Insight into tetrahydrofuran lignans from Isatis indigotica fortune with neuroprotective and acetylcholinesterase inhibitor activity

Yu-Fei Xi; Ming Bai; Xin Zhang; Zi-Lin Hou; Bin Lin; Guo-Dong Yao; Li-Li Lou; Xiao-Bo Wang; Shao-Jiang Song; Xiao-Xiao Huang

doi:10.1016/j.phytochem.2023.113609

Insight into tetrahydrofuran lignans from Isatis indigotica fortune with neuroprotective and acetylcholinesterase inhibitor activity

Phytochemistry. 2023 Apr:208:113609. doi: 10.1016/j.phytochem.2023.113609. Epub 2023 Feb 8.

Authors

Yu-Fei Xi¹, Ming Bai¹, Xin Zhang¹, Zi-Lin Hou¹, Bin Lin², Guo-Dong Yao¹, Li-Li Lou³, Xiao-Bo Wang⁴, Shao-Jiang Song¹, Xiao-Xiao Huang⁵

Affiliations

¹ Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China.
² School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, 110016, China.
³ Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China. Electronic address: lou_li_li@163.com.
⁴ Chinese People's Liberation Army Logistics Support Force No. 967 Hospital, Dalian, 116021, China.
⁵ Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China. Electronic address: xiaoxiao270@163.com.

PMID: 36758886
DOI: 10.1016/j.phytochem.2023.113609

Abstract

Nine tetrahydrofuran lignans, including three undescribed spiro-lignans, were isolated from Isatis indigotica Fortune (Brassicaceae). Extensive spectroscopic analyses achieved the structure elucidation of these tetrahydrofuran lignans, and quantum chemical calculation combined with the MAE_ΔΔδ parameter. Notably, isatispironeols A-B have a unique spiro[dienone-tetrahydrofuran] molecular core. These spiro[dienone-tetrahydrofuran] lignans showed comparable neuroprotective effects as the positive control in the H₂O₂-induced SH-SY5Y cells model. In addition, (-)-(7R,8S,1'R,7'R,8'R)-isatispironeol A possessed more significant AChE inhibitory activity, further interact sites were also predicted by the in silico assay.

Keywords: Acetylcholinesterase inhibitory; Brassicaceae; Isatis indigotica Fortune; MAE(ΔΔδ) parameter; Neuroprotective effects; Tetrahydrofuran lignans.

MeSH terms

Acetylcholinesterase
Cholinesterase Inhibitors
Furans / chemistry
Humans
Hydrogen Peroxide
Isatis* / chemistry
Lignans* / chemistry
Molecular Structure
Neuroblastoma*

Substances

Lignans
Acetylcholinesterase
Cholinesterase Inhibitors
Hydrogen Peroxide
Furans