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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 MAEΔΔδ 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.
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. [Display omitted]
•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.