Discovery of cycloneolignan enantiomers from Isatis indigotica Fortune with neuroprotective effects against MPP+-induced SH-SY5Y cell injury

[Display omitted] •Two new cycloneolignan enantiomers were isolated.•The absolute configurations were determined by ECD calculations.•Enantiomers exhibited neuroprotective activity.•Enantiomers exhibited activity by reducing the apoptosis ratio. A pair of new cycloneolignan enantiomers (1a and 1b) w...

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Published in:Bioorganic chemistry 2019-07, Vol.88, p.102926-102926, Article 102926
Main Authors: Xi, Yu-Fei, Liu, Si-Fan, Hong, Wei, Song, Xiao-Yu, Lou, Li-Li, Zhou, Le, Yao, Guo-Dong, Lin, Bin, Wang, Xiao-Bo, Huang, Xiao-Xiao, Song, Shao-Jiang
Format: Article
Language:English
Subjects:
Apoptosis
Cycloneolignan
Enantiomers
Isatis indigotica
Neuroprotective effects
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Summary:[Display omitted] •Two new cycloneolignan enantiomers were isolated.•The absolute configurations were determined by ECD calculations.•Enantiomers exhibited neuroprotective activity.•Enantiomers exhibited activity by reducing the apoptosis ratio. A pair of new cycloneolignan enantiomers (1a and 1b) were isolated from the leaves of Isatis indigotica Fortune. Their structures were elucidated by extensive spectroscopic data analysis, including 1D and 2D NMR, HRESIMS, MS/MS analysis, together with theoretical electronic circular dichroism (ECD) calculations. Compounds 1a and 1b were then evaluated for their neuroprotective effects against MPP+-induced SH-SY5Y cell injury. As a result, compounds 1a (77.64%) and 1b (78.62%) exhibited moderate neuroprotective activity at the concentration of 12.5 µM compared with that of MPP+ treated group (62.00% at 1 mM) by MTT assay. Furthermore, Annexin V-FITC/PI analysis showed that apoptosis ratios of 1a and 1b were reduced to 10.99% and 9.31%, respectively.
ISSN:0045-2068
1090-2120
DOI:10.1016/j.bioorg.2019.102926