Insight into tetrahydrofuran lignans from Isatis indigotica fortune with neuroprotective and acetylcholinesterase inhibitor activity. (April 2023)

• Record Type: Journal Article
• Authors: Xi, Yu-Fei; Bai, Ming; Zhang, Xin; Hou, Zi-Lin; Lin, Bin; Yao, Guo-Dong; Lou, Li-Li; Wang, Xiao-Bo; Song, Shao-Jiang; Huang, Xiao-Xiao
• Is Part Of: Phytochemistry. Volume 208(2023)
• Publication Date: 2023-04
• Subjects: Isatis indigotica Fortune -- Brassicaceae -- Tetrahydrofuran lignans -- MAEΔΔδ parameter -- Neuroprotective effects -- Acetylcholinesterase inhibitory; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2023.113609
• Languages: English
• ISSNs: 0031-9422

Abstract

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 MAEΔΔ δ 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 H2 O2 -induced SH-SY5Y cells model. In addition, (−)-(7 R, 8 S, 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. Graphical abstract: Nine tetrahydrofuran lignans, including three undescribed spiro-lignans, were isolated from Isatis indigotica Fortune (Brassicaceae). These undescribed spiro-lignans with a unique spiro[dienone-tetrahydrofuran] molecular core. Image 1 Highlights: Three undescribed spiro-lignans were isolated from Isatis indigotica Fortune. The structure elucidation was achieved by quantum chemical calculation. Isatispironeols A-B have a unique spiro[dienone-tetrahydrofuran] molecular core. These spiro-lignans showed comparable neuroprotective effects. (−)-isatispironeol A possessed greater AChE inhibitory activity.