Interactions between stipuol enantiomers and human serum albumin

Jiayang Feng; Xi Zhao; Yunlong Yan; Haiyao Chen; Jia Liu; Xiangyang Li; Risong Na; Qing X Li

doi:10.1016/j.foodchem.2022.132686

Interactions between stipuol enantiomers and human serum albumin

Food Chem. 2022 Aug 15:385:132686. doi: 10.1016/j.foodchem.2022.132686. Epub 2022 Mar 11.

Authors

Jiayang Feng¹, Xi Zhao², Yunlong Yan³, Haiyao Chen², Jia Liu⁴, Xiangyang Li⁵, Risong Na⁶, Qing X Li⁷

Affiliations

¹ Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Zhengzhou 450002, China.
² Institute of Theoretical Chemistry, College of Chemistry, Jilin University, Liutiao Road 2, Changchun 130021, China.
³ Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang, Guizhou Province 550025, China.
⁴ Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Zhengzhou 450002, China. Electronic address: liujia372029@henau.edu.cn.
⁵ Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang, Guizhou Province 550025, China. Electronic address: xyli1@gzu.edu.cn.
⁶ Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Zhengzhou 450002, China. Electronic address: nrs@henau.edu.cn.
⁷ Department of Molecular Biosciences and Bioengineering, University of Hawaii at Manoa, Honolulu, HI 96822, USA.

PMID: 35299022
DOI: 10.1016/j.foodchem.2022.132686

Abstract

Natural polyacetylenes occur in food and herbal plants, have a wide range of bioactivities, and are recognized as important nutraceuticals. Stipuol is a natural polyacetylene present in the edible plant Panax notoginseng. The present study was aimed to study interactions of rac-stipuol and its enantiomers with human serum albumin (HSA) using multi-spectroscopic, molecular modeling and microscale thermophoresis. Steady-state and time-resolved fluorescence spectra manifest that the fluorescence quenching mechanism is mainly static in type. The bindings of (S)-stipuol, (R)-stipuol, rac-stipuol lead to some microenvironmental and slight conformational changes of HSA. Competitive ligand displacement experiments and molecular modeling studies revealed that stipuol enantiomers bind to HSA at subdomain III (site IIA). The calculated values of K_a and K_d showed that (R)-stipuol had a stronger binding affinity than (S)-stipuol. The results are informative for use of stipuol as a nutraceutical to improve human health.

Keywords: Food safety; Human serum albumin; Molecular modeling; Natural polyacetylene; Nutraceutical.

MeSH terms

Binding Sites
Circular Dichroism
Humans
Molecular Docking Simulation
Protein Binding
Serum Albumin* / chemistry
Serum Albumin, Human* / chemistry
Spectrometry, Fluorescence
Stereoisomerism
Thermodynamics

Substances

Serum Albumin
Serum Albumin, Human