Diverse metabolites from corn silk with anti-Aβ1-42 aggregation activity

Wei-Yu Zhou; Li-Li Lou; Rui Guo; Yu-Fei Xi; Bin Lin; Xiao-Xiao Huang; Shao-Jiang Song

doi:10.1016/j.fitote.2019.104356

Diverse metabolites from corn silk with anti-Aβ_1-42 aggregation activity

Fitoterapia. 2019 Oct:138:104356. doi: 10.1016/j.fitote.2019.104356. Epub 2019 Sep 11.

Authors

Wei-Yu Zhou¹, Li-Li Lou¹, Rui Guo¹, Yu-Fei Xi¹, Bin Lin², Xiao-Xiao Huang³, Shao-Jiang Song⁴

Affiliations

¹ Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
² School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
³ Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China; Chinese People's Liberation Army Logistics support force No.967 Hospital, Dalian 116021, People's Republic of China. Electronic address: xiaoxiao270@163.com.
⁴ Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address: songsj99@163.com.

PMID: 31520649
DOI: 10.1016/j.fitote.2019.104356

Abstract

Five pairs of enantiomeric compounds (1a/1b-5a/5b) including seven undescribed compounds (1a/1b-3a/3b, 4b) along with two known ones (. and .) have been isolated from corn silk (Stigma maydis). Racemic mixtures of these enantiomers were separated by HPLC with different types of chiral columns. Their structures were elucidated based on comprehensive spectroscopic analyses together with quantum chemical calculations of ¹³C NMR data and electronic circular dichroism (ECD) curves. All the isolates were evaluated for their inhibition ability of self-induced Aβ_1-42 aggregation. Among them, compounds 4a (88.36%), 4b (74.66%) and . (85.65%) showed stronger inhibitory activity than the positive control curcumin (61.90%). The different inhibition profiles of enantiomers 4a and 4b were explained by docking simulation studies.

Keywords: Amyloid-β aggregation; Corn silk; Enantiomers.

MeSH terms

Amyloid beta-Peptides / antagonists & inhibitors*
China
Flowers / chemistry*
Molecular Docking Simulation
Molecular Structure
Peptide Fragments / antagonists & inhibitors*
Phytochemicals / isolation & purification
Phytochemicals / pharmacology*
Protein Aggregation, Pathological / prevention & control*
Zea mays / chemistry*

Substances

Amyloid beta-Peptides
Peptide Fragments
Phytochemicals
amyloid beta-protein (1-42)