargas-De-La-Cruz², Jesus Simal-Gandara³, Jianbo Xiao⁴, Qin Wang⁵

Affiliations

¹ College of Light Industry and Food, Zhongkai University of Agriculture and Engineering, Guangzhou, Guangdong 510225, China; Guangdong Provincial Key Laboratory of Lingnan Specialty Food Science and Technology, Guangzhou, Guangdong, China.
² Faculty of Pharmacy and Biochemistry, Academic Department of Pharmacology, Bromatology and Toxicology, Centro Latinoamericano de Enseñanza e Investigación en Bacteriología Alimentaria (CLEIBA), Universidad Nacional Mayor de San Marcos, Lima 15001, Peru; Research Group Biotechnology and Omics in Life Sciences, Universidad Nacional Mayor de San Marcos, Lima 15001, Peru.
³ Nutrition and Bromatology Group, Analytical and Food Chemistry Department, Faculty of Food Science and Technology, University of Vigo, Ourense Campus, E-32004 Ourense, Spain.
⁴ Nutrition and Bromatology Group, Analytical and Food Chemistry Department, Faculty of Food Science and Technology, University of Vigo, Ourense Campus, E-32004 Ourense, Spain. Electronic address: [email protected].
⁵ College of Light Industry and Food, Zhongkai University of Agriculture and Engineering, Guangzhou, Guangdong 510225, China; Guangdong Provincial Key Laboratory of Lingnan Specialty Food Science and Technology, Guangzhou, Guangdong, China. Electronic address: [email protected].

PMID: 34325244
DOI: 10.1016/j.foodchem.2021.130626

Abstract

The protective effects of the peptides Asp-Asp-Asp-Tyr (DDDY) and Asp-Tyr-Asp-Asp (DYDD) against AAPH-induced HepG2 cells are unclear. Our objective was to investigate the active sites of these peptides and their cellular antioxidant mechanism. DDDY and DYDD show a direct free radical scavenging effect in reducing ROS levels and maintained cellular antioxidant enzymes at normal levels. The quantum chemistry analysis of the electronic properties of antioxidant activity showed that DYDD has a greater energy in the highest occupied molecular orbital than DDDY, and O₅₈-H₅₉ and N₁₀-H₁₂ were identified as the active antioxidant sites in DYDD and DDDY, respectively, indicating that the inconsistent arrangement of amino acids affects the distribution of the highest occupied orbital energy as well as the active sites; thus, influences the antioxidant activity of peptides. It provide valuable insights into the antioxidant active sites of peptides.

Keywords: Active site; Antioxidant peptide; HepG2; Nrf2; Quantum chemistry.

MeSH terms

Antioxidants / pharmacology
Catalytic Domain
Dipeptides
Oxidative Stress*
Peptides*

Substances

Antioxidants
Dipeptides
Peptides
aspartyl-aspartic acid
aspartyltyrosine