Synthesis and dopaminergic neuroprotective activity of the proposed structure of bassiamide A, a caffeamide alkaloid derived from Bassia indica Wight.

Abstract

Herein, we describe the synthesis of the proposed structure of the caffeamide alkaloid bassiamide A. The amide moiety of bassiamide A was readily formed via an amide coupling reaction between caffeic acid and the known N-(3-aminopropyl)-3-methylbutanamide. However, the spectral data of the synthesized bassiamide A did not agree with that of a previous study. The structure of the synthesized bassiamide A was confirmed using combined two-dimensional NMR analysis. Extended analyses of the bioactivity of the synthesized bassiamide A revealed its efficacy in protecting dopaminergic neurons from MPP+-induced neurotoxicity in C. elegans. Additionally, treatment with bassiamide A notably ameliorated the impaired food-sensing ability and locomotion of C. elegans, suggesting a protective effect on the functionality of dopaminergic neurons.