Neuroprotective and acetylcholinesterase inhibitory activities of alkaloids from Solanum lyratum Thunb.: An in vitro and in silico analyses. (May 2023)

• Record Type: Journal Article
• Authors: Chang, Ye; Bai, Ming; Zhang, Xin; Shen, Shuai; Hou, Jiao-Yang; Yao, Guo-Dong; Huang, Xiao-Xiao; Song, Shao-Jiang
• Is Part Of: Phytochemistry. Volume 209(2023)
• Publication Date: 2023-05
• Subjects: Solanum lyratum Thunb. -- Solanaceae -- Alkaloids -- Neuroprotective activity -- Acetylcholinesterase inhibitor -- Chiral resolution -- Molecular docking; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2023.113623
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: The n -BuOH extract from the herb of Solanum lyratum Thunb. (Solanaceae) was purified by various chromatographic methods, which led to the isolation of seven undescribed alkaloids ((−)-(7′ S )– N -feruloyltyramine A, (+)-(7′ R )- N -feruloyltyramine A, (+)-(7′ S )– N- solanamide A, (−)-(7′ R )- N- solanamide A, 7′ S -perillascens, solanpyrrole A, and ( Z )-asmurratetra A) and 13 known alkaloids, including four pairs of enantiomers. Extensive spectroscopic data and electronic circular dichroism (ECD) calculations were applied to determine the structures of the undescribed compounds. In in vitro biological activity assays, (−)-(7′ S )– N -feruloyltyramine A and (+)-(7′ R )- N -feruloyltyramine A exhibited pronounced neuroprotective effects against SH-SY5Y cell damage with survival rates of 75.98% and 76.61%, respectively, at 50 μM. Additionally, (−)-(7′ S )– N -feruloyltyramine A and N - cis -feruloyl-3′-methoxy-tyramine displayed acetylcholinesterase (AChE) inhibitory effects with IC50 values of 7.41 ± 1.76 μM and 9.21 ± 0.89 μM, respectively. Molecular docking simulations revealed that (−)-(7′ S )– N -feruloyltyramine A had a binding site for AChE. These findings reveal the structural diversity of the bioactive compounds in S. lyratum and provides insights into the use of this information for the production of functional components in the pharmaceutical industry. Graphical abstract: Seven undescribed alkaloids and thirteen known alkaloids, including four pairs of enantiomers, were extracted and purified from the herb of S. lyratum, and their neuroprotective and acetylcholinesterase inhibitory activities of alkaloids were evaluated in vitro and in silico . Seven undescribed alkaloids and thirteen known alkaloids, including four pairs of enantiomers, were extracted and purified from the herb of S. lyratum, and their neuroprotective and acetylcholinesterase inhibitory activities of alkaloids were evaluated in vitro and in silico . Image 1 Highlights: Seven undescribed alkaloids and thirteen known alkaloids were purified from S. lyratum. Enantiomers were separated successfully by chiral chromatographic column. The neuroprotective and acetylcholinesterase inhibitory activities of alkaloids were evaluated in vitro and in silico.