Heliotropamide, a novel oxopyrrolidine-3-carboxamide from Heliotropium ovalifolium.

Heliotropamide (1), a new alkaloid with a novel oxopyrrolidine-3-carboxamide central moiety, has been isolated as the major product of the dicholoromethane extract of Heliotropium ovalifolium aerial parts. Its structure was elucidated by spectrometric methods including ESI-HR, EI, D/CI mass spectrometry, (1)H, (13)C, and 2D NMR experiments, and chemical derivatization. Neither heliotropamide nor its acetylated derivative (1a) showed any antifungal activity against Cladosporium cucumerinum and Candida albicans, antibacterial activity against Bacillus subtilis, radical-scavenging properties in the DPPH test, or inhibitory potential toward acetylcholinesterase.