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

J Nat Prod. 2003 Dec;66(12):1550-3. doi: 10.1021/np0302495.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Candida albicans / drug effects
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification*
  • Cholinesterase Inhibitors / pharmacology
  • Cladosporium / drug effects
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / isolation & purification*
  • Free Radical Scavengers / pharmacology
  • Heliotropium / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Pyrrolidines / chemistry
  • Pyrrolidines / isolation & purification*
  • Pyrrolidines / pharmacology
  • Zimbabwe

Substances

  • Alkaloids
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Cholinesterase Inhibitors
  • Free Radical Scavengers
  • Pyrrolidines
  • heliotropamide